TOMOXIPROLE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H20N2O
Molecular Weight	316.3963
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C2=NC3=C(C=CC4=C3C=CC=C4)N2C(C)C

InChI

InChIKey=XVDXNSRMHBAVAX-UHFFFAOYSA-N

InChI=1S/C21H20N2O/c1-14(2)23-19-13-10-15-6-4-5-7-18(15)20(19)22-21(23)16-8-11-17(24-3)12-9-16/h4-14H,1-3H3

HIDE SMILES / InChI

Molecular Formula	C21H20N2O
Molecular Weight	316.3963
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9533184 | https://www.ncbi.nlm.nih.gov/pubmed/6333688 | https://www.ncbi.nlm.nih.gov/pubmed/3082338 | https://www.ncbi.nlm.nih.gov/pubmed/4043144

Tomoxiprole belongs to the class of 3-alkyl-2-aryl-3H-naphth (1,2-d)imidazoles. It is a nonsteroidal anti-inflammatory compound that was reported to have low ulcerogenic potential. Tomoxiprole inhibition of cyclooxygenase-2 but not cyclooxygenase-1 is time-dependent. It has anti-inflammatory activity in various anti-inflammatory models such as carrageenin and nystatin oedemas, cotton pellet granuloma and adjuvant arthritis. The anti-inflammatory potency of tomoxiprole is greater than that of acetylsalicylic acid and phenylbutazone, but lower than that of indomethacin. Tomoxiprole reduced PGE2 and 6-keto-PGF1 alpha levels more effectively in inflamed tissue than in gastric mucosa when assayed in in vivo experiments, whereas indomethacin and other non-steroidal anti-inflammatory drugs are equally effective in both systems.

Approval Year

PubMed

Title	Date	PubMed
Pharmacological effects of a synthetic quinoline, a hybrid of tomoxiprole and naproxen, against acute pain and inflammation in mice: a behavioral and docking study.	2017-04	28804615
Tomoxiprole selectively inhibits cyclooxygenase-2.	1997-12	9533184
Highly selective antiinflammatory and analgesic activity of 3-(1-methylethyl)-2-(4-methoxyphenyl)-3H-naphth[1,2-d]imidazole, a new non-acidic molecule.	1986	3082338
Pharmacokinetics and metabolism of tomoxiprole, a new analgesic antiinflammatory agent, in the rat.	1985-04-01	4043144
Inhibition of PG production by MDL 035, a new non-steroidal non-acidic anti-inflammatory compound, in rat gastric mucosa and inflammatory exudate.	1984-08	6333688

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:18:41 GMT 2025` Edited by `admin` on `Mon Mar 31 18:18:41 GMT 2025`
Record UNII	EZ948T2878
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOMOXIPROLE

Official Name

English

MDL-035

Preferred Name

English

tomoxiprole [INN]

Common Name

English

3H-NAPHTH(1,2-D)IMIDAZOLE, 2-(4-METHOXYPHENYL)-3-(1-METHYLETHYL)-

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323