Azagly-nafarelin - Misplaced Pages

Chemical compound Pharmaceutical compound

Azagly-nafarelin
Clinical data

Trade names	Gonazon
Other names	6--1-9-luteinizing hormone-releasing factor (swine) 2-(aminocarbonyl)hydrazide; 6--10-deglycinamide-luteinizing hormone-releasing factor (pig) 2-(aminocarbonyl)hydrazide
Routes of administration	Implant; Injection
Drug class	GnRH 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	91991-07-0 113962-45-1 (acetate)
UNII	2N7D33X56N
CompTox Dashboard (EPA)	DTXSID30873507
Chemical and physical data
Formula	C₆₅H₈₂N₁₈O₁₃
Molar mass	1323.484 g·mol
3D model (JSmol)	Interactive image
SMILES CC(C(NC((NC((NC((NC((NC((NC(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(N8CCC8C(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

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. It is a GnRH analogue and a synthetic peptide, specifically a decapeptide. 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. The medication has also been used to treat benign prostatic hyperplasia in animals. 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. It was introduced for use by 2005.

References

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Rhodes L (April 2017). "New approaches to non-surgical sterilization for dogs and cats: Opportunities and challenges". Reproduction in Domestic Animals = Zuchthygiene. 52 (Suppl 2): 327–331. doi:10.1111/rda.12862. PMID 27892642.
Norman ST, Collop TM (30 April 2014). "Male Animal Contraception". In Chenoweth PJ, Lorton S (eds.). Animal Andrology: Theories and Applications. CABI. pp. 489–. ISBN 978-1-78064-316-8.
Christensen BW (July 2018). "Canine Prostate Disease". Veterinary Clinics of North America: Small Animal Practice. 48 (4). Elsevier Health Sciences: 701–719. doi:10.1016/j.cvsm.2018.02.012. ISBN 978-0-323-61085-8. PMID 29933768. S2CID 49381344.
Dreier HK (6 December 2010). "Hormonbehandlung bei der Hüdin". Klinik der Reproduktionsmedizin des Hundes. Schlütersche Verlagsgesellschaft mbH & Company KG. pp. 286–. ISBN 978-3-8426-8038-8.
Mylonas CC, Zohar Y (20 August 2007). "Promoting oocyte maturation, ovulation, and spawning in farmed fish". In Babin PJ, Cerdà J, Lubzens E (eds.). The Fish Oocyte: From Basic Studies to Biotechnological Applications. Springer Science & Business Media. pp. 444–. ISBN 978-1-4020-6233-9.
Haffray P, Enright WJ, Driancourt MA, 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. Archived from the original on 2018-07-29. Retrieved 2018-07-29.