Chemistry:Methandriol dipropionate

Short description: Chemical compound

Methandriol dipropionate

Clinical data
Trade names	Arbolic, Durabolic, Or-Bolic, Probolik, Protabolin
Other names	Methylandrostenediol dipropionate; Methylandrostenediol 3β,17β-dipropionate; MADP; 17α-Methylandrost-5-ene-3β,17β-diol 3,17β-dipropionate
Routes of administration	Intramuscular injection
Drug class	Androgen; Anabolic steroid; Androgen ester
Identifiers
IUPAC name [(3S,8R,9S,10R,13S,14S,17S)-10,13,17-trimethyl-17-propanoyloxy-1,2,3,4,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-yl] propanoate
CAS Number	3593-85-9
PubChem CID	546836
ChemSpider	96675
UNII	8XIW70Q5I3
KEGG	D08197
ChEBI	CHEBI:34835
Chemical and physical data
Formula	C26H40O4
Molar mass	416.602 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(=O)O[C@H]1CC[C@@]2([C@H]3CC[C@]4([C@H]([C@@H]3CC=C2C1)CC[C@]4(C)OC(=O)CC)C)C
InChI InChI=1S/C26H40O4/c1-6-22(27)29-18-10-13-24(3)17(16-18)8-9-19-20(24)11-14-25(4)21(19)12-15-26(25,5)30-23(28)7-2/h8,18-21H,6-7,9-16H2,1-5H3/t18-,19+,20-,21-,24-,25-,26-/m0/s1 Key:YUKFLTKJFMBYJM-QNSWYLPSSA-N

Methandriol dipropionate (MADP), also known as methylandrostenediol dipropionate and sold under the brand names Arbolic, Durabolic, Or-Bolic, Probolik, and Protabolin among others, is a synthetic, injected anabolic-androgenic steroid (AAS) and a 17α-alkylated derivative of 5-androstenediol. It is an androgen ester – specifically, the C3,17β dipropionate ester of methandriol (17α-methyl-5-androstenediol) – and acts as a prodrug of methandriol in the body. Methandriol dipropionate is administered by intramuscular injection and, relative to methandriol, has an extended duration via this route of several days due to a depot effect afforded by its ester. It was marketed in the United States , but is no longer available in this country.

See also

• List of androgen esters § Esters of other synthetic AAS
• Estradiol benzoate/progesterone/methandriol dipropionate

External links

• "Methandriol (methandriol, methandriol dipropionate)". William Llewellyn's Anabolic.org. https://anabolic.org/methandriol-dipropionate/. 

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(incl. AAS)

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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
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  | group1 = AR antagonists
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• Steroidal: Abiraterone acetate
• Canrenone
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• Cyproterone acetate
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• Dienogest
• Drospirenone
• Medrogestone
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• Nonsteroidal: Apalutamide
• Bicalutamide
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  | group2 = Steroidogenesis
inhibitors

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5α-Reductase	Alfatradiol Dutasteride Epristeride Finasteride Saw palmetto extract
Others	Abiraterone acetate Aminoglutethimide Bifluranol Cyproterone acetate Flutamide Ketoconazole Nilutamide Seviteronel† Spironolactone

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• 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)
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• Androstenedione immunogens: Androvax (androstenedione albumin)
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• ^#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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