TILNOPROFENIC ACID

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H15NO3
Molecular Weight	269.2952
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C(O)=O)C1=CC2=C(OC3=C(C2)C=CC(C)=N3)C=C1

InChI

InChIKey=FJDZVZSBZSMBTP-UHFFFAOYSA-N

InChI=1S/C16H15NO3/c1-9-3-4-12-8-13-7-11(10(2)16(18)19)5-6-14(13)20-15(12)17-9/h3-7,10H,8H2,1-2H3,(H,18,19)

HIDE SMILES / InChI

Molecular Formula	C16H15NO3
Molecular Weight	269.2952
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1814850
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/7996395

N,N-Dimethylcarbamoylmethyl alpha,2-dimethyl-5H-[1]- benzopyrano[2,3-b]pyridine-7-acetate (Y-23023/ Tilnoprofen arbamel) is a prodrug developed as a new non-steroidal anti-inflammatory drug (NSAID), by Yoshitomi and Japan Tobacco for treatment pain in Rheumatoid arthritis, but was discontinued. Y-23023 is rapidly hydrolysed to an active metabolite, alpha,2-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine-7-acetic acid (TILNOPROFENIC ACID), cyclo-oxygenase inhibitor.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: http://www.ncbi.nlm.nih.gov/pubmed/1814850	Inhibitor 8297
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8537074	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: http://adisinsight.springer.com/drugs/800003086	Palliative		Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Synthesis, pharmacological activity and biopharmaceutical characteristics of alpha,2-dimethyl-5H-[1]benzopyrano[2,3-b]pyridine-7-acetates].	1989 Nov	2614665
Inhibition by cyclo-oxygenase inhibitors of interleukin-6 production by human peripheral blood mononuclear cells.	1991	1814850
[Mechanism of analgesic action of Y-23023, a new non-steroidal anti-inflammatory drug].	1995 Oct	8537074

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Y-9223 (TILNOPROFENIC ACID), a novel cyclo-oxygenase inhibitor, inhibited the increases in the IL-6 level in the culture medium of both mitogen-stimulated adherent cells and non-adherent cells fractionated from mononuclear cells of human peripheral blood. Northern blotting showed that the mitogen-induced increase in the expression of IL-6 mRNA was inhibited by Y-9223, indicating that this agent inhibits IL-6 biosynthesis.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 01:24:35 GMT 2023` Edited by `admin` on `Sat Dec 16 01:24:35 GMT 2023`
Record UNII	6ON0780D7G
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TILNOPROFENIC ACID

Common Name

English

Y9223

Code

English

Y-9223

Code

English

(±)-5H-(1)BENZOPYRANO(2,3-B)PYRIDINE-7-ACETIC ACID, .ALPHA.,2-DIMETHYL-

Common Name

English

5H-(1)BENZOPYRANO(2,3-B)PYRIDINE-7-ACETIC ACID, .ALPHA.,2-DIMETHYL-

Common Name

English

Code System Code Type Description

FDA UNII

6ON0780D7G