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CHEBI:6427 - leuprolide

ChEBI IDCHEBI:6427
ChEBI Nameleuprolide
Stars
DefinitionAn oligopeptide comprising pyroglutamyl, histidyl, tryptophyl, seryl, tyrosyl, D-leucyl, 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 acetate 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
FormulaC59H84N16O12
Net Charge0
Average Mass1209.421
Monoisotopic Mass1208.64546
SMILESCCNC(=O)[C@@H]1CCCN1C(=O)[C@H](CCCNC(=N)N)NC(=O)[C@H](CC(C)C)NC(=O)[C@@H](CC(C)C)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/C59H84N16O12/c1-6-63-57(86)48-14-10-22-75(48)58(87)41(13-9-21-64-59(60)61)68-51(80)42(23-32(2)3)69-52(81)43(24-33(4)5)70-53(82)44(25-34-15-17-37(77)18-16-34)71-56(85)47(30-76)74-54(83)45(26-35-28-65-39-12-8-7-11-38(35)39)72-55(84)46(27-36-29-62-31-66-36)73-50(79)40-19-20-49(78)67-40/h7-8,11-12,15-18,28-29,31-33,40-48,65,76-77H,6,9-10,13-14,19-27,30H2,1-5H3,(H,62,66)(H,63,86)(H,67,78)(H,68,80)(H,69,81)(H,70,82)(H,71,85)(H,72,84)(H,73,79)(H,74,83)(H4,60,61,64)/t40-,41-,42-,43+,44-,45-,46-,47-,48-/m0/s1
InChIKeyGFIJNRVAKGFPGQ-LIJARHBVSA-N
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.
anti-estrogen  A drug which acts to reduce estrogenic activity in the body, either by reducing the amount of estrogen or by reducing the activity of whatever estrogen is present.
ChEBI Ontology
Outgoing Relation(s)
leuprolide (CHEBI:6427) has role anti-estrogen (CHEBI:50751)
leuprolide (CHEBI:6427) has role antineoplastic agent (CHEBI:35610)
leuprolide (CHEBI:6427) has role gonadotropin releasing hormone agonist (CHEBI:63533)
leuprolide (CHEBI:6427) is a oligopeptide (CHEBI:25676)
Incoming Relation(s)
leuprolide acetate (CHEBI:63597) has part leuprolide (CHEBI:6427)
IUPAC Name 
5-oxo-L-prolyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-N-ethyl-L-prolinamide
INNs  Source
leuprorelinaChemIDplus
leuprorelinumChemIDplus
leuprorelineChemIDplus
Synonyms  Source
LeuprorelinKEGG COMPOUND
pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5ChEBI
(D-Leu6,des-Gly-NH210,Pro-ethylamide9)-gonadotropin-releasing hormoneChemIDplus
pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEtChEBI
L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamideChEBI
Manual XrefsDatabases
C07612KEGG COMPOUND
D08113KEGG DRUG
DB00007DrugBank
DE2446005Patent
US4005063Patent
1559DrugCentral
Registry NumbersSources
Reaxys:741818Reaxys
CAS:53714-56-0KEGG COMPOUND
CAS:53714-56-0ChemIDplus