Drug

D0099 | Piroxicam

Molecular Formula C15H13N3O4S
Molecular Weight 331.3
Structure
State solid
Volume of distribution * 0.14 L/kg
Route of elimination Piroxicam and its biotransformation products are excreted in urine and feces, with about twice as much appearing in the urine as in the feces. Approximately 5% of a piroxicam dose is excreted unchanged. However, a substantial portion of piroxicam elimination occurs by hepatic metabolism. Piroxicam is excreted into human milk.
Half life 30 to 86 hours
Absorption Well absorbed following oral administration.
Trade names Feldene
Description nonsteroidal anti-inflammatory drug of the oxicam class

S

M

S01BC06 Piroxicam


[S01BC] Antiinflammatory agents, non-steroids


[S01B] ANTIINFLAMMATORY AGENTS


[S01] OPHTHALMOLOGICALS


[S] Sensory organs


M02AA07 Piroxicam


[M02AA] Antiinflammatory preparations, non-steroids for topical use


[M02A] TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN


[M02] TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN


[M] Musculoskeletal system


M01AC01 Piroxicam


[M01AC] Oxicams


[M01A] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS


[M01] ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS


[M] Musculoskeletal system


Toxicity Dose Time Species Model Method Action Positive criterion Reference
TRANSMEMBRANE POTENTIAL 796 24hr rat hepatocytes tetramethylrhodamine ethyl ester (TMRE) decrease AC50 (μM) 40
MEMBRANE POTENTIAL 8.21±1.71 human qHTS-HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 5.88 human HepG2 MMP assay decrease IC50 163
MEMBRANE POTENTIAL 4.79±1.53 rat hepatocytes MMP assay decrease IC50 163
MEMBRANE POTENTIAL 101.7 µM 30 mins mouse liver mitochondria Rh123 fluorescence (excitation 485 nm, emission 535 nm) are recorded using a fluorescence multi-well plate reader (mCICCP (20 µM) treatments was considered as the 100% baseline for ΔΨm loss) decrease EC20 36
RESPIRATION 224.5 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. decrease EC20 36
RESPIRATION 6.6 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. decrease EC20 36
STATE 2 RESPIRATION 69.0 ± 7.2 rat isolated rat liver mitochondria State 2 respiration ( 96-well plate format using a phosphorescent oxygen-sensitive probe MitoXpress) inhibit UC50 (nmol/mg mitochondrial protein) 40
STATE 3 RESPIRATION 100 nmol/mg mitochondrial protein rat isolated rat liver mitochondria State 3 respiration ( 96-well plate format using a phosphorescent oxygen-sensitive probe MitoXpress) Negative IC50 (nmol/mg mitochondrial protein) 40
LIPID METABOLISM 728 24hr rat hepatocytes LipidTox, for neutral lipid accumulation, to evaluate lipid content. accumulation AC50 (μM) 40
GLUTATHIONE METABOLISM NR 24hr rat hepatocytes glutathion depletion: cells were incubated with 50 μM monochlorobimane with 6 μg/ml Hoechst 33342 Negative AC50 (μM) 40
SWELLING > 200 µM 30 mins mouse liver mitochondria swelling assay: Absorbance at 545 nm using a fluorescence multi-well plate reader (CaCl2 (50 µM) was considered as the 100% baseline for the swelling ) increase EC20 36
ROS PRODUCTION NR rat hepatocytes use CM-H2DCFDA to monitor reactive oxygen species Negative AC50 (μM) 40
CYTOCHROME C RELEASE 598 24hr rat hepatocytes cytochrome c release (anti-cytochrome c antibody ) induce AC50 (μM) 40
ER STRESS-INDUCED 610 24hr rat hepatocytes DNA damage 153 induction (GADD153 antibodies) for ER-stress induced apoptosis induce AC50 (μM) 40

Target Dose Time Species Model Method Action Positive criterion Reference
NADH:ubiquinone reductase 224.5 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Rotenone (2µM) was used as 100% baseline for complex I inhibition. inhibit EC20 36
Succinate dehydrogenase 6.6 µM 60 mins mouse liver mitochondria Oxygen consumption was monitored with 50nM MitoXpress ( an oxygen-sensitive phosphorescent dye) using a spectrofluorimeter (Tecan Infinite 200; λExcitation 380nm; λEmission 650nm). Oligomycin A (1µM) was used as 100% baseline for complex II inhibition. inhibit EC20 36
Cytochrome c > 200 µM 30 mins mouse liver mitochondria Cytochrome c release was evaluated using ELISA kit ( 20 µg/ml Alamethicin was used as 100% baseline) release EC20 36

Pictogram Signal Statements Precautionary Statement Codes
Danger

Aggregated GHS information provided by 168 companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.


H301 (98.81%): Toxic if swallowed [Danger Acute toxicity, oral]


H360 (51.19%): May damage fertility or the unborn child [Danger Reproductive toxicity]


H372 (51.79%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]


Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.


P201, P202, P260, P264, P270, P281, P301+P310, P308+P313, P314, P321, P330, P405, and P501; (The corresponding statement to each P-code can be found at the GHS Classification page.)

Organism Test type Route Dose (normalized dose) Effect Source
mouse LD50 subcutaneous 238mg/kg (238mg/kg) Journal of Medicinal Chemistry. Vol. 28, Pg. 714, 1985.
dog LD50 oral 108mg/kg (108mg/kg) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
man TDLo oral 52mg/kg/26W-I (52mg/kg) Annals of Internal Medicine. Vol. 99, Pg. 282, 1983.
mouse LD50 intravenous 20mg/kg (20mg/kg) Journal of Pharmacology and Experimental Therapeutics. Vol. 123, Pg. 269, 1958.
rabbit LDLo intravenous 41mg/kg (41mg/kg) Acta Pharmacologica et Toxicologica. Vol. 31, Pg. 273, 1972.
rat LD50 oral 216mg/kg (216mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 28, Pg. 1714, 1978.
child TDLo oral 300mg/kg/5D-I (300mg/kg) Pediatric Emergency Care. Vol. 10, Pg. 344, 1994.
women TDLo oral 400ug/kg (0.4mg/kg) skin and appendages (skin): "dermatitis, other: after systemic exposure" Allergy. Vol. 52(Suppl,
rat LD50 rectal 400mg/kg (400mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 87, 1981.
rat LD50 skin > 5gm/kg (5000mg/kg) Yakkyoku. Pharmacy. Vol. 37(11), Pg. -, 1986.
guinea pig LDLo intravenous 65mg/kg (65mg/kg) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 130, Pg. 235, 1961.
hamster LD50 oral 170mg/kg (170mg/kg) Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
rat LD50 rectal 400mg/kg (400mg/kg) behavioral: analgesia Arzneimittel-Forschung. Drug Research. Vol. 31, Pg. 87, 1981.
man TDLo intravenous 1700ug/kg/2M- (1.7mg/kg) American Journal of Emergency Medicine. Vol. 4, Pg. 143, 1986.
mouse LD50 oral 220mg/kg (220mg/kg) Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
rat LD50 intravenous 18mg/kg (18mg/kg) United States Patent Document. Vol. #5264432,
man TDLo oral 7636mg/kg/6W- (7636mg/kg) kidney, ureter, and bladder: interstitial nephritis American Journal of Nephrology. Vol. 5, Pg. 142, 1985.
guinea pig LD50 oral 388mg/kg (388mg/kg) Archives of Toxicology, Supplement. Vol. 7, Pg. 365, 1984.
rat LD50 unreported 39400ug/kg (39.4mg/kg) Farmakologiya i Toksikologiya Vol. 54(3), Pg. 32, 1991.
rat LD50 intraperitoneal 335mg/kg (335mg/kg) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
man LDLo oral 3714mg/kg/13D (3714mg/kg) New England Journal of Medicine. Vol. 309, Pg. 795, 1983.
mouse LD50 oral 250mg/kg (250mg/kg) European Patent Application. Vol. #0079639,
women TDLo oral 39mg/kg (39mg/kg) New England Journal of Medicine. Vol. 306, Pg. 381, 1982.
rat LD50 subcutaneous 335mg/kg (335mg/kg) European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 188, 1974.
rat LD50 subcutaneous 148mg/kg (148mg/kg) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
women LDLo oral 2400ug/kg (2.4mg/kg) British Medical Journal. Vol. 293, Pg. 540, 1986.
mouse LD50 intraperitoneal 290mg/kg (290mg/kg) Russian Pharmacology and Toxicology Vol. 49, Pg. 98, 1986.
rat LD50 intraperitoneal 133mg/kg (133mg/kg) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 243, Pg. 97, 1980.
mouse LD50 subcutaneous 300mg/kg (300mg/kg) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
child TDLo oral 21mg/kg (21mg/kg) Journal of Toxicology, Clinical Toxicology. Vol. 30, Pg. 413, 1992.
child TDLo oral 7143ug/kg (7.143mg/kg) South African Medical Journal. Vol. 66, Pg. 31, 1984.
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.
guinea pig LD50 subcutaneous 120mg/kg (120mg/kg) Farmaco, Edizione Scientifica. Vol. 10, Pg. 883, 1955.
mouse LD50 intraperitoneal 102mg/kg (102mg/kg) Journal of Medicinal Chemistry. Vol. 24, Pg. 1059, 1981.
man TDLo intravenous 8643ug/kg/4H- (8.643mg/kg) behavioral: toxic psychosis Annals of Internal Medicine. Vol. 97, Pg. 149, 1982.
human TDLo intravenous 23mg/kg (23mg/kg) Archiv fuer Toxikologie. Vol. 28, Pg. 72, 1971.
rat LD50 oral 317mg/kg (317mg/kg) Bollettino Chimico Farmaceutico. Vol. 110, Pg. 330, 1971.
monkey LD50 oral 1gm/kg (1000mg/kg) Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 8, Pg. 4639, 1980.
women TDLo oral 28mg/kg (28mg/kg) Acta Medica Scandinavica. Vol. 216, Pg. 335, 1984.
women TDLo intraspinal 1mL/kg (1mL/kg) Journal of Clinical Pyschopharmacology. Vol. 10, Pg. 442, 1990.
women TDLo intravenous 16mg/kg (16mg/kg) European Journal of Clinical Pharmacology. Vol. 22, Pg. 129, 1982.

  • Ankylosing spondylitis

  • Arthritis

  • Ligament sprain

  • Osteoarthritis

  • Rheumatoid arthritis

  • Soft tissue injury

  • Tendonitis

  • Abdominal discomfort (0.057)

  • Stomatitis (0.01)

  • (4-Hydroxy-2-methyl-1,1-dioxobenzo[e]1,2-thiazin-3-yl)-N-(2-pyridyl)carboxamide (4-hydroxy-2-methyl-1,1-dioxobenzo[e]1,2-thiazin-3-yl)-N-(2-pyridyl)carboxamid e (E)-3-(hydroxy(pyridin-2-ylamino)methylene)-2-methyl-2,3-dihydro-4H-benzo[e][1,2]thiazin-4-one 1,1-dioxide
    (Z)-3-(hydroxy(pyridin-2-ylamino)methylene)-2-methyl-2H-benzo[e][1,2]thiazin-4(3H)-one 1,1-dioxide 1044566-76-8 13T4O6VMAM
    1488516-58-0 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide 2H-1,2-Benzothiazine-3-carboxamide,4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide
    3,4-Dihydro-2-methyl-4-oxo-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 3-[hydroxy(pyridin-2-ylamino)methylidene]-2-methyl-2,3-dihydro-4h-1,2-benzothiazin-4-one 1,1-dioxide 3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2H-1$l^{6},2-benzothiazine-1,1,4-trione
    3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2H-1lambda,2-benzothiazine-1,1,4-trione 3-{hydroxy[(pyridin-2-yl)amino]methylidene}-2-methyl-3,4-dihydro-2H-1lambda6,2-benzothiazine-1,1,4-trione 322P904
    36322-90-4 4-Hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-1,2-benzothiazine 1,1-Dioxide 4-Hydroxy-2-methyl-3-(pyrid-2-yl-carbamoyl)-2H-1,2-benzothiazine 1,1-dioxide
    4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzo-thiazine-3-carboxamide1,1-dioxide 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazin-3-caboxyamid-1,1-dioxid [German]
    4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine -3-carboxamide-1,1-dioxide malonic acid 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide 4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide
    4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide 4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide1,1-dioxide
    4-Hydroxy-2-methyl-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 4-hydroxy-2-methyl-1,1-dioxo-N-(2-pyridyl)-1$l^{6},2-benzothiazine-3-carboxamide 4-hydroxy-2-methyl-1,1-dioxo-N-(2-pyridyl)-1,2-dihydro-1lambda,2-benzothiazine-3-carboxamide
    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-1?^{6},2-benzothiazine-3-carboxamide 4-hydroxy-2-methyl-1,1-dioxo-N-pyridin-2-yl-1lambda6,2-benzothiazine-3-carboxamide
    4-hydroxy-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide 4-hydroxy-2-methyl-N-pyridin-2-yl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide A19556
    AB00052074-21 AB00052074-22 AB00052074_23
    AB00052074_24 AB0011706 AB2000240
    AC-24190 AK1015 AKOS000714958
    AKOS025312555 AKOS026749939 AM84917
    ANW-43611 Artroxicam BAXO
    BBL016493 BCBcMAP01_000176 BCP02919
    BCP0726000299 BDBM85245 BIDD:PXR0154
    BPBio1_000245 BRN 0627692 BSPBio_000221
    BSPBio_001030 BSPBio_002460 Bio1_000363
    Bio1_000852 Bio1_001341 Bio2_000355
    Bio2_000835 Bruxicam C01608
    C15H13N3O4S CAS-36322-90-4 CAS_36322-90-4
    CCG-36403 CCRIS 3719 CHEBI:8249
    CHEMBL1518938 CHEMBL527 CHF 1251
    CP 16171 CP-16,171 CP-16171
    CS-2233 CTK7I2700 Caliment
    Certified Reference Material D00127 DB00554
    DSSTox_CID_1170 DSSTox_GSID_21170 DSSTox_RID_75990
    DTXSID5021170 DivK1c_000369 EINECS 252-974-3
    EN300-70724 EU-0100900 Erazon
    F0001-2399 FT-0080892 FT-0630590
    Felden Feldene Feldene (TN)
    Feldene Fast Feldene Gel Flogobene
    GTPL7273 Geldene HMS1362D11
    HMS1568L03 HMS1792D11 HMS1920H22
    HMS1990D11 HMS2089B06 HMS2092A05
    HMS2095L03 HMS2231G03 HMS3262D22
    HMS3267I03 HMS3369B07 HMS3403D11
    HMS3414H17 HMS3429L03 HMS3655C04
    HMS3678H15 HMS3712L03 HMS501C11
    HY-B0253 IDI1_000369 IDI1_002110
    Improntal J10253 KBio1_000369
    KBio2_000370 KBio2_001595 KBio2_002938
    KBio2_004163 KBio2_005506 KBio2_006731
    KBio3_000719 KBio3_000720 KBio3_001680
    KBioGR_000370 KBioGR_001315 KBioSS_000370
    KBioSS_001595 KS-00000JBT KS-5322
    LP00900 LS-7663 Larapam
    Lopac-P-5654 Lopac0_000900 M-9898
    MCULE-1939282084 MFCD00057317 MLS000038002
    MLS000069644 MLS001148207 MLS001304054
    MLS004774122 N-(2-pyridyl)-4-hydroxy-2-methyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide NCGC00015823-01
    NCGC00015823-02 NCGC00015823-03 NCGC00015823-04
    NCGC00015823-05 NCGC00015823-06 NCGC00015823-07
    NCGC00015823-08 NCGC00015823-09 NCGC00015823-10
    NCGC00015823-11 NCGC00015823-12 NCGC00015823-13
    NCGC00015823-14 NCGC00015823-15 NCGC00015823-17
    NCGC00015823-18 NCGC00021244-03 NCGC00021244-05
    NCGC00021244-06 NCGC00021244-07 NCGC00021244-08
    NCGC00021244-09 NCGC00188982-01 NCGC00257705-01
    NCGC00261585-01 NCI60_022912 NINDS_000369
    NSC 666076 NSC-666076 NSC-757284
    NSC666076 NSC757284 NSC_4856
    Opera_ID_442 Oprea1_714707 P 5654
    P1905 Pharmakon1600-01500491 Pirkam
    Piroflex Piroftal Piroxicam (Feldene)
    Piroxicam (JP17/USP/INN) Piroxicam 1.0 mg/ml in Methanol Piroxicam [USAN:BAN:INN:JAN]
    Piroxicam [USAN:USP:INN:BAN:JAN] Piroxicam for system suitability Piroxicam(Feldene)
    Piroxicam, >=98% (TLC) Piroxicam, British Pharmacopoeia (BP) Reference Standard Piroxicam, European Pharmacopoeia (EP) Reference Standard
    Piroxicam, Pharmaceutical Secondary Standard Piroxicam, United States Pharmacopeia (USP) Reference Standard Piroxicam, meets USP testing specifications
    Piroxicam,(S) Piroxicam: Form Alpha1 Piroxicam: Form Alpha2
    Piroxicamum Piroxicamum [INN-Latin] Prestwick0_000211
    Prestwick1_000211 Prestwick2_000211 Prestwick3_000211
    Prestwick_573 Pyroxycam Q408676
    QYSPLQLAKJAUJT-UHFFFAOYSA-N Reudene Riacen
    Rosiden Roxam Roxam;Feldene
    Roxicam Roxiden SBI-0050875.P004
    SC-16825 SCHEMBL13462 SCHEMBL21350
    SCHEMBL3703617 SMR000035997 SPBio_001293
    SPBio_002142 SPECTRUM1500491 SR-01000000199
    SR-01000000199-12 SR-01000000199-3 SR-01000000199-5
    SR-01000000199-9 ST069379 ST2411449
    STK177288 SW219862-1 Sasulen
    Solocalm Spectrum2_001287 Spectrum3_000780
    Spectrum4_000968 Spectrum5_001445 Spectrum_001115
    TR-014899 Tocris-0960 Tox21_110231
    Tox21_110231_1 Tox21_200151 Tox21_500900
    UNII-13T4O6VMAM W-106626 Z1259192069
    ZINC12466469 ZINC51133897 ZINC87724780
    Zunden piroxicam piroxicam usp
    piroxicam:malonic acid s1713

    DrugBank Name Piroxicam
    DrugBank DB00554
    CAS Number 1044566-76-8, 137-58-6, 1488516-58-0, 36322-90-4, 942047-64-5
    PubChem Compound 54676228
    KEGG Compound ID C01608
    KEGG Drug D00127
    PubChem.Substance 46505225
    ChEBI 8249
    PharmGKB PA450985
    ChemSpider 10442653
    BindingDB 85245.0
    TTD DAP000181
    Wikipedia Piroxicam
    DPD 1996

    1. Dykens et al. (2007)
    2. Moreno-Sanchez et al. (1999)