cetrorelix   Click here for help

GtoPdb Ligand ID: 1190

Synonyms: Cetrotide® | SB-075
Approved drug Immunopharmacology Ligand
cetrorelix is an approved drug (EMA (1999), FDA (2000))
Compound class: Peptide or derivative
Comment: Cetrorelix is a synthetic GnRH receptor antagonist. Natural GnRH is a decapeptide hormone.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N1CCCC1C(=O)NC(C(=O)N)C)CCCN=C(N)N)CC(C)C)CCCNC(=O)N)Cc1ccc(cc1)O)NC(=O)C(Cc1cccnc1)NC(=O)C(Cc1ccc(cc1)Cl)NC(=O)C(Cc1ccc2c(c1)cccc2)NC(=O)C
Isomeric SMILES OC[C@@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N1CCC[C@H]1C(=O)N[C@@H](C(=O)N)C)CCCN=C(N)N)CC(C)C)CCCNC(=O)N)Cc1ccc(cc1)O)NC(=O)[C@@H](Cc1cccnc1)NC(=O)[C@@H](Cc1ccc(cc1)Cl)NC(=O)[C@@H](Cc1ccc2c(c1)cccc2)NC(=O)C
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
InChI Key SBNPWPIBESPSIF-MHWMIDJBSA-N
References
1. Ansari MA, Dhar M, Spieker S, Bakht N, Rahman AM, Moore WV, Jacobson JD. (2004)
Modulation of diabetes with gonadotropin-releasing hormone antagonists in the nonobese mouse model of autoimmune diabetes.
Endocrinology, 145 (1): 337-42. [PMID:12959992]
2. Beckers T, Marheineke K, Reiländer H, Hilgard P. (1995)
Selection and characterization of mammalian cell lines with stable over-expression of human pituitary receptors for gonadoliberin.
Eur J Biochem, 231 (3): 535-43. [PMID:7649152]
3. Beckers T, Reiländer H, Hilgard P. (1997)
Characterization of gonadotropin-releasing hormone analogs based on a sensitive cellular luciferase reporter gene assay.
Anal Biochem, 251 (1): 17-23. [PMID:9300077]
4. Chen A, Ganor Y, Rahimipour S, Ben-Aroya N, Koch Y, Levite M. (2002)
The neuropeptides GnRH-II and GnRH-I are produced by human T cells and trigger laminin receptor gene expression, adhesion, chemotaxis and homing to specific organs.
Nat Med, 8 (12): 1421-6. [PMID:12447356]
5. Jacobson JD, Nisula BC, Steinberg AD. (1994)
Modulation of the expression of murine lupus by gonadotropin-releasing hormone analogs.
Endocrinology, 134 (6): 2516-23. [PMID:8194477]
6. Kåss A, Hollan I, Fagerland MW, Gulseth HC, Torjesen PA, Førre ØT. (2015)
Rapid Anti-Inflammatory Effects of Gonadotropin-Releasing Hormone Antagonism in Rheumatoid Arthritis Patients with High Gonadotropin Levels in the AGRA Trial.
PLoS ONE, 10 (10): e0139439. [PMID:26460564]
7. Kåss AS, Førre OT, Fagerland MW, Gulseth HC, Torjesen PA, Hollan I. (2014)
Short-term treatment with a gonadotropin-releasing hormone antagonist, cetrorelix, in rheumatoid arthritis (AGRA): a randomized, double-blind, placebo-controlled study.
Scand J Rheumatol, 43 (1): 22-7. [PMID:24182325]
8. Morale MC, Batticane N, Bartoloni G, Guarcello V, Farinella Z, Galasso MG, Marchetti B. (1991)
Blockade of central and peripheral luteinizing hormone-releasing hormone (LHRH) receptors in neonatal rats with a potent LHRH-antagonist inhibits the morphofunctional development of the thymus and maturation of the cell-mediated and humoral immune responses.
Endocrinology, 128 (2): 1073-85. [PMID:1846575]
9. Neill JD. (2002)
GnRH and GnRH receptor genes in the human genome.
Endocrinology, 143 (3): 737-43. [PMID:11861490]
10. Struthers RS, Xie Q, Sullivan SK, Reinhart GJ, Kohout TA, Zhu YF, Chen C, Liu XJ, Ling N, Yang W et al.. (2007)
Pharmacological characterization of a novel nonpeptide antagonist of the human gonadotropin-releasing hormone receptor, NBI-42902.
Endocrinology, 148 (2): 857-67. [PMID:17095587]