PIROXICAM CINNAMATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H19N3O5S
Molecular Weight	461.49
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1C(C(=O)NC2=NC=CC=C2)=C(OC(=O)\C=C\C3=CC=CC=C3)C4=C(C=CC=C4)S1(=O)=O

InChI

InChIKey=GPUVGQIASQNZET-CCEZHUSRSA-N

InChI=1S/C24H19N3O5S/c1-27-22(24(29)26-20-13-7-8-16-25-20)23(18-11-5-6-12-19(18)33(27,30)31)32-21(28)15-14-17-9-3-2-4-10-17/h2-16H,1H3,(H,25,26,29)/b15-14+

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2067714 | https://www.ncbi.nlm.nih.gov/pubmed/12656905 | https://adisinsight.springer.com/drugs/800008127 | Negwer, M., Scharnow, H.-G. (2001) Organic-chemical drugs and their synonyms, page 2491, retrieved from: https://books.google.ru/books?id=zmpqAAAAMAAJ

Piroxicam cinnamate (Cinnoxicam) is the anti-inflammatory agent. It is a cyclooxygenase inhibitor. Cinnoxicam was used in patients with inflammatory-degenerative osteoarticular diseases. The treatment brought about a significant improvement in the clinical variables considered (spontaneous pain at rest and on movement and functional limitation), which was observed within a few days of starting therapy. Tolerance was good, only a few slight side-effects having been reported. Cinnoxicam is a safe and reliable therapeutic option for men with oligoasthenospermia associated with a grade III varicocele, but surgery is better for those with grade II, IV and V. Piroxicam cinnamate as a long-acting prodrug is marketed by SPA in Italy for the treatment of rheumatic disorders.

Originator

Approval Year

PubMed

Title	Date	PubMed
Reduction in sperm aneuploidy levels in severe oligoasthenoteratospermic patients after medical therapy: a preliminary report.	2012-07	22543677
Unusual coordinating behavior by three non-steroidal anti-inflammatory drugs from the oxicam family towards copper(II). Synthesis, X-ray structure for copper(II)-isoxicam, -meloxicam and -cinnoxicam-derivative complexes, and cytotoxic activity for a copper(II)-piroxicam complex.	2007-08	17592742
Male idiopathic oligoasthenoteratozoospermia.	2006-03	16491265
Cinnoxicam and L-carnitine/acetyl-L-carnitine treatment for idiopathic and varicocele-associated oligoasthenospermia.	2004-08-05	15292108
Medical therapy of oligoasthenospermia associated with left varicocele.	2003-04	12656905
[In vitro effects of L-carnitine on the inhibition of sperm mobility induced by FANS].	2000-08-25	10958050
Stability study of piroxicam and cinnoxicam in solid pharmaceuticals.	1999-06	10704033
[Clinical evaluation of 30 mg cinnoxicam in patients with osteoarthrosis. Double blind controlled trial].	1996-04	8700339
[Clinical evaluation of cinnoxicam 30 mg in patients with osteoarthrosis. A double-blind controlled study].	1996-03	8668288
Contact allergy to cinnoxicam.	1995-01	7720389
Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents.	1994-02	8162655
[Correlation of the lipophilicity of the active agents with their topical anti-inflammatory activity].	1992-07-01	1476697
[Combined clinico-thermographic findings for the evaluation of a topical anti-inflammatory agent. Study of cinnoxicam cream].	1991-07-01	1922894
[Evaluation of a new non-steroidal anti-inflammatory agent in degenerative osteo-articular pathology].	1991-06	2067714
[Analgesic activity of cinnoxicam. Findings of clinical sensimetry].	1989-12-15	2532585
[Clinical pharmacology of non-steroidal anti-inflammatory drugs. A new benzothiazine derivative: cinnoxicam].	1988-09	3050617

Patents

Name

Type

Language

PIROXICAM CINNAMIC ACID ESTER

Preferred Name

English

PIROXICAM CINNAMATE

Official Name

English

SPA-S-510

Code

English

PIROXICAM CINNAMATE [USAN]

Common Name

English

SPA-S-51O

Code

English

4-Hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide, cinnamate (ester)

Systematic Name

English

Piroxicam cinnamate [WHO-DD]

Common Name

English

PIROXICAM CINNAMIC ACID ESTER [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1323