Anagestone acetate

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Anagestone acetate
Progestin; Progestogen ester
Identifiers
  • [(6S,8R,9S,10R,13S,14S,17R)-17-acetyl-6,10,13-trimethyl-1,2,3,6,7,8,9,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
JSmol)
  • C[C@H]1C[C@@H]2[C@H](CC[C@]3([C@H]2CC[C@@]3(C(=O)C)OC(=O)C)C)[C@@]4(C1=CCCC4)C
  • InChI=1S/C24H36O3/c1-15-14-18-20(22(4)11-7-6-8-19(15)22)9-12-23(5)21(18)10-13-24(23,16(2)25)27-17(3)26/h8,15,18,20-21H,6-7,9-14H2,1-5H3/t15-,18+,20-,21-,22-,23-,24-/m0/s1
  • Key:KDLNOQQQEBKBQM-DICPTYMLSA-N

Anagestone acetate, sold under the brand names Anatropin and Neo-Novum, is a

withdrawn from medical use due to carcinogenicity observed in animal studies.[1][2][3]

Medical uses

Anagestone acetate was used in combination with the

birth control pill.[4][5]

Pharmacology

Based on its chemical structure, namely the lack of a C3 ketone, it is probable that anagestone acetate is a prodrug of medroxyprogesterone acetate (the 3-keto analogue).[6][7]

Chemistry

See also: List of progestogens, Progestogen ester, and List of progestogen esters

Anagestone acetate, also known as 3-deketo-6α-methyl-17α-acetoxyprogesterone or as 6α-methyl-17α-acetoxypregn-4-en-20-one, is a

17α-hydroxyprogesterone.[1] It is the C17α acetate ester of anagestone, which, in contrast to anagestone acetate, was never marketed.[1] Anagestone acetate is closely related structurally to medroxyprogesterone acetate (6α-methyl-17α-acetoxyprogesterone).[1]

History

Anagestone acetate was introduced in combination with mestranol as a

birth control pill in 1968 by Ortho Pharmaceutical.[4][5] It was withdrawn in 1969.[5][8]

In 1969, along with a variety of other progestogens including

hormonal contraceptives from the market (though medroxyprogesterone acetate, cyproterone acetate, and chlormadinone acetate have continued to be used).[5][9] According to Hughes et al., "It is still doubtful how much relevance these findings have for humans as the dog mammary gland seems to be the only one which can be directly maintained by progestogens."[8][11] Subsequent research revealed species differences between dogs and humans and established that there is no similar risk in humans.[12]

Society and culture

Generic names

Anagestone acetate is the

generic name of the drug and its USANTooltip United States Adopted Name.[1] It is also known by its developmental code name ORF-1658.[1]

Brand names

Anagestone acetate was marketed under the brand names Anatropin and Neo-Novum, the latter in combination with the estrogen mestranol.[1]

Availability

Anagestone acetate was withdrawn from the market and is no longer available.[5][8][10]

See also

References

  1. ^
    ISBN 978-1-4757-2085-3
    .
  2. ISBN 978-0-8155-1856-3
    .
  3. ^ IARC Working Group on the Evaluation of Carcinogenic Risks to Humans (1987). IV. OESTROGEN-PROGESTIN COMBINATIONS. International Agency for Research on Cancer. Retrieved 24 June 2022.
  4. ^
    ISBN 978-3-642-96158-8
    .
  5. ^
    ISBN 978-3-662-08422-9
    .
  6. ISBN 978-0-443-04706-0
    . Progestational activity depends on the presence of a 3-keto group in ring A of the steroid skeleton. Most of the progestogens used today do indeed carry such a group in their original molecules. However, the 3-keto group is initially missing in the case of desogestrel and norgestimate. They are prodrugs which undergo metabolic conversion to active 3-keto derivatives in the body.
  7. S2CID 5612000
    . Prodrugs (lack 3-keto): Ethylestrenol, Lynestrenol, Ethynodiol, Allylestrenol, Norgestimate
  8. ^
    PMID 107546. {{cite book}}: |journal= ignored (help
    )
  9. ^
    PMID 385985
    .
  10. ^
    ISBN 978-92-1-130230-1
    .
  11. ISBN 978-3-642-80859-3
    .
  12. ISBN 978-3-642-73790-9
    .
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