Azagly-nafarelin

Last updated
Azagly-nafarelin
Azagly-nafarelin.svg
Clinical data
Trade names Gonazon
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 class GnRH 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
UNII
CompTox Dashboard (EPA)
Chemical and physical data
Formula C65H82N18O13
Molar mass 1323.484 g·mol−1
3D model (JSmol)
  • 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=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

Related Research Articles

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<span class="mw-page-title-main">Gonadotropin-releasing hormone</span> Mammalian protein found in Homo sapiens

Gonadotropin-releasing hormone (GnRH) is a releasing hormone responsible for the release of follicle-stimulating hormone (FSH) and luteinizing hormone (LH) from the anterior pituitary. GnRH is a tropic peptide hormone synthesized and released from GnRH neurons within the hypothalamus. The peptide belongs to gonadotropin-releasing hormone family. It constitutes the initial step in the hypothalamic–pituitary–gonadal axis.

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<span class="mw-page-title-main">Gonadorelin</span> Chemical compound

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<span class="mw-page-title-main">Induced ovulation (animals)</span>

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<span class="mw-page-title-main">Lecirelin</span> Chemical compound

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<span class="mw-page-title-main">Peforelin</span> Chemical compound

Peforelin, or peforelin acetate, sold under the brand name Maprelin, is a gonadotropin-releasing hormone agonist medication which is used in veterinary medicine in Europe and Canada. It is a GnRH analogue and a synthetic peptide, specifically a decapeptide. The drug was introduced for veterinary use by 2001.

Non-surgical fertility control is the prevention of reproduction without the use of surgery. The most common form of sterilization in dogs and cats is surgical, spaying in females and castration in males. Non-surgical fertility control can either result in sterilization or temporary contraception and could offer a cheaper way to keep wild dog and cat populations under control. As of 2019, only contraceptives are commercially available. Research is ongoing into methods that could result in permanent suppression of fertility.

References

  1. 1 2 3 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. 1 2 3 4 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. Elsevier Health Sciences. 48 (4): 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.
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