Testosterone undecanoate

Short description: Chemical compound

Testosterone undecanoate

Clinical data
Pronunciation| /tɛˈstɒstəroʊn ənˈdɛkənoʊeɪt/ teh-STOS-tə-rohn ən-DEK-ə-noh-ayt
Trade names| Oral: Kyzatrex, Andriol, Jatenzo, others
IM: Aveed, Nebido, others
Other names| TU; Testosterone undecylate; Testosterone 17β-undecanoate; ORG-538; CLR-610
AHFS/Drugs.com| Monograph
MedlinePlus| a614041
License data|

* US DailyMed: Testosterone_undecanoate

Pregnancy
category|

* AU: D[1]

Routes of
administration| By mouth, intramuscular injection
Drug class| Androgen; Anabolic steroid; Androgen ester
ATC code|

* G03BA03 (WHO)

Legal status
Legal status|

* CA: Schedule IV
* US: Schedule III [2][3][4]

Pharmacokinetic data
Bioavailability| Oral: 3–7%
Intramuscular: high
Protein binding| High (testosterone)
Metabolism| Liver
Metabolites| Testosterone, undecanoic acid, metabolites of testosterone
Elimination half-life| IM (in tea seed oil): 20.9 days[5][6]
IM (in castor oil): 33.9 days[5][6]
Excretion| ~90% Urine, 6% feces
Identifiers

IUPAC name

* [(8R,9S,10R,13S,14S,17S)-10,13-Dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl] undecanoate

CAS Number|

* 5949-44-0 Y

PubChem CID|

* 65157

DrugBank|

* DB13946 Y

ChemSpider|

* 58664 Y

UNII|

* H16A5VCT9C

KEGG|

* D06087 Y

ChEBI|

* CHEBI:135741 Y

ChEMBL|

* ChEMBL2107067 Y

Chemical and physical data
Formula| C30H48O3
Molar mass| 456.711 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* CCCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CCC4=CC(=O)CC[C@]34C)C

InChI

* InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1 N

* Key:UDSFVOAUHKGBEK-CNQKSJKFSA-N N

(verify)

Testosterone undecanoate, sold under the brand names Andriol, Aveed and Nebido among others, is an androgen and anabolic steroid (AAS) medication that is used mainly in the treatment of low testosterone levels in men,[7][5][8][9][10][11][12] It is taken by mouth or given by injection into muscle.[9][13]

Side effects of testosterone undecanoate include symptoms of masculinization like acne, increased hair growth, voice changes, hypertension, elevated liver enzymes, hypertriglyceridemia, and increased sexual desire.[9] The drug is a prodrug of testosterone, the biological ligand of the androgen receptor (AR) and hence is an androgen and anabolic steroid.[14][9] It has strong androgenic effects and moderate anabolic effects, which make it useful for producing masculinization and suitable for androgen replacement therapy.[9] Testosterone undecanoate is a testosterone ester and a prodrug of testosterone in the body.[8][7][5] Because of this, it is considered to be a natural and bioidentical form of testosterone.[15]

Testosterone undecanoate was introduced in China for use by injection and in the European Union for use by mouth in the 1970s.[16][17] It became available for use by injection in the European Union in the early to mid 2000s and in the United States in 2014.[18][19] Formulations for use by mouth are approved in the United States.[2][3][20] Along with testosterone enanthate, testosterone cypionate, and testosterone propionate, testosterone undecanoate is one of the most widely used testosterone esters.[14][5][9] However, it has advantages over other testosterone esters in that it can be taken by mouth and in that it has a far longer duration when given by injection.[21][7][5][6][9] In addition to its medical use, testosterone undecanoate is used to improve physique and performance.[9] The drug is a controlled substance in many countries and so non-medical use is generally illicit.[9]

Oral administration of testosterone undecanoate is an effective method to achieve therapeutic physiological levels of serum testosterone in patients with hypogonadism. In addition, oral therapy has been found to have a positive impact on quality of life factors such as sexual function, mood, and mental status, as documented in various studies.[22]

## Contents

* 1 Medical dosage
* 2 Side effects
* 2.1 Anaphylaxis
* 3 Pharmacology
* 3.1 Pharmacodynamics
* 3.2 Pharmacokinetics
* 4 Chemistry
* 5 History
* 6 Society and culture
* 6.1 Generic names
* 6.2 Brand names
* 6.3 Availability
* 6.4 Legal status
* 7 Research
* 7.1 Non-alcoholic steatohepatitis
* 7.2 Osteoporosis
* 8 Health implications
* 8.1 Body composition
* 8.2 Bone density
* 9 References

## Medical dosage

Testosterone undecanoate is used in androgen replacement therapy in men, including trans-men. It is specifically approved only for the treatment of hypogonadism.[23][24][25] As an intramuscular injection, it is administered at a dosage of 1,000 mg (4 mL) once every 3 months.[13] Because of rare occasions of pulmonary embolism it is not recommended to inject 4 mL of Nebido into one muscle, but to split it into two 2mL injections into left and right counter muscles (e.g. gluteals).[26]

Conversely, oral testosterone undecanoate must be taken two or three times a day with food.[13][27]

## Side effects

Side effects of testosterone undecanoate include virilization among others.[9]

### Anaphylaxis

The Reandron 1000 formulation (Aveed in the United States) contains 1,000 mg of testosterone undecanoate suspended in 4 ml castor oil with benzyl benzoate for solubilization and as a preservative, and is administered by intramuscular injection. As an excipient in Reandron 1000, benzyl benzoate has been reported as a cause of anaphylaxis (a serious life-threatening allergic reaction) in a case in Australia .[28] Bayer includes this report in information for health professionals and recommends that physicians "should be aware of the potential for serious allergic reactions" to preparations of this type.[29] In Australia, reports to the Adverse Drug Reactions Advisory Committee (ADRAC), which evaluates reports of adverse drug reactions for the Therapeutic Goods Administration (TGA), show several reports of allergic reactions since the anaphylaxis case from 2011.

## Pharmacology

### Pharmacodynamics

v * d * e Androgenic vs. anabolic activity
of androgens/anabolic steroids  Medication | Ratioa

|

Testosterone | ~1:1
Androstanolone (DHT) | ~1:1
Methyltestosterone | ~1:1
Methandriol | ~1:1
Fluoxymesterone | 1:1–1:15
Metandienone | 1:1–1:8
Drostanolone | 1:3–1:4
Metenolone | 1:2–1:30
Oxymetholone | 1:2–1:9
Oxandrolone | 1:3–1:13
Stanozolol | 1:1–1:30
Nandrolone | 1:3–1:16
Ethylestrenol | 1:2–1:19
Norethandrolone | 1:1–1:20
Notes: In rodents. Footnotes: a = Ratio of androgenic to anabolic activity. Sources: See template.

Testosterone undecanoate is a prodrug of testosterone and is an androgen and anabolic–androgenic steroid (AAS). That is, it is an agonist of the androgen receptor (AR).

### Pharmacokinetics

Testosterone undecanoate has a very long elimination half-life and mean residence time when given as a depot intramuscular injection.[30][5][6] Its elimination half-life is 20.9 days and its mean residence time is 34.9 days in tea seed oil, while its elimination half-life is 33.9 days and its mean residence time is 36.0 days in castor oil.[5][6] These values are substantially longer than those of testosterone enanthate (which, in castor oil, has values of 4.5 days and 8.5 days, respectively).[30] Testosterone undecanoate is administered via intramuscular injection once every three months or so.[13][31]

## Chemistry

Testosterone undecanoate, or testosterone 17β-undecanoate, is a synthetic androstane steroid and a derivative of testosterone.[32][33] It is an androgen ester; specifically, it is the C17β undecylate (undecanoate) ester of testosterone.[32][33] A related testosterone ester with a similarly very long duration is testosterone buciclate.[7][8]

## History

In the late 1970s, testosterone undecanoate was introduced for oral use in Europe,[16] although intramuscular testosterone undecanoate had already been in use in China for several years.[17] Intramuscular testosterone undecanoate was not introduced in Europe and the United States until much later, in the early to mid 2000s and 2014, respectively.[18][19] Testosterone undecanoate was approved in the United States only in 2014 after three previous rejections due to safety concerns.[34]

## Society and culture

### Generic names

Testosterone undecanoate is the generic name of the drug and its USAN and BAN.[32][33][35][36] It is also referred to as testosterone undecylate.[32][33][35][36]

### Brand names

Testosterone undecanoate is or has been marketed under a variety of brand names, including Andriol, Androxon, Aveed, Cernos Depot, Jatenzo, Kyzatrex,[4] Nebido, Nebido-R, Panteston, Reandron 1000, Restandol, Sustanon 250, Undecanoate 250, and Undestor.[32][33][35][37][36]

### Availability

Oral testosterone undecanoate is available in Europe, Mexico, Asia, and in the United States.[38][39]

Intramuscular testosterone undecanoate has approved in over 100 countries worldwide,[38][9] including European Union, Russia and the USA.[9][38][40] Intramuscular testosterone undecanoate is marketed most commonly as Nebido in Europe and as Aveed in the United States while oral testosterone undecanoate is marketed most commonly as Andriol.[9][38][40] However, as of 2023 Nebido is not on the formulary of most US hospitals, due to several incidents of pulmonary embolism that have been reported in the country.

### Legal status

Testosterone undecanoate, along with other AAS, is a schedule III controlled substance in the United States under the Controlled Substances Act and a schedule IV controlled substance in Canada under the Controlled Drugs and Substances Act.[41][42]

In March 2019, the US Food and Drug Administration approved testosterone undecanoate (Jatenzo), an oral testosterone capsule to treat men with certain forms of hypogonadism. These men have low testosterone levels due to specific medical conditions, such as genetic disorders like Klinefelter syndrome or tumors that have damaged the pituitary gland.[20] The FDA granted the approval of Jatenzo to Clarus Therapeutics.[20][43]

In March 2022, testosterone undecanoate (Tlando) was approved for medical use in the United States.[3]

In July 2022, Kyzatrex, an oral testosterone undecanoate capsule, was approved for medical use in the United States.[4] The FDA granted the approval of Kyzatrex to Marius Pharmaceuticals.[44]

## Research

### Non-alcoholic steatohepatitis

In 2013, a phase II clinical trial testing intramuscular testosterone undecanoate for the treatment of non-alcoholic steatohepatitis (NASH) was initiated in the United Kingdom .[45] In the United States in 2018, Lipocine Inc. began investigating the potential of using an oral testosterone undecanoate formulation, known as LPCN-1144, in patients with NASH.[46]

### Osteoporosis

In 2013, a study aimed to evaluate the efficacy of testosterone undecanoate therapy on bone mineral density (BMD) and biochemical markers of bone turnover in elderly males with osteoporosis and low serum testosterone levels.

They study found that administering low-dose testosterone undecanoate (TU) at a rate of 20 mg per day to elderly men with low serum testosterone and osteoporosis effectively increases bone mineral density in the lumbar spine and femoral neck, and improves bone turnover, similar to the standard-dose TU (40 mg, per day) treatment. The treatment did not exhibit any adverse side effects on the prostate gland, including prostate-specific antigen. Therefore, low-dose TU appears to be a safe and cost-effective protocol for treating elderly male osteoporosis.[47] However, further clinical trials with larger sample sizes, multiple centers, and long-term follow-ups are required to determine the efficacy and safety of low-dose testosterone undecanoate treatment in elderly male osteoporosis with low serum testosterone.

## Health implications

### Body composition

In 2020, a study that evaluated the effects of testosterone therapy in men with testosterone deficiency and varying degrees of weight (normal weight, overweight, and obesity) on anthropometric and metabolic parameters found that long-term testosterone undecanoate therapy in hypogonadal men, regardless of their weight at the start of the study, led to improvements in several body composition parameters, including body weight, waist circumference, and body mass index. Additionally, testosterone undecanoate therapy was found to lower fasting blood glucose and HbA1c levels and improve lipid profiles in this population.[48]

### Bone density

There have been several studies that evaluate the effect of testosterone therapy on bone density or bone mineral density (BMD). One study concluded that long-term testosterone replacement therapy (TRT) in middle-aged men with late-onset hypogonadism (LOH) and metabolic syndrome (MS) led to a significant increase in both vertebral and femoral bone mineral density (BMD) after 36 months of treatment, as measured by dual-energy x-ray absorptiometry. The TRT treatment was shown to induce a 5% per year increase in BMD without changes in body mass index (BMI). The study suggests that long-term TRT could be beneficial for improving bone health in middle-aged men with LOH and MS, even in the absence of osteoporosis.[49]

## References

1. ↑ "Testosterone Use During Pregnancy". 20 August 2019. https://www.drugs.com/pregnancy/testosterone.html.
2. ↑ 2.0 2.1 "Jatenzo- testosterone undecanoate capsule, liquid filled". 11 January 2021. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=ed7b5d41-7475-4c10-99b9-b62b3434ae60.
3. ↑ 3.0 3.1 3.2 "Tlando- testosterone undecanoate capsule, liquid filled". 28 March 2022. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=479b55bd-2023-486a-8922-3b1de48b935c.
4. ↑ 4.0 4.1 4.2 "Kyzatrex- testosterone undecanoate capsule, liquid filled". 18 October 2022. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=7f7167a7-2a25-47e2-acf5-33f499fce971.
5. ↑ 5.0 5.1 5.2 5.3 5.4 5.5 5.6 5.7 Andrology: Male Reproductive Health and Dysfunction. Springer Science & Business Media. 13 January 2010. pp. 441–446. ISBN 978-3-540-78355-8. https://books.google.com/books?id=mEgckDNkonUC&pg=PA441.
6. ↑ 6.0 6.1 6.2 6.3 6.4 "Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies". European Journal of Endocrinology 140 (5): 414–419. May 1999. doi:10.1530/eje.0.1400414. PMID 10229906.
7. ↑ 7.0 7.1 7.2 7.3 Testosterone: Action, Deficiency, Substitution. Cambridge University Press. 26 July 2012. pp. 313–315, 321–322. ISBN 978-1-107-01290-5. https://books.google.com/books?id=MkrAPaQ4wJkC&pg=PA315. Retrieved 3 January 2018.
8. ↑ 8.0 8.1 8.2 Principles and Practice of Endocrinology and Metabolism. Lippincott Williams & Wilkins. 2001. pp. 1185–. ISBN 978-0-7817-1750-2. https://books.google.com/books?id=FVfzRvaucq8C&pg=PA1185. Retrieved 2018-01-03.
9. ↑ 9.00 9.01 9.02 9.03 9.04 9.05 9.06 9.07 9.08 9.09 9.10 9.11 9.12 Anabolics. Molecular Nutrition LLC. 2011. pp. 180–182, 331–334. ISBN 978-0-9828280-1-4. https://books.google.com/books?id=afKLA-6wW0oC&pg=PT180. Retrieved 2018-01-03.
10. ↑ "Testosterone therapy for transgender men". The Lancet. Diabetes & Endocrinology 5 (4): 301–311. April 2017. doi:10.1016/S2213-8587(16)00036-X. PMID 27084565.
11. ↑ "Long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals". The Journal of Sexual Medicine 4 (5): 1479–1484. September 2007. doi:10.1111/j.1743-6109.2007.00556.x. PMID 17635694.
12. ↑ "Safety aspects of 36 months of administration of long-acting intramuscular testosterone undecanoate for treatment of female-to-male transgender individuals". European Journal of Endocrinology 161 (5): 795–798. November 2009. doi:10.1530/EJE-09-0412. PMID 19749027.
13. ↑ 13.0 13.1 13.2 13.3 New Concepts for Human Disorders of Sexual Development. S. Karger AG. 28 September 2010. pp. 256–. ISBN 978-3-8055-9569-8. https://books.google.com/books?id=CQhaAgAAQBAJ&pg=PA256. Retrieved 3 November 2016.
14. ↑ 14.0 14.1 "Pharmacology of anabolic steroids". British Journal of Pharmacology 154 (3): 502–521. June 2008. doi:10.1038/bjp.2008.165. PMID 18500378.
15. ↑ "Compounded Bioidentical Hormones in Endocrinology Practice: An Endocrine Society Scientific Statement". The Journal of Clinical Endocrinology and Metabolism 101 (4): 1318–1343. April 2016. doi:10.1210/jc.2016-1271. PMID 27032319.
16. ↑ 16.0 16.1 Testosterone Dreams: Rejuvenation, Aphrodisia, Doping. University of California Press. 21 February 2005. pp. 134–. ISBN 978-0-520-93978-3. https://archive.org/details/testosteronedrea00hobe.
17. ↑ 17.0 17.1 The Scientific Basis of Urology. CRC Press. 26 July 2010. pp. 294–. ISBN 978-1-84184-749-8. https://books.google.com/books?id=h6HSBQAAQBAJ&pg=PA294. Retrieved 27 October 2017.
18. ↑ 18.0 18.1 Williams Textbook of Endocrinology. Elsevier Health Sciences. 11 November 2015. pp. 709, 711, 765. ISBN 978-0-323-34157-8. https://books.google.com/books?id=iPIACwAAQBAJ&pg=PA709. Retrieved 27 October 2017.
19. ↑ 19.0 19.1 "Testosterone Undecanoate-Schering AG". Drugs in R&D 5 (6): 368–369. 2004. doi:10.2165/00126839-200405060-00012. PMID 15563244.
20. ↑ 20.0 20.1 20.2 Meyer L (27 March 2019). "FDA approves new oral testosterone capsule for treatment of men with certain forms of hypogonadism" (Press release). U.S. Food and Drug Administration (FDA). Archived from the original on 7 September 2020. Retrieved 27 August 2020.
21. ↑ "A new oral testosterone undecanoate formulation". World Journal of Urology 21 (5): 311–315. November 2003. doi:10.1007/s00345-003-0372-x. PMID 14579074.
22. ↑ Ahmad, Syed W et al. “Is Oral Testosterone the New Frontier of Testosterone Replacement Therapy?.” Cureus vol. 14,8 e27796. 8 Aug. 2022, doi:10.7759/cureus.27796
23. ↑ "Testosterone undecanoate depot injection". AdisInsight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800017041.
24. ↑ "Testosterone undecanoate - Organon". AdisInsight. Springer Nature Switzerland AG. http://adisinsight.springer.com/drugs/800011489.
25. ↑ "Aveed- testosterone undecanoate injection". 23 August 2021. https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=f80f025b-17d8-40af-8739-20ce07902045.
26. ↑ https://www.bayer.com/sites/default/files/NEBIDO_EN_PIL.pdf
27. ↑ Pharmacology, Doping and Sports: A Scientific Guide for Athletes, Coaches, Physicians, Scientists and Administrators. Routledge. 27 October 2008. p. 25. ISBN 978-1-134-08880-5. https://books.google.com/books?id=nV3kDPoek5kC&pg=PA25. Retrieved 3 November 2016.
28. ↑ "Anaphylaxis triggered by benzyl benzoate in a preparation of depot testosterone undecanoate". Case Reports in Medicine 2012: 384054. 2012. doi:10.1155/2012/384054. 384054. PMID 22272209.
29. ↑ "Nebido Monograph - Information for Health Care Professionals". Bayer. 2016. http://www.nebido.com/en/hcp/product-information/nebido-monograph/index.php.
30. ↑ 30.0 30.1 The Leydig Cell in Health and Disease. Springer Science & Business Media. 28 October 2007. pp. 423–. ISBN 978-1-59745-453-7. https://books.google.com/books?id=x4ttqKIAOg0C&pg=PA423. Retrieved 6 October 2016.
31. ↑ Medical Care of Cancer Patients. PMPH-USA. 2009. pp. 247–. ISBN 978-1-60795-008-0. https://books.google.com/books?id=XxfjqF1A0TkC&pg=PA247. Retrieved 2017-10-30.
32. ↑ 32.0 32.1 32.2 32.3 32.4 The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. 14 November 2014. pp. 641–642. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA641. Retrieved 6 October 2016.
33. ↑ 33.0 33.1 33.2 33.3 33.4 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 1002–1004. ISBN 978-3-88763-075-1. https://books.google.com/books?id=5GpcTQD_L2oC&pg=PA1002. Retrieved 2017-12-13.
34. ↑ "FDA Approves Aveed Testosterone Jab, with Restrictions". March 7, 2014. http://www.medscape.com/viewarticle/821632.
35. ↑ 35.0 35.1 35.2 Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. 6 December 2012. ISBN 978-94-011-4439-1. https://books.google.com/books?id=tsjrCAAAQBAJ&pg=PA270. Retrieved 6 October 2016.
36. ↑ 36.0 36.1 36.2 "Testosterone". https://www.drugs.com/international/testosterone.html.
37. ↑ "Testosterone undecanoate profile and most popular brands in USA". http://downsizefitness.com/rankings/testosterone-undecanoate/.
38. ↑ 38.0 38.1 38.2 38.3 "The History of Testosterone and the Testes: From Antiquity to Modern Times". Testosterone. Springer. 2017. pp. 1–19. doi:10.1007/978-3-319-46086-4_1. ISBN 978-3-319-46084-0.
39. ↑ Hormones, Brain and Behavior, Five-Volume Set. Academic Press. 10 June 2002. pp. 20–. ISBN 978-0-12-532104-4. https://books.google.com/books?id=cGbE2nC__Q0C&pg=PA20. Retrieved 27 October 2017.
40. ↑ 40.0 40.1 "Drug Product Database - Health Canada". Health Canada. 2010-03-18. http://www.hc-sc.gc.ca/dhp-mps/prodpharma/databasdon/index-eng.php.
41. ↑ Drug Abuse Handbook, Second Edition. CRC Press. 21 December 2006. pp. 30–. ISBN 978-1-4200-0346-8. https://books.google.com/books?id=ZjrMBQAAQBAJ&pg=PA30. Retrieved 11 November 2017.
42. ↑ Pharmacology for Canadian Health Care Practice. Elsevier Health Sciences. 5 August 2016. p. 50. ISBN 978-1-77172-066-3. https://books.google.com/books?id=dNgoDwAAQBAJ&pg=PA50. Retrieved 11 November 2017.
43. ↑ "Clarus Therapeutics Receives U.S. FDA Approval of Jatenzo (Testosterone Undecanoate Capsules for Oral Use) (CIII) for Testosterone Replacement Therapy in Certain Adult Men". http://clarustherapeutics.com/content/investors-and-media/releases/clarus-receives-fda-approval-of-jatenzo.htm.
44. ↑ "Kyzatrex (testosterone undecanoate) FDA Approval History". https://www.drugs.com/history/kyzatrex.html.
45. ↑ Pilot Open Study of Testosterone Replacement in Non-alcoholic Steatohepatitis. 25 April 2017. https://clinicaltrials.gov/ct2/show/NCT01919294. Retrieved 14 March 2022.
46. ↑ "Lipocine Inc. - Clinical Trials". https://www.lipocine.com/pipeline/lpcn-1144/clinical-trials.htm.
47. ↑ "Effects of low-dose testosterone undecanoate treatment on bone mineral density and bone turnover markers in elderly male osteoporosis with low serum testosterone". International Journal of Endocrinology 2013: 570413. 2013. doi:10.1155/2013/570413. PMID 23533404.
48. ↑ "Differential effects of 11 years of long-term injectable testosterone undecanoate therapy on anthropometric and metabolic parameters in hypogonadal men with normal weight, overweight and obesity in comparison with untreated controls: real-world data from a controlled registry study". International Journal of Obesity 44 (6): 1264–1278. June 2020. doi:10.1038/s41366-019-0517-7. PMID 32060355.
49. ↑ "Effects of long-acting testosterone undecanoate on bone mineral density in middle-aged men with late-onset hypogonadism and metabolic syndrome: results from a 36 months controlled study". The Aging Male 15 (2): 96–102. June 2012. doi:10.3109/13685538.2011.631230. PMID 22439807.

* v
* t
* e

Testosterone

Topics|

* Testosterone (as a hormone)
* Testosterone (as a medication)
* Pharmacodynamics of testosterone
* Pharmacokinetics of testosterone
* Androgen (as a hormone)
* Androgen/anabolic steroid (as a medication)
* Androgen replacement therapy
* Transgender hormone therapy (female-to-male)

Esters|

* Androgen ester
* Testosterone ester
* Testosterone buciclate
* Testosterone caproate
* Testosterone cypionate
* Testosterone decanoate
* Testosterone enanthate
* Testosterone isobutyrate
* Testosterone isocaproate
* Testosterone phenylpropionate
* Testosterone propionate
* Testosterone undecanoate
* Mixed testosterone esters

Related|

* Dihydrotestosterone (DHT; androstanolone)
* Methyltestosterone
* Nandrolone (19-nortestosterone)
* Dehydroepiandrosterone (DHEA; prasterone)
* Estradiol

{{Navbox

| name = Androgens and antiandrogens
| title = Androgens and antiandrogens
| state = collapsed
| listclass = hlist
| groupstyle = text-align:center;

| group1 = Androgens
(incl. AAS)

| list1 =

AR agonists|

* Testosterone derivatives: Androstenediol dipropionate
* Boldenone undecylenate
* Clostebol
* Clostebol acetate
* Clostebol caproate
* Clostebol propionate
* Cloxotestosterone acetate
* Prasterone (dehydroepiandrosterone, DHEA)
* Prasterone enanthate (DHEA enanthate)
* Prasterone sulfate (DHEA sulfate)
* Quinbolone
* Testosterone#
* Testosterone esters (e.g., testosterone cypionate, testosterone enanthate]], testosterone propionate]], testosterone undecanoate]], testosterone ester mixture]]s (Deposterona, Omnadren, Sustanon, Testoviron Depot))

* Dihydrotestosterone derivatives: Androstanolone (stanolone, dihydrotestosterone, DHT)
* Androstanolone esters
* Bolazine capronate
* Drostanolone propionate (dromostanolone propionate)
* Epitiostanol
* Mepitiostane
* Mesterolone
* Metenolone acetate (methenolone acetate)
* Metenolone enanthate (methenolone enanthate)
* Stenbolone acetate

* 19-Nortestosterone derivatives: Bolandiol dipropionate
* Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
* Norclostebol
* Norclostebol acetate
* Oxabolone cipionate (oxabolone cypionate)
* Trenbolone acetate
* Trenbolone hexahydrobenzylcarbonate (trenbolone cyclohexylmethylcarbonate)

* 17α-Alkylated testosterone derivatives: Bolasterone
* Calusterone
* Chlorodehydromethyltestosterone (CDMT)
* Fluoxymesterone
* Formebolone
* Metandienone (methandienone, methandrostenolone)
* Methandriol (methylandrostenediol)
* Methandriol bisenanthoyl acetate
* Methandriol dipropionate
* Methandriol propionate
* Methyltestosterone
* Methyltestosterone 3-hexyl ether
* Oxymesterone
* Penmesterol
* Tiomesterone (thiomesterone)

* 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
* Furazabol
* Mebolazine (dimethazine)
* Mestanolone
* Oxandrolone
* Oxymetholone
* Stanozolol

* 17α-Alkylated 19-nortestosterone derivatives: Ethylestrenol
* Mibolerone
* Norethandrolone
* Normethandrone (methylestrenolone, normethisterone)
* Propetandrol (propethandrol)

* 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)

* 17α-Ethynyltestosterone derivatives: Danazol
* Gestrinone
* Progestins (e.g., ethisterone (ethynyltestosterone), levonorgestrel, norgestrel, norethisterone (norethindrone), [[Chemistry:Lynestrlynestrenol, Norgestrienone|norgestrienone]])
* Tibolone

* Progesterone derivatives: Medroxyprogesterone acetate

|

Progonadotropins|

* Antiestrogens (e.g., tamoxifen, Chemistry:Clomifene

| group2 = Antiandrogens
| list2 = {{Navbox|child
| groupstyle = text-align:center;
| groupwidth = 9em;

| group1 = AR antagonists
| list1 =

* Steroidal: Abiraterone acetate
* Canrenone
* Chlormadinone acetate
* Cyproterone acetate
* Delmadinone acetate
* Dienogest
* Drospirenone
* Medrogestone
* Megestrol acetate
* Nomegestrol acetate
* Osaterone acetate
* Oxendolone
* Potassium canrenoate
* Spironolactone

* Nonsteroidal: Apalutamide
* Bicalutamide
* Cimetidine
* Darolutamide
* Enzalutamide
* Flutamide
* Ketoconazole
* Nilutamide
* Seviteronel†
* Topilutamide (fluridil)

| group2 = Steroidogenesis
inhibitors

| list2 =

5α-Reductase|

* Alfatradiol
* Dutasteride
* Epristeride
* Finasteride
* Saw palmetto extract

|

Others|

* Abiraterone acetate
* Aminoglutethimide
* Bifluranol
* Cyproterone acetate
* Flutamide
* Ketoconazole
* Nilutamide
* Seviteronel†
* Spironolactone

| group3 = Antigonadotropins
| list3 =

* D2 receptor antagonists (prolactin releasers) (e.g., domperidone, metoclopramide, risperidone, haloperidol, chlorpromazine, sulpiride)
* Estrogens (e.g., bifluranol, [[diethylstilbestrol, estradiol, estradiol esters, ethinylestradiol, ethinylestradiol sulfonate, paroxypropione)
* GnRH agonists (e.g., leuprorelin)
* GnRH antagonists (e.g., cetrorelix)
* Progestogens (incl., chlormadinone acetate, [[cyproterone acetate, hydroxyprogesterone caproate, gestonorone caproate, [[Chemistry:Medroxyprogesterone medroxyprogesterone acetate, Chemistry:Megestrol acetate|megestrol acetate]])

| group4 = Others
| list4 =

* Androstenedione immunogens: Androvax (androstenedione albumin)
* Ovandrotone albumin (Fecundin)

| liststyle = background:#DDDDFF;

| list3 =

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

See also
Androgen receptor modulators
Estrogens and antiestrogens
Progestogens and antiprogestogens
List of androgens/anabolic steroids

* v
* t
* e

Androgen receptor modulators

AR|

| Agonists|

* Testosterone derivatives: 4-Androstenediol
* 4-Dehydroepiandrosterone (4-DHEA)
* 4-Hydroxytestosterone
* 4,17α-Dimethyltestosterone
* 5-Androstenedione
* 11-Ketotestosterone
* 11β-Hydroxyandrostenedione
* Adrenosterone (11-ketoandrostenedione, 11-oxoandrostenedione)
* Androstenediol (5-androstenediol)
* Androstenediol 3β-acetate
* Androstenediol 17β-acetate
* Androstenediol diacetate
* Androstenediol dipropionate
* Androstenedione (4-androstenedione)
* Atamestane
* Boldenone
* Boldenone undecylenate
* Boldione (1,4-androstadienedione)
* Clostebol
* Clostebol acetate
* Clostebol caproate
* Clostebol propionate
* Cloxotestosterone
* Cloxotestosterone acetate
* Dehydroandrosterone
* DHEA (androstenolone, prasterone; 5-DHEA)
* DHEA enanthate (prasterone enanthate)
* DHEA sulfate
* Exemestane
* Formestane
* Plomestane
* Quinbolone
* Silandrone
* Testosterone# (+dutasteride)
* Testosterone esters
* Polytestosterone phloretin phosphate

* Dihydrotestosterone derivatives: 1-Androstenediol
* 1-Androstenedione
* 1-Androsterone (1-andro, 1-DHEA)
* 1-Testosterone
* 3α-Androstanediol
* 5α-Androst-2-en-17-one
* 7β-Hydroxyepiandrosterone
* 11-Ketodihydrotestosterone
* Androsterone
* Bolazine
* Bolazine capronate
* Dihydroethisterone
* Dihydroethyltestosterone
* Dihydrofluoxymesterone
* Dihydromethylandrostenediol
* Dihydrotestosterone (DHT) (androstanolone, stanolone)
* Dihydrotestosterone esters
* Drostanolone
* Drostanolone propionate
* Epiandrosterone
* Epitiostanol
* Mepitiostane
* Mesabolone
* Mesterolone
* Mesterolone cipionate
* Methyldiazinol
* Nisterime
* Nisterime acetate
* Prostanozol
* Stenbolone
* Stenbolone acetate
* Testifenon (testiphenon, testiphenone)

* 19-Nortestosterone derivatives: 7α-Methyl-19-norandrostenedione (MENT dione, trestione)
* 11β-Methyl-19-nortestosterone
* 11β-Methyl-19-nortestosterone dodecylcarbonate
* 19-Nor-5-androstenediol
* 19-Nor-5-androstenedione
* 19-Nordehydroepiandrosterone
* Bolandiol
* Bolandiol dipropionate
* Bolandione (19-nor-4-androstenedione)
* Bolmantalate (nandrolone adamantoate)
* Dienedione
* Dienolone
* Dimethandrolone
* Dimethandrolone buciclate
* Dimethandrolone dodecylcarbonate
* Dimethandrolone undecanoate
* LS-1727 (nandrolone 17β-N-(2-chloroethyl)-N-nitrosocarbamate)
* Methoxydienone (methoxygonadiene)
* Nandrolone
* Nandrolone esters
* Norclostebol
* Norclostebol acetate
* Normethandrone (methylestrenolone, normethisterone)
* Oxabolone
* Oxabolone cipionate (oxabolone cypionate)
* Trenbolone
* Trenbolone acetate
* Trenbolone enanthate
* Trenbolone hexahydrobenzylcarbonate
* Trenbolone undecanoate
* Trendione
* Trestolone (MENT)
* Trestolone acetate
* Trestolone enanthate

* Dihydrotestosterone and 19-nortestosterone derivatives: 5α-Dihydrolevonorgestrel
* 5α-Dihydronandrolone
* 5α-Dihydronorethandrolone
* 5α-Dihydronorethisterone
* 5α-Dihydronormethandrone
* 5α-Dihydrotrestolone
* 19-Norandrosterone

* 17α-Alkylated testosterone derivatives: Bolasterone
* Calusterone
* Chlorodehydromethylandrostenediol (CDMA)
* Chlorodehydromethyltestosterone (CDMT)
* Chloromethylandrostenediol (CMA)
* Enestebol
* Ethyltestosterone
* Fluoxymesterone
* Formebolone
* Hydroxystenozole
* Metandienone (methandrostenolone)
* Methandriol (methylandrostenediol)
* Methandriol bisenanthoyl acetate
* Methandriol diacetate
* Methandriol dipropionate
* Methandriol propionate
* Methylclostebol (chloromethyltestosterone)
* Methyltestosterone (+esterified estrogens)
* Methyltestosterone 3-hexyl ether
* Oxymesterone
* Penmesterol
* Tiomesterone

* 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
* Desoxymethyltestosterone
* Furazabol
* Mebolazine (dimethazine)
* Mestanolone
* Metenolone
* Metenolone acetate
* Metenolone enanthate
* Methasterone
* Methyl-1-testosterone
* Methylepitiostanol
* Methylstenbolone
* Oxandrolone
* Oxymetholone
* Stanozolol

* 17α-Alkylated 19-nortestosterone derivatives: Bolenol
* Dimethyldienolone
* Dimethyltrienolone
* Ethyldienolone
* Ethylestrenol
* Methyldienolone
* Methylhydroxynandrolone (MOHN, MHN)
* Metribolone
* Mibolerone
* Norboletone
* Norethandrolone
* Propetandrol
* RU-2309
* Tetrahydrogestrinone

* 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
* Vinyltestosterone

* 17α-Ethynyltestosterone derivatives: Δ4-Tibolone
* Danazol
* Desogestrel
* Ethisterone (ethynyltestosterone)
* Etonogestrel
* Etynodiol
* Etynodiol diacetate
* Gestodene
* Gestrinone
* Levonorgestrel
* Levonorgestrel esters (e.g., levonorgestrel butanoate)
* Lynestrenol
* Lynestrenol phenylpropionate
* Norethisterone
* Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
* Norgestrel
* Norgestrienone
* Quingestanol
* Quingestanol acetate
* Tibolone

* Progesterone derivatives: Medroxyprogesterone acetate
* Megestrol acetate

* Others/unsorted: 3-Keto-5α-abiraterone
* 5α-Androstane
* Alternariol
* Cl-4AS-1
* Drupanol
* ZM-182345

|

Mixed
(SARMs)|

* Nonsteroidal: 198RL26
* ACP-105
* AC-262536
* Acetothiolutamide
* Andarine (acetamidoxolutamide, androxolutamide, GTx-007, S-4)
* BMS-564929
* DTIB
* Enobosarm (ostarine, MK-2866, GTx-024, S-22)
* FTBU-1
* GSK-4336A
* GSK-8698
* LG-121071 (LGD-121071)
* LGD-2226
* LGD-2941 (LGD-122941)
* LGD-3303
* LGD-4033
* JNJ-26146900
* JNJ-28330835
* JNJ-37654032
* ORM-11984
* R-1
* RAD140
* RU-59063
* S-1
* S-23
* S-40503
* S-101479
* Triclosan

* Steroidal: EM-9017
* MK-0773
* TFM-4AS-1
* YK-11

Antagonists|

* Steroidal: 7α-Thioprogesterone
* 7α-Thiospironolactone
* 7α-Thiomethylspironolactone
* 11α-Hydroxyprogesterone
* 15β-Hydroxycyproterone acetate
* Abiraterone
* Abiraterone acetate
* Allyltestosterone
* Benorterone
* BOMT
* Canrenoic acid
* Canrenone
* Chlormadinone acetate
* Clascoterone
* Clometerone
* Cyproheptadine
* Cyproterone
* Cyproterone acetate
* Delanterone
* Delmadinone acetate
* Dicirenone
* Dienogest
* Drospirenone
* DU-41165
* Edogestrone
* EM-4350
* EM-5854
* EM-5855
* EM-6537
* Epitestosterone
* Galeterone
* Guggulsterone
* Medrogestone
* Megestrol acetate
* Mespirenone
* Metogest
* Mexrenone
* Mifepristone
* Nomegestrol acetate
* Nordinone
* Osaterone
* Osaterone acetate
* Oxendolone
* Potassium canrenoate
* Promegestone
* Prorenone
* Rosterolone
* RU-15328
* SC-5233 (spirolactone)
* Spironolactone
* Spirorenone
* Spiroxasone
* Topterone
* Trimegestone
* Trimethyltrienolone (R-2956)
* Zanoterone

* Nonsteroidal: 5N-Bicalutamide
* AA560
* Antarlides
* Arabilin
* Apalutamide
* Atraric acid
* AZD-3514
* Bakuchiol
* BAY-1024767
* Bicalutamide
* Bisphenols (e.g., BADGE, BFDGE, bisphenol A, bisphenol F, bisphenol S)
* BMS-501949
* BMS-570511
* BMS-641988
* CH5137291
* Cimetidine
* Cioteronel
* Cyanonilutamide
* Darolutamide
* DDT (via metabolite p,p’-DDE)
* Dieldrin
* DIMP
* Endosulfan
* Enzalutamide
* EPI-001
* Fenarimol
* Flutamide
* Hydroxyflutamide
* Inocoterone
* Inocoterone acetate
* Ketoconazole
* Ketodarolutamide
* Lavender oil
* LG-105
* LG-120907
* LGD-1331
* Linuron
* Methiocarb
* N-Butylbenzenesulfonamide
* N-Desmethylapalutamide
* N-Desmethylenzalutamide
* Nilutamide
* ONC1-13B
* Pentomone
* PF-998425
* Phenothrin
* Prochloraz
* Procymidone
* Proxalutamide
* Ralaniten (EPI-002)
* Ralaniten acetate (EPI-506)
* RD-162
* Ro 2-7239
* Ro 5-2537
* RU-22930
* RU-56187
* RU-57073
* RU-58642
* RU-58841
* Seviteronel
* Thalidomide
* Topilutamide (fluridil)
* Valproic acid
* Vinclozolin
* YM-580
* YM-92088
* YM-175735

GPRC6A|

| Agonists|

* Cations (incl. aluminum, calcium, Gadolinium

|

See also
Receptor/signaling modulators
Androgens and antiandrogens
Estrogen receptor modulators
Progesterone receptor modulators
List of androgens/anabolic steroids

* v
* t
* e

Estrogen receptor modulators

ER|

| Agonists|

* Steroidal: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* 3-Methyl-19-methyleneandrosta-3,5-dien-17β-ol
* 3α-Androstanediol
* 3α,5α-Dihydrolevonorgestrel
* 3β,5α-Dihydrolevonorgestrel
* 3α-Hydroxytibolone
* 3β-Hydroxytibolone
* 3β-Androstanediol
* 4-Androstenediol
* 4-Androstenedione
* 4-Hydroxyestradiol
* 4-Hydroxyestrone
* 4-Methoxyestradiol
* 4-Methoxyestrone
* 5-Androstenediol
* 7-Oxo-DHEA
* 7α-Hydroxy-DHEA
* 7α-Methylestradiol
* 7β-Hydroxyepiandrosterone
* 8,9-Dehydroestradiol
* 8,9-Dehydroestrone
* 8β-VE2
* 10β,17β-Dihydroxyestra-1,4-dien-3-one (DHED)
* 16α-Fluoroestradiol
* 16α-Hydroxy-DHEA
* 16α-Hydroxyestrone
* 16α-Iodoestradiol
* 16α-LE2
* 16β,17α-Epiestriol (16β-hydroxy-17α-estradiol)
* 17α-Estradiol (alfatradiol)
* 17α-Dihydroequilenin
* 17α-Dihydroequilin
* 17α-Epiestriol (16α-hydroxy-17α-estradiol)
* 17β-Dihydroequilenin
* 17β-Dihydroequilin
* Abiraterone
* Abiraterone acetate
* Alestramustine
* Almestrone
* Anabolic steroids (e.g., testosterone and esters, methyltestosterone, metandienone (methandrostenolone), nandrolone and esters, many others; via estrogenic metabolites)
* Atrimustine
* Bolandiol
* Bolandiol dipropionate
* Butolame
* Clomestrone
* Cloxestradiol
* Cloxestradiol acetate
* Conjugated estriol
* Conjugated estrogens
* Cyclodiol
* Cyclotriol
* DHEA
* DHEA-S
* Epiestriol (16β-epiestriol, 16β-hydroxy-17β-estradiol)
* Epimestrol
* Equilenin
* Equilin
* ERA-63 (ORG-37663)
* Esterified estrogens
* Estetrol
* Estradiol
* Estradiol esters
* Lipoidal estradiol
* Polyestradiol phosphate
* Estramustine
* Estramustine phosphate
* Estrapronicate
* Estrazinol
* Estriol
* Estriol esters
* Polyestriol phosphate
* Estrofurate
* Estromustine
* Estrone
* Estrone esters
* Estrone methyl ether
* Estropipate
* Etamestrol (eptamestrol)
* Ethinylestradiol
* Ethinylestradiol 3-benzoate
* Ethinylestradiol sulfonate
* Ethinylestriol
* Ethylestradiol
* Etynodiol
* Etynodiol diacetate
* Hexolame
* Hippulin
* Hydroxyestrone diacetate
* Lynestrenol
* Lynestrenol phenylpropionate
* Mestranol
* Methylestradiol
* Moxestrol
* Mytatrienediol
* Nilestriol
* Norethisterone
* Noretynodrel
* Orestrate
* Pentolame
* Prodiame
* Prolame
* Promestriene
* RU-16117
* Quinestradol
* Quinestrol
* Tibolone

* Nonsteroidal: (R,R)-THC
* (S,S)-THC
* 2,8-DHHHC
* β-LGND1
* β-LGND2 (GTx-878)
* AC-186
* Allenestrol
* Allenolic acid
* Benzestrol
* Bifluranol
* Bisdehydrodoisynolic acid
* Carbestrol
* D-15414
* DCW234
* Diarylpropionitrile
* Dienestrol
* Dienestrol diacetate
* Diethylstilbestrol
* Diethylstilbestrol esters
* Dimestrol (dianisylhexene)
* Doisynoestrol (fenocycline)
* Doisynolic acid
* Efavirenz
* ERB-196 (WAY-202196)
* Erteberel (SERBA-1, LY-500307)
* Estrobin (DBE)
* Fenestrel
* FERb 033
* Fosfestrol (diethylstilbestrol diphosphate)
* Furostilbestrol (diethylstilbestrol difuroate)
* GTx-758
* Hexestrol
* Hexestrol esters
* ICI-85966 (Stilbostat)
* Mestilbol
* Methallenestril
* Methestrol
* Methestrol dipropionate
* Paroxypropione
* Pentafluranol
* Phenestrol
* Prinaberel (ERB-041, WAY-202041)
* Propylpyrazoletriol
* Quadrosilan
* SC-4289
* SERBA-2
* SKF-82,958
* Terfluranol
* Triphenylbromoethylene
* Triphenylchloroethylene
* Triphenyliodoethylene
* Triphenylmethylethylene (triphenylpropene)
* WAY-166818
* WAY-169916
* WAY-200070
* WAY-204688 (SIM-688)
* WAY-214156

* Unknown/unsorted: ERB-26
* ERA-45
* ERB-79
* ZK-283197

* Xenoestrogens: Anise-related (e.g., anethole, anol, dianethole, dianol, photoanethole)
* Chalconoids (e.g., isoliquiritigenin, phloretin, phlorizin (phloridzin), wedelolactone)
* Coumestans (e.g., coumestrol, psoralidin)
* Flavonoids (incl. 7,8-DHF, 8-prenylnaringenin, apigenin, baicalein, baicalin, biochanin A, calycosin, catechin, daidzein, daidzin, ECG, EGCG, [[Chemistry:Epicateepicatechin, Chemistry:Equol|equol]], formononetin, glabrene, glabridin, Genistein|genistein]], genistin, glycitein, kaempferol, Chemistry:Liquiritigenin

|

Mixed
(SERMs)|

* 2-Phenylbenzofuran
* 2-Phenylbenzothiophene
* 4'-Hydroxynorendoxifen
* 27-Hydroxycholesterol
* Acefluranol
* Acolbifene
* Afimoxifene
* Anordiol
* Anordrin
* Arzoxifene
* Bazedoxifene
* Brilanestrant
* Broparestrol
* Chlorotrianisene
* Clomifene
* Clomifenoxide
* Cyclofenil
* D-15413
* Droloxifene
* Elacestrant
* Enclomifene
* Endoxifen
* Etacstil (GW-5638, DPC-974)
* Ethamoxytriphetol (MER-25)
* Femarelle
* Fispemifene
* GW-7604
* ICI-55548
* Idoxifene
* Lasofoxifene
* Levormeloxifene
* LN-1643
* LN-2299
* LY-117018
* Menerba
* Miproxifene
* Miproxifene phosphate
* Nafoxidine
* Nitromifene
* NNC 45-0095
* NNC 45-0320
* NNC 45-0781
* NNC 45-1506
* Ormeloxifene
* Ospemifene
* Panomifene
* Pipendoxifene
* Promensil
* Raloxifene
* Rimostil (P-081)
* Spironolactone
* SS1010
* Tamoxifen
* TAS-108 (SR-16234)
* Toremifene
* Trioxifene
* TZE-5323
* Y-134
* Zindoxifene
* Zuclomifene

Antagonists|

* (R,R)-THC
* 7β-Hydroxy-DHEA
* Chloroindazole
* Cytestrol acetate
* EM-800
* Epitiostanol
* ERA-90
* ERB-88
* Fulvestrant (ICI-182780)
* Glyceollins (I, II, III, IV)
* ICI-164384
* Mepitiostane
* Methylepitiostanol
* Methylpiperidinopyrazole
* MIBE
* Oxabicycloheptene sulfonate
* Phenytoin
* PHTPP
* Prochloraz
* RU-58668
* SS1020
* TAS-108 (SR-16234)
* ZB716
* ZK-164015
* ZK-191703

* Coregulator-binding modulators: ERX-11

GPER|

| Agonists|

* 2-Methoxyestradiol
* 7β-Hydroxyepiandrosterone
* Afimoxifene (4-hydroxytamoxifen)
* Atrazine
* Bisphenol A
* Daidzein
* DDT (p,p'-DDT, o',p'-DDE)
* Equol
* Estradiol
* Ethinylestradiol
* Fulvestrant (ICI-182780)
* G-1
* Genistein
* GPER-L1
* GPER-L2
* Hydroxytyrosol
* Kepone
* Niacin
* Nicotinamide
* Nonylphenol
* Oleuropein
* PCBs (2,2',5'-PCB-4-OH)
* Propylpyrazoletriol
* Quercetin
* Raloxifene
* Resveratrol
* Tamoxifen
* Tectoridin
* Zearalanone
* Zearalenol
* Zearalenone
* Zeranol (zearalanol))

|

Antagonists|

* CCL18
* Estriol
* G-15
* G-36
* MIBE

See also
Receptor/signaling modulators
Estrogens and antiestrogens
Androgen receptor modulators
Progesterone receptor modulators
List of estrogens

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Original source: https://en.wikipedia.org/wiki/Testosterone undecanoate. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Chemistry:Testosterone_undecanoate&oldid=3336079"
*[US]: United States
*[AU]: Australia
*[CA]: Canada
*[IM]: Intramuscular injection
*[CID]: Compound ID
*[DHT]: dihydrotestosterone
*[USAN]: United States Adopted Name
*[BAN]: British Approved Name
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AAS]: anabolic–androgenic steroid
*[AR]: Androgen receptor
*[SARMs]: Selective androgen receptor modulator
*[GPRC6A]: G protein-coupled receptor family C group 6 member A
*[ER]: Estrogen receptor
*[SERMs]: Selective estrogen receptor modulators
*[GPER]: G protein-coupled estrogen receptor