Nafarelin Acetate Hydrate

Nafarelin Acetate is the acetate salt form of nafarelin, a modified synthetic porcine luteinizing hormone (LH)-releasing hormone peptide analog, with gonadotropin-releasing hormone (GnRH) agonist activity. Upon nasal inhalation, nafarelin acetate binds to the GnRH receptor. This initially results in the release of the gonadotropins, follicle-stimulating hormone (FSH) and LH, from the pituitary gland; however, prolonged stimulation of the GnRH receptor desensitizes the receptor, which leads to decreased secretion of FSH and LH.

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

CAT No: R1952

Synonyms/Alias:RS-94991-298; Nafarelin acetate; Nafarelin acetate hydrate; Synarel; L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide; acetic acid; hydrate

Chemical Name:acetic acid;(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(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]-3-naphthalen-2-yl-1-oxopropan-2-yl]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;hydrate

Custom Peptide Synthesis
cGMP Peptide
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  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C68H89N17O16
M.W/Mr.
1400.5
Sequence
One Letter Code: XHWSYXLRPG Three Letter Code: H-Pyr-His-Trp-Ser-Tyr-D-2Nal-Leu-Arg-Pro-Gly-NH2.CH3CO2H.H2O
Appearance
Solid powder
Target
Gonadotropin-releasing hormone (GnRH)

Nafarelin Acetate Hydrate is a synthetic decapeptide analog of gonadotropin-releasing hormone (GnRH), engineered for enhanced potency and stability compared to its natural counterpart. As a member of the peptide hormone family, it features structural modifications that confer increased receptor affinity and resistance to enzymatic degradation. These properties have made it a valuable tool in the study of hypothalamic-pituitary-gonadal (HPG) axis regulation and reproductive endocrinology. Its ability to modulate the secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) underpins its significance in both basic research and applied biochemical investigations.

Endocrine signaling research: Nafarelin Acetate Hydrate serves as a robust model compound for dissecting GnRH receptor-mediated pathways. In vitro and ex vivo studies utilize it to stimulate or suppress downstream hormonal cascades, enabling researchers to map the molecular events involved in pituitary hormone release. Its high receptor specificity and predictable activity profile allow for precise modulation of gonadotropin secretion, supporting detailed mechanistic studies of endocrine feedback loops and signal transduction.

Reproductive biology studies: The compound is widely employed in investigations of reproductive system function, particularly in elucidating the physiological roles of GnRH analogs in mammalian species. By providing a controllable means to alter gonadotropin levels, it facilitates experiments that explore the regulation of gametogenesis, steroidogenesis, and sexual maturation. Researchers leverage its activity to probe ovarian and testicular function, dissecting the temporal dynamics of hormone-dependent reproductive processes.

Peptide receptor pharmacology: Nafarelin Acetate Hydrate is instrumental in characterizing the pharmacological properties of GnRH receptors, including binding affinity, receptor desensitization, and internalization kinetics. Its use in ligand-receptor interaction assays helps clarify the structural requirements for receptor activation and downregulation. Such studies are essential for advancing understanding of peptide-receptor dynamics and for the rational design of novel GnRH analogs with tailored biological profiles.

Peptide synthesis and analytical validation: The compound is frequently used as a reference standard in peptide synthesis laboratories and analytical development settings. Its well-defined sequence and physicochemical properties make it suitable for validating chromatographic methods, mass spectrometry protocols, and peptide quantification assays. These applications ensure the reliability of peptide production workflows and support quality control in research environments focused on synthetic peptide analogs.

Cell signaling and gene expression analysis: Nafarelin Acetate Hydrate provides a controlled stimulus for examining the downstream effects of GnRH receptor activation on cellular signaling networks and gene regulation. Researchers use it to induce or suppress specific gene expression patterns in pituitary or gonadal cell models, facilitating the identification of regulatory elements and transcriptional responses associated with reproductive hormone signaling. Such studies contribute to a broader understanding of how peptide hormones orchestrate complex physiological functions at the molecular level.

Long-term Storage Conditions
Soluble in DMSO, not in water
InChI
InChI=1S/C66H83N17O13.C2H4O2.H2O/c1-36(2)25-48(58(89)76-47(13-7-23-71-66(68)69)65(96)83-24-8-14-54(83)64(95)73-33-55(67)86)77-60(91)50(28-38-15-18-39-9-3-4-10-40(39)26-38)78-59(90)49(27-37-16-19-43(85)20-17-37)79-63(94)53(34-84)82-61(92)51(29-41-31-72-45-12-6-5-11-44(41)45)80-62(93)52(30-42-32-70-35-74-42)81-57(88)46-21-22-56(87)75-46;1-2(3)4;/h3-6,9-12,15-20,26,31-32,35-36,46-54,72,84-85H,7-8,13-14,21-25,27-30,33-34H2,1-2H3,(H2,67,86)(H,70,74)(H,73,95)(H,75,87)(H,76,89)(H,77,91)(H,78,90)(H,79,94)(H,80,93)(H,81,88)(H,82,92)(H4,68,69,71);1H3,(H,3,4);1H2/t46-,47-,48-,49-,50+,51-,52-,53-,54-;;/m0../s1
InChI Key
FSBTYDWUUWLHBD-UDXTWCDOSA-N
Canonical SMILES
CC(C)CC(C(=O)NC(CCCN=C(N)N)C(=O)N1CCCC1C(=O)NCC(=O)N)NC(=O)C(CC2=CC3=CC=CC=C3C=C2)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(CO)NC(=O)C(CC5=CNC6=CC=CC=C65)NC(=O)C(CC7=CN=CN7)NC(=O)C8CCC(=O)N8.CC(=O)O.O
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)[C@@H](CC2=CC3=CC=CC=C3C=C2)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC5=CNC6=CC=CC=C65)NC(=O)[C@H](CC7=CN=CN7)NC(=O)[C@@H]8CCC(=O)N8.CC(=O)O.O

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