Gonadorelin Hydrochloride
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Gonadorelin Hydrochloride

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Gonadorelin is a synthetic decapeptide prepared by solid-phase peptide synthesis. It is used to assess the functional ability and response of gonadotropin in the anterior pituitary gland, as well as after pituitary resection. It is mainly used for cows to estrus at the same time to treat abnormal ovarian function.

Category
Peptide Inhibitors
Catalog number
BAT-010044
CAS number
51952-41-1
Molecular Formula
C55H75N17O13.xHCl
Molecular Weight
1182.29 (free base)
Gonadorelin Hydrochloride
IUPAC Name
(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[2-[[(2S)-1-[[(2S)-1-[(2S)-2-[(2-amino-2-oxoethyl)carbamoyl]pyrrolidin-1-yl]-5-(diaminomethylideneamino)-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; hydrochloride
Synonyms
Luteinizing hormone-releasing factor (swine), hydrochloride (1:x); Luteinizing hormone-releasing factor (pig), hydrochloride; Factrel; Gonadorelin hydrochloride; LH-RH hydrochloride; Gonadorelin HCl; H-Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2.xHCl; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycinamide hydrochloride
Related CAS
51952-40-0 (monohydrochloride) 53716-42-0 (Deleted CAS) 129311-55-3 (monoacetate) 33515-09-2 (free base)
Purity
95%
Sequence
Pyr-HWSYGLRPG-NH2.xHCl
Storage
Store at -20°C
Solubility
Soluble in DMSO
InChI
InChI=1S/C55H75N17O13.ClH/c1-29(2)19-38(49(80)67-37(9-5-17-60-55(57)58)54(85)72-18-6-10-43(72)53(84)62-25-44(56)75)66-46(77)26-63-47(78)39(20-30-11-13-33(74)14-12-30)68-52(83)42(27-73)71-50(81)40(21-31-23-61-35-8-4-3-7-34(31)35)69-51(82)41(22-32-24-59-28-64-32)70-48(79)36-15-16-45(76)65-36; /h3-4,7-8,11-14,23-24,28-29,36-43,61,73-74H,5-6,9-10,15-22,25-27H2,1-2H3,(H2,56,75)(H,59,64)(H,62,84)(H,63,78)(H,65,76)(H,66,77)(H,67,80)(H,68,83)(H,69,82)(H,70,79)(H,71,81)(H4,57,58,60); 1H/t36-,37-,38-,39-,40-,41-,42-,43-; /m0./s1
InChI Key
UPRWQSQENCASAD-HBBGHHHDSA-N
Canonical SMILES
CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)CNC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6.Cl
1.Does lower dose of long-acting triptorelin maintain pituitary suppression and produce good live birth rate in long down-regulation protocol for in-vitro fertilization?
Chen X1, Feng SX1, Guo PP1, He YX1, Liu YD1, Ye DS1, Chen SL2. J Huazhong Univ Sci Technolog Med Sci. 2016 Apr;36(2):215-20. doi: 10.1007/s11596-016-1569-8. Epub 2016 Apr 13.
The effects of pituitary suppression with one-third depot of long-acting gonadotropin-releasing hormone (GnRH) agonist in GnRH agonist long protocol for in vitro fertilization (IVF)/intracytoplasmic sperm injection (ICSI) were investigated. A retrospective cohort study was performed on 3186 cycles undergoing IVF/ICSI with GnRH agonist long protocol in a university-affiliated infertility center. The pituitary was suppressed with depot triptorelin of 1.25 mg or 1.875 mg. There was no significant difference in live birth rate between 1.25 mg triptorelin group and 1.875 mg triptorelin group (41.2% vs. 43.7%). The mean luteinizing hormone (LH) level on follicle-stimulating hormone (FSH) starting day was significantly higher in 1.25 mg triptorelin group. The mean LH level on the day of human chorionic gonadotrophin (hCG) administration was slightly but statistically higher in 1.25 mg triptorelin group. There was no significant difference in the total FSH dose between the two groups.
2.Recurrence after robotic myomectomy: is it associated with use of GnRH agonist?
Sangha R1, Katukuri V2, Palmer M2, Khangura RK2. J Robot Surg. 2016 Apr 12. [Epub ahead of print]
Gonadotropin-releasing hormone (GnRH) agonist therapy is used before myomectomy to decrease the size of the fibroids, but its association with fibroid recurrence postoperatively remains unsettled. We undertook a retrospective study of robotic-assisted myomectomy (RM) patients at our academic medical center to determine symptomatic recurrence and reoperation rates in those who did versus did not receive preoperative GnRH therapy. Only patients, who had their index myomectomy at least 2 years prior to the chart review, were included in this study. Of 118 RM patients identified between January 2005 and December 2009, 17 patients (14.4 %) had symptomatic recurrence as early as 5 months to as late as 30 months postoperatively. The symptomatic recurrence group had significantly higher preoperative GnRH use (35 vs 9 % non-recurrence; p = 0.009). A total of 7.6 % of all patients underwent reoperation. GnRH agonist use was significantly higher in the reoperation group (56 vs 9 % no reoperation; p = 0.
3.Molecular basis for regulating seasonal reproduction in vertebrates.
Nishiwaki-Ohkawa T1, Yoshimura T2. J Endocrinol. 2016 Apr 11. pii: JOE-16-0066. [Epub ahead of print]
Animals that inhabit mid- to high-latitude regions exhibit various adaptive behaviors such as migration, reproduction, molting, and hibernation in response to seasonal cues. These adaptive behaviors are tightly regulated by seasonal changes in photoperiod, the relative day length versus night. Recently, the regulatory pathway of seasonal reproduction was elucidated using quail. In birds, deep-brain photoreceptors receive and transmit light information to the pars tuberalis in the pituitary gland, which induces the secretion of thyroid-stimulating hormone. Thyroid-stimulating hormone locally activates thyroid hormone via induction of type 2 deiodinase in the mediobasal hypothalamus. Thyroid hormone then induces morphological changes in the terminals of neurons that express gonadotropin-releasing hormone and facilitates gonadotropin secretion from the pituitary gland. In mammals, light information is received by photoreceptors in the retina and neurally transmitted to the pineal gland, where it inhibits the synthesis and secretion of melatonin, which is crucial for seasonal reproduction.
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