Altrenogest

Source: Wikipedia, the free encyclopedia.
Altrenogest
Progestin
ATCvet code
Legal status
Legal status
Identifiers
  • (8S,13S,14S,17R)-17-Hydroxy-13-methyl-17-prop-2-enyl-1,2,6,7,8,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
JSmol)
  • C[C@]12C=CC3=C4CCC(=O)C=C4CC[C@H]3[C@@H]1CC[C@]2(CC=C)O
  • InChI=1S/C21H26O2/c1-3-10-21(23)12-9-19-18-6-4-14-13-15(22)5-7-16(14)17(18)8-11-20(19,21)2/h3,8,11,13,18-19,23H,1,4-7,9-10,12H2,2H3/t18-,19+,20+,21+/m1/s1
  • Key:VWAUPFMBXBWEQY-ANULTFPQSA-N

Altrenogest, sold under the brand names Swinemate and Altren manufactured by Aurora Pharmaceutical and Regumate manufactured by Merck, is a

estrus in horses and pigs.[3][4][5][6][7] It is available for veterinary use in both Europe (as Regumate) and the United States (as Matrix).[8]

Uses

Veterinary

Altrenogest is used in veterinary medicine.

Pharmacology

Pharmacodynamics

An

anabolic–androgenic steroids (AAS).[9] The observed potency of altrenogest even exceeded that of metribolone (methyltrienolone, R-1881), which was the second most potent compound.[9] In the study, it showed an EC50 of 0.64 nM for the AR and 688% of the relative activational potency of testosterone and an EC50 of 0.3 nM and 1,300% of the relative activational potency of progesterone, with an AR/PR activational potency ratio of 0.53.[9]

Although very potent in both activities in vitro, the AR/PR activational potency ratio of altrenogest was in the same range as that of other 19-nortestosterone progestins such as norethisterone, noretynodrel, norgestrel, and allylestrenol (ratio for all < 1.0), whereas the AR/PR activational potency ratio of its 17α-deallylated AAS analogue trenbolone was, at 64, profoundly increased (although the ratio of metribolone (the 17α-methylated variant of altrenogest), at 0.56, was almost the same as that of altrenogest).[9]

According to its

anabolic and androgenic activity equivalent to 1/20th of that of testosterone.[10] However, no significant androgenic effects have been observed in young stallions or mature mares,[11] and altrenogest has notably been used to maintain pregnancy in mares (similarly to the use of allylestrenol to maintain pregnancy in women) with no incidence of virilization or other abnormalities in filly offspring.[12] On the other hand, minor potential anabolic/androgenic effects have been suggested for altrenogest in pigs.[11]

Chemistry

See also: List of progestogens

Altrenogest, also known as 17α-allyl-19-nor-δ9,11-testosterone or as 17α-allylestra-4,9,11-trien-17β-ol-3-one, is a

17α-alkylated (with a methyl or ethyl group).[3][4] Altrenogest is the 17α-allylated derivative of the AAS trenbolone (and hence can also be referred to as allyltrenbolone or allyltrienolone), which itself is the 9,11-didehydro analogue of the AAS nandrolone (19-nortestosterone).[3][4] Altrenogest is also closely related to norgestrienone.[3][4]

History

Altrenogest has been marketed as Regumate since the early 1980s.[11]

Society and culture

Generic names

Altrenogest is the

INNTooltip International Nonproprietary Name, USANTooltip United States Adopted Name, and BANTooltip British Approved Name, while altrénogest is its DCFTooltip Dénomination Commune Française.[3][4][5]

Brand names

Altrenogest is marketed under the brand names Regumate and Matrix among others.[3][4][5]

References

  1. ISBN 978-0-8018-8304-0
    .
  2. ^ "Health product highlights 2021: Annexes of products approved in 2021". Health Canada. 3 August 2022. Retrieved 25 March 2024.
  3. ^
    ISBN 978-1-4757-2085-3
    .
  4. ^
    ISBN 978-3-88763-075-1
    .
  5. ^ a b c "Altrenogest". Drugs.com. Archived from the original on 2017-12-01. Retrieved 2017-11-25.
  6. ISBN 978-1-118-68590-7
    .
  7. ^
    ISBN 978-0-444-88727-6
    . Other examples are allylestrenol (42), a pro-drug converted to the 3-keto analogue (43), which is used in the treatment of threatened abortion [78,79] and altrenogest (44), used in sows and mares to suppress ovulation and estrus behaviour [80]. [...] Progestins with a 17a-allyl side chain: (42) allylestrenol, (43), (44) altrenogest.
  8. ISBN 978-1-907284-53-3
    .
  9. ^
    S2CID 5612000
    .
  10. PMID 3131291
    .
  11. ^
    ISBN 978-0-470-96187-2
    .
  12. ISBN 978-0-309-26494-5
    .
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