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.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.

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

Gonadorelin Hydrochloride is a synthetic decapeptide that functions as an analog of the natural gonadotropin-releasing hormone (GnRH). Structurally identical to endogenous GnRH, this peptide is widely utilized in biochemical and endocrine research due to its precise regulatory role in the hypothalamic-pituitary-gonadal axis. By stimulating the release of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) from the anterior pituitary, Gonadorelin Hydrochloride offers a controlled means to investigate reproductive hormone pathways, making it a valuable tool for elucidating mechanisms of hormonal regulation, feedback, and signal transduction in mammalian systems.

Endocrine signaling studies: As a potent GnRH receptor agonist, Gonadorelin Hydrochloride is extensively used in research focused on hypothalamic-pituitary communication. Its application allows for the controlled activation of GnRH receptors, enabling the study of downstream signaling cascades and gene expression changes in pituitary cells. Researchers can utilize this peptide to dissect the molecular dynamics of hormone secretion and receptor desensitization, providing critical insights into neuroendocrine regulation.

Reproductive physiology research: The compound serves as a foundational reagent in investigations of reproductive endocrinology. By inducing LH and FSH release in vitro or in animal models, it supports the study of gonadal development, gametogenesis, and steroidogenesis. Its use facilitates the exploration of feedback mechanisms between the gonads and the hypothalamic-pituitary axis, helping to clarify the physiological roles of these hormones in both male and female reproductive systems.

Assay development and standardization: Gonadorelin Hydrochloride is frequently employed as a reference agonist in the development and calibration of bioassays designed to measure GnRH receptor activity. Its well-characterized action profile makes it suitable for validating assay sensitivity, specificity, and reproducibility. Laboratories benefit from its use in establishing baseline responses, ensuring consistency across experimental platforms and facilitating the comparison of novel GnRH analogs or antagonists.

Peptide-receptor interaction studies: The compound is instrumental in characterizing the binding dynamics and activation mechanisms of GnRH receptors. By providing a defined ligand, it enables detailed analyses of receptor-ligand affinity, signal transduction kinetics, and structure-activity relationships. These studies are essential for advancing the understanding of peptide hormone receptor pharmacology and for guiding the rational design of new modulators targeting the reproductive axis.

Peptide synthesis and analytical validation: Gonadorelin Hydrochloride also serves as a model peptide in synthetic chemistry and analytical method development. Researchers utilize it to optimize solid-phase peptide synthesis protocols, assess peptide purity, and validate chromatographic or spectrometric techniques. Its well-established sequence and physicochemical properties make it an ideal standard for benchmarking peptide production and quality control processes, supporting both academic and industrial research initiatives.

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

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