U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of PIROXICAM CINNAMATE

SMILES

CN1C(C(=O)NC2=CC=CC=N2)=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
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.

Approval Year

PubMed

PubMed

TitleDatePubMed
[Clinical pharmacology of non-steroidal anti-inflammatory drugs. A new benzothiazine derivative: cinnoxicam].
1988 Sep
[Clinical evaluation of cinnoxicam 30 mg in patients with osteoarthrosis. A double-blind controlled study].
1996 Mar
Male idiopathic oligoasthenoteratozoospermia.
2006 Mar
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 Aug
Patents
Name Type Language
PIROXICAM CINNAMATE
USAN   WHO-DD  
USAN  
Official Name English
PIROXICAM CINNAMIC ACID ESTER
MI  
Common 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
Created by admin on Fri Dec 15 15:49:15 GMT 2023 , Edited by admin on Fri Dec 15 15:49:15 GMT 2023
Code System Code Type Description
CAS
87234-24-0
Created by admin on Fri Dec 15 15:49:14 GMT 2023 , Edited by admin on Fri Dec 15 15:49:14 GMT 2023
PRIMARY
EVMPD
SUB14900MIG
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PRIMARY
RXCUI
33787
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PRIMARY RxNorm
EPA CompTox
DTXSID10236212
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PRIMARY
MERCK INDEX
m8889
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PRIMARY Merck Index
USAN
W-149
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PRIMARY
ChEMBL
CHEMBL2106889
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PRIMARY
MESH
C057291
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PRIMARY
NCI_THESAURUS
C73032
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PRIMARY
DRUG CENTRAL
655
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FDA UNII
7E8Q32N75N
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PRIMARY
SMS_ID
100000079144
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PRIMARY
PUBCHEM
6436090
Created by admin on Fri Dec 15 15:49:15 GMT 2023 , Edited by admin on Fri Dec 15 15:49:15 GMT 2023
PRIMARY