TILNOPROFEN ARBAMEL

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H22N2O4
Molecular Weight	354.3997
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=ZAKRMJAETCUYKK-UHFFFAOYSA-N

InChI=1S/C20H22N2O4/c1-12-5-6-15-10-16-9-14(7-8-17(16)26-19(15)21-12)13(2)20(24)25-11-18(23)22(3)4/h5-9,13H,10-11H2,1-4H3

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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
[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.

Name

Type

Language

TILNOPROFEN ARBAMEL

Official Name

English

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

Common Name

English

MEPRANOPROFEN ARBAMEL

Common Name

English

tilnoprofen arbamel [INN]

Common Name

English

MEPRANOPROFEN ARBAMEL [JAN]

Common Name

English

Y-23023

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C257