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5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)-chinolin-7-carbonsäure
oxolinic · 5-ETHYL-8-OXO-5,8-DIHYDRO-[1,3]DIOXOLO[4,5-G]QUINOLINE-7-CARBOXYLIC ACID · w4565 · utibid · ossian · oxoboi · pietil · s-0208
Identifikatoren & physikalische Daten
| CAS No. | 14698-29-4 |
|---|---|
| Summenformel | C13H11NO5 |
| Durchschnittliche Molmasse | 261,23 g/mol |
| Monoisotopische Masse | 261,06372245 g/mol |
| SMILES | CCn1cc(C(=O)O)c(=O)c2cc3c(cc21)OCO3 |
| InChIKey | KYGZCKSPAKDVKC-UHFFFAOYSA-N |
| PubChem CID | 4628 |
| ChEMBL | CHEMBL416755 |
| ChEBI | CHEBI:138856 |
| EC No. | 238-750-8 |
| DTXSID | DTXSID1021089 |
| Lokaler Name | 5-Ethyl-5,8-dihydro-8-oxo-1,3-dioxolo(4,5-g)-chinolin-7-carbonsäure |
Chemische & physikalische Eigenschaften
| XLogP | -0,2 |
|---|---|
| Polarare Oberfläche (TPSA) | 76,1 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 6 |
| Frei drehbare Bindungen | 2 |
| Schwere Atome | 19 |
| Formalladung | 0 |
| Komplexität | 446 |
| Arzneimittel | Pharmaceuticals -> Antibiotics (Quinolones)Pharmaceuticals -> Antibiotics |
| LogP (Verteilungskoeffizient) | 1.01 |
| Color/Form | CRYSTALS FROM DIMETHYLFORMAMIDE |
| Schmelzpunkt | 314-316 °C314-316°C (dec.) |
| Collision Cross Section | 152.6 Ų [M+H]+ [CCS Type: DTBuffer gas: N2Ionization: APCI+Dataset: TOXCASTSource Identifier: DTXSID1021089]147.8 Ų [M+H]+ [CCS Type: TW]167.2 Ų [M+Na]+ [CCS Type: TWMethod: calibrated with Waters Major Mix]149.1 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]150.35 Ų [M+H]+ |
| Siedepunkt | 473℃ |
| Dichte | 1.3038 (rough estimate) |
| Brechungsindex | 1.5500 (estimate) |
| Flammpunkt | >110°(230°F) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | Soluble in 0.5N NaOH with warming3.214mg/L(temperature not stated) |
| Aggregatzustand | Crystalline Powder |
| pKa (Säurekonstante) | 5.94±0.20(Predicted) |
| Farbe | White |
| Merck | 13,7014 |
| BRN | 620635 |
| Stabilität | Stable. Combustible. |
| Hauptanwendungen | clinical testing |
| InChI | 1S/C13H11NO5/c1-2-14-5-8(13(16)17)12(15)7-3-10-11(4-9(7)14)19-6-18-10/h3-5H,2,6H2,1H3,(H,16,17) |
| InChIKey | KYGZCKSPAKDVKC-UHFFFAOYSA-N |
| SMILES | CCN1C=C(C(O)=O)C(=O)c2cc3OCOc3cc12 |
| CAS Datenbank | 14698-29-4(CAS DataBase Reference) |
| EPA chemische Informationen | Oxolinic acid (14698-29-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (98.9%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 93 reports by companies from 5 notifications to the ECHA C&L Inventory.H332: Harmful if inhaled [Warning Acute toxicity, inhalation] |
|---|---|
| Regulatorische Informationen | Oxolinic acid: Does not have an individual approval but may be used under an appropriate group standard |
| Weitere Sicherheitsinformationen | IMAP assessments - 1,3-Dioxolo[4,5-g]quinoline-7-carboxylic acid, 5-ethyl-5,8-dihydro-8-oxo-: Environment tier I assessment |
| Hazard Classes and Categories | Acute Tox. 4 (98.9%)Acute toxicity (Inhalation: Dusts and mists) - Category 4 |
| Wechselwirkungen | OXOLINIC ACID ANTAGONIZED HYPNOTIC ACTION OF SODIUM BARBITOL IN MICE & RATS. EFFECTS OF OXOLINIC ACID WERE ANTAGONIZED BY ALPHA-METHYLTYROSINE, PIMOZIDE, RESERPINE, & DIAZEPAM. |
| Human Toxicity Excerpts | CNS TOXICITY HAS INCL INSOMNIA (MOST FREQUENT), RESTLESSNESS, DIZZINESS, HEADACHE, DROWSINESS, & VISUAL DISTURBANCES. ... GI REACTIONS INCL NAUSEA (MOST FREQUENT), VOMITING, ABDOMINAL DISCOMFORT & DIARRHEA.LESS FREQUENT...REACTIONS INCL FEVER, SKIN ERUPTIONS, PHOTOSENSITIVITY, PALPITATIONS, DYSPNEA & SENSE OF CHEST TIGHTNESS. TRANSIENT ELEVATIONS OF SERUM BILIRUBIN, SGOT & ALKALINE PHOSPHATASE, AS WELL AS LEUKOPENIA & HEMOLYTIC ANEMIA HAVE ALSO BEEN DESCRIBED.OCCASIONAL REACTIONS INCL ANOREXIA...CONSTIPATION, WEAKNESS...PRURITUS... RARELY, DRUG MAY CAUSE SWELLING OF EXTREMITIES, URTICARIA, SORENESS OF MOUTH & GUMS, METALLIC TASTE... |
| F | 10 |
| Wassergefährdungsklasse (WGK) | 3 |
| Zollcode | 29349990 |
| RTECS-Nr. | JI5075000 |
| R-Sätze (R) | 22 |
| Toxizität | LD50 in mice, rats (mg/kg): >6000, >2000 orally (Turner) |
Anwendungen & Verwendung
Beschreibung
Bacterial DNA gyrase is a heterodimeric type II topoisomerase that negatively supercoils circular double-stranded DNA. Oxolinic acid is a quinolone antibiotic that inhibits bacterial DNA gyrase, but not eukaryotic topoisomerases, reversibly binding gyrase subunit A in gyrase-DNA complexes, blocking supercoiling activity and inhibiting DNA synthesis at 0.5-5 μg/ml. Oxolinic acid also blocks neuronal uptake of dopamine in mammals (IC50 = 4.3 μM), leading to an increase in locomotor activity.
Verwenden
Oxolinic acid is a quinolone antibiotic used for studies on DNA winding and coiling and for studies on dopaminergic neurotransmission processes. It is used to study new transmissible resistance mechanisms qnrA, qnrB, qnrS, and aac(6′)Ib-cr, in Escherichia