CAS 36322-90-4|piroxicam| Feldene|Roxam|Piroxicam|4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1$l^{6},2-benzothiazine-3-carboxamide|Sasulen|Roxicam|Bruxicam|Roxiden|4-Hydroxy-2-methyl-N-2-pyrid...

General Information

Structure

Molecular Formula

C₁₅H₁₃N₃O₄S

Molecular Mass

331.34642

Exact Mass

331.06267691

Charge

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

Canonic Smiles

O=C(C1=C(O)c2ccccc2S(=O)(=O)N1C)Nc1ccccn1

Isomeric Smiles

c1cnc(cc1)NC(=O)C1=C(c2c(S(=O)(=O)N1C)cccc2)O

Calculated Properties

JChem

LogD (pH = 7.4)

-1.28

LogD (pH = 5.5)

0.35

Log P

0.67

Rotatable Bonds

H Donor

H Acceptors

Lipinski's Rule of Five

true

Acid pKa

5.06

Polar Surface Area

99.60

Polarizability

32.19

Molar Refractivity

87.04

LOG S

-3.27

Data Source

Names and Identifiers

Synonyms

FeldeneRoxamPiroxicamSasulenCP 16171BruxicamRoxidenBaxoRoxicamArtroxicamCalimentCHF 1251Solocalm4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxideReudene;LarapamCycladolFasaxFlamatrolPiroflamBrexinPiroxicamPirozipPiroxImprontal4-Hydroxy-2-methyl-3-(pyrid-2-yl-carbamoyl)-2H-1,2-benzothiazine 1,1-dioxide2-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4-Hydroxy-2-methyl-3[pyrid-2-yl-carbamoyl]-2H-1,2-benzothiazine 1,1-dioxide吡罗昔康piroxicam4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxidPyroxycamPiroxicam

IUPAC Traditional name

piroxicam 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-1lambda6,2-benzothiazine-3-carboxamide

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 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide

Brand Name

FeldeneFELDENE

International Nonproprietary Name (INN)

piroxicampiroxicamum

Names and Identifiers

Registration numbers

PubChem SID

242786411620377122489813257304811

CAS Number

EC Number

MDL Number

KEGG ID

Medline Plus

Unique Ingredient Identifier

13T4O6VMAM

CHEBI ID

8249CHEBI:8249

ATC CODE

S01BC06M02AA07M01AC01

Wikipedia Title

Chemspider ID

CHEMBL

PubChem CID

DrugBank ID

KEGG DRUG Database

BRENDA Database

5.3.2.12.8.2.11.14.99.12.1.1.677.2.2.192.8.2.41.1.1.1882.7.11.11

SureChEMBL Database

SCHEMBL13462

Drug Central Database

2,210

Patent number

DE1943265US3591584

BRENDA Ligand Database

BKMS React Database

Beilstein Number

BindingDB Database

PubMed Citation Links

111424132816621712154043

Reaxys Registry

627692

ACToR Database

36322-90-4

CompTox Database

DTXSID5021170

MetaboLights Database

MTBLS2267

HMDB Database

HMDB0014694

Registration numbers

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C15H13N3O4S

Suitability

meets USP testing specifications

Purity

≥98% (TLC)

95+%

Application(s)

Antiinflammatory agent

Physical Property

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Selleck Chemicals

S1713

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

MP Biomedicals

02156277

Cyclooxygenase inhibitor

Wikipedia

Piroxicam

Sigma Aldrich

P0847

Biochem/physiol Actions
Cyclooxygenase inhibitor.

P5654

Biochem/physiol Actions
Cyclooxygenase inhibitor.
Non-steroidal anti-inflamatory agent (NSAID) shown to be effective in the prevention of colon cancer.

TRC

P510000

Non-steroidal anti-inflammatory with long half-life. Cyclooxygenase inhibitor. Clinically useful NSAID.

ChEBI

CHEBI:8249

A monocarboxylic acid amide resulting from the formal condensation of the carboxy group of 4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxylic acid 1,1-dioxide with the exocyclic nitrogen of 2-aminopyridine. A non-steroidal anti-inflammatory drug of the oxicam class, it is used to relieve pain and works by preventing the production of endogenous prostaglandins involved in the mediation of pain, stiffness, tenderness and swelling.

Molecule Details

References

PubChem Literature

From Data Sources

• Oyanagui Y et al. Life Sci. 2003 Jul 25; 73(10)

• Brogden, R.N., et al.: Drugs, 22, 165 (1980)

• Carty, T.J., et al.: Prostaglandins, 47, 55 (1980)

• Mihalic, M., et al.: Anal. Profiles Drug Subs., 15, 509 (1980)

• Laneauville., O., et al.: J. Pharmacol. Exp. Ther., 271, 927 (1980)

• Bernhard, E. et al., Arzneim.-Forsch., 1984, 34, 647, (pKa)

• Takcs-Novk, K. et al., Helv. Chim. Acta, 1995, 78, 553, (props, bibl)

• Brogden, R.N. et al., Drugs, 1984, 28, 292, (rev, pharmacol)

• Mihalic, M. et al., Anal. Profiles Drug Subst., 1986, 15, 509, (rev, synth, anal)

• Lee, C.R. et al., Drugs, 1994, 48, 907, (rev)

• Lombardino, J.G. et al., J. Med. Chem., 1973, 16, 493, (synth, pharmacol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4443, (synonyms)

• Maya, M.T. et al., J. Pharm. Biomed. Anal., 1995, 13, 319; 785, (hplc)

• U.S. Pat., 1984, 4 434 164; CA, 100, 191894, (salts)

• Wiseman, E.H. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 524, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 80

• Whipple, E.B., Org. Magn. Reson., 1977, 10, 23, (cmr)

• 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)

• Svoboda, J. et al., Coll. Czech. Chem. Comm., 1986, 51, 1133, (synth)

• Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (props)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

Synonyms

IUPAC Traditional name

piroxicam 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-2H-1λ⁶,2-benzothiazine-3-carboxamide 4-hydroxy-2-methyl-1,1-dioxo-N-(pyridin-2-yl)-1lambda6,2-benzothiazine-3-carboxamide

IUPAC name

Brand Name

FeldeneFELDENE

International Nonproprietary Name (INN)

piroxicampiroxicamum

Registration numbers

PubChem SID

242786411620377122489813257304811

CAS Number

EC Number

MDL Number

KEGG ID

Medline Plus

Unique Ingredient Identifier

13T4O6VMAM

CHEBI ID

8249CHEBI:8249

ATC CODE

S01BC06M02AA07M01AC01

Wikipedia Title

Chemspider ID

CHEMBL

PubChem CID

DrugBank ID

KEGG DRUG Database

BRENDA Database

5.3.2.12.8.2.11.14.99.12.1.1.677.2.2.192.8.2.41.1.1.1882.7.11.11

SureChEMBL Database

SCHEMBL13462

Drug Central Database

2,210

Patent number

DE1943265US3591584

BRENDA Ligand Database

BKMS React Database

Beilstein Number

BindingDB Database

PubMed Citation Links

111424132816621712154043

Reaxys Registry

627692

ACToR Database

36322-90-4

CompTox Database

DTXSID5021170

MetaboLights Database

MTBLS2267

HMDB Database

HMDB0014694

Properties

Product Information

Salt Data

Free Base

Certificate of Analysis

Download link

Empirical Formula (Hill Notation)

C15H13N3O4S

Suitability

meets USP testing specifications

Purity

≥98% (TLC)

95+%

Application(s)

Antiinflammatory agent

Physical Property

Molecule Details

Selleck Chemicals

S1713

MP Biomedicals

02156277

Cyclooxygenase inhibitor

Wikipedia

Piroxicam

Sigma Aldrich

P0847

Biochem/physiol Actions
Cyclooxygenase inhibitor.

P5654

Biochem/physiol Actions
Cyclooxygenase inhibitor.
Non-steroidal anti-inflamatory agent (NSAID) shown to be effective in the prevention of colon cancer.

TRC

P510000

Non-steroidal anti-inflammatory with long half-life. Cyclooxygenase inhibitor. Clinically useful NSAID.

ChEBI

CHEBI:8249

References

PubChem Literature

From Data Sources

• Oyanagui Y et al. Life Sci. 2003 Jul 25; 73(10)

• Brogden, R.N., et al.: Drugs, 22, 165 (1980)

• Carty, T.J., et al.: Prostaglandins, 47, 55 (1980)

• Mihalic, M., et al.: Anal. Profiles Drug Subs., 15, 509 (1980)

• Laneauville., O., et al.: J. Pharmacol. Exp. Ther., 271, 927 (1980)

• Bernhard, E. et al., Arzneim.-Forsch., 1984, 34, 647, (pKa)

• Takcs-Novk, K. et al., Helv. Chim. Acta, 1995, 78, 553, (props, bibl)

• Brogden, R.N. et al., Drugs, 1984, 28, 292, (rev, pharmacol)

• Mihalic, M. et al., Anal. Profiles Drug Subst., 1986, 15, 509, (rev, synth, anal)

• Lee, C.R. et al., Drugs, 1994, 48, 907, (rev)

• Lombardino, J.G. et al., J. Med. Chem., 1973, 16, 493, (synth, pharmacol)

• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 4443, (synonyms)

• Maya, M.T. et al., J. Pharm. Biomed. Anal., 1995, 13, 319; 785, (hplc)

• U.S. Pat., 1984, 4 434 164; CA, 100, 191894, (salts)

• Wiseman, E.H. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 524, (rev, pharmacol)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 80

• Whipple, E.B., Org. Magn. Reson., 1977, 10, 23, (cmr)

• 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)

• Svoboda, J. et al., Coll. Czech. Chem. Comm., 1986, 51, 1133, (synth)

• Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (props)

Bioactivity

PubChem BioAssay

Molecule

ID:72791