Lecirelin

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.[1][2][3][4] It is a GnRH analogue and a synthetic peptide, specifically a nonapeptide.[1][2][3] The drug was introduced for veterinary use by 2000.[5] It is used in form of the acetate salt.[6]

Lecirelin
Clinical data
Trade namesDalmarelin, Ovucron, Reproreline
Other namesH-Pyr-His-Trp-Ser-Tyr-D-Gly(tBu)-Leu-Arg-Pro-NHEt; XHWSYXLRP
Routes of
administration		Injection
Drug classGnRH agonist
Identifiers
IUPAC 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
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.224.787
Chemical and physical data
FormulaC59H84N16O12
Molar mass1209.421 g·mol−1
3D model (JSmol)
SMILES
  • CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@H](NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1cnc[nH]1)NC(=O)[C@@H]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

See also
  • Gonadotropin-releasing hormone receptor § Agonists

References
  2. 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.
  3. 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.
  4. 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.
  5. Ahmad, G. (2000). Use of GNRH to improve the conception rate of Nili-Ravi buffaloes during low breeding season (Report).
  6. Haberfeld H, ed. (2020). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Dalmarelin 25 Mikrogramm/ml Injektionslösung für Rinder und Kaninchen.


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