Lecirelin - Misplaced Pages

Chemical compound Pharmaceutical compound

Lecirelin
Clinical data

Trade names	Dalmarelin, Ovucron, Reproreline
Other names	H-Pyr-His-Trp-Ser-Tyr-D-Gly(tBu)-Leu-Arg-Pro-NHEt; XHWSYXLRP
Routes of administration	Injection
Drug class	GnRH agonist
Identifiers
IUPAC name (2S)-N--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
CAS Number	61012-19-9
PubChem CID	66577115
ChemSpider	25027162
UNII	ZD8NZ8J5LN
CompTox Dashboard (EPA)	DTXSID00735365
ECHA InfoCard	100.224.787
Chemical and physical data
Formula	C₅₉H₈₄N₁₆O₁₂
Molar mass	1209.421 g·mol
3D model (JSmol)	Interactive image
SMILES CCNC(=O)1CCCN1C(=O)(CCCN=C(N)N)NC(=O)(CC(C)C)NC(=O)(NC(=O)(Cc1ccc(O)cc1)NC(=O)(CO)NC(=O)(Cc1cc2ccccc12)NC(=O)(Cc1cnc1)NC(=O)1CCC(=O)N1)C(C)(C)C
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 Key:XJWIEWPGHRSZJM-MGZASHDBSA-N

Lecirelin, sold under the brand names Dalmarelin, Ovucron, and Reproreline, is a short-acting gonadotropin-releasing hormone agonist (GnRH agonist) medication which is used in veterinary medicine in Europe and Israel. It is a GnRH analogue and a synthetic peptide, specifically a nonapeptide. The drug was introduced for veterinary use by 2000. It is used in form of the acetate salt.

References

^
^ Farkas E, Ryadnov M (31 August 2013). Amino Acids, Peptide and Proteins. Royal Society of Chemistry. pp. 226–227. ISBN 978-1-84973-585-8.
^ Löscher W, Richter A, Potschka H (3 September 2014). Pharmakotherapie bei Haus- und Nutztieren: Begründet von W. Löscher, F.R. Ungemach und R. Kroker. Enke. pp. 435–. ISBN 978-3-8304-1251-9.
Speer B (21 December 2015). Current Therapy in Avian Medicine and Surgery - E-Book. Elsevier Health Sciences. pp. 448–. ISBN 978-0-323-24367-4.
Ahmad, G. (2000). Use of GNRH to improve the conception rate of Nili-Ravi buffaloes during low breeding season (Report).
Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Dalmarelin 25 Mikrogramm/ml Injektionslösung für Rinder und Kaninchen.

GnRHTooltip Gonadotropin-releasing hormone and gonadotropins

Preparations	Follicle-stimulating hormone Human chorionic gonadotropin Luteinizing hormone Menotropin Urofollitropin

Others
(indirect)

Sex steroid antagonists (via disinhibition of the HPG axis): Antiandrogens (e.g., flutamide, bicalutamide, enzalutamide)
Antiestrogens/SERMsTooltip Selective estrogen receptor modulators (e.g., tamoxifen, clomifene, enclomifene)
Aromatase inhibitors (e.g., anastrozole)
GnRH agonists (e.g., GnRHTooltip gonadotropin-releasing hormone)

See also: GnRH and gonadotropin receptor modulators; Androgens and antiandrogens; Estrogens and antiestrogens; Progestogens and antiprogestogens

GnRHTooltip Gonadotropin-releasing hormone receptor and gonadotropin receptor modulators

GnRHTooltip Gonadotropin-releasing hormone receptor

LH/hCGTooltip Luteinizing hormone/choriogonadotropin receptor

FSHTooltip Follicle-stimulating hormone receptor

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