Gonadorelin Hydrochloride

Gonadorelin Hydrochloride is a synthetic peptide corresponding to a hypothalamic hormone also known as LHRH or GnRH. As a single dose it stimulates the release of LH and FSH from the anterior pituitary, whereas continuous administration results in downregulation of LH and FSH levels followed by suppression of ovarian and testicular steroid biosynthesis.

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CAT No: 10-101-86

CAS No: 33515-09-2 (net), 51952-41-1 (hydrochloride)

Synonyms/Alias: Gonadotropin-releasing hormone; Luteinizing hormone-releasing factor; Fertagyl; Gonadoliberin; Hypocrine; Lutrefact; Relefact; Gonadorelin hydrochloride; Gonadorelin HCl; Factrel; 5-Oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosylglycyl-L-leucyl-L-arginyl-L-prolylglycinamide hydrochloride; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-glycyl-L-leucyl-L-arginyl-L-prolyl-glycinamide hydrochloride

Chemical 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

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M.F/Formula	C55H75N17O13
M.W/Mr.	1218.76
Sequence	One Letter Code: XHWSYGLRPG Three Letter Code: H-Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-Gly-NH2.HCl
Labeling Target	Gonadotropin-releasing hormone (GNRH) Receptor
Application	Gonadorelin hydrochloride stimulates anterior pituitary to release the gonadotropin LH.
Activity	Agonist
Areas of Interest	Pituitary & Hypothalamic Hormones Veterinary Medicine
Target	Gonadotropin-releasing hormone receptor

Source#	Synthetic
Length	10
Solubility	−20°C
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
Isomeric SMILES	CC(C)C[C@@H](C(=O)N[C@@H](CCCN=C(N)N)C(=O)N1CCC[C@H]1C(=O)NCC(=O)N)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.Cl
BoilingPoint	N/A
References	Recently a patient with severe hypogonadotropic hypogonadism who was given luteinizing hormone-releasing hormone (Factrel) through an infusion pump developed a wheat-and-flare reaction at the sites of injection. Treatment with luteinizing hormone-releasing hormone was discontinued and the immune response was characterized. Skin testing by skin prick test was positive for luteinizing hormone-releasing hormone but negative for vehicle. Radioallergosorbent testing was performed with allergic (patient serum with an elevated serum immunoglobulin E concentration and allergic to inhalant allergens including ragweed pollen) and nonallergic controls. Radioallergosorbent testing was negative for luteinizing hormone-releasing hormone-reactive immunoglobulin E antibodies. Radioimmunoassay of serum of the allergic patient antibody to luteinizing hormone-releasing hormone was positive only for immunoglobulin E. Maximum binding occurred at a dilution of 1:10. Sera from nonallergic and unchallenged patients were negative. It is concluded that this patient developed hypersensitivity reactions caused by IgE antibody to luteinizing hormone-releasing hormone. Foster, W. G., Jarrell, J. F., Dolovich, J., & YoungLai, E. V. (1989). Immunoglobulin-mediated hypersensitivity in response to long-term treatment with gonadorelin hydrochloride (Factrel) in a female patient. American journal of obstetrics and gynecology, 160(4), 979-983.
Melting Point	N/A

1. Store-operated Ca2+ entry sustains the fertilization Ca2+ signal in pig eggs

2. Identification, Localization in the Central Nervous System and Novel Myostimulatory Effect of Allatostatins in Tenebrio molitor Beetle

3. Myotropic activity and immunolocalization of selected neuropeptides of the burying beetle Nicrophorus vespilloides (Coleoptera: Silphidae)

4. Investigating Potential Interactions Between Neurohypophyseal Peptides, their Drug Analogs, and Coagulation Factor VIII

5. GLP-1, exendin-4 and C-peptide regulate pancreatic islet microcirculation, insulin secretion and glucose tolerance in rats

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