Mibolerone

Mibolerone
Clinical data


AHFS/Drugs.com	International Drug Names
Routes of administration	Oral
ATC code	none
Legal status
Legal status	CA: Schedule IV US: Schedule III
Pharmacokinetic data
Metabolism	Hepatic
Biological half-life	2–4 hours
Identifiers
IUPAC name (7R,8R,9S,10R,13S,14S,17S)-17-hydroxy-7,13,17-trimethyl-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one
Synonyms	U-10997; CDB-904; 7α,17α-dimethyl-19-nortestosterone; 7α,17α-Dimethylestr-4-en-17β-ol-3-one
CAS Number	3704-09-4^N
PubChem CID	251636
IUPHAR/BPS	2859
ChemSpider	220460^Y
UNII	9OGY4BOR8D
KEGG	D05025^Y
ChEBI	CHEBI:34849^N
ChEMBL	CHEMBL425863^Y
ECHA InfoCard	100.020.951
Chemical and physical data
Formula	C₂₀H₃₀O₂
Molar mass	302.4558 g/mol
3D model (Jmol)	Interactive image
SMILES O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)C)[C@@H]2[C@H](C)C3)C)CC4
InChI InChI=1S/C20H30O2/c1-12-10-13-11-14(21)4-5-15(13)16-6-8-19(2)17(18(12)16)7-9-20(19,3)22/h11-12,15-18,22H,4-10H2,1-3H3/t12-,15+,16-,17+,18-,19+,20+/m1/s1^Y Key:PTQMMNYJKCSPET-OMHQDGTGSA-N^Y
^NY (what is this?)

Mibolerone (INN, USAN, BAN) (brand names Cheque Drops, Matenon; developmental code name U-10997), also known as 7α,17α-dimethyl-19-nortestosterone (DMNT), is a potent, orally active anabolic-androgenic steroid (AAS) and 17α-alkylated derivative of nandrolone (19-nortestosterone) that was marketed by Upjohn for use as a veterinary drug. It was indicated as an oral treatment for prevention of estrus (heat) in adult female dogs. Mibolerone is the 17α-methyl derivative of trestolone (7α-methyl-19-nortestosterone; MENT). It has both higher affinity and greater selectivity for the androgen receptor (AR) than does the related potent AAS metribolone (17α-methyl-19-nor-δ^9,11-testosterone), although potent and significant progestogenic activity remains present. However, another study found that mibolerone and metribolone had similar affinity for the progesterone receptor (PR) but that mibolerone only had around half the affinity of metribolone for the AR.

Nandrolone (1) appears to be used to make mibolerone. For comparison, also see bolasterone and calusterone. The first step involves extending the conjugation of the enone function by an additional double bond. Chloranil (tetrachloroquinone) is the forerunner of dichlorodicyanoquinone (DDQ), a reagent used extensively for introducing additional unsaturation in the progestin and corticoid series.

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