CHEBI:5739 - histrelin

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ChEBI Name histrelin
ChEBI ID CHEBI:5739
Definition An oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, 1-benzyl-D-histidyl, leucyl, arginyl, and N-ethylprolinamide residues joined in sequence. It is a synthetic nonapeptide analogue of gonadotropin-releasing hormone, and is used as a subcutaneous hydrogel implant (particularly as the diacetate salt) for the treatment of prostate cancer and for the suppression of gonadal sex hormone production in children with central precocious puberty.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C66H86N18O12
Net Charge 0
Average Mass 1323.50240
Monoisotopic Mass 1322.667
InChI InChI=1S/C66H86N18O12/c1-4-70-64(95)55-17-11-25-84(55)65(96)48(16-10-24-71-66(67)68)76-58(89)49(26-38(2)3)77-62(93)53(30-43-34-83(37-74-43)33-40-12-6-5-7-13-40)81-59(90)50(27-39-18-20-44(86)21-19-39)78-63(94)54(35-85)82-60(91)51(28-41-31-72-46-15-9-8-14-45(41)46)79-61(92)52(29-42-32-69-36-73-42)80-57(88)47-22-23-56(87)75-47/h5-9,12-15,18-21,31-32,34,36-38,47-55,72,85-86H,4,10-11,16-17,22-30,33,35H2,1-3H3,(H,69,73)(H,70,95)(H,75,87)(H,76,89)(H,77,93)(H,78,94)(H,79,92)(H,80,88)(H,81,90)(H,82,91)(H4,67,68,71)/t47-,48-,49-,50-,51-,52-,53+,54-,55-/m0/s1
InChIKey HHXHVIJIIXKSOE-QILQGKCVSA-N
SMILES CCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(N)=N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](Cc1cn(Cc2ccccc2)cn1)NC(=O)[C@H](Cc1ccc(O)cc1)NC(=O)[C@H](CO)NC(=O)[C@H](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1
Roles Classification
Biological Role(s): gonadotropin releasing hormone agonist
Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
Application(s): antineoplastic agent
A substance that inhibits or prevents the proliferation of neoplasms.
gonadotropin releasing hormone agonist
Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing histrelin (CHEBI:5739) has role antineoplastic agent (CHEBI:35610)
histrelin (CHEBI:5739) has role gonadotropin releasing hormone agonist (CHEBI:63533)
histrelin (CHEBI:5739) is a oligopeptide (CHEBI:25676)
Incoming histrelin acetate (CHEBI:63530) has part histrelin (CHEBI:5739)
IUPAC Name
5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-1-benzyl-D-histidyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide
INNs Sources
histrelin ChemIDplus
histrelina ChemIDplus
histreline ChemIDplus
histrelinum ChemIDplus
Synonyms Sources
5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Nτ-benzyl-D-histidyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide ChemIDplus
[(im-Bzl)-D-His6,Pro9-NEt]-gonadotropin releasing hormone ChEBI
L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-Nim-benzyl-histidyl-L-leucyl-L-arginyl-L-proline ethylamide ChEBI
ORF 17070 ChemIDplus
RWJ 17070 ChemIDplus
Database Links Databases
2975 DrugCentral
C07671 KEGG COMPOUND
D02369 KEGG DRUG
Histrelin Wikipedia
US4244946 Patent
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Registry Numbers Types Sources
4290557 Reaxys Registry Number Reaxys
76712-82-8 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
19920916 PubMed citation Europe PMC
19956699 PubMed citation Europe PMC
20329807 PubMed citation Europe PMC
21851539 PubMed citation Europe PMC
Last Modified
22 February 2017