Azagly-nafarelin

Chemical compound
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
  • (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 checkY
    113962-45-1 (acetate)
UNII
  • 2N7D33X56N
CompTox Dashboard (EPA)
  • DTXSID30873507 Edit this at Wikidata
Chemical and physical data
FormulaC65H82N18O13
Molar mass1323.484 g·mol−1
3D model (JSmol)
  • Interactive image
  • 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

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]

See also

References

  1. ^ a b c Driancourt MA, Rodes L (29 June 2018). "Male Contraception in Animal Species". In Skinner MK (ed.). Encyclopedia of Reproduction. Elsevier Science. pp. 554–556. ISBN 978-0-12-815145-7.
  2. ^ a b c d 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.
  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". Molecular Reproduction and Development. 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". Reproduction in Domestic Animals = Zuchthygiene. 52 (Suppl 2): 327–331. doi:10.1111/rda.12862. PMID 27892642.
  5. ^ 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.
  6. ^ 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.
  7. ^ 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.
  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.
  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.
  • v
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GnRHTooltip Gonadotropin-releasing hormone and gonadotropins
GnRH modulators
(incl. analogues)
Agonists
Antagonists
Gonadotropins
Preparations
Others
(indirect)
Progonadotropins
Antigonadotropins
See also
GnRH and gonadotropin receptor modulators
Androgens and antiandrogens
Estrogens and antiestrogens
Progestogens and antiprogestogens
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  • e
GnRHTooltip Gonadotropin-releasing hormone receptor and gonadotropin receptor modulators
GnRHTooltip Gonadotropin-releasing hormone receptor
Gonadotropin
LH/hCGTooltip Luteinizing hormone/choriogonadotropin receptor
FSHTooltip Follicle-stimulating hormone receptor
  • NAMs: Non-peptides: ADX-61623


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