Norgestomet

Last updated
Norgestomet
Norgestomet.svg
Clinical data
Trade names Syncro-Mate B, Crestar
Other namesNorgestamet; SC-21009; 11β-Methyl-17α-acetoxy-19-norprogesterone; 17α-Hydroxy-11β-methyl-19-norpregn-4-ene-3,20-dione acetate
Drug class Progestogen; Progestin; Progestogen ester
Identifiers
  • [(8R,9S,10R,11S,13S,14S,17R)-17-acetyl-11,13-dimethyl-3-oxo-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-17-yl] acetate
CAS Number
PubChem CID
ChemSpider
UNII
ECHA InfoCard 100.042.359 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C23H32O4
Molar mass 372.505 g·mol−1
3D model (JSmol)
  • CC1CC2(C(CCC2(C(=O)C)OC(=O)C)C3C1C4CCC(=O)C=C4CC3)C
  • InChI=1S/C23H32O4/c1-13-12-22(4)20(9-10-23(22,14(2)24)27-15(3)25)19-7-5-16-11-17(26)6-8-18(16)21(13)19/h11,13,18-21H,5-10,12H2,1-4H3/t13-,18-,19-,20-,21+,22-,23-/m0/s1
  • Key:IWSXBCZCPVUWHT-VIFKTUCRSA-N

Norgestomet, or norgestamet, sold under the brand name Syncro-Mate B and Crestar, is a progestin medication which is used in veterinary medicine to control estrus and ovulation in cattle. [1] [2]

Contents

Uses

Veterinary

Norgestomet is used in veterinary medicine.

Pharmacology

Pharmacodynamics

Norgestomet is a progestogen. In addition to the progesterone receptor, it possesses weak (micromolar) affinity for the glucocorticoid receptor. [3]

Chemistry

Norgestomet, also known as 11β-methyl-17α-acetoxy-19-norprogesterone or as 17α-hydroxy-11β-methyl-19-norpregn-4-ene-3,20-dione acetate, is a synthetic norpregnane steroid and a derivative of progesterone. [1] [4]

History

Norgestomet was developed and introduced for veterinary use in the mid-1970s. [5]

Society and culture

Generic names

Norgestomet is the generic name of the drug and its INN, USAN, and BAN. [1] [4] It also known as norgestamet and is known by its developmental code name SC-21009. [1] [4] [6]

Brand names

Norgestomet is marketed under the brand names Syncro-Mate B and Crestar. [1] [4]

Related Research Articles

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

17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids.

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

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

Normethandrone, also known as methylestrenolone or methylnortestosterone and sold under the brand name Metalutin among others, is a progestin and androgen/anabolic steroid (AAS) medication which is used in combination with an estrogen in the treatment of amenorrhea and menopausal symptoms in women. It is taken by mouth.

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

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<span class="mw-page-title-main">19-Norprogesterone</span> Chemical compound

19-Norprogesterone, also known as 19-norpregn-4-ene-3,20-dione, is a steroidal progestin and close analogue of the sex hormone progesterone, lacking only the C19 methyl group of that molecule. It was first synthesized in 1944 in the form of a mixture that also included unnatural stereoisomers of progesterone, and this mixture was found to be at least equivalent to progesterone in terms of progestogenic activity. Subsequent investigations revealed that 17-isoprogesterone and 14-iso-17-isoprogesterone are devoid of progestogenic activity. 19-Norprogesterone was resynthesized in 1951 with an improved method, and was confirmed to be the component of the mixture synthesized in 1944 that was responsible for its progestogenic activity. In 1953, a paper was published showing that 19-norprogesterone possessed 4- to 8-fold the activity of progesterone in the Clauberg assay in rabbits, and at the time of this discovery, 19-norprogesterone was the most potent progestogen known.

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

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

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

Norgesterone, also known as norvinodrel or vinylestrenolone and sold under the brand name Vestalin, is a progestin medication which was formerly used in birth control pills for women but is now no longer marketed. It was used in combination with the estrogen ethinylestradiol. It is taken by mouth.

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

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<span class="mw-page-title-main">Progestogen ester</span> Drug class

A progestogen ester is an ester of a progestogen or progestin. The prototypical progestogen is progesterone, an endogenous sex hormone. Esterification is frequently employed to improve the pharmacokinetics of steroids, including oral bioavailability, lipophilicity, and elimination half-life. In addition, with intramuscular injection, steroid esters are often absorbed more slowly into the body, allowing for less frequent administration. Many steroid esters function as prodrugs.

<span class="mw-page-title-main">Flugestone acetate</span> Progestin medication

Flugestone acetate (FGA), sold under the brand name Cronolone among others, is a progestin medication which is used in veterinary medicine.

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

Acetomepregenol (ACM), also known as mepregenol diacetate and sold under the brand name Diamol, is a progestin medication which is used in Russia for the treatment of gynecological conditions and as a method of birth control in combination with an estrogen. It has also been studied in the treatment of threatened abortion. It has been used in veterinary medicine as well. It has been marketed since at least 1981.

<span class="mw-page-title-main">11-Ketoprogesterone</span> Chemical compound

11-Ketoprogesterone, or 11-oxoprogesterone, also known as pregn-4-ene-3,11,20-trione, is a pregnane steroid related to cortisone (11-keto-17α,21-dihydroxyprogesterone) that was formerly used in veterinary medicine in the treatment of bovine ketosis. It was synthesized in 1940. The steroid has profound effects on carbohydrate metabolism and possesses activities associated with adrenal cortex hormones like cortisone. However, it is non-toxic even in high dosages, suggesting that it lacks conventional glucocorticoid activity, and it does not possess mineralocorticoid activity, unlike other adrenocortical hormones. 11-Ketoprogesterone may act through membrane glucocorticoid receptors.

References

  1. 1 2 3 4 5 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 887–. ISBN   978-1-4757-2085-3.
  2. ↑ Favero RJ, Henderson EA, Kesler DJ (1 July 1990). "The Ability of Norgesomet Impregnated Poly(dimethylsiloxane) to Maintain Pregnancy Subsequent to Ovarietomy". In Gebelein CG, Dunn RL (eds.). Progress in Biomedical Polymers. Springer Science & Business Media. pp. 356–. ISBN   978-0-306-43523-2.
  3. ↑ Moffatt RJ, Zollers WG, Welshons WV, Kieborz KR, Garverick HA, Smith MF (January 1993). "Basis of norgestomet action as a progestogen in cattle". Domestic Animal Endocrinology. 10 (1): 21–30. doi:10.1016/0739-7240(93)90005-v. PMID   8467644.
  4. 1 2 3 4 "Norgestomet". Drugs.com. Archived from the original on 28 February 2018.
  5. ↑ Gordon U (22 October 2013). "Artificial Control O Oestrus and Ovulation". Controlled Breeding in Farm Animals. Elsevier. pp. 40–. ISBN   978-1-4832-8569-6.
  6. ↑ Houghton PL (1979). "Effect of time of insemination and calf removal after estrus synchronization in beef cattle".
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