Methandriol dipropionate

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.^[2][1] 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.^[2][1] 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.^[1] It was marketed in the United States,^[2] but is no longer available in this country.^[3]

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[1]
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
CompTox Dashboard (EPA)	DTXSID801016686
ECHA InfoCard	100.020.669
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

See also

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