Azagly-nafarelin

Azagly-nafarelin, sold under the brand name Gonazon, is a gonadotropin-releasing hormone agonist (GnRH agonist) medication which is used in veterinary medicine in Europe.[1][2] It is a GnRH analogue and a synthetic peptide, specifically a decapeptide.[1][2][3] The medication has been approved in Europe as a solid silicone-based matrix implant for use as a contraceptive in animals such as male dogs, cats, and others, but is no longer or was never commercially available.[1][2][4][5] The medication has also been used to treat benign prostatic hyperplasia in animals.[6][7] In addition to its use in mammals, azagly-nafarelin has been approved for use in aquaculture fish, specifically to control ovulation in salmonids, and was the first GnRH agonist to be available for use in fish.[2][8] It was introduced for use by 2005.[9]

Azagly-nafarelin
Clinical data
Trade namesGonazon
Other names6-[3-(2-Naphthalenyl)-D-alanine]-1-9-luteinizing hormone-releasing factor (swine) 2-(aminocarbonyl)hydrazide; 6-[3-(2-Naphthalenyl)-D-alanine]-10-deglycinamide-luteinizing hormone-releasing factor (pig) 2-(aminocarbonyl)hydrazide
Routes of
administration		Implant; Injection
Drug classGnRH agonist
Identifiers
IUPAC name
  • (S)-N-((6S,9S,12R,15S,18S,21S,24S)-21-((1H-indol-3-yl)methyl)-1,1-diamino-6-((S)-2-(2-carbamoylhydrazine-1-carbonyl)pyrrolidine-1-carbonyl)-15-(4-hydroxybenzyl)-18-(hydroxymethyl)-25-(1H-imidazol-5-yl)-9-isobutyl-12-(naphthalen-2-ylmethyl)-8,11,14,17,20,23-hexaoxo-2,7,10,13,16,19,22-heptaazapentacos-1-en-24-yl)-5-oxopyrrolidine-2-carboxamide
CAS Number
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC65H82N18O13
Molar mass1323.484 g·mol−1
3D model (JSmol)
SMILES
  • CC(C[C@H](NC([C@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H](NC([C@@H]1CCC(N1)=O)=O)CC2=CN=CN2)=O)CC3=CNC4=CC=CC=C43)=O)CO)=O)CC5=CC=C(O)C=C5)=O)CC6=CC7=CC=CC=C7C=C6)=O)C(N[C@H](C(N8CCC[C@H]8C(NNC(N)=O)=O)=O)CCC/N=C(N)\N)=O)C
InChI
  • InChI=1S/C65H82N18O13/c1-35(2)25-47(56(88)74-46(13-7-23-70-64(66)67)63(95)83-24-8-14-53(83)62(94)81-82-65(68)96)75-58(90)49(28-37-15-18-38-9-3-4-10-39(38)26-37)76-57(89)48(27-36-16-19-42(85)20-17-36)77-61(93)52(33-84)80-59(91)50(29-40-31-71-44-12-6-5-11-43(40)44)78-60(92)51(30-41-32-69-34-72-41)79-55(87)45-21-22-54(86)73-45/h3-6,9-12,15-20,26,31-32,34-35,45-53,71,84-85H,7-8,13-14,21-25,27-30,33H2,1-2H3,(H,69,72)(H,73,86)(H,74,88)(H,75,90)(H,76,89)(H,77,93)(H,78,92)(H,79,87)(H,80,91)(H,81,94)(H4,66,67,70)(H3,68,82,96)/t45-,46-,47-,48-,49+,50-,51-,52-,53-/m0/s1
  • Key:FDOMSRGNWHJMGI-XRSSZCMZSA-N

See also
  • Gonadotropin-releasing hormone receptor § Agonists

References
  1. Encyclopedia of Reproduction. Elsevier Science. 29 June 2018. pp. 554–556. ISBN 978-0-12-815145-7.
  2. Wolfgang Löscher; Angelika Richter; Heidrun Potschka (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.
  3. Bulldan A, Shihan M, Goericke-Pesch S, Scheiner-Bobis G (December 2016). "Signaling events associated with gonadotropin releasing hormone-agonist-induced hormonal castration and its reversal in canines". Mol. Reprod. Dev. 83 (12): 1092–1101. doi:10.1002/mrd.22751. PMID 27764533. S2CID 29559009.
  4. Rhodes L (April 2017). "New approaches to non-surgical sterilization for dogs and cats: Opportunities and challenges". Reprod. Domest. Anim. 52 Suppl 2: 327–331. doi:10.1111/rda.12862. PMID 27892642.
  5. Peter J Chenoweth; Steven Lorton (30 April 2014). Animal Andrology: Theories and Applications. CABI. pp. 489–. ISBN 978-1-78064-316-8.
  6. Bruce W. Christensen (23 June 2018). Theriogenology, An Issue of Veterinary Clinics of North America: Small Animal Practice, E-Book. Elsevier Health Sciences. pp. 707–. ISBN 978-0-323-61085-8.
  7. Hans-Klaus Dreier (6 December 2010). Klinik der Reproduktionsmedizin des Hundes. Schlütersche Verlagsgesellschaft mbH & Company KG. pp. 286–. ISBN 978-3-8426-8038-8.
  8. Patrick J. Babin; Joan Cerdà; Esther Lubzens (20 August 2007). The Fish Oocyte: From Basic Studies to Biotechnological Applications. Springer Science & Business Media. pp. 444–. ISBN 978-1-4020-6233-9.
  9. Haffray, P.; Enright, W. J.; Driancourt, M. A.; Mikolajczyk, T.; Rault, P.; Breton, B. (2005). "Optimization of breeding of salmonids: Gonazon, the first officially approved inducer of ovulation in the EU". World Aquaculture.



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