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CHEBI:5739 - histrelin

ChEBI IDCHEBI:5739
ChEBI Namehistrelin
Stars
DefinitionAn 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.
Last Modified22 February 2017
DownloadsMolfile
FormulaC66H86N18O12
Net Charge0
Average Mass1323.528
Monoisotopic Mass1322.66726
SMILESCCNC(=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](Cc1cnc2ccccc12)NC(=O)[C@H](Cc1cncn1)NC(=O)[C@@H]1CCC(=O)N1
InChIInChI=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
InChIKeyHHXHVIJIIXKSOE-QILQGKCVSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Role:
gonadotropin releasing hormone agonist  Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
Applications:
gonadotropin releasing hormone agonist  Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
antineoplastic agent  A substance that inhibits or prevents the proliferation of neoplasms.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
histrelinaChemIDplus
histrelineChemIDplus
histrelinChemIDplus
histrelinumChemIDplus
Synonyms  Source
ORF 17070ChemIDplus
RWJ 17070ChemIDplus
[(im-Bzl)-D-His6,Pro9-NEt]-gonadotropin releasing hormoneChEBI
L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-Nim-benzyl-histidyl-L-leucyl-L-arginyl-L-proline ethylamideChEBI
5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-Nτ-benzyl-D-histidyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamideChemIDplus
Manual XrefsDatabases
C07671KEGG COMPOUND
D02369KEGG DRUG
HistrelinWikipedia
US4244946Patent
2975DrugCentral
Registry NumbersSources
Reaxys:4290557Reaxys
CAS:76712-82-8KEGG COMPOUND
CAS:76712-82-8ChemIDplus
Citations