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36322-90-4 molecular structure
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4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1$l^{6},2-benzothiazine-3-carboxamide

ChemBase ID: 72791
Molecular Formular: C15H13N3O4S
Molecular Mass: 331.34642
Monoisotopic Mass: 331.06267691
SMILES and InChIs

SMILES:
c1cnc(cc1)NC(=O)C1=C(c2c(S(=O)(=O)N1C)cccc2)O
Canonical SMILES:
O=C(C1=C(O)c2ccccc2S(=O)(=O)N1C)Nc1ccccn1
InChI:
InChI=1S/C15H13N3O4S/c1-18-13(15(20)17-12-8-4-5-9-16-12)14(19)10-6-2-3-7-11(10)23(18,21)22/h2-9,19H,1H3,(H,16,17,20)
InChIKey:
QYSPLQLAKJAUJT-UHFFFAOYSA-N

Cite this record

CBID:72791 http://www.chembase.cn/molecule-72791.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1$l^{6},2-benzothiazine-3-carboxamide
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ6,2-benzothiazine-3-carboxamide
IUPAC Traditional name
piroxicam
4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ6,2-benzothiazine-3-carboxamide
Brand Name
Feldene
Synonyms
Feldene
Roxam
Piroxicam
4-Hydroxy-2-methyl-3[pyrid-2-yl-carbamoyl]-2H-1,2-benzothiazine 1,1-dioxide
4-Hydroxy-2-methyl-3-(pyrid-2-yl-carbamoyl)-2H-1,2-benzothiazine 1,1-dioxide
Piroxicam
4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide
Artroxicam
Baxo
Bruxicam
CHF 1251
CP 16171
Caliment
Roxicam
Roxiden
Sasulen
Solocalm
Brexin
Cycladol
Fasax
Flamatrol
Improntal
Larapam
Piroflam
Pirox
Pirozip
Reudene;
4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide
2-甲基-4-羟基-N-(2-吡啶基)-2H-1,2-苯并噻嗪-3-甲酰胺-1,1-二氧化物
吡罗昔康
CAS Number
36322-90-4
EC Number
252-974-3
MDL Number
MFCD00057317
PubChem SID
162037712
24898132
24278641
PubChem CID
54676228
5280452
CHEBI ID
8249
ATC CODE
M01AC01
M02AA07
S01BC06
CHEMBL
527
Chemspider ID
10442653
DrugBank ID
DB00554
KEGG ID
D00127
Unique Ingredient Identifier
13T4O6VMAM
Wikipedia Title
Piroxicam
Medline Plus
a684045

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 4.7604237  H Acceptors
H Donor LogD (pH = 5.5) 0.033200305 
LogD (pH = 7.4) -1.5190158  Log P 0.59988385 
Molar Refractivity 87.0435 cm3 Polarizability 32.634167 Å3
Polar Surface Area 99.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Ethyl Acetate expand Show data source
Apperance
Off-White to Pale Yellow Solid expand Show data source
Melting Point
198-200°C expand Show data source
198-200°C expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
2-8°C expand Show data source
RTECS
DL0705000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
26-36 expand Show data source
S:36/37/39 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301 expand Show data source
GHS Precautionary statements
P301 + P310 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Target
COX expand Show data source
Admin Routes
PO expand Show data source
Excretion
4 to 10% renal expand Show data source
Half Life
30 to 86 hours expand Show data source
Metabolism
4 to 10% renal expand Show data source
Legal Status
POM expand Show data source
Pregnancy Category
C, D if used in the third trimester or near delivery expand Show data source
Gene Information
human ... PTGS1(5742), PTGS2(5743)rat ... Alox5(25290) expand Show data source
Mechanism of Action
Piroxicam also inhibits the migration of leukocytes into sites of inflammation and prevents the formation of thromboxane A2, an aggregating agent, by the platelets expand Show data source
Piroxicam blocks the Cox-1 enzyme, resulting into the disruption of production of prostaglandins. expand Show data source
Reversible inhibitor of cyclooxygenase, causing the peripheral inhibition of prostaglandin synthesis. expand Show data source
The prostaglandins are produced by an enzyme called Cox-1. expand Show data source
Purity
≥98% (TLC) expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Suitability
meets USP testing specifications expand Show data source
Application(s)
Antiinflammatory agent expand Show data source
Empirical Formula (Hill Notation)
C15H13N3O4S expand Show data source

DETAILS

DETAILS

Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia TRC TRC MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich
Selleck Chemicals - S1713 external link
Research Area: Inflammtion
Biological Activity:
Piroxicam (Feldene) is a non-selective COX inhibitor with an IC50 of 6 mM. It is a non-steroidal anti-inflammatory drug used to relieve the symptoms of rheumatoid and osteoarthritis, primary dysmenorrhoea, postoperative pain; and acts as an analgesic, especially where there is an inflammatory component. [1][2]References on Piroxicam (Feldene)[] Life Sciences , 2003, 73:333–1346
Toronto Research Chemicals - P510000 external link
Non-steroidal anti-inflammatory with long half-life. Cyclooxygenase inhibitor. Clinically useful NSAID.
MP Biomedicals - 02156277 external link
Cyclooxygenase inhibitor
Sigma Aldrich - P5654 external link
Biochem/physiol Actions
Cyclooxygenase inhibitor.
Non-steroidal anti-inflamatory agent (NSAID) shown to be effective in the prevention of colon cancer.
Sigma Aldrich - P0847 external link
Biochem/physiol Actions
Cyclooxygenase inhibitor.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
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  • • Brogden, R.N., et al.: Drugs, 22, 165 (1980)
  • • Mihalic, M., et al.: Anal. Profiles Drug Subs., 15, 509 (1980)
  • • Laneauville., O., et al.: J. Pharmacol. Exp. Ther., 271, 927 (1980)
  • • Lombardino, J.G. et al., J. Med. Chem., 1973, 16, 493, (synth, pharmacol)
  • • Whipple, E.B., Org. Magn. Reson., 1977, 10, 23, (cmr)
  • • Wiseman, E.H. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 524, (rev, pharmacol)
  • • Kojic-Prodic, B. et al., Acta Cryst. B, 1982, 38, 2948, (cryst struct)
  • • Bordner, J. et al., Acta Cryst. C, 1984, 40, 989, (cryst struct)
  • • Bernhard, E. et al., Arzneim.-Forsch., 1984, 34, 647, (pKa)
  • • Brogden, R.N. et al., Drugs, 1984, 28, 292, (rev, pharmacol)
  • • U.S. Pat., 1984, 4 434 164; CA, 100, 191894, (salts)
  • • Mihalic, M. et al., Anal. Profiles Drug Subst., 1986, 15, 509, (rev, synth, anal)
  • • Svoboda, J. et al., Coll. Czech. Chem. Comm., 1986, 51, 1133, (synth)
  • • Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (props)
  • • Lee, C.R. et al., Drugs, 1994, 48, 907, (rev)
  • • Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4443, (synonyms)
  • • Takcs-Novk, K. et al., Helv. Chim. Acta, 1995, 78, 553, (props, bibl)
  • • Maya, M.T. et al., J. Pharm. Biomed. Anal., 1995, 13, 319; 785, (hplc)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 80
  • •  Oyanagui Y et al. Life Sci. 2003 Jul 25; 73(10)
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PATENTS

PATENTS

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INTERNET

INTERNET

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