CHEBI:59224 - cetrorelix

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ChEBI Name cetrorelix
ChEBI ID CHEBI:59224
Definition A synthetic ten-membered oligopeptide comprising N-acetyl-3-(naphthalen-2-yl)-D-alanyl, 4-chloro-D-phenylalanyl, 3-(pyridin-3-yl)-D-alanyl, L-seryl, L-tyrosyl, N5-carbamoyl-D-ornithyl, L-leucyl, L-arginyl, L-prolyl, and D-alaninamide residues coupled in sequence. A gonadotrophin-releasing hormone (GnRH) antagonist, it is used for treatment of infertility and of hormone-sensitive cancers of the prostate and breast.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C70H92ClN17O14
Net Charge 0
Average Mass 1431.03800
Monoisotopic Mass 1429.66982
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
InChIKey SBNPWPIBESPSIF-MHWMIDJBSA-N
SMILES CC(C)C[C@H](NC(=O)[C@@H](CCCNC(N)=O)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)N[C@@H](CCCNC(N)=N)C(=O)N1CCC[C@H]1C(=O)N[C@H](C)C(N)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): GnRH antagonist
A chemical substance which inhibits the function of gonadotrophin-releasing hormone (GnRH).
Application(s): GnRH antagonist
A chemical substance which inhibits the function of gonadotrophin-releasing hormone (GnRH).
antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing cetrorelix (CHEBI:59224) has role antineoplastic agent (CHEBI:35610)
cetrorelix (CHEBI:59224) has role GnRH antagonist (CHEBI:59229)
cetrorelix (CHEBI:59224) is a oligopeptide (CHEBI:25676)
Incoming cetrorelix acetate (CHEBI:31387) has part cetrorelix (CHEBI:59224)
IUPAC Name
N-acetyl-3-(naphthalen-2-yl)-D-alanyl-4-chloro-D-phenylalanyl-3-(pyridin-3-yl)-D-alanyl-L-seryl-L-tyrosyl-N5-carbamoyl-D-ornithyl-L-leucyl-L-arginyl-L-prolyl-D-alaninamide
INNs Sources
cetrorelix ChemIDplus
cetrorelixum ChemIDplus
Manual Xrefs Databases
583 DrugCentral
Cetrorelix Wikipedia
D07665 KEGG DRUG
DB00050 DrugBank
EP299402 Patent
US4800191 Patent
View more database links
Registry Numbers Types Sources
120287-85-6 CAS Registry Number ChemIDplus
5860649 Beilstein Registry Number Beilstein
Last Modified
22 February 2017