Alfatradiol

Short description: Medication

Alfatradiol

Clinical data
Trade names| Avicis, Avixis, Ell-Cranell Alpha, Pantostin
Other names| 17α-Estradiol; 17-Epiestradiol; MX-4509; Estra-1,3,5(10)-triene-3,17α-diol; β-Estradiol (obsolete, misleading)[1]
AHFS/Drugs.com| International Drug Names
Pregnancy
category|

* US: C (Risk not ruled out)

* No studies

Routes of
administration| Topical
Drug class| Estrogen; 5α-Reductase inhibitor
ATC code|

* None

Legal status
Legal status|

* US: ℞-only

Identifiers

IUPAC name

* (8R,9S,13S,14S,17R)-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthrene-3,17-diol

CAS Number|

* 57-91-0 Y

PubChem CID|

* 68570

ChemSpider|

* 61840 Y

UNII|

* 3VQ38D63M7

ChEBI|

* CHEBI:17160 Y

ChEMBL|

* ChEMBL286452 Y

Chemical and physical data
Formula| C18H24O2
Molar mass| 272.388 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* OC1CCC3C1(C)CCC(c2cc4)C3CCc2cc4O

InChI

* InChI=1S/C18H24O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h3,5,10,14-17,19-20H,2,4,6-9H2,1H3/t14-,15-,16+,17-,18+/m1/s1 Y

* Key:VOXZDWNPVJITMN-SFFUCWETSA-N Y

(verify)

Alfatradiol, also known as 17α-estradiol and sold under the brand names Avicis, Avixis, Ell-Cranell Alpha, and Pantostin, is a weak estrogen and 5α-reductase inhibitor medication which is used topically in the treatment of pattern hair loss (androgenic alopecia or pattern baldness) in men and women.[1][2][3][4] It is a stereoisomer of the endogenous steroid hormone and estrogen 17β-estradiol (or simply estradiol).[1]

## Contents

* 1 Medical uses
* 2 Contraindications
* 3 Side effects
* 4 Pharmacology
* 4.1 Pharmacodynamics
* 5 Society and culture
* 5.1 Generic names
* 5.2 Brand names
* 5.3 Availability
* 6 Research
* 7 See also
* 8 References
* 9 External links

## Medical uses

Alfatradiol is used in form of an ethanolic solution for topical application on the scalp. Similarly to other drugs against alopecia, topical or oral, it has to be applied continuously to prevent further hair loss.[5] Regrowth of hair that was already lost is only possible to a limited extent. In general, advanced alopecia does not respond well to medical treatment, which has historically been thought to be a consequence of the hair roots being lost.[6]

A university-led study (including several authors who are advisors to companies such as Pfizer) in 103 women comparing alfatradiol to minoxidil, another topical hair loss treatment, found the latter to be more effective. In contrast to minoxidil, alfatradiol did not result in an increase of hair density or thickness, but only in slowing down or stabilization of hair loss in this study.[7] In an earlier study, no systemic side effects were noted, and 17α-estradiol was found to reduce androgenic hair loss, though it was not effective at growing new hair.[8]

Other efforts of alfatradiol had been directed at neurodegenerative diseases including Parkinson's.[9]

Other hair loss medications include ketoconazole, finasteride, and dutasteride.

## Contraindications

Nothing is known about the use of alfatradiol during pregnancy or lactation, or in patients under 18 years of age. The package leaflet recommends against using it under these circumstances.[10]

## Side effects

Local burning or itching is not an effect of alfatradiol, but of the ethanol in the solvent. The solution can stimulate sebum production.[10]

## Pharmacology

### Pharmacodynamics

Alfatradiol (top) and 17β-estradiol (bottom).

Alfatradiol (17α-estradiol) is distinguished from estradiol (17β-estradiol), the predominant sex hormone in females, only by the stereochemistry of the carbon atom 17. In contrast to 17β-estradiol, 17α-estradiol, while it still binds to the estrogen receptor, has less or no feminizing estrogenic activity depending on its dosage and the tissue it is affecting.[11] Alfatradiol acts as an inhibitor of the enzyme 5α-reductase, which is responsible for the activation of testosterone to dihydrotestosterone, and which plays a role in regulating hair growth.[5] 17α-Estradiol has been studied as a therapeutic with potential to treat Alzheimer's and Parkinson's disease and other patients with neurodegenerative diseases.[12] 17α-Estradiol (as the sodium salt of its sulfated form) is a minor component (<10%) of hormone replacement products (such as conjugated estrogens, brand name Premarin), which have been studied and/or marketed in women and men since the 1930s. A survey of the effects of various forms of 17α-estradiol in humans on biochemical parameters, efficacy, estrogenicity, metabolism, safety, and tolerability has been published.[13]

Alfatradiol binds to the ERα and ERβ with 58% and 11% of the relative binding affinity of 17β-estradiol.[14] However, it has 100-fold lower estrogenic activity relative to estradiol,[15] which may in part be due to differences in the intrinsic activity of the two compounds.[citation needed] On the other hand, alfatradiol has been found to bind to and activate the brain-expressed ER-X with a greater potency than estradiol, indicating that it may be the predominant endogenous ligand for the receptor.[16] In contrast to estradiol, alfatradiol is not a ligand of the G protein-coupled estrogen receptor (affinity >10 μM).[17]

## Society and culture

### Generic names

Alfatradiol is the generic name of the drug and its INN.[2] It is also known as 17α-estradiol.[1]

### Brand names

Alfatradiol is marketed under the brand names Avicis, Avixis, Ell-Cranell Alpha, and Pantostin.[2]

### Availability

Alfatradiol is available in Germany and several Latin American countries, including Argentina , Brazil , and Mexico.

## Research

Alfatradiol administered systemically improved metabolic function, reduced insulin resistance, decreased intra-abdominal fat, and decreased inflammation in old male mice without inducing feminization, suggesting potential usefulness in the treatment of type 2 diabetes.[18]

## See also

* Alfatradiol/dexamethasone (Ell-Cranell Dexa)
* Estradiol 17α-dehydrogenase
* List of estrogens

## References

1. ↑ 1.0 1.1 1.2 1.3 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 897. ISBN 978-1-4757-2085-3. https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA897.
2. ↑ 2.0 2.1 2.2 "Alfatradiol". Drugs.com International. https://www.drugs.com/international/alfatradiol.html.
3. ↑ (in de) Hunnius Pharmazeutisches Wörterbuch (8 ed.). Walter de Gruyter Verlag. 1998. p. 486. ISBN 978-3-11-015793-2. https://books.google.com/books?id=WSGmQgAACAAJ.
4. ↑ "Recommended International Nonproprietary Names (rec. Inn): List 46". WHO Drug Information 15 (3&4). 2001. http://apps.who.int/medicinedocs/en/d/Jh2989e/10.html.
5. ↑ 5.0 5.1 (in de) Arzneimittelwirkungen (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. 2001. p. 453. ISBN 978-3-8047-1763-3. https://books.google.com/books?id=pOM5SQAACAAJ.
6. ↑ (in de) Austria-Codex. 4 (2007/2008 ed.). Vienna: Österreichischer Apothekerverlag. 2007. p. 9673. ISBN 978-3-85200-181-4.
7. ↑ "Comparison of the efficacy and safety of topical minoxidil and topical alfatradiol in the treatment of androgenetic alopecia in women". Journal der Deutschen Dermatologischen Gesellschaft 5 (5): 391–5. May 2007. doi:10.1111/j.1610-0387.2007.06295.x. PMID 17451383.
8. ↑ "[Local therapy of androgenetic alopecia with 17 alpha-estradiol. A controlled, randomized double-blind study (author's transl)]" (in de). Dermatologica 161 (2): 124–32. 1980. doi:10.1159/000250344. PMID 7398983.
9. ↑ "Alfatradiol". Adis Insight. https://adisinsight.springer.com/drugs/800020680.
10. ↑ 10.0 10.1 (in de) Rote Liste (2005 ed.). Aulendorf: Editio Cantor Verlag. 2005. 32 369. ISBN 978-3-87193-306-6. https://books.google.com/books?id=zZ5KAQAAIAAJ.
11. ↑ "17α-Estradiol: A Less-Feminizing Estrogen". Drug Development Research 69 (4): 177–184. 2008. doi:10.1002/ddr.20244.
12. ↑ "Development of 17alpha-estradiol as a neuroprotective therapeutic agent: rationale and results from a phase I clinical study". Annals of the New York Academy of Sciences 1052 (1): 116–35. June 2005. doi:10.1196/annals.1347.008. PMID 16024755. Bibcode: 2005NYASA1052..116D.
13. ↑ "Review of the Effects of 17α-Estradiol in Humans: A Less Feminizing Estrogen with Neuroprotective Potential". Drug Development Research 70: 1–21. 2009. doi:10.1002/ddr.20284.
14. ↑ "Comparison of the ligand binding specificity and transcript tissue distribution of estrogen receptors alpha and beta". Endocrinology 138 (3): 863–70. March 1997. doi:10.1210/endo.138.3.4979. PMID 9048584.
15. ↑ Male Alopecia: Guide to Successful Management. Springer Science & Business Media. 13 February 2014. p. 93. ISBN 978-3-319-03233-7. https://books.google.com/books?id=0ue5BAAAQBAJ&pg=PA93.
16. ↑ "17alpha-estradiol: a brain-active estrogen?". Endocrinology 146 (9): 3843–50. September 2005. doi:10.1210/en.2004-1616. PMID 15947006.
17. ↑ "International Union of Basic and Clinical Pharmacology. XCVII. G Protein-Coupled Estrogen Receptor and Its Pharmacologic Modulators". Pharmacol. Rev. 67 (3): 505–40. July 2015. doi:10.1124/pr.114.009712. PMID 26023144.
18. ↑ "17α-Estradiol Alleviates Age-related Metabolic and Inflammatory Dysfunction in Male Mice Without Inducing Feminization". The Journals of Gerontology. Series A, Biological Sciences and Medical Sciences 72 (1): 3–15. January 2017. doi:10.1093/gerona/glv309. PMID 26809497.

## External links

* Alfatradiol (17α-estradiol)

* v
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* e

Estrogens and antiestrogens

Estrogens|

| ER agonists|

* Steroidal: Alfatradiol
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* #WHO-EM
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See also
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Androgens and antiandrogens
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List of estrogens

{{Navbox

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| group2 = Antiandrogens
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| group4 = Others
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| 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

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* 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/Alfatradiol. Read more

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Retrieved from "https://handwiki.org/wiki/index.php?title=Biology:Alfatradiol&oldid=2628354"
*[US]: United States
*[CID]: Compound ID
*[INN]: International Nonproprietary Name
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[ER]: Estrogen receptor
*[GnRH]: gonadotropin-releasing hormone
*[FSH]: follicle-stimulating hormone
*[LH]: luteinizing hormone
*[SERMs]: Selective estrogen receptor modulators
*[SERDs]: selective estrogen receptor downregulators
*[AAS]: anabolic–androgenic steroid
*[AR]: Androgen receptor
*[GPER]: G protein-coupled estrogen receptor