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 namesArbolic, Durabolic, Or-Bolic, Probolik, Protabolin
Other namesMethylandrostenediol dipropionate; Methylandrostenediol 3β,17β-dipropionate; MADP; 17α-Methylandrost-5-ene-3β,17β-diol 3,17β-dipropionate
Routes of
administration		Intramuscular injection[1]
Drug classAndrogen; 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
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ECHA InfoCard100.020.669
Chemical and physical data
FormulaC26H40O4
Molar mass416.602 g·mol−1
3D model (JSmol)
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

References
  1. Llewellyn W (1 November 2008). Anabolics: Anabolic Steroid Reference Guide. William Llewellyn. pp. 294–296. ISBN 978-0-9679304-7-3.
  2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 663–. ISBN 978-3-88763-075-1.
  3. "Drugs@FDA: FDA Approved Drug Products". United States Food and Drug Administration. Retrieved 29 November 2016.


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