Ganirelix
Identification
- Summary
Ganirelix is a GnRH antagonist used in assisted reproduction in women undergoing controlled ovarian hyperstimulation to control ovulation by inhibiting the premature LH surges.
- Brand Names
- Orgalutran
- Generic Name
- Ganirelix
- DrugBank Accession Number
- DB06785
- Background
Ganirelix is an injectable competitive gonadotropin-releasing hormone antagonist (GnRH antagonist). It is utilized frequently in assisted reproduction therapy to control the occurrence of ovulation. The drug exerts its effects by inhibiting the action of GnRH in the pituitary gland, leading to fast suppression of luteinizing hormone (LH) and follicle-stimulating hormone (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. Ganirelix is marketed by Merck & Co., Inc. as Orgalutran®.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Ganirelix (DB06785)
- Weight
- Average: 1570.35
Monoisotopic: 1568.8423035 - Chemical Formula
- C80H113ClN18O13
- Synonyms
- Ganirelix
- External IDs
- Org 37462
- RS 26306
- SML0241
Pharmacology
- Indication
For the inhibition of premature LH surges in women undergoing controlled ovarian hyperstimulation.
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- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- Pharmacodynamics
Not Available
- Mechanism of action
Ganirelix acts by competitively blocking the GnRH receptors on the pituitary gonadotroph and subsequent transduction pathway. It induces a rapid, reversible suppression of gonadotropin secretion. The suppression of pituitary LH secretion by ganirelix is more pronounced than that of FSH. An initial release of endogenous gonadotropins has not been detected with ganirelix, which is consistent with an antagonist effect. Upon discontinuation of ganirelix, pituitary LH and FSH levels are fully recovered within 48 hours.
Target Actions Organism AGonadotropin-releasing hormone receptor antagonistHumans - Absorption
Ganirelix is rapidly absorbed following subcutaneous injection with maximum serum concentrations reached approximately one hour after dosing.
- Volume of distribution
The mean (SD) volume of distribution of Ganirelix in healthy females following intravenous administration of a single 250 mg dose is 43.7 (11.4) L.
- Protein binding
81.9%.
- Metabolism
Following single-dose intravenous administration of radiolabeled ganirelix acetate to healthy female volunteers, ganirelix Acetate is the major compound present in the plasma (50–70% of total radioactivity in the plasma) up to 4 hours and urine (17.1–18.4% of administered dose) up to 24 hours. Ganirelix Acetate is not found in the feces. The 1–4 peptide and 1–6 peptide of Ganirelix Acetate are the primary metabolites observed in the feces.
- Route of elimination
On average, 97.2% of the total radiolabeled ganirelix dose is recovered in the feces and urine (75.1% and 22.1%, respectively) over 288 h following intravenous single dose administration of 1 mg [14 75 C]-ganirelix acetate. Urinary excretion is virtually complete in 24 h, whereas fecal excretion starts to plateau 192 h after dosing.
- Half-life
16.2 hours.
- Clearance
Single dose: 2.4L/hour Multiple dose: 3.3L/hour
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Comprehensive & structured drug product infoFrom application numbers to product codes, connect different identifiers through our commercial datasets.Easily connect various identifiers back to our datasets- Product Ingredients
Ingredient UNII CAS InChI Key Ganirelix acetate 56U7906FQW 129311-55-3 OVBICQMTCPFEBS-SATRDZAXSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ganirelix Acetate Injection, solution 250 ug/0.5mL Subcutaneous Organon USA Inc. 1999-07-29 Not applicable US 
Orgalutran Injection, solution 0.25 mg/0.5mL Subcutaneous Merck Sharp And Dohme B.V 2016-09-08 Not applicable EU 
Orgalutran Injection, solution 0.25 mg/0.5mL Subcutaneous Merck Sharp And Dohme B.V 2016-09-08 Not applicable EU Orgalutran Solution 250 mcg / 0.5 mL Subcutaneous Organon Canada Inc. 2002-08-23 Not applicable Canada 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Ganirelix Acetate Injection, solution 250 ug/0.5mL Subcutaneous Sun Pharmaceutical Industries, Inc. 2019-11-07 2020-01-18 US Ganirelix Acetate Injection, solution 250 ug/0.5mL Subcutaneous Ferring Pharmaceuticals Inc. 2019-01-01 Not applicable US
Categories
- ATC Codes
- H01CC01 — Ganirelix
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Anti-Gonadotropin-Releasing Hormones
- Decreased GnRH Secretion
- Gonadotropin Releasing Hormone Receptor Antagonists
- Gonadotropin-releasing Hormone Antagonists
- Gonadotropin-Releasing Hormone, antagonists & inhibitors
- Hormone Antagonists
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hypothalamic Hormones
- Nerve Tissue Proteins
- Neuropeptides
- Oligopeptides
- Peptide Hormones
- Peptides
- Pituitary and Hypothalamic Hormones and Analogues
- Pituitary Hormone-Releasing Hormones
- Proteins
- Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as polypeptides. These are peptides containing ten or more amino acid residues.
- Kingdom
- Organic compounds
- Super Class
- Organic Polymers
- Class
- Polypeptides
- Sub Class
- Not Available
- Direct Parent
- Polypeptides
- Alternative Parents
- Peptides / Tyrosine and derivatives / Phenylalanine and derivatives / Leucine and derivatives / N-acyl-alpha amino acids and derivatives / Proline and derivatives / Serine and derivatives / Alpha amino acid amides / Alanine and derivatives / Naphthalenes show 23 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / Acetamide / Alanine or derivatives / Alcohol / Alpha peptide / Alpha-amino acid amide / Alpha-amino acid or derivatives / Amphetamine or derivatives / Aromatic heteropolycyclic compound / Aryl chloride show 46 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- IX503L9WN0
- CAS number
- 124904-93-4
- InChI Key
- GJNXBNATEDXMAK-PFLSVRRQSA-N
- 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
- IUPAC Name
- (2R)-6-{[bis(ethylamino)methylidene]amino}-N-[(1S)-1-{[(2S)-6-{[bis(ethylamino)methylidene]amino}-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxohexan-2-yl]carbamoyl}-3-methylbutyl]-2-[(2S)-2-[(2S)-2-[(2R)-2-[(2R)-3-(4-chlorophenyl)-2-[(2R)-2-acetamido-3-(naphthalen-2-yl)propanamido]propanamido]-3-(pyridin-3-yl)propanamido]-3-hydroxypropanamido]-3-(4-hydroxyphenyl)propanamido]hexanamide
- 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
References
- Synthesis Reference
"Patent Link":http://www.google.ca/patents/US5767082
- General References
- Oberye J, Mannaerts B, Huisman J, Timmer C: Local tolerance, pharmacokinetics, and dynamics of ganirelix (Orgalutran) administration by Medi-Jector compared to conventional needle injections. Hum Reprod. 2000 Feb;15(2):245-9. [Article]
- Royster GD, Retzloff MG, Robinson RD, King JA, Propst AM: Effect of length of controlled ovarian hyperstimulation using a gonadotropin-releasing hormone antagonist on in vitro fertilization pregnancy rates. J Reprod Med. 2012 Sep-Oct;57(9-10):415-20. [Article]
- External Links
- KEGG Drug
- D08010
- PubChem Compound
- 16130957
- PubChem Substance
- 310264884
- ChemSpider
- 17287671
- BindingDB
- 50102454
- 35825
- ChEBI
- 135910
- ChEMBL
- CHEMBL1251
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- PDRhealth
- PDRhealth Drug Page
- Wikipedia
- Ganirelix
- AHFS Codes
- 92:40.00 — Gonadotropin-releasing Hormone Antagonists
- FDA label
- Download (62.6 KB)
- MSDS
- Download (60.9 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Other Infertility 1 4 Completed Treatment Controlled Ovarian Stimulation 1 4 Completed Treatment Egg Donation 1 4 Completed Treatment Fertility / Optimal Stimulation Protocol / Reproductive Endocrinology 1 4 Completed Treatment Infertile Women Undergoing Assisted Reproductive Technology (ART) 1 4 Completed Treatment Infertility 2 4 Completed Treatment Infertility / IVF Treatment 1 4 Completed Treatment Infertility / Premature Ovarian Failure (POF) 1 4 Recruiting Treatment Infertility / IVF 2 4 Terminated Treatment In Vitro Fertilization (IVF) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, solution Injection, solution Subcutaneous 250 ug/0.5mL Injection, solution Parenteral Injection, solution Subcutaneous Injection, solution Subcutaneous 0.25 mg/0.5mL Solution Subcutaneous 250 mcg / 0.5 mL Solution Subcutaneous Solution Subcutaneous 0.5 mg/1ml - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5767082 No 1998-06-16 2015-06-16 US US6653286 No 2003-11-25 2018-06-16 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00531 mg/mL ALOGPS logP 3.42 ALOGPS logP 1.62 ChemAxon logS -5.5 ALOGPS pKa (Strongest Acidic) 9.5 ChemAxon pKa (Strongest Basic) 12.14 ChemAxon Physiological Charge 2 ChemAxon Hydrogen Acceptor Count 20 ChemAxon Hydrogen Donor Count 16 ChemAxon Polar Surface Area 451.49 Å2 ChemAxon Rotatable Bond Count 44 ChemAxon Refractivity 423.46 m3·mol-1 ChemAxon Polarizability 170.37 Å3 ChemAxon Number of Rings 6 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Peptide binding
- Specific Function
- Receptor for gonadotropin releasing hormone (GnRH) that mediates the action of GnRH to stimulate the secretion of the gonadotropic hormones luteinizing hormone (LH) and follicle-stimulating hormone...
- Gene Name
- GNRHR
- Uniprot ID
- P30968
- Uniprot Name
- Gonadotropin-releasing hormone receptor
- Molecular Weight
- 37730.355 Da
References
- Oberye J, Mannaerts B, Huisman J, Timmer C: Local tolerance, pharmacokinetics, and dynamics of ganirelix (Orgalutran) administration by Medi-Jector compared to conventional needle injections. Hum Reprod. 2000 Feb;15(2):245-9. [Article]
Drug created on September 14, 2010 16:21 / Updated on May 15, 2021 12:14