CHEBI:60564 - felypressin

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ChEBI Name felypressin
ChEBI ID CHEBI:60564
Definition A synthetic nonapeptide comprising cysteinyl, phenylalanyl, phenylalanyl, glutaminyl, asparaginyl, cysteinyl, prolyl, lysyl, and glycinamide residues in sequence, with a disulfide bridge joining the two cysteine residues. Its antidiuretic effects are less than those of vasopressin. It is used as a vasoconstrictor in local anaesthetic injections for dental use, and is an ingredient of preparations that have been used for treatment of pain and inflammation of the mouth.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information
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Formula C46H65N13O11S2
Net Charge 0
Average Mass 1040.21900
InChI InChI=1S/C46H65N13O11S2/c47-18-8-7-14-29(40(64)52-23-38(51)62)54-45(69)35-15-9-19-59(35)46(70)34-25-72-71-24-28(48)39(63)55-31(20-26-10-3-1-4-11-26)43(67)56-32(21-27-12-5-2-6-13-27)42(66)53-30(16-17-36(49)60)41(65)57-33(22-37(50)61)44(68)58-34/h1-6,10-13,28-35H,7-9,14-25,47-48H2,(H2,49,60)(H2,50,61)(H2,51,62)(H,52,64)(H,53,66)(H,54,69)(H,55,63)(H,56,67)(H,57,65)(H,58,68)/t28-,29-,30-,31-,32-,33-,34-,35-/m0/s1
InChIKey SFKQVVDKFKYTNA-DZCXQCEKSA-N
SMILES NCCCC[C@H](NC(=O)[C@@H]1CCCN1C(=O)[C@@H]1CSSC[C@H](N)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](Cc2ccccc2)C(=O)N[C@@H](CCC(N)=O)C(=O)N[C@@H](CC(N)=O)C(=O)N1)C(=O)NCC(N)=O
Roles Classification
Biological Role(s): vasopressin receptor agonist
Any drug which binds to vasopressin receptors and triggers a response.
Application(s): vasoconstrictor agent
Drug used to cause constriction of the blood vessels.
vasopressin receptor agonist
Any drug which binds to vasopressin receptors and triggers a response.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing felypressin (CHEBI:60564) has role vasoconstrictor agent (CHEBI:50514)
felypressin (CHEBI:60564) has role vasopressin receptor agonist (CHEBI:59727)
felypressin (CHEBI:60564) is a heterodetic cyclic peptide (CHEBI:24533)
IUPAC Name
1-{[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13,16-dibenzyl-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-L-prolyl-L-lysylglycinamide
INNs Sources
felipresina ChemIDplus
felypressin ChemIDplus
felypressine ChemIDplus
felypressinum ChemIDplus
Synonyms Sources
2-(L-phenylalanine)-8-L-lysinevasopressin ChemIDplus
L-cysteinyl-L-phenylalanyl-L-phenylalanyl-L-glutaminyl-L-asparaginyl-L-cysteinyl-L-prolyl-L-lysylglycinamide cyclic (1-6)disulfide ChemIDplus
Phe2-Lys8-vasopressin ChEBI
PLV-2 ChEBI
Database Links Databases
D04137 KEGG DRUG
DB00093 DrugBank
GB928607 Patent
US3232923 Patent
View more database links
Registry Numbers Types Sources
13260124 Reaxys Registry Number Reaxys
56-59-7 CAS Registry Number KEGG DRUG
56-59-7 CAS Registry Number ChemIDplus
Last Modified
04 November 2010