AMPIROXICAM

Details

Stereochemistry	RACEMIC
Molecular Formula	C20H21N3O7S
Molecular Weight	447.462
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCOC(=O)OC(C)OC1=C(N(C)S(=O)(=O)C2=CC=CC=C12)C(=O)NC3=NC=CC=C3

InChI

InChIKey=LSNWBKACGXCGAJ-UHFFFAOYSA-N

InChI=1S/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)

HIDE SMILES / InChI

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/8304243
Curator's Comment: description was created based on several sources, including http://www.selleckchem.com/products/ampiroxicam.html http://www.ncbi.nlm.nih.gov/pubmed/8162655

Ampiroxicam is a non-steroidal anti-inflammatory drug (NSAID) that exhibits anti-inflammatory and analgesic activities; it inhibits COX-1 and COX-2. Ampiroxicam is a prodrug of piroxicam that does not inhibit prostaglandin synthesis itself. In animal models of inflammation, ampiroxicam decreases paw edema. Ampiroxicam has been synthesised to reduce piroxicam-related gastrointestinal irritation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Cyclooxygenase 89 Target ID: CHEMBL2094253 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16788159	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Arthritis 89 Sources: http://www.ncbi.nlm.nih.gov/pubmed/8304243	Secondary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[Preemptive analgesia for postoperative pain after frontotemporal craniotomy].	2002 Feb	11857941
Evaluation of gastric acid secretion in two patients (each aged over 90 years) with Helicobacter pylori-negative nonsteroidal anti-inflammatory drug-caused duodenal ulcers.	2003	12640531
Premedication with cyclooxygenase-2 inhibitor meloxicam reduced postoperative pain in patients after oral surgery.	2006 Jul	16540287
3-Benzoyl-4-hydr-oxy-2-methyl-2H-1,2-benzothia-zine 1,1-dioxide.	2010 Mar 27	21580768

Patents

Sample Use Guides

In Vivo Use Guide

in rats: ED50 of 28 mg/kg at single oral dose and 7.8 mg/kg at 5 daily oral dose

Route of Administration: Oral

In Vitro Use Guide

Ampiroxicam (50 μM) results in decreased expression of Sp1, Sp3, Sp4, and VEGFR1 proteins in Panc-1 cells and L3.6pl cells as determined by Western blot analysis. Ampiroxicam (50 μM) results in increased phosphorylation of MAPK1/2 in Panc-1 cells and L3.6pl cells.

Name

Type

Language

AMPIROXICAM

Official Name

English

AMPIROXICAM [MI]

Common Name

English

AMPIROXICAM [MART.]

Common Name

English

(±)-4-(1-HYDROXYETHOXY)-2-METHYL-N-2-PYRIDYL-2H-1,2-BENZOTHIAZINE-3-CARBOXAMIDE ETHYL CARBONATE (ESTER), 1,1-DIOXIDE

Common Name

English

CP-65703

Code

English

CP-65,703

Code

English

NSC-759807

Code

English

FLUCAM

Brand Name

English

Ampiroxicam [WHO-DD]

Common Name

English

ampiroxicam [INN]

Common Name

English

AMPIROXICAM [JAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C257