Lecirelin

Lecirelin (6-(3-methyl-d-valine)-9-(N-ethyl-L-prolynamide)-10-deglycinamide) luteinizing hormone releasing factor, is a synthetic hypothalamic gonadotropin releasing hormone (GnRH) analogue. Lecirelin is a nonapeptide, while the natural compound is a decapeptide. Moreover, the glycine aminoacid in the 6th position has been substituted by leucine.

Designed for biological research and industrial applications, not intended for individual clinical or medical purposes.
Lecirelin(CAS 61012-19-9)

CAT No: 10-101-89

CAS No:61012-19-9

Synonyms/Alias:LECIRELIN;61012-19-9;Dalmarelin;Gestran;ZD8NZ8J5LN;Lecrelin;UNII-ZD8NZ8J5LN;DTXSID00735365;GLXC-25476;DA-69143;MS-32049;F85421;(Des-Gly10,tBu-D-Gly6,Pro-NHEt9)-LHRH trifluoroacetate salt;

Chemical Name:(2S)-N-[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2R)-1-[[(2S)-1-[[(2S)-5-(diaminomethylideneamino)-1-[(2S)-2-(ethylcarbamoyl)pyrrolidin-1-yl]-1-oxopentan-2-yl]amino]-4-methyl-1-oxopentan-2-yl]amino]-3,3-dimethyl-1-oxobutan-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

Custom Peptide Synthesis
cGMP Peptide
  • Registration of APIs
  • CMC information required for an IND
  • IND and NDA support
  • Drug master files (DMF) filing
M.F/Formula
C59H84N16O12
M.W/Mr.
1209.4
Sequence
One Letter Code:XHWSYXLRP
Three Letter Code:H-Pyr-His-Trp-Ser-Tyr-D-Gly(tBu)-Leu-Arg-Pro-NHEt
Activity
Agonist
Biological Activity
Lecirelin, a synthetic gonadotropin-releasing hormone (GnRH) analogue, acts as a GnRH agonist. Lecirelin is widely used for the research of bovine ovarian follicular cysts.
Target
GnRH Receptor

Lecirelin is a synthetic peptide analog of gonadotropin-releasing hormone (GnRH), designed to mimic the activity of endogenous GnRH in the regulation of reproductive hormone secretion. As a decapeptide, Lecirelin exhibits high affinity for GnRH receptors, making it a valuable tool for probing the hypothalamic-pituitary-gonadal axis in various animal models. Its robust biological activity and well-characterized mechanism of action have established Lecirelin as a standard reagent in reproductive endocrinology research, facilitating the investigation of hormonal regulation, signal transduction, and peptide-receptor interactions. The compound's stability and specificity offer distinct advantages for controlled experimental manipulation of gonadotropin release in both in vitro and in vivo systems.

Reproductive endocrinology research: Lecirelin is extensively utilized to study the physiological and molecular mechanisms underlying the regulation of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) secretion from the anterior pituitary. By serving as a potent GnRH receptor agonist, it enables researchers to induce synchronized gonadotropin release, thereby facilitating investigations into the feedback regulation of reproductive hormones, pituitary cell signaling pathways, and the dynamics of hormone synthesis and secretion. Such studies are crucial for elucidating the neuroendocrine control of fertility and reproductive cycles in a range of vertebrate species.

Peptide-receptor interaction studies: The compound's structural similarity to native GnRH, combined with its enhanced receptor affinity and metabolic stability, makes it an ideal probe for dissecting the molecular determinants of ligand-receptor binding. Lecirelin is frequently employed in binding assays, receptor activation studies, and structure-activity relationship (SAR) analyses to characterize the specificity and signaling efficacy of GnRH receptor subtypes. These applications contribute to a deeper understanding of peptide hormone action and receptor pharmacology, supporting the development of novel analogs and molecular tools.

Signal transduction pathway analysis: By selectively activating GnRH receptors, Lecirelin enables precise modulation of downstream signaling cascades, including the activation of phospholipase C, inositol phosphate turnover, and intracellular calcium mobilization. Researchers leverage its predictable activity to map the intracellular events that follow GnRH receptor engagement, assess second messenger dynamics, and explore cross-talk with other hormonal pathways. Such mechanistic insights are essential for unraveling the complexities of endocrine signaling networks and their physiological outcomes.

Animal model development: In experimental animal studies, Lecirelin is applied to induce controlled ovulation, synchronize estrous cycles, or modulate reproductive parameters, thereby providing a standardized means of manipulating reproductive physiology. Its use supports the creation of reproducible animal models for investigating fertility regulation, ovarian function, and reproductive toxicology. The compound's reliability and well-defined pharmacodynamics make it a preferred choice for generating consistent experimental conditions in reproductive biology research.

Peptide synthesis and analytical validation: Lecirelin also serves as a reference standard and quality control reagent in peptide synthesis workflows. Its defined sequence and bioactivity allow for the calibration of analytical assays, validation of chromatographic methods, and benchmarking of synthetic peptide quality. By ensuring the accuracy and reproducibility of peptide-based experimental systems, Lecirelin supports advancements in peptide chemistry, analytical biochemistry, and the development of new GnRH analogs for research use.

Shipping Condition
Room temperature in continental US; may vary elsewhere.
InChI
InChI=1S/C59H84N16O12/c1-7-63-55(85)46-15-11-23-75(46)57(87)40(14-10-22-64-58(60)61)68-50(80)41(24-32(2)3)72-56(86)48(59(4,5)6)74-53(83)42(25-33-16-18-36(77)19-17-33)69-54(84)45(30-76)73-51(81)43(26-34-28-65-38-13-9-8-12-37(34)38)70-52(82)44(27-35-29-62-31-66-35)71-49(79)39-20-21-47(78)67-39/h8-9,12-13,16-19,28-29,31-32,39-46,48,65,76-77H,7,10-11,14-15,20-27,30H2,1-6H3,(H,62,66)(H,63,85)(H,67,78)(H,68,80)(H,69,84)(H,70,82)(H,71,79)(H,72,86)(H,73,81)(H,74,83)(H4,60,61,64)/t39-,40-,41-,42-,43-,44-,45-,46-,48-/m0/s1
InChI Key
XJWIEWPGHRSZJM-MGZASHDBSA-N
Canonical SMILES
CCNC(=O)C1CCCN1C(=O)C(CCCN=C(N)N)NC(=O)C(CC(C)C)NC(=O)C(C(C)(C)C)NC(=O)C(CC2=CC=C(C=C2)O)NC(=O)C(CO)NC(=O)C(CC3=CNC4=CC=CC=C43)NC(=O)C(CC5=CN=CN5)NC(=O)C6CCC(=O)N6
Isomeric SMILES
CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](C(C)(C)C)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@H](CC3=CNC4=CC=CC=C43)NC(=O)[C@H](CC5=CN=CN5)NC(=O)[C@@H]6CCC(=O)N6

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