Fertirelin acetate | CAS# 66002-66-2 | GnRH agonist

MedKoo Cat#: 574357 | Name: Fertirelin acetate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fertirelin acetate is a gonadotropin-releasing hormone (GnRH) agonist.

Chemical Structure

Fertirelin acetate

CAS#66002-66-2

Theoretical Analysis

MedKoo Cat#: 574357

Name: Fertirelin acetate

CAS#: 66002-66-2

Chemical Formula: C57H80N16O14

Exact Mass: 0.0000

Molecular Weight: 1213.37

Elemental Analysis: C, 56.42; H, 6.65; N, 18.47; O, 18.46

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Synonym

Fertirelin acetate; Fertilerine acetate; Conceral; Ovalyse; Fertirelin monoacetate; Des-Gly(sup 10)-GNRH-ethylamide; TAP031 acetate; TAP 031 acetate; TAP-031 acetate;

IUPAC/Chemical Name

acetic acid;(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

InChi Key

BXPQWJDAPUWFRD-AQJXLSMYSA-N

InChi Code

InChI=1S/C55H74N16O13/c1-29(2)19-38(50(80)66-37(9-5-17-60-55(57)58)54(84)71-18-6-10-43(71)44(74)23-45(56)75)65-47(77)26-62-48(78)39(20-30-11-13-33(73)14-12-30)67-53(83)42(27-72)70-51(81)40(21-31-24-61-35-8-4-3-7-34(31)35)68-52(82)41(22-32-25-59-28-63-32)69-49(79)36-15-16-46(76)64-36/h3-4,7-8,11-14,24-25,28-29,36-43,61,72-73H,5-6,9-10,15-23,26-27H2,1-2H3,(H2,56,75)(H,59,63)(H,62,78)(H,64,76)(H,65,77)(H,66,80)(H,67,83)(H,68,82)(H,69,79)(H,70,81)(H4,57,58,60)/t36-,37-,38-,39-,40-,41-,42-,43-/m0/s1

SMILES Code

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](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6.CC(=O)O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 1,213.37 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Chenault JR. Effect of fertirelin acetate or buserelin on conception rate at first or second insemination in lactating dairy cows. J Dairy Sci. 1990 Mar;73(3):633-8. doi: 10.3168/jds.S0022-0302(90)78714-0. PMID: 2111339. 2: Chenault JR, Kratzer DD, Rzepkowski RA, Goodwin MC. LH and FSH response of Holstein heifers to fertirelin acetate, gonadorelin and buserelin. Theriogenology. 1990 Jul;34(1):81-98. doi: 10.1016/0093-691x(90)90579-i. PMID: 16726818. 3: Yamada K, Nakao T, Nakada K, Matsuda G. Influence of GnRH analogue (fertirelin acetate) doses on synchronization of ovulation and fixed-time artificial insemination in lactating dairy cows. Anim Reprod Sci. 2002 Nov 15;74(1-2):27-34. doi: 10.1016/s0378-4320(02)00161-6. PMID: 12379372. 4: Nariai K, Ishinazaka T, Suzuki K, Uchiyama H, Sato K, Asano R, Tsumagari S, Yukawa M, Kanayama K. Optimum dose of LH-RH analogue Fertirelin Acetate for the induction of superovulation in mice. Exp Anim. 2005 Jan;54(1):97-9. doi: 10.1538/expanim.54.97. PMID: 15725686. 5: Nakao T, Sugihashi A, Kawata K, Nakamura H, Shirakawa J, Iinuma M, Tsurubayashi M, Horiuchi S. Effects of an analog of PGF2(alpha) (ONO-1052) on cows with luteinized ovarian cysts following treatment with GnRH analog (fertirelin acetate). Theriogenology. 1985 Oct;24(4):425-33. doi: 10.1016/0093-691x(85)90049-4. PMID: 16726097. 6: Coleman DA, Bartol FF, Rahe CH, Chenault JR. Endocrine and reproductive responses of beef cattle to a synthetic gonadotropin-releasing hormone agonist (fertirelin acetate). Theriogenology. 1988 Jul;30(1):149-57. doi: 10.1016/0093-691x(88)90272-5. PMID: 16726458. 7: Osawa T, Nakao T, Kimura M, Kaneko K, Takagi H, Moriyoshi M, Kawata K. Fertirelin and buserelin compared by LH release, milk progesterone and subsequent reproductive performance in dairy cows treated for follicular cysts. Theriogenology. 1995 Oct 15;44(6):835-47. doi: 10.1016/0093-691x(95)00269-e. PMID: 16727779. 8: Hartman PA, Stodola JD. Reversed-phase high-performance liquid chromatography of fertirelin acetate and related compounds. J Chromatogr. 1988 Jul 1;444:177-82. doi: 10.1016/s0021-9673(01)94020-8. PMID: 3060475. 9: Yamada K. JSAR Innovative Technology Award. Development of ovulation synchronization and fixed time artificial insemination in dairy cows. J Reprod Dev. 2005 Apr;51(2):177-86. doi: 10.1262/jrd.16103. PMID: 15883484. 10: Rettmer I, Stevenson JS, Corah LR. Endocrine responses and ovarian changes in inseminated dairy heifers after an injection of a GnRH agonist 11 to 13 days after estrus. J Anim Sci. 1992 Feb;70(2):508-17. doi: 10.2527/1992.702508x. PMID: 1548214. 11: Nakao T, Harada A, Kimura M, Takagi H, Kaneko K, Sugiyama S, Saito A, Moriyoshi M, Kawata K. Effect of fenprostalene 14 days after fertirelin treatment on intervals from treatment to conception in cows with follicular cysts diagnosed by milk progesterone test. J Vet Med Sci. 1993 Apr;55(2):207-10. doi: 10.1292/jvms.55.207. PMID: 8512999. 12: Inaba T, Tani H, Gonda M, Nakagawa A, Ohmura M, Mori J, Torii R, Tamada H, Sawada T. Induction of fertile estrus in bitches using a sustained-release formulation of a GnRH agonist (leuprolide acetate). Theriogenology. 1998 Apr 1;49(5):975-82. doi: 10.1016/s0093-691x(98)00046-6. PMID: 10732105. 13: Kutzler MA. Induction and synchronization of estrus in dogs. Theriogenology. 2005 Aug;64(3):766-75. doi: 10.1016/j.theriogenology.2005.05.025. PMID: 15993937. 14: Nakao T, Sugihashi A, Saga N, Tsunoda N, Kawata K. A further study on the dosage of an analog of luteinizing hormone-releasing hormone (fertirelin; Des- Gly10-LH-RH-ethylamide) for treatment of ovarian follicular cyst in cows. Nihon Juigaku Zasshi. 1983 Apr;45(2):269-73. doi: 10.1292/jvms1939.45.269. PMID: 6355595. 15: Okada J, Seo T, Kasahara F, Takeda K, Kondo S. New degradation product of des-Gly10-NH2-LH-RH-ethylamide (fertirelin) in aqueous solution. J Pharm Sci. 1991 Feb;80(2):167-70. doi: 10.1002/jps.2600800217. PMID: 2051323. 16: Rettmer I, Stevenson JS, Corah LR. Pregnancy rates in beef cattle after administering a GnRH agonist 11 to 14 days after insemination. J Anim Sci. 1992 Jan;70(1):7-12. doi: 10.2527/1992.7017. PMID: 1582922. 17: Kutzler MA. Estrus induction and synchronization in canids and felids. Theriogenology. 2007 Aug;68(3):354-74. doi: 10.1016/j.theriogenology.2007.04.014. Epub 2007 Jun 19. PMID: 17582484. 18: Hirata T, Hoshina T, Sasaki S, Sasaki O, Osawa T. Applicability of a progesterone-based timed artificilal insemination protocol after follicular fluid aspiration using the ovum pick-up technique in suckled beef cows. J Reprod Dev. 2007 Apr;53(2):171-7. doi: 10.1262/jrd.18089. Epub 2006 Nov 1. PMID: 17077579. 19: Tungmahasuk D, Fungbun N, Laoharatchatathanin T, Terashima R, Kurusu S, Kawaminami M. Effects of gonadotropin-releasing hormone agonist on human chorionic gonadotropin activity in granulosa cells of immature female rats. J Reprod Dev. 2018 Apr 13;64(2):129-134. doi: 10.1262/jrd.2017-142. Epub 2017 Dec 15. PMID: 29249775; PMCID: PMC5902900. 20: Okada J, Kondo S. Enzyme immunoassay for the determination of des- Gly10-NH2-LH-RH-ethylamide (fertirelin) in bovine plasma. Chem Pharm Bull (Tokyo). 1985 Oct;33(10):4464-70. doi: 10.1248/cpb.33.4464. PMID: 3912070.