Ganirelix

Ganirelix

Clinical data
Trade names	Orgalutran, Antagon, others
AHFS/Drugs.com	Monograph
License data	US DailyMed: Ganirelix
Pregnancy category	AU: D
Routes of administration	Subcutaneous injection
Drug class	GnRH analogue; GnRH antagonist; Antigonadotropin
ATC code	H01CC01 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[1] CA: ℞-only[2] US: ℞-only EU: Rx-only[3]
Pharmacokinetic data
Bioavailability	91.1%
Protein binding	81.9%
Elimination half-life	16.2 hours
Excretion	Feces: 75% Urine: 22%
Identifiers
IUPAC name (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	124904-93-4 N
PubChem CID	16186319
IUPHAR/BPS	3877
DrugBank	DB06785 N
ChemSpider	16736620 Y
UNII	IX503L9WN0
KEGG	D08010 N as salt: D04302 N
ChEMBL	ChEMBL1251 N
CompTox Dashboard (EPA)	DTXSID401027283
ECHA InfoCard	100.216.077
Chemical and physical data
Formula	C80H113ClN18O13
Molar mass	1570.35 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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 Y Key:GJNXBNATEDXMAK-PFLSVRRQSA-N Y
NY (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]