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Abandoned drugs
Mibolerone
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    Mibolerone

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    Mibolerone
    Mibolerone structure.png
    Mibolerone molecule ball.png
    Clinical data
    Trade names Cheque Drops, Matenon
    Other names U-10997; CDB-904; Dimethylnandrolone; Dimethylnortestosterone; DMNT; 7α,17α-Dimethyl-19-nortestosterone; 7α,17α-Dimethylestr-4-en-17β-ol-3-one
    AHFS/Drugs.com International Drug Names
    Routes of
    administration    		 By mouth
    Drug class Androgen; Anabolic steroid; Progestogen
    ATC code
    • None
    Legal status
    Legal status
    Pharmacokinetic data
    Metabolism Liver
    Identifiers
    • (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
    CAS Number
    PubChem CID
    IUPHAR/BPS
    ChemSpider
    UNII
    KEGG
    ChEBI
    ChEMBL
    CompTox Dashboard (EPA)
    ECHA InfoCard 100.020.951
    Chemical and physical data
    Formula C20H30O2
    Molar mass 302.458 g·mol−1
    3D model (JSmol)
    • C[C@@H]1CC2=CC(=O)CC[C@@H]2[C@@H]3[C@@H]1[C@@H]4CC[C@]([C@]4(CC3)C)(C)O
    • 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 checkY
    • Key:PTQMMNYJKCSPET-OMHQDGTGSA-N checkY
      (verify)

    Mibolerone, also known as dimethylnortestosterone (DMNT) and sold under the brand names Cheque Drops and Matenon, is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was marketed by Upjohn for use as a veterinary drug. It was indicated specifically as an oral treatment for prevention of estrus (heat) in adult female dogs.

    Side effects

    See also: Anabolic steroid § Adverse effects

    Pharmacology

    Pharmacodynamics

    Mibolerone has both higher affinity and greater selectivity for the androgen receptor (AR) than does the related potent AAS metribolone (17α-methyl-19-nor-δ9,11-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.

    Relative affinities (%) of mibolerone and related steroids
    Compound Chemical name PR AR ER GR MR
    Testosterone T 1.0 100 <0.1 0.17 0.9
    Nandrolone 19-NT 20 154 <0.1 0.5 1.6
    Trenbolone ∆9,11-19-NT 74 197 <0.1 2.9 1.33
    Trestolone 7α-Me-19-NT 50–75 100–125 ? <1 ?
    Normethandrone 17α-Me-19-NT 100 146 <0.1 1.5 0.6
    Metribolone ∆9,11-17α-Me-19-NT 208 204 <0.1 26 18
    Mibolerone 7α,17α-DiMe-19-NT 214 108 <0.1 1.4 2.1
    Dimethyltrienolone ∆9,11-7α,17α-DiMe-19-NT 306 180 0.1 22 52
    Values are percentages (%). Reference ligands (100%) were progesterone for the PR, testosterone for the AR, estradiol for the ER, DEXA for the GR, and aldosterone for the MR.

    Chemistry

    See also: List of androgens/anabolic steroids

    Mibolerone, also known as 7α,17α-dimethyl-19-nortestosterone (DMNT) or as 7α,17α-dimethylestr-4-en-17β-ol-3-one, is a synthetic estrane steroid and a 17α-alkylated derivative of nandrolone (19-nortestosterone). It is the 17α-methyl derivative of trestolone (7α-methyl-19-nortestosterone; MENT). Other related AAS include metribolone (17α-methyl-δ9,11-19-nortestosterone) and dimethyltrienolone (7α,17α-dimethyl-δ9,11-19-nortestosterone).

    Synthesis

    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.

    Preparation of Mibolerone: BE 610385 ; J. C. Babcock, J. A. Campbell, U.S. Patent 3,341,557 (1962, 1967 both to Upjohn).

    In the case at hand, heating acetate (1) with chloranil gives the conjugated dienone (2), 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 (3). The stereochemistry of the product again illustrates the preference for additions from the backside. The alcohol at C17 is then oxidized to a ketone (4). 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 intermediate with pyrrolidine gives dienamine (5). This transformation emphasizes the clear difference in reactivity between ketones at C7 and C17. A second methyl Grignard addition gives the corresponding 17α-methyl derivative. Hydrolysis of the enamine function then affords mibolerone (6).

    The same structure of 3 and 4 also containing an 11β-fluoro group has also been described in the patent literature.

    History

    Mibolerone was first synthesized in 1963.

    Society and culture

    Generic names

    Mibolerone is the generic name of the drug and its INN, USAN, and BAN. It is also known as dimethylnortestosterone (DMNT) and by its former developmental code name U-10997.

    Brand names

    Mibolerone has been marketed under the brand names Cheque Drops and Matenon.

    External links



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