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Details

Stereochemistry ACHIRAL
Molecular Formula C19H16ClNO4
Molecular Weight 357.788
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLOMETACIN

SMILES

COC1=CC2=C(C=C1)C(C(=O)C3=CC=C(Cl)C=C3)=C(C)N2CC(O)=O

InChI

InChIKey=DGMZLCLHHVYDIS-UHFFFAOYSA-N
InChI=1S/C19H16ClNO4/c1-11-18(19(24)12-3-5-13(20)6-4-12)15-8-7-14(25-2)9-16(15)21(11)10-17(22)23/h3-9H,10H2,1-2H3,(H,22,23)

HIDE SMILES / InChI

Molecular Formula C19H16ClNO4
Molecular Weight 357.788
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/2940571 https://www.ncbi.nlm.nih.gov/pubmed/6991549 http://www.biomedcentral.com/content/supplementary/s12916-014-0262-7-s2.pdf

The NSAID clometacin is an indometacin derivative. Clometacin is an analgesic drug that binds to human serum albumin (HSA) and inhibits the binding of indomethacin, warfarin, clofibrate and salicylic acid to HSA. Clometacin (DUPERAN) was approved in France in 1977. All preparations containing clometacin were withdrawn in 1987 due to their hepatotoxicity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
200.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
DUPERAN

Approved Use

Pain

Launch Date

1976
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.6%
CLOMETACIN serum
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
150 mg 1 times / day multiple, oral
Studied dose
Dose: 150 mg, 1 times / day
Route: oral
Route: multiple
Dose: 150 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.
2006-08
Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies.
1985-09-01
[Acute renal insufficiency with ketoprofen and clometacin].
1983-05-26
[Acute renal insufficiency caused by clometacin. Relapse with diclofenac. Inhibition of the synthesis of prostaglandins].
1982-12
[Liver damage following clomethacin treatment. 6 cases, including 2 deaths (author's transl)].
1981-09-19
Patents

Sample Use Guides

clometacin (450 to 600 mg) daily
Route of Administration: Oral
Clometacin at a concentration of 6 x 10(-4) M induced hepatitis in normal human hepatocytes culture
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:33:46 GMT 2025
Edited
by admin
on Mon Mar 31 18:33:46 GMT 2025
Record UNII
L9M34YK25C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CLOMETACIN
INN   MART.   MI   WHO-DD  
INN  
Official Name English
C 1656
Preferred Name English
CLOMETACIN [MART.]
Common Name English
Clometacin [WHO-DD]
Common Name English
R-3959
Code English
CLOMETACIN [MI]
Common Name English
MINDOLIC ACID
Common Name English
clometacin [INN]
Common Name English
R 3959
Code English
3-(P-CHLOROBENZOYL)-6-METHOXY-2-METHYLINDOLE-1-ACETIC ACID
Systematic Name English
C-1656
Code English
Classification Tree Code System Code
NCI_THESAURUS C257
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
Code System Code Type Description
PUBCHEM
33176
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
EPA CompTox
DTXSID7048827
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
NCI_THESAURUS
C77348
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
MERCK INDEX
m1080
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
247-271-3
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
FDA UNII
L9M34YK25C
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
ChEMBL
CHEMBL13376
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
DRUG CENTRAL
698
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
EVMPD
SUB06718MIG
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
INN
3041
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
SMS_ID
100000084543
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
CAS
25803-14-9
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
MESH
C017136
Created by admin on Mon Mar 31 18:33:46 GMT 2025 , Edited by admin on Mon Mar 31 18:33:46 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY