Fertirelin

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]

Fertirelin

Clinical data
Trade names	Ovalyse
Other names	TAP-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	QH01CA91 (WHO)
Identifiers
IUPAC name (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	38234-21-8 Y acetate: 66002-66-2 Y
PubChem CID	188304
ChemSpider	163670
UNII	Q041AO6T91 acetate: JD54DU77I8 Y
KEGG	D07957
ChEMBL	ChEMBL3272563
CompTox Dashboard (EPA)	DTXSID8057728
ECHA InfoCard	100.164.570
Chemical and physical data
Formula	C55H76N16O12
Molar mass	1153.313 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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

See also

• Gonadotropin-releasing hormone receptor § Agonists

References

1. 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. Index Nominum 2000: International Drug Directory. Taylor & Francis. 2000. pp. 441–. ISBN 978-3-88763-075-1.
3. 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.