Substance Name: Piroxicam [USAN:USP:INN:BAN:JAN]
RN: 36322-90-4
InChIKey: QYSPLQLAKJAUJT-UHFFFAOYSA-N

Note

  • A cyclooxygenase inhibiting, non-steroidal anti-inflammatory agent (NSAID) that is well established in treating rheumatoid arthritis and osteoarthritis and used for musculoskeletal disorders, dysmenorrhea, and postoperative pain. Its long half-life enables it to be administered once daily.

Molecular Formula

  • C15-H13-N3-O4-S

Molecular Weight

  • 331.3507
2D chemical structure of 36322-90-4
 

Classification Codes

  • Analgesics
  • Analgesics, Non-Narcotic
  • Anti-inflammatory
  • Anti-Inflammatory Agents
  • Anti-inflammatory agents, non-steroidal
  • Antirheumatic Agents
  • Cyclooxygenase inhibitors
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Human Data
  • Peripheral Nervous System Agents
  • Reproductive Effect
  • Sensory System Agents

Names and Synonyms

Name of Substance

  • Piroxicam
  • Piroxicam [USAN:USP:INN:BAN:JAN]

MeSH Heading

  • Piroxicam

Synonyms

  • 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid
  • 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid [German]
  • 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
  • 4-Hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
  • BAXO
  • BRN 0627692
  • CCRIS 3719
  • CHF 1251
  • CP 16171
  • CP-16,171
  • EINECS 252-974-3
  • Feldene
  • NSC 666076
  • Piroftal
  • Piroxicam
  • Piroxicamum
  • Piroxicamum [INN-Latin]
  • Pyroxycam
  • Rosiden
  • Roxicam
  • UNII-13T4O6VMAM

Systematic Names

  • 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide
  • Piroxicam

Registry Numbers

CAS Registry Number

  • 36322-90-4

System Generated Number

  • 0036322904

Structure Descriptors

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

Smiles

CN1C(=C(c2ccccc2S1(=O)=O)O)C(=O)Nc3ccccn3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 7143ug/kg (7.143mg/kg) BLOOD: APLASTIC ANEMIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
South African Medical Journal. Vol. 66, Pg. 31, 1984.
dog LD50 oral 108mg/kg (108mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
guinea pig LD50 oral 388mg/kg (388mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
Link to PubMed
hamster LD50 oral 170mg/kg (170mg/kg)   Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
Link to PubMed
man LDLo oral 3714mg/kg/13D (3714mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, ALLERGIC: AFTER SYSTEMIC EXPOSURE"

BLOOD: AGRANULOCYTOSIS
New England Journal of Medicine. Vol. 309, Pg. 795, 1983.
man TDLo oral 52mg/kg/26W-I (52mg/kg)   Annals of Internal Medicine. Vol. 99, Pg. 282, 1983.
man TDLo oral 7636mg/kg/6W- (7636mg/kg) KIDNEY, URETER, AND BLADDER: INTERSTITIAL NEPHRITIS American Journal of Nephrology. Vol. 5, Pg. 142, 1985.
Link to PubMed
monkey LD50 oral 1gm/kg (1000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
mouse LD50 intraperitoneal 290mg/kg (290mg/kg)   Russian Pharmacology and Toxicology Vol. 49, Pg. 98, 1986.
mouse LD50 oral 250mg/kg (250mg/kg)   European Patent Application. Vol. #0079639,
mouse LD50 subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
rat LD50 intraperitoneal 335mg/kg (335mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
rat LD50 oral 216mg/kg (216mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1714, 1978.
Link to PubMed
rat LD50 rectal 400mg/kg (400mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 87, 1981.
Link to PubMed
rat LD50 rectal 400mg/kg (400mg/kg) BEHAVIORAL: ANALGESIA Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 87, 1981.
Link to PubMed
rat LD50 skin > 5gm/kg (5000mg/kg)   Yakkyoku. Pharmacy. Vol. 37(11), Pg. -, 1986.
rat LD50 subcutaneous 148mg/kg (148mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
women LDLo oral 2400ug/kg (2.4mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"
British Medical Journal. Vol. 293, Pg. 540, 1986.
Link to PubMed
women TDLo oral 400ug/kg (.4mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Allergy. Vol. 52(Suppl,
women TDLo oral 1200ug/kg/3D- (1.2mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE" Journal of Rheumatology. Vol. 11, Pg. 554, 1984.
Link to PubMed
women TDLo oral 28mg/kg (28mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM DUODENUM

BEHAVIORAL: HEADACHE
Acta Medica Scandinavica. Vol. 216, Pg. 335, 1984.
Link to PubMed

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 198-200 deg C   EXP
pKa Dissociation Constant 6.3 (none)   EXP
log P (octanol-water) 3.06 (none)   EXP
Water Solubility 23 mg/L 22 EXP
Vapor Pressure 4.67E-15 mm Hg 25 EST
Henry's Law Constant 2.90E-19 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.30E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by Syracuse Research Corporation.
See all available property data for this compound, including references.