U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31N5O5
Molecular Weight 505.5655
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRILETIDE

SMILES

COC(=O)[C@H](CC1=CN=CN1)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC3=CC=CC=C3)NC(C)=O

InChI

InChIKey=ZHAGGRWTJXROKV-HJOGWXRNSA-N
InChI=1S/C27H31N5O5/c1-18(33)30-22(13-19-9-5-3-6-10-19)25(34)31-23(14-20-11-7-4-8-12-20)26(35)32-24(27(36)37-2)15-21-16-28-17-29-21/h3-12,16-17,22-24H,13-15H2,1-2H3,(H,28,29)(H,30,33)(H,31,34)(H,32,35)/t22-,23-,24-/m0/s1

HIDE SMILES / InChI
Triletide is a tripeptide derivative which shows cytoprotective and antiulcerogenic activity. It is a thromboxane synthase inhibitor. Analysis of both individual and pooled data indicated that triletide was well absorbed after oral administration, with a lag time of 0.3 hours and the blood peak was reached after about 1.1 to 1.3 hours. Metabolization to desmethyl, desacetyl, desmethyl-desacetyl and hydroxylated derivatives plays a major role in the biotransformation of the drug and thus in its disappearance from blood, the distribution half-life being about 1 hour. A greater proportion of patients given the combination cimetidine and triletide was found to be endoscopically healed after treatment in comparison with those who had cimetidine alone (53% vs 40%). Intensity of symptoms decreased significantly faster and to a significantly greater extent in the same patients, as did antacid intake. Triletide appears to be equally well tolerated as, but significantly more effective than, aluminium hydroxide and magnesium hydroxide in relieving symptoms and promoting healing in patients with mild to moderate duodenal ulcer. There were no complaints of possible side-effects with either triletide treatment and no evidence of any significant changes in blood pressure, heart rate or routine haematology and haematochemistry investigations.

Approval Year

PubMed

PubMed

TitleDatePubMed
The tripeptide ZAMI-420 inhibits thromboxane-induced gastric vasoconstriction and ischaemia.
1983
Prevention of experimentally induced gastric damage with the tripeptide ZAMI-420, a new thromboxane synthesis inhibitor.
1983
Preliminary human pharmacokinetics of triletide.
1985
Effects of combined treatment with triletide and cimetidine in gastric and duodenal ulcer patients, and a retrospective comparison with cimetidine alone.
1985
Clinical evaluation of triletide versus antacids in the treatment of duodenal ulcer out-patients.
1985
Dose-finding clinical assay of triletide in gastric and duodenal ulceration.
1985
Cytoprotective approach to peptic ulcer therapy: a preliminary dose-finding clinical investigation with triletide.
1985
Triletide and ranitidine for the management of chronic duodenal ulcer: a controlled clinical investigation.
1985
Triletide in a cimetidine-controlled clinical evaluation in duodenal ulcer patients.
1985
Cytoprotective therapy of gastric ulcers: a controlled clinical evaluation of triletide versus carbenoxolone.
1985
Controlled clinical assessment of the efficacy and tolerance of triletide versus antacids in patients with gastric and duodenal ulcers.
1985
Name Type Language
TRILETIDE
INN   MART.  
INN  
Official Name English
triletide [INN]
Common Name English
TRILETIDE [MART.]
Common Name English
N-(N-(N-ACETYL-3-PHENYL-L-ALANYL)-3-PHENYL-L-ALANYL)-L-HISTIDINE, METHYL ESTER
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29701
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152744
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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ChEMBL
CHEMBL2105562
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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EVMPD
SUB11296MIG
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INN
5368
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EPA CompTox
DTXSID801174335
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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PUBCHEM
21114913
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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MESH
C040183
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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FDA UNII
50Q6LI773L
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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ECHA (EC/EINECS)
263-401-1
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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SMS_ID
100000076919
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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CAS
62087-96-1
Created by admin on Sat Dec 16 16:31:37 GMT 2023 , Edited by admin on Sat Dec 16 16:31:37 GMT 2023
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