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Nabumetone
RELAFEN · relifex · Nabumeton · brl147777 · BRL-14777 · NABUMETONE · Nabumetone RS · Naftobumedone
Identifikatoren & physikalische Daten
| CAS No. | 42924-53-8 |
|---|---|
| Summenformel | C15H16O2 |
| Durchschnittliche Molmasse | 228,29 g/mol |
| Monoisotopische Masse | 228,11502975 g/mol |
| SMILES | COc1ccc2cc(CCC(C)=O)ccc2c1 |
| InChIKey | BLXXJMDCKKHMKV-UHFFFAOYSA-N |
| PubChem CID | 4409 |
| ChEMBL | CHEMBL1070 |
| ChEBI | CHEBI:7443 |
| EC No. | 641-917-1 |
| DTXSID | DTXSID4045472 |
Chemische & physikalische Eigenschaften
| XLogP | 3,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 26,3 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 4 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 262 |
| Arzneimittel | PharmaceuticalsPharmaceuticals -> Listed in ZINC15 |
| LogP (Verteilungskoeffizient) | 3.13.45 |
| Löslichkeit | Practically insoluble1.93e-03 g/LSoluble in alcohol or chloroform6mg/L(22.5 ºC) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnalgesic AgentsAnti-inflammatory Agents, NonsteroidalFDA approved drugs -> Active ingredientPharmaceuticals |
| Schmelzpunkt | 78-8280 °C80-810C |
| Physical Description | Solid |
| Collision Cross Section | 148.38 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]148 Ų [M+H]+ [CCS Type: TW |
| Siedepunkt | 330.1°C (rough estimate) |
| Dichte | 1.0657 (rough estimate) |
| Brechungsindex | 1.5542 (estimate) |
| Lagerbedingungen | Sealed in dry,2-8°C |
| Aggregatzustand | Solid |
| Farbe | White |
| BCS Class | 2/4 |
| Hauptanwendungen | forensics and toxicologypharmaceutical (small molecule)veterinary |
| InChI | InChI=1S/C15H16O2/c1-11(16)3-4-12-5-6-14-10-15(17-2)8-7-13(14)9-12/h5-10H,3-4H2,1-2H3 |
| InChIKey | BLXXJMDCKKHMKV-UHFFFAOYSA-N |
| SMILES | CC(=O)CCC1=CC=C2C(=C1)C=CC(OC)=C2 |
| CAS Datenbank | 42924-53-8(CAS DataBase Reference) |
| NIST chemische Informationen | Nabumetone(42924-53-8) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 14.3% (1 of 7) of reports.WarningH302 (42.9%): Harmful if swallowed [Warning Acute toxicity, oral]P203, P260, P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P318, P319, P321, P330, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 7 reports by companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 4 (42.9%) |
| Protective Action Criteria (PAC) | 1.0 [mg/m3]11 [mg/m3]66 [mg/m3] |
| Hepatotoxicity | Prospective studies show that 1% to 5% of patients taking nabumetone experience at least transient serum aminotransferase elevations. These may resolve even with drug continuation. Marked aminotransferase elevations (above 3 times ULN) occur in 0.5% of patients, a rate similar to that in placebo treated controls. Clinically apparent liver injury with jaundice from nabumetone is rare and in large clinical trials, no instances of acute liver injury with jaundice were reported. Since its approval and release, nabumetone has been reported to cause rare instances of serious hepatic adverse events (~1.3 per million prescriptions), but there have been no cases of clinically apparent liver injury due to nabumetone described in the published literature. Furthermore, nabumetone is not mentioned as a cause in large case series on drug induced liver injury or acute liver failure. Thus, the latency, clinical features and outcome of nabumetone induced liver injury have not been described and clinically apparent hepatotoxicity due to nabumetone must be very rare. |
| Drug Induced Liver Injury | Drug Induced Liver Injury Rank (DILIrank 2.0)NabumetoneAmbiguous-DILI-concern3Warnings & precautionsDOI:10.1016/j.drudis.2016.02.015 |
| Effects During Pregnancy and Lactation | ◉ Summary of Use during Lactation |
| Wassergefährdungsklasse (WGK) | 2 |
| Zollcode | 2914500000 |
| RTECS-Nr. | EL9085000 |
| R-Sätze (R) | 22-40 |
| Gefahrensymbole | Xn |
| Sicherheitshinweise (S) | 36/37 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Nabumetone is a non-acidic, nonsteroidal antiinflammatory agent formally related to naproxen. Its main circulating metabolite is 6-methoxy-2-naphthylacetic acid (α-nornaproxen). Administered once daily (Tsub>1/2 * 30 hrs), nabumetone is reported to be effective in the treatment of rheumatoid and osteoarthritis.
Verwenden
Nabumetone is an anti-inflammatory and antibacterial agent (1). A non-steroidal anti-inflammatory prodrug used for treatment of inflammatory and degenerative rheumatic diseases.