Ganirelix

Ganirelix
Clinical data
Trade namesOrgalutran, Antagon, others
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: D
Routes of
administration		Subcutaneous injection
Drug classGnRH analogue; GnRH antagonist; Antigonadotropin
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability91.1%
Protein binding81.9%
Elimination half-life16.2 hours
ExcretionFeces: 75%
Urine: 22%
Identifiers
  • (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-2-ylpropanoyl]amino]-3-(4-chlorophenyl)propanoyl]amino]-3-pyridin-3-ylpropanoyl]amino]-3-hydroxypropanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]amino]-4-methylpentanoyl]amino]-6-[bis(ethylamino)methylideneamino]hexanoyl]-N-[(2R)-1-amino-1-oxopropan-2-yl]pyrrolidine-2-carboxamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.216.077 Edit this at Wikidata
Chemical and physical data
FormulaC80H113ClN18O13
Molar mass1570.35 g·mol−1
3D model (JSmol)
  • CCNC(=NCCCC[C@H](NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CCCCN=C(NCC)NCC)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(Cl)cc1)NC(=O)[C@@H](Cc1ccc2ccccc2c1)NC(C)=O)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O)NCC
  • InChI=1S/C80H113ClN18O13/c1-9-84-79(85-10-2)88-38-17-15-24-60(70(104)94-62(41-49(5)6)71(105)93-61(25-16-18-39-89-80(86-11-3)87-12-4)78(112)99-40-20-26-68(99)77(111)90-50(7)69(82)103)92-73(107)64(44-53-30-35-59(102)36-31-53)97-76(110)67(48-100)98-75(109)66(46-55-21-19-37-83-47-55)96-74(108)65(43-52-28-33-58(81)34-29-52)95-72(106)63(91-51(8)101)45-54-27-32-56-22-13-14-23-57(56)42-54/h13-14,19,21-23,27-37,42,47,49-50,60-68,100,102H,9-12,15-18,20,24-26,38-41,43-46,48H2,1-8H3,(H2,82,103)(H,90,111)(H,91,101)(H,92,107)(H,93,105)(H,94,104)(H,95,106)(H,96,108)(H,97,110)(H,98,109)(H2,84,85,88)(H2,86,87,89)/t50-,60-,61+,62+,63-,64+,65-,66-,67+,68+/m1/s1 checkY
  • Key:GJNXBNATEDXMAK-PFLSVRRQSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Ganirelix acetate (or diacetate), sold under the brand names Orgalutran and Antagon among others, is an injectable competitive gonadotropin-releasing hormone antagonist (GnRH antagonist). It is primarily used in assisted reproduction to control ovulation. The drug works by blocking the action of gonadotropin-releasing hormone (GnRH) upon the pituitary, thus rapidly suppressing the production and action of LH and FSH. Ganirelix is used in fertility treatment to prevent premature ovulation that could result in the harvesting of eggs that are too immature to be used in procedures such as in vitro fertilization.[4]

GnRH agonists are also sometimes used in reproductive therapy, as well as to treat disorders involving sex-steroid hormones, such as endometriosis.[5] One advantage of using GnRH antagonists is that repeated administration of GnRH agonists results in decreased levels of gonadotropins and sex steroids due to desensitization of the pituitary. This is avoided when using GnRH antagonists such as ganirelix.[5] The success of ganirelix in reproductive therapy has been shown to be comparable to that when using GnRH agonists.[4]

  1. ^ "Ganirelix Theramex (Theramex Australia Pty Ltd)". Therapeutic Goods Administration (TGA). 13 January 2023. Retrieved 9 April 2023.
  2. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  3. ^ "Orgalutran EPAR". European Medicines Agency (EMA). 17 May 2000. Retrieved 1 June 2024.
  4. ^ a b Cite error: The named reference ema was invoked but never defined (see the help page).
  5. ^ a b Oberyé J, Mannaerts B, Huisman J, Timmer C (February 2000). "Local tolerance, pharmacokinetics, and dynamics of ganirelix (Orgalutran) administration by Medi-Jector compared to conventional needle injections". Human Reproduction. 15 (2): 245–9. doi:10.1093/humrep/15.2.245. PMID 10655292.