Nafarelin Acetate

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.

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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;

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M.F/FormulaC10H18N2O7
M.W/Mr.1322.5
SequenceOne Letter Code:XHWSYXLRPG
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-2Nal-Leu-Arg-Pro-Gly-NH2.CH3CO2H
Labeling TargetGonadotropin-releasing hormone (GNRH) Receptor
ApplicationNafarelin acetate is a potent synthetic agonist of gonadotropin-releasing hormone. Nafarelin has been used in the treatments of central precocious puberty and endometriosis.
AppearanceSolid powder
Purity>98% (or refer to the Certificate of Analysis)
ActivityAgonist
Areas of InterestCardiovascular System & Diseases
Pituitary & Hypothalamic Hormones
FunctionsPeptide binding
TargetGonadotropin-releasing hormone (GnRH)
Source#Synthetic
Long-term Storage ConditionsSoluble in DMSO, not in water
Shipping ConditionShipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Short-term Storage ConditionsDry, dark and at 0 - 4 °C
Solubility-20 °C
OrganismHuman
BoilingPointN/A
ShelfLife>2 years if stored properly
References

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.

Melting PointN/A
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