Altrenogest

Last updated
Altrenogest
Altrenogest.svg
Clinical data
Trade names Regumate, Matrix
Other namesAllyltrenbolone; Allyltrienolone; RU-2267; RH-2267; A-35957; A-41300; 17α-Allylestra-4,9,11-trien-17β-ol-3-one; 17α-Allyl-19-nor-δ9,11-testosterone
Routes of
administration 		By mouth [1]
Drug class Progestogen; Progestin
ATCvet code
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
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.011.549 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H26O2
Molar mass 310.437 g·mol−1
3D model (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 progestin of the 19-nortestosterone group which is widely used in veterinary medicine to suppress or synchronize estrus in horses and pigs. [2] [3] [4] [5] [6] It is available for veterinary use in both Europe (as Regumate) and the United States (as Matrix). [7]

Contents

Uses

Veterinary

Altrenogest is used in veterinary medicine.

Pharmacology

Pharmacodynamics

An in vitro yeast structure–activity relationships bioassay study found that altrenogest was the most potent agonist of both the progesterone receptor (PR) and the androgen receptor (AR) of a large selection of other progestogens as well as anabolic–androgenic steroids (AAS). [8] The observed potency of altrenogest even exceeded that of metribolone (methyltrienolone, R-1881), which was the second most potent compound. [8] 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. [8]

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). [8]

According to its manufacturer Roussel Uclaf, altrenogest has weak anabolic and androgenic activity equivalent to 1/20th of that of testosterone. [9] However, no significant androgenic effects have been observed in young stallions or mature mares, [10] 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. [11] On the other hand, minor potential anabolic/androgenic effects have been suggested for altrenogest in pigs. [10]

Chemistry

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 synthetic estrane steroid and derivative of 19-nortestosterone and 17α-allyltestosterone, or of 17α-allyl-19-nortestosterone. [2] [3] [6] It is one of only two marketed progestins that possesses a 17α-allyl group, the other being allylestrenol. [2] [3] Most other progestins possess a 17α-ethynyl group, while AAS, if they are 17α-substituted, are usually 17α-alkylated (with a methyl or ethyl group). [2] [3] 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). [2] [3] Altrenogest is also closely related to norgestrienone. [2] [3]

History

Altrenogest has been marketed as Regumate since the early 1980s. [10]

Society and culture

Generic names

Altrenogest is the generic name of the drug and its INN, USAN, and BAN, while altrénogest is its DCF. [2] [3] [4]

Brand names

Altrenogest is marketed under the brand names Regumate and Matrix among others. [2] [3] [4]

Related Research Articles

<span class="mw-page-title-main">Tetrahydrogestrinone</span> Synthetic and orally active anabolic–androgenic steroid (AAS)

Tetrahydrogestrinone (THG), known by the nickname The Clear, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed for medical use. It was developed by Patrick Arnold and was used by a number of high-profile athletes such as Marion Jones, Barry Bonds, and Dwain Chambers.

<span class="mw-page-title-main">Nandrolone</span> Anabolic steroid

Nandrolone, also known as 19-nortestosterone, is an endogenous androgen which exists in the male body at a ratio of 1:50 compared to testosterone. It is also an anabolic steroid (AAS) which is medically used in the form of esters such as nandrolone decanoate and nandrolone phenylpropionate. Nandrolone esters are used in the treatment of anemias, cachexia, osteoporosis, breast cancer, and for other indications. They are not used by mouth and instead are given by injection into muscle or fat.

<span class="mw-page-title-main">Trenbolone</span> Anabolic steroid

Trenbolone is an androgen and anabolic steroid (AAS) of the nandrolone group which itself was never marketed. Trenbolone ester prodrugs, including trenbolone acetate and trenbolone hexahydrobenzylcarbonate, are or have been marketed for veterinary and clinical use. Trenbolone acetate is used in veterinary medicine in livestock to increase muscle growth and appetite, while trenbolone hexahydrobenzylcarbonate was formerly used clinically in humans but is now no longer marketed. In addition, although it is not approved for clinical or veterinary use, trenbolone enanthate is sometimes sold on the black market under the nickname Trenabol.

<span class="mw-page-title-main">Ethylestrenol</span> Chemical compound

Ethylestrenol, also known as ethyloestrenol or ethylnandrol and sold under the brand names Maxibolin and Orabolin among others, is an androgen and anabolic steroid (AAS) medication which has been used in the past for a variety of indications such as to promote weight gain and to treat anemia and osteoporosis but has been discontinued for use in humans. It is still available for veterinary use in Australia and New Zealand however. It is taken by mouth.

<span class="mw-page-title-main">Norethandrolone</span> Chemical compound

Norethandrolone, sold under the brand names Nilevar and Pronabol among others, is an androgen and anabolic steroid (AAS) medication which has been used to promote muscle growth and to treat severe burns, physical trauma, and aplastic anemia but has mostly been discontinued. It is still available for use in France however. It is taken by mouth.

<span class="mw-page-title-main">Trenbolone acetate</span> Chemical compound

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<span class="mw-page-title-main">Mibolerone</span> Chemical compound

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.

<span class="mw-page-title-main">Metribolone</span> Chemical compound

Metribolone is a synthetic and orally active anabolic–androgenic steroid (AAS) and a 17α-alkylated nandrolone (19-nortestosterone) derivative which was never marketed for medical use but has been widely used in scientific research as a hot ligand in androgen receptor (AR) ligand binding assays (LBAs) and as a photoaffinity label for the AR. More precisely, metribolone is the 17α-methylated derivative of trenbolone. It was investigated briefly for the treatment of advanced breast cancer in women in the late 1960s and early 1970s, but was found to produce signs of severe hepatotoxicity at very low dosages, and its development was subsequently discontinued.

<span class="mw-page-title-main">Anabolic steroid</span> Steroidal androgen that is structurally related and has similar effects to testosterone

Anabolic steroids, also known as anabolic-androgenic steroids (AAS), are synthetic substances that mimic the effects of testosterone, the male sex hormone. They are used to increase muscle size, strength, and performance and are commonly associated with athletic performance enhancement and bodybuilding. Anabolic steroids are classified as Schedule III controlled substances in many countries due to their potential for abuse and adverse health effects.

<span class="mw-page-title-main">Allylestrenol</span> Chemical compound

Allylestrenol, sold under the brand names Gestanin and Turinal among others, is a progestin medication which is used to treat recurrent and threatened miscarriage and to prevent premature labor in pregnant women. However, except in the case of proven progesterone deficiency, its use for such purposes is no longer recommended. It is also used in Japan to treat benign prostatic hyperplasia (BPH) in men. The medication is used alone and is not formulated in combination with an estrogen. It is taken by mouth.

<span class="mw-page-title-main">Dienolone</span> Chemical compound

Dienolone, or nordienolone, also known as 19-nor-δ9(10)-testosterone, δ9(10)-nandrolone, or estra-4,9(10)-dien-17β-ol-3-one, is a synthetic anabolic-androgenic steroid (AAS) of the 19-nortestosterone group that was never marketed. It has been found to possess slightly lower affinity for the androgen receptor (AR) and progesterone receptor (PR) relative to nandrolone in rat and rabbit tissue bioassays, whereas trenbolone was found to possess the same affinity for the AR as dienolone but several-fold increased affinity for the PR. Dienedione is thought to be a prohormone of dienolone, while methyldienolone and ethyldienolone are orally active 17α-alkylated AAS derivatives of dienolone. In contrast, dienogest, the 17α-cyanomethyl derivative of dienolone, is a potent progestogen and antiandrogen.

<span class="mw-page-title-main">Ethyltestosterone</span> Synthetic anabolic steroid

Ethyltestosterone, or 17α-ethyltestosterone, also known as 17α-ethylandrost-4-en-17β-ol-3-one or 17α-pregn-4-en-17-ol-3-one, is a synthetic, orally active anabolic–androgenic steroid (AAS) of the 17α-alkylated group related to methyltestosterone which was never marketed. Like methyltestosterone, ethyltestosterone is the parent compound of many AAS. Derivatives of ethyltestosterone include norethandrolone, ethylestrenol (ethylnandrol), norboletone, ethyldienolone, tetrahydrogestrinone, bolenol (ethylnorandrostenol), and propetandrol.

<span class="mw-page-title-main">Dimethyltrienolone</span> Anabolic–androgenic steroid

Dimethyltrienolone is a synthetic, orally active, and extremely potent anabolic–androgenic steroid (AAS) and 17α-alkylated 19-nortestosterone (nandrolone) derivative which was never marketed for medical use. It has among the highest known affinity of any AAS for the androgen receptors, and has been said to be perhaps the most potent AAS to have ever been developed.

<span class="mw-page-title-main">Vinyltestosterone</span> Chemical compound

Vinyltestosterone is a synthetic anabolic–androgenic steroid (AAS) that was never marketed. However, two 19-nortestosterone derivatives of vinyltestosterone, norvinisterone (17α-vinyl-19-nortestosterone) and norgesterone, have been marketed. They are used as progestins for female hormonal contraception, rather than as AAS.

<span class="mw-page-title-main">Allyltestosterone</span> Chemical compound

Allyltestosterone, or 17α-allyltestosterone, also known as 17α-allylandrost-4-en-17β-ol-3-one, is a steroid derived from testosterone that was first synthesized in 1936 and was never marketed. Along with propyltestosterone (topterone), it has been patented as a topical antiandrogen and hair growth inhibitor. Allyltestosterone is the parent structure of two marketed 19-nortestosterone progestins, allylestrenol and altrenogest. These progestins are unique among testosterone derivatives in that they appear to be associated with few or no androgenic effects.

<span class="mw-page-title-main">5α-Dihydronandrolone</span> Chemical compound

5α-Dihydronandrolone is a naturally occurring anabolic–androgenic steroid (AAS) and a 5α-reduced derivative of nandrolone (19-nortestosterone). It is a major metabolite of nandrolone and is formed from it by the actions of the enzyme 5α-reductase analogously to the formation of dihydrotestosterone (DHT) from testosterone.

<span class="mw-page-title-main">5α-Dihydronorethisterone</span> Chemical compound

5α-Dihydronorethisterone is a major active metabolite of norethisterone (norethindrone). Norethisterone is a progestin with additional weak androgenic and estrogenic activity. 5α-DHNET is formed from norethisterone by 5α-reductase in the liver and other tissues.

<span class="mw-page-title-main">17α-Allyl-19-nortestosterone</span> Chemical compound

17α-Allyl-19-nortestosterone, also known as 3-ketoallylestrenol or as 17α-allylestr-4-en-17β-ol-3-one, is a progestin which was never marketed. It is a combined derivative of the anabolic–androgenic steroid and progestogen nandrolone (19-nortestosterone) and the antiandrogen allyltestosterone (17α-allyltestosterone). The drug is a major active metabolite of allylestrenol, which is thought to be a prodrug of 17α-allyl-19-nortestosterone.

<span class="mw-page-title-main">Structure–activity relationships of anabolic steroids</span>

The structure–activity relationships (SAR) of anabolic steroids (AAS) have been extensively studied.

References

  1. ↑ Cheryl S. Asa; Ingrid J. Porton (24 August 2005). Wildlife Contraception: Issues, Methods, and Applications. JHU Press. pp. 35–. ISBN   978-0-8018-8304-0.
  2. 1 2 3 4 5 6 7 8 J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 35–. ISBN   978-1-4757-2085-3.
  3. 1 2 3 4 5 6 7 8 Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 33–. ISBN   978-3-88763-075-1.
  4. 1 2 3 "Archived copy". Archived from the original on 2017-12-01. Retrieved 2017-11-25.{{cite web}}: CS1 maint: archived copy as title (link)
  5. ↑ Jim E. Riviere; Mark G. Papich (13 May 2013). Veterinary Pharmacology and Therapeutics. John Wiley & Sons. pp. 727–. ISBN   978-1-118-68590-7.
  6. 1 2 F. J. Zeelen (1990). Medicinal chemistry of steroids. Elsevier Science Limited. pp. 108–109. 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.
  7. ↑ Heriberto Rodriguez-Martinez (1 April 2010). Control of Pig Reproduction VIII. Nottingham University Press. pp. 189–. ISBN   978-1-907284-53-3.
  8. 1 2 3 4 McRobb L, Handelsman DJ, Kazlauskas R, Wilkinson S, McLeod MD, Heather AK (2008). "Structure-activity relationships of synthetic progestins in a yeast-based in vitro androgen bioassay". J. Steroid Biochem. Mol. Biol. 110 (1–2): 39–47. doi:10.1016/j.jsbmb.2007.10.008. PMID   18395441. S2CID   5612000.
  9. ↑ Kluber EF, Minton JE, Stevenson JS, Hunt MC, Davis DL, Hoagland TA, Nelssen JL (1988). "Growth, carcass traits, boar odor and testicular and endocrine functions of male pigs fed a progestogen, altrenogest". J. Anim. Sci. 66 (2): 470–8. doi:10.2527/jas1988.662470x. PMID   3131291.
  10. 1 2 3 Angus O. McKinnon; Edward L. Squires; Wendy E. Vaala; Dickson D. Varner (5 July 2011). Equine Reproduction. John Wiley & Sons. pp. 4462–. ISBN   978-0-470-96187-2.
  11. ↑ Committee to Review the Bureau of Land Management Wild Horse and Burro Management Program; Board on Agriculture and Natural Resources; Division on Earth and Life Studies; National Research Council (4 October 2013). Using Science to Improve the BLM Wild Horse and Burro Program: A Way Forward. National Academies Press. pp. 120–. ISBN   978-0-309-26494-5.
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