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

Molecular Formula	C20H21N3O7S
Molecular Weight	447.462
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/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
Preoperative ampiroxicam reduces postoperative pain after hand surgery.	2001 Aug	11469844
Randomized clinical trial of primary treatment for temporomandibular joint disk displacement without reduction and without osseous changes: a combination of NSAIDs and mouth-opening exercise versus no treatment.	2001 Jun	11402280
[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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:37:06 GMT 2023` Edited by `admin` on `Fri Dec 15 15:37:06 GMT 2023`
Record UNII	0PV32JZB1J
Record Status	`Validated (UNII)`
Record Version

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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