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13710-19-5

13710-19-5 structure
13710-19-5 structure
  • Name: Tolfenamic acid
  • Chemical Name: tolfenamic acid
  • CAS Number: 13710-19-5
  • Molecular Formula: C14H12ClNO2
  • Molecular Weight: 261.704
  • Catalog: Biochemical Inhibitor Neuronal Signaling COX inhibitor
  • Create Date: 2018-09-02 17:45:25
  • Modify Date: 2024-01-02 14:19:16
  • 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.
Name tolfenamic acid
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
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
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
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
Storage condition Refrigerator

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
Symbol GHS06
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
12775-96-1 structure

12775-96-1

87-60-5 structure

87-60-5

88-65-3 structure

88-65-3

~%

13710-22-0 structure

13710-22-0

Detail
Literature: US4092430 A1, ;
16497-87-3 structure

16497-87-3

87-60-5 structure

87-60-5

~39%

13710-19-5 structure

13710-19-5

Literature: Kovala-Demertzi, Dimitra; Hadjipavlou-Litin, Dimitra; Primikiri, Alexandra; Staninska, Malgorzata; Kotoglou, Chronis; Demertzis, Mavroudis A. Chemistry and Biodiversity, 2009 , vol. 6, # 6 p. 948 - 960
Precursor  2

DownStream  0

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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title: CAS No. 13710-19-5 | Chemsrc address: https://www.chemsrc.com/en/baike/325183.html

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