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Tolmetin
C07149 · olmetin · McN 2559 · Tolmetin · Methyiin · Tolmetine · TOLMETINUM · pyrolyzate
Identifikatoren & physikalische Daten
| CAS No. | 26171-23-3 |
|---|---|
| Summenformel | C15H15NO3 |
| Durchschnittliche Molmasse | 257,28 g/mol |
| Monoisotopische Masse | 257,10519334 g/mol |
| SMILES | Cc1ccc(C(=O)c2ccc(CC(=O)O)n2C)cc1 |
| InChIKey | UPSPUYADGBWSHF-UHFFFAOYSA-N |
| PubChem CID | 5509 |
| ChEMBL | CHEMBL1020 |
| ChEBI | CHEBI:71941 |
| EC No. | 247-497-2 |
| DTXSID | DTXSID2043951 |
| Lokaler Name | Tolmetin |
Chemische & physikalische Eigenschaften
| XLogP | 2,8 |
|---|---|
| Polarare Oberfläche (TPSA) | 59,3 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 347 |
| Arzneimittel | DEA NFLIS-Drug Category -> AnalgesicsPharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 2.6 |
| Color/Form | CRYSTALS FROM ACETONITRILE |
| Löslichkeit | 1.31e-01 g/LChloroform (Slightly), Methanol (Slightly)222 mg/L |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalPharmaceuticals |
| Schmelzpunkt | 155-157 °C (DECOMPOSES)156 °C |
| Physical Description | Solid |
| Dissociation Constants | 3.5 |
| Collision Cross Section | 163.1 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]156.7 Ų [M+H]+ [CCS Type: TW] |
| Other Experimental Properties | PYRROLE-ACETIC ACID DERIVATIVE /TOLMETIN SODIUM/ |
| Siedepunkt | 400.53°C (rough estimate) |
| Dichte | 1.1391 (rough estimate) |
| Brechungsindex | 1.5200 (estimate) |
| Lagerbedingungen | 2-8°C |
| pKa (Säurekonstante) | pKa 3.5(H2O t undefined I undefined) (Uncertain) |
| Aggregatzustand | Solid |
| Farbe | Off-White to Pale Yellow |
| InChI | InChI=1S/C15H15NO3/c1-10-3-5-11(6-4-10)15(19)13-8-7-12(16(13)2)9-14(17)18/h3-8H,9H2,1-2H3,(H,17,18) |
| InChIKey | UPSPUYADGBWSHF-UHFFFAOYSA-N |
| SMILES | N1(C)C(C(=O)C2=CC=C(C)C=C2)=CC=C1CC(O)=O |
| NIST chemische Informationen | Tolmetin(26171-23-3) |
| EPA chemische Informationen | 1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)- (26171-23-3) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (33.3%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 3 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - 1H-Pyrrole-2-acetic acid, 1-methyl-5-(4-methylbenzoyl)-: Environment tier I assessment |
| Special Reports | REVIEW ARTICLE INCLUDES TOLMETIN.[SIMON LS, MILLS JANONSTEROIDAL ANTIINFLAMMATORY DRUGS (SECOND OF TWO PARTS)N ENGL J MED 302 (22) 1237 (1980)]TOLMETIN'S PHARMACOLOGICAL PROPERTIES & THERAPEUTIC EFFICACY IN RHEUMATIC DISEASES ARE REVIEWED.[BROGDEN RN ET ALTOLMETIN: A REVIEW OF ITS PHARMACOLOGICAL PROPERTIES & THERAPEUTIC EFFICACY IN RHEUMATIC DISEASESDRUGS 15(6) 429 (1978)]THE HISTORY OF RESEARCH & DEVELOPMENT OF NONSTEROIDAL ANTI-INFLAMMATORY AGENTS, INCL TOLMETIN.[GRINGAUZ ANONSTEROIDAL ANTI-INFLAMMATORY AGENTS--ANYTHING NEW UNDER THE SUN?HOSP FORMUL 14(MAR) 290 (1979)] |
| Hazard Classes and Categories | Acute Tox. 3 (33.3%) |
| Wechselwirkungen | PT RECEIVING CORTICOSTEROID OR GOLD THERAPY OBTAINED GREATER RELIEF OF SYMPTOMS WHEN TOLMETIN WAS ADDED TO THE REGIMEN, & THERE WAS EVIDENCE THAT TOLMETIN HAD A STEROID-SPARING EFFECT. /TOLMETIN SODIUM/CONCOMITANT ADMIN OF TOLMETIN & ACETAMINOPHEN PRODUCED A GREATER IMPROVEMENT IN SYMPTOMS THAN WITH TOLMETIN ALONE, BUT FURTHER STUDIES ARE NEEDED TO SUBSTANTIATE THIS EFFECT. /TOLMETIN SODIUM/CONCOMITANT ASPIRIN REDUCES PLASMA LEVELS OF TOLMETIN BY ABOUT 20%, BUT THE INTERACTION PROBABLY IS NOT CLINICALLY IMPORTANT. /TOLMETIN SODIUM/IN DOGS, PROSTAGLANDIN SYNTHETASE INHIBITORS INDOMETHACIN & TOLMETIN BLOCKED FUROSEMIDE-INDUCED INCR IN RENIN SECRETION WHETHER FUROSEMIDE WAS GIVEN IV OR INTO RENAL ARTERY.DESPITE ITS EXTENSIVE BINDING TO ALBUMIN...NO CHANGE IN PROTHROMBIN TIME WHEN WARFARIN & TOLMETIN WERE GIVEN TOGETHER. |
| Hepatotoxicity | Up to 5% of patients taking tolmetin chronically experience at least transient serum aminotransferase elevations. These may resolve even with drug continuation. Marked aminotransferase elevations (>3 fold elevated) occur in |
| Human Toxicity Excerpts | MOST FREQUENTLY REPORTED ADVERSE REACTIONS ARE GI DISTURBANCES... EPIGASTRIC DISTRESS, INCL HEARTBURN, DYSPEPSIA, & ABDOMINAL PAIN, WAS MOST COMMONOTHER REACTIONS INCL NAUSEA, VOMITING, & CONSTIPATION. GI BLEEDING WAS REPORTED OCCASIONALLY... IN CLINICAL STUDIES, PEPTIC ULCER OCCURRED IN APPROX 2% OF PT. /TOLMETIN SODIUM/CNS REACTIONS REPORTED INCL HEADACHE, DIZZINESS, LIGHTHEADEDNESS, NERVOUSNESS, & DROWSINESS. ... OTHER REACTIONS OBSERVED OCCASIONALLY WERE RASH OR URTICARIA, PRURITUS, TINNITUS, & MILD EDEMA, WHICH WAS RELATED TO SODIUM RETENTION. /TOLMETIN SODIUM/THE CASE OF A 51-YR-OLD MAN WHO DEVELOPED ANAPHYLAXIS AFTER RESTARTING ORAL THERAPY WITH TOLMETIN SODIUM FOR A PULLED GROIN MUSCLE IS PRESENTED.A 56-YR-OLD MAN WITH RHEUMATOID ARTHRITIS, BEING TREATED WITH TOLMETIN SODIUM 1800 MG/DAY, DEVELOPED A DRUG FEVER BELIEVED TO BE DUE TO TOLMETIN SODIUM THERAPY.For more Human Toxicity Excerpts (Complete) data for TOLMETIN (9 total), please visit the HSDB record page. |
| Drug Induced Liver Injury | Drug-Induced Liver Injury Severity and Toxicity (DILIst)tolmetinDILI PositiveOralDOI:10.1016/j.drudis.2019.09.022 |
| Non-Human Toxicity Excerpts | MAX ANTIINFLAMMATORY ACTIVITY OF RECTALLY ADMIN TOLMETIN WAS OBSERVED IN RATS AFTER 125 MG/KG DOSE. TOLMETIN ALSO SHOWED GREATER ACTIVITY WHEN ADMIN RECTALLY THAN ORALLY. THE LD50 OF RECTALLY ADMIN TOLMETIN WAS 743.6 MG/KG IN MALE & 843.4 MG/KG IN FEMALE RATS.TOLMETIN (100-150 MUG/L) DOSE-DEPENDENTLY INHIBITED DNA SYNTHESIS BY MOUSE SPLEEN CELLS & HUMAN LYMPHOCYTES IN VITRO. |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Gefahrstoffdaten | 26171-23-3(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
An antiinflammatory, analgesic, and antipyretic that is as efficacious as moderate doses of aspirin and better tolerated. Tolmetin produces a number of adverse effects including epigastric pain, dyspepsia, nausea, and vomiting. Tolmetin is approximately 99% plasma protein bound, yet does not interfere with concurrent treatment with oral hypoglycemics. Tolmetin has been found to be effective in the treatment of osteoarthritis and rheumatoid arthritis.
Verwenden
Tolmetine is an NSAID.