CLOMETACIN

Possibly Marketed Outside US

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 Search

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

Description
Sources: http://www.trc-canada.com/product-detail/?C586995
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 All preparations containing clometacin were withdrawn in 1987 due to their hepatotoxicity.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Prostaglandin-H2 D-isomerase 1 Target ID: CHEMBL4334 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1900533	Inhibitor 8504		200.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 619 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6991549	Palliative		Approved 8583	DUPERAN Approved Use Pain Launch Date 1976

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.6% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6626262/			CLOMETACIN serum	Homo sapiens

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/6991549/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6991549/	Sources: https://pubmed.ncbi.nlm.nih.gov/6991549/

PubMed

Title	Date	PubMed
Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems.	2006-08	16867024
Drug-induced hepatitis associated with anticytoplasmic organelle autoantibodies.	1985-09-01	4029887
[Acute renal insufficiency with ketoprofen and clometacin].	1983-05-26	6310774
[Acute renal insufficiency caused by clometacin. Relapse with diclofenac. Inhibition of the synthesis of prostaglandins].	1982-12	7163673
[Liver damage following clomethacin treatment. 6 cases, including 2 deaths (author's transl)].	1981-09-19	7290927

Patents

Sample Use Guides

In Vivo Use Guide

clometacin (450 to 600 mg) daily

Route of Administration: Oral

In Vitro Use Guide

Clometacin at a concentration of 6 x 10(-4) M induced hepatitis in normal human hepatocytes culture

Name

Type

Language

CLOMETACIN

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