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36322-90-4

36322-90-4 structure
36322-90-4 structure
Name piroxicam
Synonyms 2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide
4-Hydroxy-2-methyl-N-pyridin-2-yl-2H-1,2-benzothiazin-3-carboxamid-1,1-dioxid
Riacen
1,2-benzothiazine-3-carboxamide
Reudene
Zunden
Baxo
Roxiden
Larapam
Feldene
4-hydroxy-2-méthyl-N-pyridin-2-yl-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxyde
Piroxicam
4-hydroxy-2-methyl-N-(pyridin-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
Erazon
4-Hydroxy-2-methyl-3-(pyrid-2-yl-carbamoyl)-2H-1,2-benzothiazine 1,1-dioxide
Artroxicam
Bruxicam
4-Hydroxy-2-methyl-N-(2-pyridinyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
4-Hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-1,2-benzothiazine 1,1-Dioxide
Caliment
chf1251
Improntal
Piroflex
MFCD00057317
Geldene
Sasulen
4-Hydroxy-2-methyl-N-(pyridin-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide
Solocalm
EINECS 252-974-3
4-Hydroxy-2-methyl-N-(2-pyridyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide
Flogobene
Pirkam
Description Piroxicam is a non-steroidal anti-inflammatory drugs, acts as a COX inhibitor, with IC50s of 47, 25 μM for human monocyte COX-1 and COX-2, respectively.
Related Catalog
Target

COX-2:25 μM (IC50, in human monocytes)

COX-1:47 μM (IC50, in human monocytes)

In Vitro Piroxicam is a non-steroidal anti-inflammatory drugs, acts as a COX inhibitor, with IC50s of 47, 25 μM for human monocyte COX-1 and COX-2, respectively[1]. Piroxicam (167, 333, 500 μM) decreases cell population of T24 and the 5637 cells. Piroxicam (500 μM) also reduces the cell viability of T24 and 5637 cell, and is significantly effective when combined with 0.05 μM carboplatin. The combination also inhibits Ki-67 expression in booth cells[3].
In Vivo Piroxicam (0.3 mg/kg qd 24-h p.o.) reduces tumor volume in 12 of 18 dogs, and such and effect is via induction of apoptosis and reduction in urine basic fibroblast growth factor concentration[2].
Cell Assay Urinary bladder cancer cell lines are treated with graded concentrations of carboplatin (0.05, 0.5 and 1 μM) and Piroxicam (167, 333 and 500 μM) for 72 h to assess dose-response profiles. For the combination approach, 0.05 μM of carboplatin is used with 333 μM Piroxicam. Both drugs are freshly prepared before each experiment. An untreated control group (cells not exposed to carboplatin and Piroxicam) is used for all assays[3].
Animal Admin Dogs[2] Dogs undergo tumor staging, including thoracic and abdominal radiography, cystography, ultrasonography, and cystoscopy (with collection of tissue samples) before treatment and after 4 weeks of Piroxicam (0.3 mg/kg qd 24-h p. o.) treatment. Dogs receive no other cancer treatment during the 4 weeks of Piroxicam treatment. Tissue samples are immediately frozen in liquid nitrogen for PGE2 analysis or fixed in 10% neutral buffered formalin for immunohistochemical examination. Urine is also collected before and after Piroxicam treatment, aliquoted, and then stored at −80°C until analyzed[2].
References

[1]. Kato M, et al. Cyclooxygenase-1 and cyclooxygenase-2 selectivity of non-steroidal anti-inflammatory drugs: investigation using human peripheral monocytes. J Pharm Pharmacol. 2001 Dec;53(12):1679-85.

[2]. Mohammed SI, et al. Effects of the cyclooxygenase inhibitor, piroxicam, on tumor response, apoptosis, and angiogenesis in a canine model of human invasive urinary bladder cancer. Cancer Res. 2002 Jan 15;62(2):356-8.

[3]. Silva J, et al. Synergistic Effect of Carboplatin and Piroxicam on Two Bladder Cancer Cell Lines. Anticancer Res. 2017 Apr;37(4):1737-1745.
Density 1.5±0.1 g/cm3
Boiling Point 568.5±60.0 °C at 760 mmHg
Melting Point 198-200°C
Molecular Formula C15H13N3O4S
Molecular Weight 331.346
Flash Point 297.6±32.9 °C
Exact Mass 331.062683
PSA 107.98000
LogP 2.23
Vapour Pressure 0.0±1.6 mmHg at 25°C
Index of Refraction 1.692
Storage condition 2-8°C

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DL0705000
CHEMICAL NAME :
2H-1,2-Benzothiazine-3-carboxamide, 4-hydroxy-2-methyl-N-2-pyridinyl-, 1,1-dioxide
CAS REGISTRY NUMBER :
36322-90-4
LAST UPDATED :
199801
DATA ITEMS CITED :
29
MOLECULAR FORMULA :
C15-H13-N3-O4-S
MOLECULAR WEIGHT :
331.37
WISWESSER LINE NOTATION :
T66 BSWNJ C1 EQ DVM- BT6NJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
7636 mg/kg/6W-I
TOXIC EFFECTS :
Kidney, Ureter, Bladder - interstitial nephritis
REFERENCE :
AJNED9 American Journal of Nephrology. (S. Karger Pub., Inc., 79 Fifth Ave., New York, NY 10003) V.1- 1981- Volume(issue)/page/year: 5,142,1985
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
7143 ug/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Blood - aplastic anemia Nutritional and Gross Metabolic - other changes
REFERENCE :
SAMJAF South African Medical Journal. (Medical Assoc. of South Africa, Secy., P.O. Box 643, Cape Town, S. Africa) V.6- 1932- Volume(issue)/page/year: 66,31,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
52 mg/kg/26W-I
TOXIC EFFECTS :
Nutritional and Gross Metabolic - metabolic acidosis
REFERENCE :
AIMEAS Annals of Internal Medicine. (American College of Physicians, 4200 Pine St., Philadelphia, PA 19104) V.1- 1927- Volume(issue)/page/year: 99,282,1983
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
1200 ug/kg/3D-I
TOXIC EFFECTS :
Skin and Appendages - dermatitis, other (after systemic exposure)
REFERENCE :
JRHUA9 Journal of Rheumatology. (920 Yonge St., Suite 608, Toronto, Ont., Canada) V.1- 1974- Volume(issue)/page/year: 11,554,1984
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
3714 mg/kg/13D-I
TOXIC EFFECTS :
Blood - agranulocytosis Skin and Appendages - dermatitis, allergic (after systemic exposure)
REFERENCE :
NEJMAG New England Journal of Medicine. (Massachusetts Medical Soc., 10 Shattuck St., Boston, MA 02115) V.198- 1928- Volume(issue)/page/year: 309,795,1983
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
2400 ug/kg
TOXIC EFFECTS :
Liver - hepatitis, fibrous (cirrhosis, post-necrotic scarring) Liver - jaundice, other or unclassified Kidney, Ureter, Bladder - other changes in urine composition
REFERENCE :
BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 293,540,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
28 mg/kg
TOXIC EFFECTS :
Behavioral - headache Gastrointestinal - ulceration or bleeding from duodenum Gastrointestinal - nausea or vomiting
REFERENCE :
AMSVAZ Acta Medica Scandinavica. (Almqvist & Wiksell, POB 45150, S-10430 Stockholm, Sweden) V.52-224, 1919-88. Volume(issue)/page/year: 216,335,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
216 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 28,1714,1978
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 37(11),-,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
335 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4639,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
148 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4639,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Behavioral - analgesia Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 31,87,1981
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
250 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0079639
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
290 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 49,98,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4639,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
108 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4639,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Primate - monkey
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity) Behavioral - changes in motor activity (specific assay) Lungs, Thorax, or Respiration - respiratory depression
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4639,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
388 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) No.1- 1978- Volume(issue)/page/year: 7,365,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
170 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ATSUDG Archives of Toxicology, Supplement. (Springer-Verlag New York, Inc., Service Center, 44 Hartz Way, Secaucus, NJ 07094) No.1- 1978- Volume(issue)/page/year: 7,365,1984 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
600 mg/kg/30D-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from small intestine Blood - normocytic anemia
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35(1),-,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1825 mg/kg/1Y-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach Kidney, Ureter, Bladder - other changes Blood - normocytic anemia
REFERENCE :
YKYUA6 Yakkyoku. Pharmacy. (Nanzando, 4-1-11, Yushima, Bunkyo-ku, Tokyo, Japan) V.1- 1950- Volume(issue)/page/year: 35(1),-,1984 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
35 mg/kg
SEX/DURATION :
female 15-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition
REFERENCE :
TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 30,59,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
110 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Maternal Effects - parturition Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4655,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
110 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - stillbirth Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive) Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4655,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
110 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4655,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
55 mg/kg
SEX/DURATION :
female 7-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4655,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
34 mg/kg
SEX/DURATION :
female 1-17 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - viability index (e.g., # alive at day 4 per # born alive)
REFERENCE :
TXCYAC Toxicology. (Elsevier Scientific Pub. Ireland, Ltd., POB 85, Limerick, Ireland) V.1- 1973- Volume(issue)/page/year: 30,59,1984
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
260 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4655,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
910 mg/kg
SEX/DURATION :
female 6-18 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
REFERENCE :
YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 8,4655,1980
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301
Precautionary Statements Missing Phrase - N15.00950417
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn:Harmful
Risk Phrases R22
Safety Phrases S26-S36
RIDADR UN 2811
RTECS DL0705000
Packaging Group III
Hazard Class 6.1(b)
HS Code 3005101000
HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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