Mibolerone

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Mibolerone
Mibolerone structure.png
Mibolerone2.png
Systematic (IUPAC) name
(7α,17β)-17-hydroxy-7,17-dimethylestr-4-en-3-one
Clinical data
AHFS/Drugs.com International Drug Names
Legal status
  • Schedule 3 (US)
Routes Oral
Pharmacokinetic data
Metabolism Hepatic
Half-life 2-4 hours
Identifiers
CAS number 3704-09-4 N
ATC code None
PubChem CID 251636
IUPHAR ligand 2859
ChemSpider 220460 YesY
UNII 9OGY4BOR8D YesY
KEGG D05025 YesY
ChEBI CHEBI:34849 N
ChEMBL CHEMBL425863 YesY
Synonyms (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
Chemical data
Formula C20H30O2 
Mol. mass 302.4558 g/mol
 N (what is this?)  (verify)

Mibolerone[pronunciation?] is a potent anabolic steroid which is both higher affinity[1] and more selective[2] for the androgen receptor than metribolone.

Under the brand name "Cheque Drops", Mibolerone was marketed as a veterinary drug by the Upjohn company. It was indicated as an oral treatment for estrous (heat) prevention in adult female dogs.

Synthesis[edit]

Nandrolone appears to be used to make Mibolerone. For comparison, also see bolasterone and calusterone.

Preparation of Mibolerone: U.S. Patent 3,341,557 John C Babcock, Campbell J. Upjohn Co (1967).

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. In the case at hand, heating acetate with chloranil gives the diene, and reaction of that compound with methylmagnesium bromide in the presence of cuprous chloride leads to addition of the methyl group to position 7 at the end of the conjugated system. The stereochemistry of the product again illustrates the preference for additions from the backside. The alcohol at C17 is then oxidized to a ketone. Enamines are commonly used to activate adjacent functions; they are also not infrequently used, as in this case, as protecting groups. Thus, reaction of the intermediatewith pyrrolidine gives enamine. This transformation emphasizes the clear difference in reactivity between ketones at C7 and C17. A second methyl Grignard addition gives the corresponding 17a-methyl derivative. Hydrolysis of the enamine function then affords mibolerone.[3]

References[edit]

  1. ^ Murthy LR, Johnson MP, Rowley DR, Young CY, Scardino PT, Tindall DJ (1986). "Characterization of steroid receptors in human prostate using mibolerone". Prostate 8 (3): 241–53. doi:10.1002/pros.2990080305. PMID 2422638. 
  2. ^ Schilling K, Liao S (1984). "The use of radioactive 7 alpha, 17 alpha-dimethyl-19-nortestosterone (mibolerone) in the assay of androgen receptors". Prostate 5 (6): 581–8. doi:10.1002/pros.2990050603. PMID 6333679. 
  3. ^ US patent 3341557, Babcock JC, Campbell JC, "7-Methyltestosterones", published 1967-09-12, assigned to Upjohn Company