Fertirelin

Last updated
Fertirelin
Fertirelin.svg
Clinical data
Trade names Ovalyse
Other namesTAP-031; U-69689; 9-(N-Ethyl-L-prolinamide)-10-deglycinamide; 9-(N)-Et-ProNH2-10-des-GlyNH2-LHRH; Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-NHEt
Drug class GnRH analogue; GnRH agonist; Antigonadotropin
ATCvet code
Identifiers
  • (2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-2-oxoethyl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-hydroxy-1-oxopropan-2-yl]amino]-3-(1H-indol-3-yl)-1-oxopropan-2-yl]amino]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]-5-oxopyrrolidine-2-carboxamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.164.570 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C55H76N16O12
Molar mass 1153.313 g·mol−1
3D model (JSmol)
  • CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)CNC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]1CCC(=O)N1
  • InChI=1S/C55H76N16O12/c1-4-59-53(82)44-12-8-20-71(44)54(83)38(11-7-19-60-55(56)57)66-49(78)39(21-30(2)3)65-46(75)27-62-47(76)40(22-31-13-15-34(73)16-14-31)67-52(81)43(28-72)70-50(79)41(23-32-25-61-36-10-6-5-9-35(32)36)68-51(80)42(24-33-26-58-29-63-33)69-48(77)37-17-18-45(74)64-37/h5-6,9-10,13-16,25-26,29-30,37-44,61,72-73H,4,7-8,11-12,17-24,27-28H2,1-3H3,(H,58,63)(H,59,82)(H,62,76)(H,64,74)(H,65,75)(H,66,78)(H,67,81)(H,68,80)(H,69,77)(H,70,79)(H4,56,57,60)/t37-,38-,39-,40-,41-,42-,43-,44-/m0/s1
  • Key:DGCPIBPDYFLAAX-YTAGXALCSA-N

Fertirelin, or fertirelin acetate, sold under the brand name Ovalyse, is a gonadotropin-releasing hormone agonist (GnRH agonist) which has been marketed in the United Kingdom and Austria. [1] [2] [3] It may no longer be available. [4] Fertirelin has been used in veterinary medicine. [2] It may have been used in the treatment of sex hormone-dependent conditions and infertility in women. [3] The drug was first introduced in 1981 in Japan to treat various kinds of ovarian failure in cattle. [5] Fertirelin is a synthetic peptide and GnRH analogue. [1] [2] It is used as the acetate salt. [2]

See also

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

Azagly-nafarelin, sold under the brand name Gonazon, is a gonadotropin-releasing hormone agonist medication which is used in veterinary medicine in Europe. It is a GnRH analogue and a synthetic peptide, specifically a decapeptide. The medication has been approved in Europe as a solid silicone-based matrix implant for use as a contraceptive in animals such as male dogs, cats, and others, but is no longer or was never commercially available. The medication has also been used to treat benign prostatic hyperplasia in animals. In addition to its use in mammals, azagly-nafarelin has been approved for use in aquaculture fish, specifically to control ovulation in salmonids, and was the first GnRH agonist to be available for use in fish. It was introduced for use by 2005.

References

  1. 1 2 Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 549–. ISBN   978-1-4757-2085-3.
  2. 1 2 3 4 Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 441–. ISBN   978-3-88763-075-1.
  3. 1 2 Morton IK, Hall JM (6 December 2012). Concise Dictionary of Pharmacological Agents: Properties and Synonyms. Springer Science & Business Media. pp. 120–. ISBN   978-94-011-4439-1.
  4. ↑ "List of Gonadotropin releasing hormones". Drugs.com.
  5. ↑ Okada J, Seo T, Kasahara F, Takeda K, Kondo S (February 1991). "New degradation product of des-Gly10-NH2-LH-RH-ethylamide (fertirelin) in aqueous solution". Journal of Pharmaceutical Sciences. 80 (2): 167–170. doi:10.1002/jps.2600800217. PMID   2051323.
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