Dimethandrolone

Dimethandrolone (DMA), also known by its developmental code name CDB-1321, is an experimental androgen/anabolic steroid (AAS) and progestogen medication which is under investigation for potential clinical use.[1][2][3]

Dimethandrolone is an AAS, and hence is an agonist of the androgen receptor, the biological target of androgens like testosterone.[1] It is also a progestin, or a synthetic progestogen, and hence is an agonist of the progesterone receptor, the biological target of progestogens like progesterone.[1] Due to its androgenic and progestogenic activity, dimethandrolone has antigonadotropic effects.[1] It has no estrogenic activity.[1][4]

Dimethandrolone was first described in 1997.[5] It was developed by the Contraceptive Development Branch of the National Institute of Child Health and Human Development, an agency in the United States government.[1][6]

An ester and prodrug of dimethandrolone, dimethandrolone undecanoate (DMAU) (CDB-4521), is under development for potential use as a birth control pill for men and in androgen replacement therapy for men.[1][2][3][7]

## Contents

* 1 Side effects
* 2 Pharmacology
* 2.1 Pharmacodynamics
* 3 Chemistry
* 3.1 Synthesis
* 3.2 Esters
* 3.3 Analogues
* 4 History
* 5 References

## Side effects

## Pharmacology

### Pharmacodynamics

Dimethandrolone is an AAS, though it has also been described as a selective androgen receptor modulator (SARM).[1][2][3] As an AAS, it is a potent agonist of the androgen receptor (AR).[1][2]

Unlike testosterone and various other AAS, dimethandrolone is not metabolized by 5α-reductase.[2] In addition, the 5α-reduced derivative of dimethandrolone, 5α-dihydrodimethandrolone (5α-DHDMA), possesses only 30 to 40% of the potency of dimethandrolone as an agonist of the AR, indicating that dimethandrolone does not require potentiation by 5α-reductase for its activity as an AAS and that even if it were a substrate for 5α-reductase, it would not be potentiated in androgenic tissues like the skin and prostate.[2] As such, dimethandrolone and ester prodrugs of it like DMAU are thought to have a reduced risk of androgenic side effects and conditions such as benign prostatic hyperplasia, prostate cancer, pattern scalp hair loss, and acne relative to testosterone and certain other AAS.[2]

Dimethandrolone is not a substrate for aromatase, and for this reason, is not converted into the corresponding aromatic A-ring derivative 7α,11β-dimethylestradiol, a potent estrogen.[3][4] As such, dimethandrolone is not estrogenic.[4] This is in contrast to nandrolone, which, although its rate of aromatization into the estrogen estradiol is reduced relative to that of testosterone, is still converted to a significant extent.[4]

Similarly to nandrolone and other 19-nortestosterone derivatives, dimethandrolone is a potent progestogen in addition to AAS.[1] This property may serve to augment its antigonadotropic activity, which in turn may improve its effectiveness as an antispermatogenic agent and male contraceptive.[1] This is salient and potentially beneficial as male contraceptives based on androgens alone have failed to produce satisfactory azoospermia in around one-third of men.[1]

Dimethandrolone has shown minimal potential for hepatotoxicity in animal studies, which is in accordance with the fact that it is not a 17α-alkylated AAS.[6]

## Chemistry

Dimethandrolone, also known as 7α,11β-dimethyl-19-nortestosterone or as 7α,11β-dimethylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a non-17α-alkylated derivative of nandrolone (19-nortestosterone).[1]

### Synthesis

The chemical synthesis has been described.[8] Cook's alternative syntheses:[9][10][11] The following synthesis is based on almestrone.[8]

The starting 7a-methyl-estrone-3-methylester, PC14306575 (1) was reacted with antimony pentafluoride and hydrogen fluoride to yield a mixture of 7alpha-Methyl-estra-4,9(10)-diene-3,17-dione, PC9943709 (2a) and the isomeric by-product (2b) in a 2:1 ratio. The products were separated by chromatography to provide 39.6% yield of 2a. The 17-keto group was reduced with Lithium tri-tert-butoxyaluminum hydride (LTBA) and the product was ketalized. The product of this step was 5(10),9(11) diene due to olefin migration, PC67331809 (3). Treatment with hydrogen peroxide in hexafluoroacetone solvent gave the oxirane, (4), as a mixture of epimers, which was used for the next step without further purification. Conjugate addition of methylmagnesium bromide in the presence of a catalytic amount of cuprous chloride added to the olefin with concomitant opening of the oxirane ring to an alcohol (5). The product of this step was predominantly the 11α-methyl epimer as would be mandated based on the steric shielding of the incoming nucleophile by 18-methyl group. Treatment with acid caused deprotection of the ketal and dehydration of the alcohol (6) Ketalization with ethyleneglycol again was accompanied by olefin bond migration with the 11-methyl now occupying group an sp2 bond (7). Upon deprotecting the ketal in acid the 11-methyl group was now 90% beta stereochemistry which must reflect the thermodynamically favoured geometry of the system (8). Reduction of the diene with lithium in ammonia in the presence of a small amount of butanol reduced the compound to the C5(10) olefin (9). Migration of the remaining olefin occurred in acid to give the conjugated enone and hence dimethandrolone (10). Esterification with trans-4-Butylcyclohexane-1-carbonyl chloride (11) gave the bucyclate prodrug, CDB-4386A (12).

N.B. The deketalization steps resulted in the lowest yields. Changing the alcohol from ethylene glycol to methanol might theoretically result in higher yields since the acyclic ketal is easier to remove owing to the absence of a chelate-type of effect when ethylene glycol is used.

### Esters

Aside from the C17β undecanoate ester of dimethandrolone, DMAU (CDB-4521),[1][2][3] a few other esters, such as dimethandrolone buciclate (CDB-4386A) and dimethandrolone dodecylcarbonate (CDB-4730), have also been developed.[8][12]

### Analogues

Other AAS that are closely related to dimethandrolone (besides nandrolone) include trestolone (also known as 7α-methyl-19-nortestosterone (MENT)) and 11β-methyl-19-nortestosterone (11β-MNT) and their respective C17β esters trestolone acetate and 11β-MNT dodecylcarbonate (11β-MNTDC).[1][2]

## History

A patent for dimethandrolone was filed in 1997 and was granted in 1999.[5] Subsequently, a patent for DMAU and dimethandrolone buciclate was filed in 2002 and was granted to the United States government in 2003.[8] Dimethandrolone was developed under the code name CDB-1321 by the Contraceptive Development Branch of the National Institute of Child Health and Human Development, one of the National Institutes of Health in the United States Department of Health and Human Services.[1][6]

## References

1. ↑ 1.00 1.01 1.02 1.03 1.04 1.05 1.06 1.07 1.08 1.09 1.10 1.11 1.12 1.13 1.14 1.15 "Dimethandrolone undecanoate: a new potent orally active androgen with progestational activity". Endocrinology 147 (6): 3016–26. June 2006. doi:10.1210/en.2005-1524. PMID 16497801.
2. ↑ 2.0 2.1 2.2 2.3 2.4 2.5 2.6 2.7 2.8 "The potent synthetic androgens, dimethandrolone (7α,11β-dimethyl-19-nortestosterone) and 11β-methyl-19-nortestosterone, do not require 5α-reduction to exert their maximal androgenic effects". The Journal of Steroid Biochemistry and Molecular Biology 122 (4): 212–8. October 2010. doi:10.1016/j.jsbmb.2010.06.009. PMID 20599615.
3. ↑ 3.0 3.1 3.2 3.3 3.4 "Hormonal approaches to male contraception". Current Opinion in Urology 20 (6): 520–4. November 2010. doi:10.1097/MOU.0b013e32833f1b4a. PMID 20808223.
4. ↑ 4.0 4.1 4.2 4.3 "Dimethandrolone (7alpha,11beta-dimethyl-19-nortestosterone) and 11beta-methyl-19-nortestosterone are not converted to aromatic A-ring products in the presence of recombinant human aromatase". The Journal of Steroid Biochemistry and Molecular Biology 110 (3–5): 214–22. June 2008. doi:10.1016/j.jsbmb.2007.11.009. PMID 18555683.
5. ↑ 5.0 5.1 Cook CE, Kepler JA, Lee YW, Wani MW, "Androgenic steroid compounds and a method of making and using the same", US patent 5952319, published 1999, assigned to Research Triangle Institute
6. ↑ 6.0 6.1 6.2 "Development of dimethandrolone 17beta-undecanoate (DMAU) as an oral male hormonal contraceptive: induction of infertility and recovery of fertility in adult male rabbits". Journal of Andrology 32 (5): 530–40. September–October 2011. doi:10.2164/jandrol.110.011817. PMID 21164142.
7. ↑ "Dimethandrolone undecanoate shows promise as a male birth control pill". Press Release. Endocrine Society. March 18, 2018. https://www.endocrine.org/news-room/2018/dimethandrolone-undecanoate-shows-promise-as-a-male-birth-control-pill.
8. ↑ 8.0 8.1 8.2 8.3 Blye R, Kim H, "Methods of making and using 7a, 11b-dimethyl-17b-hydroxy-4-estren-3-one 17b-trans-4-n-butylcyclohexane carboxylate and 7a, 11b-dimethyl-17b-hydroxyestr-4-en-3-one 17-undecanoate.", US patent 20030069215, assigned to US Government
9. ↑ Edgar C. Cook, et al. WO1999026962 (to RTI International Inc).
10. ↑ "7α,11β-Dimethyl-19-nortestosterone: a potent and selective androgen response modulator with prostate-sparing properties". Bioorganic & Medicinal Chemistry Letters 15 (4): 1213–1216. February 2005. doi:10.1016/j.bmcl.2004.11.076. https://linkinghub.elsevier.com/retrieve/pii/S0960894X04014477.
11. ↑ "7α,11β‐Dimethyl‐19‐nortestosterone: A Potent and Selective Androgen Response Modulator with Prostate‐Sparing Properties.". ChemInform 36 (26). 28 June 2005. doi:10.1002/chin.200526118. https://onlinelibrary.wiley.com/doi/10.1002/chin.200526118.
12. ↑ Blye R, Kim H, "Nandrolone 17β-carbonates", US patent 7820642, published 26 October 2010, assigned to US Government

* v
* t
* e

Androgen receptor modulators

AR|

| Agonists|

* Testosterone derivatives: 4-Androstenediol
* 4-Dehydroepiandrosterone (4-DHEA)
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* 1-Testosterone
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* 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
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* 19-Nordehydroepiandrosterone
* Bolandiol
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* 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
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* Chlorodehydromethylandrostenediol (CDMA)
* Chlorodehydromethyltestosterone (CDMT)
* Chloromethylandrostenediol (CMA)
* Enestebol
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* Methyltestosterone 3-hexyl ether
* Oxymesterone
* Penmesterol
* Tiomesterone

* 17α-Alkylated dihydrotestosterone derivatives: Androisoxazole
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* Mestanolone
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* Methasterone
* Methyl-1-testosterone
* Methylepitiostanol
* Methylstenbolone
* Oxandrolone
* Oxymetholone
* Stanozolol

* 17α-Alkylated 19-nortestosterone derivatives: Bolenol
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* Methylhydroxynandrolone (MOHN, MHN)
* Metribolone
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* RU-2309
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* 17α-Vinyltestosterone derivatives: Norvinisterone (vinylnortestosterone)
* Vinyltestosterone

* 17α-Ethynyltestosterone derivatives: Δ4-Tibolone
* Danazol
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* Norgestrel
* Norgestrienone
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* 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)
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* DTIB
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* ORM-11984
* R-1
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* 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
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* RU-15328
* SC-5233 (spirolactone)
* Spironolactone
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* Trimegestone
* Trimethyltrienolone (R-2956)
* Zanoterone

* Nonsteroidal: 5N-Bicalutamide
* AA560
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* Bicalutamide
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* BMS-501949
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* CH5137291
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* Pentomone
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* Phenothrin
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* Ralaniten (EPI-002)
* Ralaniten acetate (EPI-506)
* RD-162
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* RU-58642
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* 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

Progesterone receptor modulators

PR|

| Agonists|

* Progesterone derivatives: 3β-Dihydroprogesterone
* 5α-Dihydroprogesterone
* 9α-Bromo-11-ketoprogesterone
* 11-Dehydroprogesterone
* 11-Deoxycorticosterone
* 16α-Hydroxyprogesterone
* 20α-Dihydroprogesterone
* 20β-Dihydroprogesterone
* Dimepregnen
* Diosgenin
* P1-185
* Progesterone
* Progesterone 3-acetyl enol ether
* Quingestrone

* Retroprogesterone derivatives: 20α-Dihydrodydrogesterone
* 20α-Dihydrotrengestone
* DU-41164
* DU-41165
* Dydrogesterone
* Retroprogesterone
* Ro 6-3129
* Trengestone

* 17α-Substituted progesterone derivatives: 6α-Methyl-17α-bromoprogesterone
* 15β-Hydroxycyproterone acetate
* 16-Methylene-17α-hydroxyprogesterone acetate
* 17α-Bromoprogesterone
* 17α-Hydroxyprogesterone (hydroxyprogesterone)
* 17α-Methylprogesterone
* Acetomepregenol (mepregenol diacetate)
* Algestone
* Algestone acetonide
* Algestone acetophenide
* Anagestone
* Anagestone acetate
* Bromethenmadinone
* Bromethenmadinone acetate
* Butagest (buterol)
* Chlormadinone
* Chlormadinone acetate
* Chlormadinone caproate
* Chlormethenmadinone
* Chlormethenmadinone acetate
* Cismadinone
* Cismadinone acetate
* Clogestone
* Clogestone acetate
* Clomegestone
* Clomegestone acetate
* Cymegesolate
* Cyproterone acetate
* Delmadinone
* Delmadinone acetate
* Edogestrone
* Flugestone
* Flugestone acetate
* Fluorometholone
* Fluorometholone acetate
* Flumedroxone
* Flumedroxone acetate
* Fluoromedroxyprogesterone acetate
* Gestaclone
* Haloprogesterone
* Hydromadinone
* Hydromadinone acetate
* Hydroxyprogesterone acetate
* Hydroxyprogesterone caproate (hydroxyprogesterone hexanoate)
* Hydroxyprogesterone heptanoate (hydroxyprogesterone enanthate)
* Hydroxyprogesterone heptanoate benzilic acid hydrazone
* Mecigestone (pentarane B)
* Medrogestone
* Medroxyprogesterone
* Medroxyprogesterone acetate
* Medroxyprogesterone caproate
* Megestrol
* Megestrol acetate
* Megestrol caproate
* Melengestrol
* Melengestrol acetate
* Methenmadinone
* Methenmadinone acetate
* Methenmadinone caproate
* Mometasone
* Mometasone furoate
* Osaterone
* Osaterone acetate
* Pentagestrone
* Pentagestrone acetate
* Pentarane A
* Proligestone

* 19-Norprogesterone derivatives: 17α-Methyl-19-norprogesterone
* 18-Methylsegesterone acetate
* 19-Norprogesterone
* Amadinone
* Amadinone acetate
* Demegestone
* Fluoro ethyl norprogesterone
* Fluoro furanyl norprogesterone
* Gestadienol
* Gestadienol acetate
* Gestonorone acetate (gestronol acetate)
* Gestonorone caproate (gestronol hexanoate)
* Gestronol (gestonorone)
* Nomegestrol
* Nomegestrol acetate
* Norgestomet
* ORG-2058
* Oxogestone
* Oxogestone phenpropionate (xinogestone)
* Promegestone
* Segesterone
* Segesterone acetate (nestorone)
* Trimegestone

* Testosterone derivatives: Progestins: 6,6-Difluoronorethisterone
* 6,6-Difluoronorethisterone acetate
* 17α-Allyl-19-nortestosterone
* Allylestrenol
* Altrenogest
* Chloroethynylnorgestrel
* Cingestol
* Danazol
* Desogestrel
* Dienogest
* Ethisterone
* Ethynerone
* Etonogestrel
* Etynodiol
* Etynodiol diacetate
* Gestodene
* Gestrinone
* Levonorgestrel
* Levonorgestrel esters (e.g., levonorgestrel butanoate)
* Lynestrenol
* Lynestrenol phenylpropionate
* Metynodiol
* Metynodiol diacetate
* Norelgestromin
* Norethisterone (norethindrone)
* Norethisterone esters (e.g., norethisterone acetate, norethisterone enanthate)
* Noretynodrel
* Norgesterone
* Norgestimate
* Norgestrel
* Norgestrienone
* Norvinisterone
* Oxendolone
* Quingestanol
* Quingestanol acetate
* Tibolone
* Tigestol
* Tosagestin; Anabolic–androgenic steroids: 11β-Methyl-19-nortestosterone
* 11β-Methyl-19-nortestosterone dodecylcarbonate
* 19-Nor-5-androstenediol
* 19-Nor-5-androstenedione
* 19-Nordehydroepiandrosterone
* Bolandiol
* Bolandiol dipropionate
* Bolandione
* Dimethisterone
* Dienedione
* Dienolone
* Dimethandrolone
* Dimethandrolone buciclate
* Dimethandrolone dodecylcarbonate
* Dimethandrolone undecanoate
* Dimethyldienolone
* Dimethyltrienolone
* Ethyldienolone
* Ethylestrenol (ethylnandrol)
* Methyldienolone
* Metribolone (R-1881)
* Methoxydienone (methoxygonadiene)
* Mibolerone
* Nandrolone
* Nandrolone esters (e.g., nandrolone decanoate, nandrolone phenylpropionate)
* Norethandrolone
* Normethandrone (methylestrenolone, normethandrolone, normethisterone)
* RU-2309
* Tetrahydrogestrinone
* Trenbolone (trienolone)
* Trenbolone esters (e.g., trenbolone acetate, trenbolone enanthate)
* Trendione
* Trestolone
* Trestolone acetate

* Spirolactone derivatives: Canrenoic acid
* Canrenone
* Drospirenone
* Mespirenone
* Potassium canrenoate
* Prorenone
* SC-5233 (spirolactone)
* SC-8109
* Spironolactone
* Spirorenone

* Nonsteroidal: 3,8-Dihydrodiligustilide
* LG-2527
* LG-100128
* Riligustilide
* RWJ-26819
* RWJ-49853
* RWJ-60130
* Tanaproget
* ZM-182345

* Unknown: ORG-47241
* ORG-201745

|

Mixed
(SPRMs)|

* Steroidal: Dihydroethisterone
* 5α-Dihydrolevonorgestrel
* 5α-Dihydronorethisterone
* Asoprisnil
* Asoprisnil ecamate
* Guggulsterone
* J1042
* LG-120838
* Metapristone (RU-42633)
* Mifepristone (RU-486)
* ORF-9371
* ORF-9326
* ORG-31710
* ORG-33628
* RMI-12936
* Telapristone
* Ulipristal acetate
* Vilaprisan
* ZK-137316

* Nonsteroidal: Apigenin
* Kaempferol
* LG-120920
* Naringenin
* PRA-910
* Syringic acid

Antagonists|

* Steroidal: Aglepristone
* Lilopristone
* Lonaprisan
* Onapristone
* ORG-31710
* ORG-31806
* ORG-33628
* RTI 3021–022
* Toripristone
* Zanoterone

* Nonsteroidal: Darolutamide
* LG-001447
* LG-100127
* LG-100128
* LG-120830
* LG-121046
* Valproic acid
* ZM-150271
* ZM-172406

mPR
(PAQR)|

| Agonists|

* 5α-Dihydroprogesterone
* 5β-Dihydroprogesterone
* 11-Deoxycortisone (21-hydroxyprogesterone)
* 11-Deoxycortisol (17α,21-dihydroxyprogesterone)
* 17α-Hydroxyprogesterone
* Allopregnanolone
* Mifepristone
* Pregnenolone
* Progesterone

|

Antagonists|

* Mifepristone

See also
Receptor/signaling modulators
Progestogens and antiprogestogens
Androgen receptor modulators
Estrogen receptor modulators
List of progestogens

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

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*[AR]: Androgen receptor
*[SARMs]: Selective androgen receptor modulator
*[GPRC6A]: G protein-coupled receptor family C group 6 member A
*[PR]: Progesterone receptor
*[SPRMs]: Selective progesterone receptor modulators
*[mPR]: Membrane progesterone receptor
*[PAQR]: Progestin and adipoQ receptor