Fertirelin

Fertirelin is a GnRH and LH-RH analogue; it also becomes the treatment choice for reversing cow follicular cysts.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Fertirelin(CAS 38234-21-8)

CAT No: R1348

CAS No:38234-21-8

Synonyms/Alias:Fertirelin;38234-21-8;Fertirelina;Fertireline;Fertirelinum;Fertireline [INN-French];Fertirelin [INN:BAN];Fertirelinum [INN-Latin];Fertirelina [INN-Spanish];Fertirelin (INN);UNII-Q041AO6T91;DTXSID8057728;9-(N-Ethyl-L-prolinamide)-10-deglycinamide;DTXCID9031517;TAP 031;TAP-031;Q041AO6T91;1-9-Luteinizing hormone-releasing factor (swine),9-(N-ethyl-L-prolinamide)-;fertilerine acetate;FERTIRELIN [INN];Fertireline (INN-French);Fertirelinum (INN-Latin);Fertirelina (INN-Spanish);fertilerine;fertirelin acetat;DGNH-LHRH;FERTIRELIN [MI];FERTIRELIN [JAN];5-oxo-l-prolyl-l-histidyl-l-tryptophyl-l-seryl-l-tyrosylglycyl-l-leucyl-l-arginyl-n-ethyl-l-prolinamide;GTPL9341;CHEMBL3272563;CHEBI:177856;GnRH, (N)-Et-ProNH2(9)-;LHRH, (N)-Et-ProNH2(9)-;Tox21_113925;AKOS015896030;desGly(10)-Pro(9)-LHRH ethylamide;AC-8920;NCGC00262930-01;FD109163;MS-32015;9-(N)-Et-ProNH2-10-des-GlyNH2-LHRH;CAS-38234-21-8;NS00120978;D07957;F85427;LHRH, (N)-ethylprolinamide(9)-des-glycinamide(10)-;Q27286835;(2S)-1-[(2S)-5-CARBAMIMIDAMIDO-2-[(2S)-2-{2-[(2S)-2-[(2S)-3-HYDROXY-2-[(2S)-2-[(2S)-3-(1H-IMIDAZOL-4-YL)-2-{[(2S)-5-OXOPYRROLIDIN-2-YL]FORMAMIDO}PROPANAMIDO]-3-(1H-INDOL-3-YL)PROPANAMIDO]PROPANAMIDO]-3-(4-HYDROXYPHENYL)PROPANAMIDO]ACETAMIDO}-4-METHYLPENTANAMIDO]PENTANOYL]-N-ETHYLPYRROLIDINE-2-CARBOXAMIDE;LUTEINIZING HORMONE-RELEASING FACTOR (PIG), 9-(N-ETHYL-L-PROLINAMIDE)-10-DEGLYCINAMIDE-;

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M.F/Formula
C55H76N16O12
M.W/Mr.
1153.3
Sequence
One Letter Code:XHWSYGLRP
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-Gly-Leu-Arg-Pro-NHEt
Activity
Antagonist
Target
Gonadotropin-releasing hormone (GnRH)

Fertirelin is a synthetic decapeptide analog of gonadotropin-releasing hormone (GnRH), closely related to the endogenous peptide responsible for regulating the release of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) from the anterior pituitary. As a potent GnRH agonist, Fertirelin exhibits enhanced receptor binding affinity and increased resistance to enzymatic degradation compared to the native hormone, making it a valuable tool in the study of reproductive endocrinology and peptide-receptor interactions. Its well-characterized structure and bioactivity profile have established it as a fundamental research reagent for probing hypothalamic-pituitary-gonadal axis mechanisms and for developing novel peptide-based technologies.

Endocrine signaling research: In basic and applied studies of reproductive biology, Fertirelin serves as a model GnRH agonist for dissecting the molecular and cellular pathways involved in gonadotropin release. By stimulating GnRH receptors on pituitary gonadotrophs, it enables precise control over LH and FSH secretion in vitro and in vivo experimental systems. This capability is essential for elucidating feedback mechanisms, signal transduction pathways, and hormonal regulation within the hypothalamic-pituitary-gonadal axis.

Peptide-receptor interaction studies: As a synthetic analog with well-defined modifications, Fertirelin is widely utilized to investigate peptide-receptor binding dynamics. Its structural stability and high receptor affinity facilitate detailed mapping of ligand-receptor interactions, receptor activation kinetics, and downstream signaling events. Such studies support the rational design of next-generation GnRH analogs and inform broader research into peptide hormone pharmacology.

Assay development and validation: The consistent biological activity and robust receptor engagement of Fertirelin make it a preferred standard in the development and validation of bioassays for GnRH receptor function. Researchers employ it to calibrate assay sensitivity, assess the potency of test compounds, and benchmark the performance of new analytical platforms. Its use in reference protocols enhances reproducibility and comparability across laboratories engaged in neuroendocrine research.

Peptide synthesis and analytical controls: Owing to its defined sequence and functional relevance, Fertirelin is frequently used as a reference compound in solid-phase peptide synthesis and peptide purification workflows. It provides a benchmark for method optimization, process validation, and quality control in the production of GnRH analogs and related peptides. Analytical laboratories also utilize it as a control standard in chromatographic and mass spectrometric assays, ensuring accuracy in peptide identification and quantification.

Structure-activity relationship (SAR) investigations: The availability of Fertirelin as a research-grade peptide enables systematic exploration of structure-activity relationships within the GnRH family. By comparing its bioactivity and receptor interactions to those of other analogs and native GnRH, scientists can delineate the impact of specific amino acid substitutions on potency, stability, and receptor selectivity. These insights drive the development of improved peptide therapeutics and advance the understanding of peptide hormone function at the molecular level.

InChI
InChI=1S/C55H76N16O12/c1-4-59-53(82)44-12-8-20-71(44)54(83)38(11-7-19-60-55(56)57)66-49(78)39(21-30(2)3)65-46(75)27-62-47(76)40(22-31-13-15-34(73)16-14-31)67-52(81)43(28-72)70-50(79)41(23-32-25-61-36-10-6-5-9-35(32)36)68-51(80)42(24-33-26-58-29-63-33)69-48(77)37-17-18-45(74)64-37/h5-6,9-10,13-16,25-26,29-30,37-44,61,72-73H,4,7-8,11-12,17-24,27-28H2,1-3H3,(H,58,63)(H,59,82)(H,62,76)(H,64,74)(H,65,75)(H,66,78)(H,67,81)(H,68,80)(H,69,77)(H,70,79)(H4,56,57,60)/t37-,38-,39-,40-,41-,42-,43-,44-/m0/s1
InChI Key
DGCPIBPDYFLAAX-YTAGXALCSA-N

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