Nafarelin

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.

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

CAT No: 10-101-211

CAS No:76932-56-4, 76932-60-0, 86220-42-0

Synonyms/Alias:NAFARELIN;76932-56-4;Nafareline;NAFARELIN ACETATE;Nafarelina;Nafarelinum;Nafarelinum [Latin];UNII-1X0094V6JV;LHRH, Ala(2-naphthyl)(6)-;1X0094V6JV;Nafarelinum (Latin);Nafareline [French];Nafarelina [Spanish];Nafarelin [INN:BAN];(S)-1-(((R)-2-((S)-2-((S)-2-((S)-2-((S)-3-(1H-imidazol-4-yl)-2-((S)-5-oxopyrrolidine-2-carboxamido)propanamido)-3-(1H-indol-3-yl)propanamido)-3-hydroxypropanamido)-3-(4-hydroxyphenyl)propanamido)-3-(naphthalen-2-yl)propanoyl)-L-leucyl-L-arginyl)-N-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide;NAFARELIN [INN];CHEBI:7445;Nafarelin?;HS-2018;NAFARELIN [MI];NAFARELIN [VANDF];NAFARELIN [WHO-DD];SCHEMBL22518;BIDD:GT0760;GTPL3902;6-D-(2-naphthyl)alanyl-GnRH;BDBM84707;H01CA02;DTXSID001031284;(6-D-(2-naphthyl)alanine)-GnRH;AKOS015895038;CCG-270673;DB00666;FN65097;NS00078790;C76463;EN300-7480908;Q3869873;5-OXOPRO-HIS-TRP-SER-TYR-D-NAL(2)-LEU-ARG-PRO-GLY-NH2;(2S)-N-(2-amino-2-oxoethyl)-1-((2S,5S,8R,11S,14S,17S,20S)-2-(3-carbamimidamidopropyl)-11-(4-hydroxybenzyl)-14-(hydroxymethyl)-20-(1H-imidazol-4-ylmethyl)-17-(1H-indol-3-ylmethyl)-5-(2-methylpropyl)-8-(naphthalen-2-ylmethyl)-4,7,10,13,16,19,22-heptaoxo-22-((2S)-5-oxopyrrolidin-2-yl)-3,6,9,12,15,18,21-heptaazadocosan-1-oyl)pyrrolidine-2-carboxamide;(S)-1-((3S,6S,9S,12S,15R,18S,21S)-3-((1H-imidazol-5-yl)methyl)-6-((1H-indol-3-yl)methyl)-21-(3-guanidinopropyl)-12-(4-hydroxybenzyl)-9-(hydroxymethyl)-18-isobutyl-15-(naphthalen-2-ylmethyl)-1,4,7,10,13,16,19-heptaoxo-1-((S)-5-oxopyrrolidin-2-yl)-2,5,8,11,14,17,20-heptaazadocosan-22-oyl)-N-(2-amino-2-oxoethyl)pyrrolidine-2-carboxamide;5-oxo-L-prolyl L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolylglycinamide;L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-3-(2-naphthyl)-D-alanyl-L-leucyl-L-arginyl-L-prolyl-glycinamide;

Custom Peptide Synthesis
cGMP Peptide
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M.F/Formula
C66H83N17O13
M.W/Mr.
1322.5
Sequence
One Letter Code:XHWSYXLRPG
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-2Nal-Leu-Arg-Pro-Gly-NH2
Application
Three Letter Code: Pyr-His-Trp-Ser-Tyr-D-2-Nal-Leu-Arg-Pro-Gly-NH2
Activity
Agonist
Biological Activity
Synthetic gonadotropin-releasing hormone (GnRH) agonist that stimulates secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH). Repeated administration causes desensitization of pituitary GnRH receptors resulting in inhibition of gonadotropin release and decreased steroid hormone synthesis. Induces atrophy and regression of experimentally induced endometriosis in rat and shrinks hypertrophic tissue in benign prostatic hyperplasia.
Target
Gonadotropin-releasing hormone (GnRH)

Nafarelin, also known as a potent gonadotropin-releasing hormone (GnRH) agonist, is a synthetic decapeptide widely recognized for its role in modulating hormonal pathways. Characterized by its high receptor affinity and ability to regulate the secretion of key pituitary hormones, Nafarelin has become an invaluable tool in both basic and applied research settings. With its robust stability and predictable pharmacological profile, this peptide is favored for studies that require precise control over the hypothalamic-pituitary-gonadal axis. Researchers appreciate its capacity to induce reversible suppression of gonadotropin secretion, making it an essential reagent for exploring endocrine system dynamics and reproductive biology.

Endocrine Research: Nafarelin is extensively utilized in endocrine research to investigate the mechanisms underlying hormone regulation and feedback loops within the hypothalamic-pituitary axis. By serving as a GnRH analog, it enables scientists to modulate the release of luteinizing hormone (LH) and follicle-stimulating hormone (FSH), thus allowing for the detailed study of downstream effects on gonadal steroidogenesis. The use of this peptide facilitates the examination of hormonal rhythms, receptor desensitization, and the physiological consequences of altered gonadotropin levels in various experimental models.

Reproductive Biology Studies: In reproductive biology, Nafarelin provides a controlled means to manipulate reproductive hormone levels, offering insight into the timing and regulation of ovulation, spermatogenesis, and sexual maturation. Researchers employ it to create models of hypo- or hypergonadotropic states, which are crucial for understanding fertility, puberty onset, and the interplay between external stimuli and reproductive function. Its reversible action is particularly valuable for studies requiring the restoration of normal hormonal cycles following experimental intervention.

Animal Model Development: Nafarelin is instrumental in the development of animal models that mimic human endocrine disorders. By administering this peptide to laboratory animals, scientists can induce conditions such as hypogonadism or delayed puberty, thereby creating reliable platforms for investigating disease mechanisms, genetic influences, and the impact of environmental factors on reproductive health. These models are essential for the preclinical evaluation of new therapeutic strategies targeting hormonal pathways.

Cell Signaling Investigations: The peptide's ability to selectively activate GnRH receptors makes it an important tool for dissecting cell signaling pathways in pituitary and gonadal tissues. Researchers utilize Nafarelin to map intracellular cascades triggered by GnRH receptor engagement, including the activation of second messengers, kinases, and transcription factors. Such studies contribute to a deeper understanding of how hormonal signals are transduced at the molecular level and how dysregulation may lead to pathological conditions.

Peptide Therapeutics Research: Nafarelin's structural and functional properties serve as a model for the design and optimization of new peptide-based therapeutics. By analyzing its receptor binding characteristics, metabolic stability, and biological effects, pharmaceutical scientists can develop next-generation GnRH analogs with improved efficacy, selectivity, and duration of action. Investigations into its structure-activity relationships inform the rational design of peptides targeting other hormone receptors, broadening the scope of drug discovery in the peptide therapeutics field.

Comparative Endocrinology: Comparative studies employing Nafarelin across different species provide valuable information on the evolutionary conservation and divergence of GnRH signaling mechanisms. By observing species-specific responses to the peptide, researchers gain insight into the adaptive significance of reproductive strategies and hormonal control systems. These findings have implications for both basic science and the management of breeding programs in wildlife and agriculture, highlighting the versatile utility of Nafarelin in advancing the field of comparative endocrinology.

Shipping Condition
Room temperature in continental US; may vary elsewhere.
InChI
InChI=1S/C66H83N17O13/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/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)/t46-,47-,48-,49-,50+,51-,52-,53-,54-/m0/s1
InChI Key
RWHUEXWOYVBUCI-ITQXDASVSA-N

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