Nafarelin acetate is a potent LHRH agonist. After a transient increase, continuous administration results in downregulation of LH and FSH levels followed by a suppression of ovarian and testicular steroid biosynthesis.
CAT No: 10-101-24
CAS No:76932-56-4 (net)
Synonyms/Alias:Synarela;NAFARELIN ACETATE;76932-60-0;Nafarelin acetate anhydrous;TH2HMT9YBQ;UNII-TH2HMT9YBQ;(6-D-(2-Naphthyl)alanine)LHRH acetate;nafarelin acetate (anhydrous);UNII-8ENZ0QJW4H;CHEBI:167202;DTXSID50227720;Nasanyl;NAFARELIN ACETATE (MART.);RS-94991;Synrelina;6-[3-(2-Naphthalenyl)-D-alanine]-luteinizing Hormone-releasing Factor (pig) Acetate Salt; Nafareline Acetate; [6-D-(2-naphthyl)-alanine]LH-RH Acetate;;Nafarelin (acetate);5-OXO-PRO-HIS-TRP-SER-TYR-3-(2-NAPHTHYL)-D-ALA-LEU-ARG-PRO-GLYCINAMIDE ACETATE;Nafarelin Acetate, Hydrate;SCHEMBL166006;(D-2-Nal6)-LHRH Acetate;DTXCID00150211;NAFARELIN ACETATE [WHO-DD];MFCD01716231;AKOS040744807;NAFARELIN ACETATE ANHYDROUS [MI];Nafarelin acetate(76932-56-4 free base);RS-94991298;Q27289963;
Nafarelin Acetate is a synthetic decapeptide and potent gonadotropin-releasing hormone (GnRH) agonist widely utilized in biochemical and endocrinological research. Structurally analogous to natural GnRH but featuring specific amino acid substitutions, it exhibits enhanced metabolic stability and receptor affinity, making it a valuable tool for probing the hypothalamic-pituitary-gonadal (HPG) axis. Its ability to modulate the secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) through receptor desensitization underpins its central role in studies of reproductive biology, neuroendocrinology, and peptide-receptor interactions.
Neuroendocrine regulation studies: Nafarelin Acetate is frequently employed to investigate the regulatory mechanisms governing the HPG axis. By acting as a GnRH receptor agonist, it initially stimulates, then suppresses, pituitary gonadotropin release through receptor downregulation following continuous exposure. This property is instrumental in dissecting feedback loops and temporal dynamics of hormone secretion, enabling researchers to elucidate the molecular basis of endocrine signaling and its physiological consequences in various animal models.
Peptide-receptor interaction research: The compound serves as a model ligand for exploring GnRH receptor binding, signal transduction, and desensitization phenomena. Its defined sequence and high receptor affinity allow for detailed kinetic and structural analyses of ligand-receptor engagement. Studies utilizing nafarelin have contributed to mapping critical residues involved in receptor activation and internalization, supporting the rational design of novel analogs and antagonists.
Endocrine disruptor screening: Nafarelin is valuable in the assessment of environmental or synthetic compounds that may interfere with reproductive hormone signaling. By providing a controlled, reproducible means of activating or suppressing GnRH pathways, the peptide facilitates in vitro and in vivo assays to evaluate the impact of potential endocrine disruptors on gonadotropin release and downstream reproductive endpoints. Such applications are crucial for toxicological profiling and risk assessment in environmental health research.
Reproductive physiology modeling: Researchers utilize nafarelin to induce reversible suppression of gonadotropin secretion, thereby creating experimental models of hypoestrogenism or hypogonadism. These models are essential for studying the physiological effects of altered sex steroid levels on target tissues, including the gonads, bone, and central nervous system. The ability to precisely modulate hormone levels with a well-characterized agonist supports investigations into the developmental, metabolic, and behavioral consequences of reproductive hormone deprivation.
Peptide synthesis and analytical validation: Nafarelin Acetate is also utilized as a reference standard or positive control in peptide synthesis, purification, and analytical method development. Its defined structure and bioactivity make it suitable for validating chromatographic, mass spectrometric, and bioassay protocols designed for peptide therapeutics. Such applications ensure the reliability and accuracy of analytical workflows in peptide research and quality control environments.
Nafarelin acetate (less than Glu-His-Trp-Ser-Tyr-3-(2-naphthyl)-D-Ala-Leu-Arg-Pro-Gly-NH2) is a potent agonistic analogue of luteinizing hormone-releasing hormone. After a single iv administration of nafarelin acetate (with 14C label at C-3 of 3-(2-naphthyl)-D-Ala) to female rhesus monkeys, about 80% of the radioactivity was eliminated in urine. Five major radioactive urinary metabolites were isolated and purified by reversed phase HPLC. Four of these metabolites, identified by amino acid analysis, were short peptides: the 5-10-hexapeptide amide, the 6-10-pentapeptide amide, the 5-7-tripeptide, and the 6-7-dipeptide. The fifth metabolite, which accounted for about 15% of the radioactivity administered, was shown by NMR and mass spectrometry to be 2-naphthylacetic acid. A possible pathway of its formation is by oxidative deamination of 3-(2-napthyl)-D-Ala to give the corresponding alpha-keto acid, followed by oxidative decarboxylation of the alpha-keto acid. These five metabolites together accounted for about 70% of the radioactivity recovered in the urine of rhesus monkeys, or more than half of the radioactivity in the administered dose. A minor metabolite, which was not isolated, coeluted with 3-(2-naphthyl)-D-Ala in two solvent systems on HPLC. Nafarelin acetate was also present in small amounts. Several of these metabolites were also present in plasma of the rhesus monkey.
Chan, R. L., & Chaplin, M. D. (1985). Identification of major urinary metabolites of nafarelin acetate, a potent agonist of luteinizing hormone-releasing hormone, in the rhesus monkey. Drug metabolism and disposition, 13(5), 566-571.
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