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26171-23-3

26171-23-3 structure
26171-23-3 structure
  • Name: 1-Methyl-5-p-toluoylpyrrole-2-acetic acid
  • Chemical Name: tolmetin
  • CAS Number: 26171-23-3
  • Molecular Formula: C15H15NO3
  • Molecular Weight: 257.284
  • Catalog: Signaling Pathways Immunology/Inflammation COX
  • Create Date: 2018-03-29 08:00:00
  • Modify Date: 2024-01-02 14:03:05
  • Tolmetin is an orally active and potent COX inhibitor with IC50s of 0.35 µM and 0.82 µM human COX-1 and COX-2, respectively. Tolmetin is a non-steroidal anti-inflammatory drug (NSAID)[1][2].
Name tolmetin
Synonyms [3H]-Tolmetin
[1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl]acetic acid
EINECS 247-497-2
Tolmetino
1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)-
Tolmetine
Tolmetina
TOLMETIN
Tolmetinum
2-[1-methyl-5-(4-methylbenzoyl)pyrrol-2-yl]acetic acid
Tolectin
5-(p-toluoyl)-1-methylpyrrole-2-acetic acid
5-(4-methylbenzoyl)-1-methyl-pyrrol-2-ylacetic acid
1-Methyl-5-p-toluoylpyrrole-2-acetic acid
Tolmetine [INN-French]
2-(1-Methyl-5-(4-methylbenzoyl)-1H-pyrrol-2-yl)acetic acid
1-methyl-5-(4-methylbenzoyl)pyrrol-2-acetic acid
1-Methyl-5-(p-toluoyl)-2-pyrroleacetic acid
Tolmetina [DCIT]
1-methyl-5-(4-methylbenzoyl)-1H-pyrrole-2-acetic acid
1-METHYL-5-P-TOLUOYL-PYRROLE-2-ACETIC ACID
Description Tolmetin is an orally active and potent COX inhibitor with IC50s of 0.35 µM and 0.82 µM human COX-1 and COX-2, respectively. Tolmetin is a non-steroidal anti-inflammatory drug (NSAID)[1][2].
Related Catalog
Target

Human COX-1:0.35 μM (IC50)

Human COX-2:0.82 μM (IC50)

In Vitro Tolmetin (0.25 mM) does not attenuate lipid peroxidation in rat brain homogenate. Tolmetin (0.25, 0.5, 0.75, 1 mM) shows radical scavenging properties but without superoxide anion generation in rat brain homogenat[3]. Tolmetin (0.001-100 μM) shows anticancer activity againts HT-29 colon cancer cell line in a dose-dependent manner[4]. Tolmetin (0-100 μM) shows no effect on osteoblast growth[5].
In Vivo Tolmetin (30,100 mg/kg; gavage; single dose or twice daily for 3 and 14 days) shows maximal ulcerogenic effect 4 h after the single dose, while potently decreases after 3 and 14 days of repeated administration in male Wistar rats weighing 180-200 g. Tolmetin causes gastric lesions in 100 mg/kg[2]. Tolmetin (5 mg/kg twice a day for 5 days) pre-treatment considerably attenuates quinolinic acid (QA)-induced neurotoxicity[3].
References

[1]. T D Warner, et al. Nonsteroid drug selectivities for cyclo-oxygenase-1 rather than cyclo-oxygenase-2 are associated with human gastrointestinal toxicity: a full in vitro analysis. Proc Natl Acad Sci U S A. 1999 Jun 22;96(13):7563-8.

[2]. DADAŞ, Yakup, et al. Synthesis and anticancer activity of some novel tolmetin thiosemicarbazides. Marmara Pharmaceutical Journal 19(3) • April 2015

[3]. Etcheverry SB, et al. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. J Inorg Biochem. 2002 Jan 1;88(1):94-100.

[4]. Etcheverry SB, et al. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. J Inorg Biochem. 2002 Jan 1;88(1):94-100.

[5]. Etcheverry SB, et al. Three new vanadyl(IV) complexes with non-steroidal anti-inflammatory drugs (Ibuprofen, Naproxen and Tolmetin). Bioactivity on osteoblast-like cells in culture. J Inorg Biochem. 2002 Jan 1;88(1):94-100.
Density 1.2±0.1 g/cm3
Boiling Point 483.2±40.0 °C at 760 mmHg
Melting Point 156ºC
Molecular Formula C15H15NO3
Molecular Weight 257.284
Flash Point 246.0±27.3 °C
Exact Mass 257.105194
PSA 59.30000
LogP 1.55
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.582
Water Solubility 222 mg/L

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UX9287000
CHEMICAL NAME :
Pyrrole-2-acetic acid, 1-methyl-5-p-toluoyl-
CAS REGISTRY NUMBER :
26171-23-3
BEILSTEIN REFERENCE NO. :
0485305
LAST UPDATED :
199612
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C15-H15-N-O3
MOLECULAR WEIGHT :
257.31
WISWESSER LINE NOTATION :
T5NJ A1 BVR D1& E1VQ

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 :
293 mg/kg
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 25,1526,1975
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
744 mg/kg
TOXIC EFFECTS :
Biochemical - Metabolism (Intermediary) - effect on inflammation or mediation of inflammation
REFERENCE :
AFTOD7 Archivos de Farmacologia y Toxicologia. (Universidad Complutense, Facultad de Medicina, Departamento Coordinado de Farmacologia, Ciudad Universitaria, Madrid 3, Spain) V.1- 1975- Volume(issue)/page/year: 5,257,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
914 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 38,90,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
600 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FRPSAX Farmaco, Edizione Scientifica. (Casella Postale 227, 27100 Pavia, Italy) V.8-43 1953-88 For publisher information, see FRMCE8 Volume(issue)/page/year: 38,90,1983
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
680 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: 8,45,1977
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Unreported
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1107 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
YHTPAD Yaoxue Tongbao. Bulletin of Pharmacology. (China International Book Trading Corp., POB 2820, Beijing, Peop. Rep. China) V.13-23, 1978-88. For publisher information, see ZYZAEU. Volume(issue)/page/year: 19,460,1984
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - species unspecified
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 81,621,1985 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 mg/kg/4D-I
TOXIC EFFECTS :
Gastrointestinal - ulceration or bleeding from stomach
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 52,454,1980
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1680 mg/kg/8W-I
TOXIC EFFECTS :
Brain and Coverings - other degenerative changes Liver - other changes Nutritional and Gross Metabolic - changes in metals, not otherwise specified
REFERENCE :
TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: (Suppl),245,1992 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
20600 ug/kg
SEX/DURATION :
female 21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - cardiovascular (circulatory) system
REFERENCE :
TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 30(1),25A,1984
Hazard Codes Xi
HS Code 2933990090
HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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