Ganirelix

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

Chemical data

Formula: C80H113ClN18O13
Molecular weight: 1570.3 g/mol
IUPAC name: (2S)-1-[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2S)-2-[[(2S)-2-[[(2R)-2-[[(2R)-2-[[(2R)-2-acetamido-3-naphthalen-1-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
SMILES: CCNC(=NCCCC[C@H](C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(=O)N)NC(=O)[C@H](CC2=CC=C(C=C2)O)NC(=O)[C@H](CO)NC(=O)[C@@H](CC3=CN=CC=C3)NC(=O)[C@@H](CC4=CC=C(C=C4)Cl)NC(=O)[C@@H](CC5=CC=CC6=CC=CC=C65)NC(=O)C)NCC
InChIKey: BJQRBVMMHKUPPY-YYXZGPOZSA-N
XLogP: 5.4
Polar surface area: 451 Å²
H-bond donors: 16
H-bond acceptors: 16
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Protein
First approval: 1999
Admin. routes: parenteral
Indications: infertility, polycystic ovary syndrome, female infertility, Reproductive Techniques, Assisted

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Research

305 papers

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 1568.8423033559993
Has use: medication

Show 6 more facts

chemical formula: C₈₀H₁₁₃ClN₁₈O₁₃
medical condition treated: ovarian hyperstimulation syndrome
defined daily dose: 0.25
isomeric SMILES: CCNC(NCC)=NCCCC[C@@H](NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC1=CC=CN=C1)NC(=O)[C@@H](CC1=CC=C(Cl)C=C1)NC(=O)[C@@H](CC1=CC2=CC=CC=C2C=C1)NC(C)=O)C(=O)N[C@@H](CC(C)C)C(=O)N[C@@H](CCCCN=C(NCC)NCC)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O
NCI Thesaurus ID: C77423
canonical SMILES: CCNC(=NCCCCC(NC(=O)C(Cc1ccc(O)cc1)NC(=O)C(CO)NC(=O)C(Cc1cccnc1)NC(=O)C(Cc1ccc(Cl)cc1)NC(=O)C(Cc1ccc2ccccc2c1)NC(C)=O)C(=O)NC(CC(C)C)C(=O)NC(CCCCN=C(NCC)NCC)C(=O)N1CCCC1C(=O)NC(C)C(N)=O)NCC

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Encyclopedic overview

10 sections

Contents

Medical uses
Contraindications
Side effects
Birth defects
Pharmacology
Pharmacodynamics
Pharmacokinetics
Chemistry
History
References

GnRH agonists are also sometimes used in reproductive therapy, as well as to treat disorders involving sex-steroid hormones, such as endometriosis. 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. The success of ganirelix in reproductive therapy has been shown to be comparable to that when using GnRH agonists.

Excerpted from Wikipedia’s “Ganirelix” article, available under the CC BY-SA 4.0 licence.

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