CHEBI:6427 - leuprolide

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ChEBI Name leuprolide
ChEBI ID CHEBI:6427
Definition An 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.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
Download Molfile XML SDF
Formula C59H84N16O12
Net Charge 0
Average Mass 1209.39830
Monoisotopic Mass 1208.64546
InChI InChI=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
InChIKey GFIJNRVAKGFPGQ-LIJARHBVSA-N
SMILES CCNC(=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](Cc1c[nH]c2ccccc12)NC(=O)[C@H](Cc1c[nH]cn1)NC(=O)[C@@H]1CCC(=O)N1
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): gonadotropin releasing hormone agonist
Any drug which binds to gonadotropin-releasing hormone receptors and triggers a response.
Application(s): 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.
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 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 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 Sources
leuprorelina ChemIDplus
leuproreline ChemIDplus
leuprorelinum ChemIDplus
Synonyms Sources
(D-Leu6,des-Gly-NH210,Pro-ethylamide9)-gonadotropin-releasing hormone ChemIDplus
L-pyroglutamyl-L-histidyl-L-tryptophyl-L-seryl-L-tyrosyl-D-leucyl-L-leucyl-L-arginyl-L-proline ethylamide ChEBI
Leuprorelin KEGG COMPOUND
pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHC2H5 ChEBI
pGlu-His-Trp-Ser-Tyr-D-Leu-Leu-Arg-Pro-NHEt ChEBI
Manual Xrefs Databases
1559 DrugCentral
C07612 KEGG COMPOUND
D08113 KEGG DRUG
DB00007 DrugBank
DE2446005 Patent
US4005063 Patent
View more database links
Registry Numbers Types Sources
53714-56-0 CAS Registry Number ChemIDplus
741818 Reaxys Registry Number Reaxys
Last Modified
22 February 2017