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

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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, a synthetic analogue of gonadotropin-releasing hormone (GnRH), is widely recognized for its biochemical stability and high receptor affinity, making it a valuable tool in various research and laboratory settings. Characterized by its robust peptide structure, Lecirelin mimics the action of endogenous GnRH, enabling precise modulation of the hypothalamic-pituitary-gonadal axis in experimental models. Its enhanced resistance to enzymatic degradation and prolonged biological activity allow for sustained interaction with target receptors, which is particularly advantageous in studies requiring consistent hormonal stimulation or suppression. Researchers benefit from its well-documented pharmacological profile and predictable physiological responses, supporting a broad spectrum of investigative and analytical applications.

Reproductive Endocrinology Studies: Lecirelin serves as a critical reagent in the investigation of reproductive hormone regulation, especially in studies focused on the mechanisms controlling luteinizing hormone (LH) and follicle-stimulating hormone (FSH) secretion. By administering this GnRH analogue in vitro or in vivo, scientists can precisely stimulate pituitary cells to release gonadotropins, facilitating detailed exploration of the feedback loops and signaling pathways involved in reproductive endocrinology. Such applications are essential for understanding the hormonal dynamics that underpin fertility, ovulation, and gonadal function in various animal models.

Animal Reproductive Physiology Research: In the field of animal science, Lecirelin is extensively employed to elucidate the physiological processes governing estrus synchronization, ovulation timing, and reproductive efficiency. Its use enables researchers to induce synchronized ovulatory events or analyze the temporal patterns of hormone release, thereby advancing knowledge of reproductive cycles and breeding management. Studies utilizing this peptide often focus on optimizing reproductive protocols in livestock, enhancing the understanding of species-specific reproductive physiology, and supporting the development of innovative reproductive technologies.

Cell Signaling and Receptor Interaction Analysis: Leveraging its high receptor specificity, Lecirelin is instrumental in dissecting the intricacies of GnRH receptor-mediated signaling pathways. By applying this peptide to cultured pituitary or hypothalamic cells, investigators can monitor downstream effects, such as the activation of second messenger systems and gene transcription events. These analyses contribute to a deeper comprehension of receptor-ligand interactions, signal transduction mechanisms, and the modulation of cellular responses, which are fundamental to the broader field of neuroendocrinology and hormone action research.

Pharmacological Screening and Drug Discovery: Lecirelin is a preferred positive control in pharmacological assays designed to evaluate the efficacy and selectivity of novel GnRH analogues or antagonists. Its consistent biological activity provides a reliable benchmark for comparing the potency and duration of action of experimental compounds. This application is vital in the early stages of drug discovery, where accurate assessment of candidate molecules' interactions with the GnRH receptor informs the design and optimization of new therapeutic agents targeting reproductive disorders or hormone-dependent conditions.

Comparative Endocrinology and Evolutionary Biology: The use of Lecirelin extends to comparative studies aimed at understanding the evolution and diversity of endocrine regulation across species. By examining the responses of different animal models to this synthetic peptide, researchers can identify conserved and divergent features of GnRH signaling pathways. These investigations shed light on the adaptive significance of hormonal control mechanisms, support phylogenetic analyses, and contribute to the broader field of evolutionary biology by elucidating the molecular underpinnings of reproductive strategies in vertebrates.

Lecirelin continues to be a cornerstone reagent in the advancement of reproductive biology, endocrinology, and pharmacological research. Its versatility, stability, and predictable activity profile make it indispensable for probing hormone-driven processes, optimizing experimental protocols, and fostering innovation in the study of complex biological systems. As research in these fields evolves, the applications of this GnRH analogue are expected to expand, reinforcing its role as a fundamental tool in scientific discovery.

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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