Identification
- Summary
Cetrorelix is a synthetic peptide antagonist of gonadotropin releasing hormone used to prevent luteinizing hormone surges in women undergoing assisted reproduction therapy.
- Brand Names
- Cetrotide
- Generic Name
- Cetrorelix
- DrugBank Accession Number
- DB00050
- Background
Cetrorelix is a man-made hormone that blocks the effects of Gonadotropin Releasing Hormone (GnRH). GnRH controls another hormone that is called luteinizing hormone (LH), which is the hormone that starts ovulation during the menstrual cycle. When undergoing hormone treatment sometimes premature ovulation can occur, leading to eggs that are not ready for fertilization to be released. Cetrorelix does not allow the premature release of these eggs to occur.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Cetrorelix (DB00050)
- Weight
- Average: 1431.038
Monoisotopic: 1429.669818444 - Chemical Formula
- C70H92ClN17O14
- Synonyms
- Cetrorelix
- Cetrorelixum
- External IDs
- SB 75
- SB-75
Pharmacology
- Indication
For the inhibition of premature LH surges in women undergoing controlled ovarian stimulation
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- Contraindications & Blackbox Warnings
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Cetrorelix is a synthetic decapeptide with gonadotropin-releasing hormone (GnRH) antagonistic activity. GnRH induces the production and release of luteinizing hormone (LH) and follicle stimulating hormone (FSH) from the gonadotrophic cells of the anterior pituitary. Due to a positive estradiol (E2) feedback at midcycle, GnRH liberation is enhanced resulting in an LH-surge. This LH-surge induces the ovulation of the dominant follicle, resumption of oocyte meiosis and subsequently luteinization as indicated by rising progesterone levels. Cetrorelix competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner.
- Mechanism of action
Cetrorelix binds to the gonadotropin releasing hormone receptor and acts as a potent inhibitor of gonadotropin secretion. It competes with natural GnRH for binding to membrane receptors on pituitary cells and thus controls the release of LH and FSH in a dose-dependent manner.
Target Actions Organism AGonadotropin-releasing hormone receptor antagonistHumans ULutropin-choriogonadotropic hormone receptor Not Available Humans - Absorption
Rapidly absorbed following subcutaneous injection. The mean absolute bioavailability following subcutaneous administration to healthy female subjects is 85%.
- Volume of distribution
- 1.16 L/kg
- Protein binding
86%
- Metabolism
In in vitro studies, cetrorelix was stable against phase I- and phase II-metabolism. Cetrorelix was transformed by peptidases, and the (1-4) peptide was the predominant metabolite.
- Route of elimination
Following subcutaneous administration of 10 mg cetrorelix to males and females, only unchanged cetrorelix was detected in urine.
- Half-life
~62.8 hours
- Clearance
- 1.28 ml/min·kg [adult healthy female with 3 mg single SC administration]
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.No interactions found.
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Cetrorelix acetate W9Y8L7GP4C 130143-01-0 DTPVYWHLQLAXFT-SMCUOGPFSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cetrotide Injection, powder, for solution 0.25 mg Subcutaneous Merck Europe B.V. 2016-09-08 Not applicable EU 
Cetrotide Kit 0.25 mg/1mL Subcutaneous EMD Serono, Inc. 2000-08-11 Not applicable US 
Cetrotide Powder, for solution 3 mg / vial Subcutaneous Emd Serono, A Division Of Emd Inc., Canada 2004-02-25 2014-10-20 Canada 
Cetrotide Kit 3 mg/3mL Subcutaneous EMD Serono, Inc. 2008-04-24 2008-04-24 US Cetrotide Injection, powder, for solution 0.25 mg Subcutaneous Merck Europe B.V. 2016-09-08 Not applicable EU - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Cetrorelix Kit 0.25 mg/1mL Subcutaneous Teva Pharmaceuticals, Inc. 2023-12-14 Not applicable US Cetrorelix Kit 0.25 mg/1mL Subcutaneous Akorn 2022-10-24 Not applicable US
Categories
- ATC Codes
- H01CC02 — Cetrorelix
- Drug Categories
- Amino Acids, Peptides, and Proteins
- Anti-Gonadotropin-Releasing Hormones
- Decreased GnRH Secretion
- Fertility Agents
- Fertility Agents, Female
- Gonadotropin Releasing Hormone Receptor Antagonists
- Gonadotropin-releasing Hormone Antagonists
- 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
- Reproductive Control Agents
- 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 24 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 47 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- oligopeptide (CHEBI:59224)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- OON1HFZ4BA
- CAS number
- 120287-85-6
- InChI Key
- SBNPWPIBESPSIF-MHWMIDJBSA-N
- InChI
- InChI=1S/C70H92ClN17O14/c1-39(2)31-52(61(94)82-51(15-9-28-77-69(73)74)68(101)88-30-10-16-58(88)67(100)79-40(3)59(72)92)83-60(93)50(14-8-29-78-70(75)102)81-63(96)54(34-43-20-25-49(91)26-21-43)86-66(99)57(38-89)87-65(98)56(36-45-11-7-27-76-37-45)85-64(97)55(33-42-18-23-48(71)24-19-42)84-62(95)53(80-41(4)90)35-44-17-22-46-12-5-6-13-47(46)32-44/h5-7,11-13,17-27,32,37,39-40,50-58,89,91H,8-10,14-16,28-31,33-36,38H2,1-4H3,(H2,72,92)(H,79,100)(H,80,90)(H,81,96)(H,82,94)(H,83,93)(H,84,95)(H,85,97)(H,86,99)(H,87,98)(H4,73,74,77)(H3,75,78,102)/t40-,50-,51+,52+,53-,54+,55-,56-,57+,58+/m1/s1
- IUPAC Name
- (2S)-N-[(2S)-5-carbamimidamido-1-[(2S)-2-{[(1R)-1-carbamoylethyl]carbamoyl}pyrrolidin-1-yl]-1-oxopentan-2-yl]-2-[(2R)-5-(carbamoylamino)-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]pentanamido]-4-methylpentanamide
- SMILES
- CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)NC(=O)[C@H](CC1=CC=C(O)C=C1)NC(=O)[C@H](CO)NC(=O)[C@@H](CC1=CN=CC=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](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014261
- KEGG Drug
- D07665
- PubChem Compound
- 25074887
- PubChem Substance
- 46505494
- ChemSpider
- 10482082
- BindingDB
- 50369965
- 68147
- ChEBI
- 59224
- ChEMBL
- CHEMBL1200490
- Therapeutic Targets Database
- DAP000096
- PharmGKB
- PA164764506
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Cetrorelix
- FDA label
- Download (221 KB)
- MSDS
- Download (35.2 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Not Available Effect of Two Protocols of Ovarian Stimulation on Oocyte Quality 1 4 Completed Not Available Uterine Fibroids (Leiomyomas) 1 4 Completed Prevention Ovarian Hyper Stimulation Syndrome (OHSS) 1 4 Completed Treatment Assisted Reproduction 1 4 Completed Treatment Female Infertility 1
Pharmacoeconomics
- Manufacturers
- Emd serono inc
- Packagers
- Baxter International Inc.
- EMD Canada Inc.
- Solvay Pharmaceuticals
- Dosage Forms
Form Route Strength Injection, powder, for solution Subcutaneous 0.25 mg/ml Injection, powder, lyophilized, for solution Subcutaneous 3 mg Kit Subcutaneous 0.25 mg/1mL Kit Subcutaneous 3 mg/3mL Powder, for solution Subcutaneous 0.25 mg / vial Powder, for solution Subcutaneous 3 mg / vial Injection, powder, for solution Subcutaneous 0.25 mg Injection Subcutaneous 0.25 MG Injection, powder, lyophilized, for solution Subcutaneous 0.25 mg Injection, solution 0.25 MG Powder 0.25 mg/1vial - Prices
Unit description Cost Unit Cetrotide 3 mg kit 689.92USD kit Cetrotide 0.25 mg kit 137.99USD kit DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US5198533 No 1993-03-30 2010-10-24 US CA2115943 No 2003-08-05 2014-02-18 Canada US6319192 No 2001-11-20 2019-04-23 US
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.00694 mg/mL ALOGPS logP 1.33 ALOGPS logP -1.7 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 9.5 Chemaxon pKa (Strongest Basic) 11.79 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 18 Chemaxon Hydrogen Donor Count 17 Chemaxon Polar Surface Area 495.67 Å2 Chemaxon Rotatable Bond Count 38 Chemaxon Refractivity 384.16 m3·mol-1 Chemaxon Polarizability 148.93 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
Property Value Probability Human Intestinal Absorption + 0.913 Blood Brain Barrier - 0.9647 Caco-2 permeable - 0.748 P-glycoprotein substrate Substrate 0.8796 P-glycoprotein inhibitor I Non-inhibitor 0.8235 P-glycoprotein inhibitor II Inhibitor 0.6194 Renal organic cation transporter Non-inhibitor 0.6856 CYP450 2C9 substrate Non-substrate 0.7609 CYP450 2D6 substrate Non-substrate 0.7938 CYP450 3A4 substrate Substrate 0.6358 CYP450 1A2 substrate Non-inhibitor 0.7491 CYP450 2C9 inhibitor Non-inhibitor 0.6987 CYP450 2D6 inhibitor Non-inhibitor 0.8339 CYP450 2C19 inhibitor Non-inhibitor 0.7056 CYP450 3A4 inhibitor Inhibitor 0.6531 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9001 Ames test Non AMES toxic 0.6327 Carcinogenicity Non-carcinogens 0.7553 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.7014 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.7601 hERG inhibition (predictor II) Inhibitor 0.649
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 363.36618 predictedDeepCCS 1.0 (2019) [M+H]+ 365.07416 predictedDeepCCS 1.0 (2019) [M+Na]+ 371.231 predictedDeepCCS 1.0 (2019)
Targets
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- 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
- Volker P, Grundker C, Schmidt O, Schulz KD, Emons G: Expression of receptors for luteinizing hormone-releasing hormone in human ovarian and endometrial cancers: frequency, autoregulation, and correlation with direct antiproliferative activity of luteinizing hormone-releasing hormone analogues. Am J Obstet Gynecol. 2002 Feb;186(2):171-9. [Article]
- Zapatero-Caballero H, Sanchez-Franco F, Guerra-Perez N, Fernandez-Mendez C, Fernandez-Vazquez G: Gonadotropin-releasing hormone receptor gene expression during pubertal development of male rats. Biol Reprod. 2003 May;68(5):1764-70. Epub 2002 Dec 11. [Article]
- Zapatero-Caballero H, Sanchez-Franco F, Fernandez-Mendez C, Garcia-San Frutos M, Botella-Cubells LM, Fernandez-Vazquez G: Gonadotropin-releasing hormone receptor gene expression during pubertal development of female rats. Biol Reprod. 2004 Feb;70(2):348-55. Epub 2003 Oct 15. [Article]
- Roth C, Hegemann F, Hildebrandt J, Balzer I, Witt A, Wuttke W, Jarry H: Pituitary and gonadal effects of GnRH (gonadotropin releasing hormone) analogues in two peripubertal female rat models. Pediatr Res. 2004 Jan;55(1):126-33. Epub 2003 Nov 6. [Article]
- Castellon E, Clementi M, Hitschfeld C, Sanchez C, Benitez D, Saenz L, Contreras H, Huidobro C: Effect of leuprolide and cetrorelix on cell growth, apoptosis, and GnRH receptor expression in primary cell cultures from human prostate carcinoma. Cancer Invest. 2006 Apr-May;24(3):261-8. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Luteinizing hormone receptor activity
- Specific Function
- Receptor for lutropin-choriogonadotropic hormone. The activity of this receptor is mediated by G proteins which activate adenylate cyclase.
- Gene Name
- LHCGR
- Uniprot ID
- P22888
- Uniprot Name
- Lutropin-choriogonadotropic hormone receptor
- Molecular Weight
- 78642.01 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Ascoli M, Fanelli F, Segaloff DL: The lutropin/choriogonadotropin receptor, a 2002 perspective. Endocr Rev. 2002 Apr;23(2):141-74. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55