CAS 13710-19-5|Tolfenamic acid

Introduction：Basic information about CAS 13710-19-5|Tolfenamic acid, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Tolfenamic acid BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles49
8. Synonyms

Common Name	Tolfenamic acid
CAS Number	13710-19-5	Molecular Weight	261.704
Density	1.3±0.1 g/cm3	Boiling Point	405.4±40.0 °C at 760 mmHg
Molecular Formula	C₁₄H₁₂ClNO₂	Melting Point	210-214°C
MSDS	ChineseUSA	Flash Point	199.0±27.3 °C
Symbol	GHS06	Signal Word	Danger

Names

Name	tolfenamic acid
Synonym	More Synonyms

Tolfenamic acid BiologicalActivity

Description	Tolfenamic Acid is a non-steroidal anti-inflammatory and anti-cancer agent, selectively inhibits COX-2, with an IC50 of 13.49 μM (3.53 μg/mL) in LPS-treated (COX-2) canine DH82 monocyte/macrophage cells, but shows no effect on COX-1.
Related Catalog	Research Areas >>Inflammation/Immunology
Target	COX-2:13.49 μM (IC50, in cell)
In Vitro	Tolfenamic Acid is a nonsteroidal antiinflammatory agent, selectively inhibits COX-2, with an IC50 of 13.49 μM (3.53 μg/mL) in LPS-treated (COX-2) canine DH82 monocyte/macrophage cells, but shows no effect on COX-1[1]. Tolfenamic Acid (100 μM) inhibits >70% of cell viability of BE3, OE33, and SKGT5. Tolfenamic Acid also acts as a potent Sp protein inhibitor, decreases Sp1 and Sp4 and suppresses c-Met expression in esophageal cancer cells BE3 and SKGT5[2]. Tolfenamic Acid (50 μM) significantly affects gene expression in L3.6pl cells, and downregulates CENPF, KIF20A, LMNB1, MYB, SKP2, CCNE2, and DDIT3[3].
In Vivo	Tolfenamic Acid (50 mg/kg 3 times/wk, p.o.) inhibits tumor formation and tumor incidence in N-nitrosomethylbenzylamine (NMBA)-induced esophageal tumor model. Tolfenamic Acid also causes decreases in tumor multiplicity and tumor volume in rats treated with NMBA[2].
Cell Assay	All cells are grown in media (RPMI1640) supplemented with 5% serum and cultured at 37°C in a humidified atmosphere of 95% air and 5% CO2. Twenty four hours after seeding, cells are treated with vehicle (0.1% DMSO) or various concentrations of Tolfenamic Acid (25/50/100 μM). Cell viability assays are conducted at 24, 48 and 72 h post-treatment. Cells are treated with 50 μM Tolfenamic Acid and the cell pellets are harvested at 48 h post-treatment. These pellets are used to prepare cell lysates that are used in Western blot analyses[2].
Animal Admin	Mice[2] The Fischer 344 (F-344) rat model of esophageal SCC are initially housed two per cage, but eventually separated to one per cage due to increase in size, and are maintained under standard, humane conditions (20±2°C, 50±10% relative humidity, 12-h light/dark cycles). Food and water are provided ad libitum. Body weights are recorded at the time of each dosing. Two weeks after arrival in the animal facility, the rats are randomLy assigned into 4 groups: C: NMBA (1-5 week); NTA: (NMBA 1-5 week and then Tolfenamic Acid 6-25 week); NC: Negative control (vehicle); and TA: Tolfenamic Acid negative control. Control (C) and NTA groups are injected s.c. with NMBA (0.5 mg/kg) in 0.2 mL vehicle three times per week for 5 weeks while negative control groups are injected with vehicle alone. NTA and Tolfenamic Acid groups also receive 50 mg/kg Tolfenamic Acid by oral gavage from week 6 through week 25. After the 25th week, the animals are sacrificed, esophagi are cut open longitudinally, and surface tumors are mapped and counted. The number and the size of lesions, including polyps are recorded and images captured. Tumor volume is calculated using the formula for a prolate spheroid: length × width × height × p/6[2].
References	[1]. Kay-Mugford P, et al. In vitro effects of nonsteroidal anti-inflammatory drugs on cyclooxygenase activity in dogs. Am J Vet Res. 2000 Jul;61(7):802-10. [2]. Maliakal P, et al. Chemopreventive effects of tolfenamic acid against esophageal tumorigenesis in rats. Invest New Drugs. 2012 Jun;30(3):853-61. [3]. Sankpal UT, et al. Tolfenamic acid-induced alterations in genes and pathways in pancreatic cancer cells. Oncotarget. 2017 Feb 28;8(9):14593-14603

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	405.4±40.0 °C at 760 mmHg
Melting Point	210-214°C
Molecular Formula	C₁₄H₁₂ClNO₂
Molecular Weight	261.704
Flash Point	199.0±27.3 °C
Exact Mass	261.055664
PSA	49.33000
LogP	5.76
Vapour Pressure	0.0±1.0 mmHg at 25°C
Index of Refraction	1.658
InChIKey	YEZNLOUZAIOMLT-UHFFFAOYSA-N
SMILES	Cc1c(Cl)cccc1Nc1ccccc1C(=O)O
Storage condition	Refrigerator

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: CB2687500

CHEMICAL NAME :: Anthranilic acid, N-(3-chloro-o-tolyl)-

CAS REGISTRY NUMBER :: 13710-19-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C14-H12-Cl-N-O2

MOLECULAR WEIGHT :: 261.72

WISWESSER LINE NOTATION :: QVR BMR CG B1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 225 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 28,99,1981

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 238 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 29,851,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 246 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,838,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,838,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 185 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,838,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 267 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 14,838,1983

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rabbit

DOSE/DURATION :: 562 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - respiratory stimulation

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 29,851,1983 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 1 mg/kg

SEX/DURATION :: female 21 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 27,117,1984

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 648 mg/kg

SEX/DURATION :: female 17-22 day(s) after conception lactating female 21 day(s) post-birth

TOXIC EFFECTS :: Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 29,889,1983

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 264 mg/kg

SEX/DURATION :: female 7-17 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: TOIZAG Toho Igakkai Zasshi. Journal of Medical Society of Toho University. (Toho Daigaku Igakkai, 21-16, Omori-nishi, 5-chome, Ota-ku, Tokyo 143, Japan) V.1- 1954- Volume(issue)/page/year: 29,889,1983

Safety Information

Symbol	GHS06
Signal Word	Danger
Hazard Statements	H301
Precautionary Statements	P301 + P310
Personal Protective Equipment	dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes	Xn:Harmful
Risk Phrases	R22
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS	CB2687500
HS Code	2922499990

Customs

HS Code	2922499990
Summary	HS:2922499990 other amino-acids, other than those containing more than one kind of oxygen function, and their esters; salts thereof VAT:17.0% Tax rebate rate:9.0% Supervision conditions:AB(certificate of inspection for goods inward,certificate of inspection for goods outward) MFN tariff:6.5% General tariff:30.0%

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Synonyms

Clotam

N-(3-Chloro-ortho-tolyl) anthranilic acid

2-[(3-Chloro-2-methylphenyl)amino]benzoic acid

Tolfenamic acid

MFCD00133865

N-(3-Chloro-o-tolyl)-anthranilic acid

EINECS 237-264-3

Tolfedine

2-((3-Chloro-2-methylphenyl)amino)benzoic acid

2-(3-Chloro-o-toluidino)benzoic Acid

N-(3-Chloro-ortho-tolyl)anthranilic acid

N-(2-Methyl-3-chlorophenyl)anthranilic acid

Benzoic acid, 2-[(3-chloro-2-methylphenyl)amino]-

N-(3-Chloro-2-methylphenyl)anthranilic Acid

2 (3-Chloro-2-methylanilino)benzoic acid

2-(3-chloro-2-methylanilino)benzoic acid

Anthranilic acid, N-(3-chloro-o-tolyl)-

N-(3-chloro-o-tolyl)anthranilic acid

Tolfine

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