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=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

Molecular Formula	C24H19N3O5S
Molecular Weight	461.49
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

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
[Clinical pharmacology of non-steroidal anti-inflammatory drugs. A new benzothiazine derivative: cinnoxicam].	1988 Sep	3050617
[Analgesic activity of cinnoxicam. Findings of clinical sensimetry].	1989 Dec 15	2532585
[Combined clinico-thermographic findings for the evaluation of a topical anti-inflammatory agent. Study of cinnoxicam cream].	1991 Jul-Aug	1922894
[Correlation of the lipophilicity of the active agents with their topical anti-inflammatory activity].	1992 Jul-Aug	1476697
Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents.	1994 Feb	8162655
Contact allergy to cinnoxicam.	1995 Jan	7720389
[In vitro effects of L-carnitine on the inhibition of sperm mobility induced by FANS].	2000 May-Jun	10958050
Medical therapy of oligoasthenospermia associated with left varicocele.	2003 Apr	12656905
Cinnoxicam and L-carnitine/acetyl-L-carnitine treatment for idiopathic and varicocele-associated oligoasthenospermia.	2004 Sep-Oct	15292108
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	17592742
Reduction in sperm aneuploidy levels in severe oligoasthenoteratospermic patients after medical therapy: a preliminary report.	2012 Jul	22543677

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:49:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:49:14 GMT 2023`
Record UNII	7E8Q32N75N
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PIROXICAM CINNAMATE

Official Name

English

PIROXICAM CINNAMIC ACID ESTER

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

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Code System Code Type Description

CAS

87234-24-0

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EVMPD

SUB14900MIG

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RXCUI

33787

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RxNorm

EPA CompTox

DTXSID10236212

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MERCK INDEX

m8889

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Merck Index

USAN

W-149

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ChEMBL

CHEMBL2106889

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MESH

C057291

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NCI_THESAURUS

C73032

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DRUG CENTRAL

655

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FDA UNII

7E8Q32N75N

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SMS_ID

100000079144

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PUBCHEM

6436090

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