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

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
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 All preparations containing clometacin were withdrawn in 1987 due to their hepatotoxicity.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 8297		200.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6991549	Palliative		Approved 8429	DUPERAN Approved Use Pain Launch Date 1976

PubMed

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

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

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:39:30 GMT 2023` Edited by `admin` on `Fri Dec 15 16:39:30 GMT 2023`
Record UNII	L9M34YK25C
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CLOMETACIN

Official 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

C 1656

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