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2-Phenyl-1H-inden-1,3(2H)-dion
PHENINDIONE · PID · Indion · MTA2 · Hedulin · 2-Phenyl-1H-indene-1,3(2H)-dione · 1H-Indene-1,3(2H)-dione, 2-phenyl- · Indon
Identifikatoren & physikalische Daten
| CAS No. | 83-12-5 |
|---|---|
| Summenformel | C15H10O2 |
| Durchschnittliche Molmasse | 222,24 g/mol |
| Monoisotopische Masse | 222,06807956 g/mol |
| SMILES | O=C1c2ccccc2C(=O)C1c1ccccc1 |
| InChIKey | NFBAXHOPROOJAW-UHFFFAOYSA-N |
| PubChem CID | 4760 |
| ChEMBL | CHEMBL711 |
| ChEBI | CHEBI:8066 |
| EC No. | 201-454-4 |
| DTXSID | DTXSID5023453 |
| Lokaler Name | 2-Phenyl-1H-inden-1,3(2H)-dion |
Chemische & physikalische Eigenschaften
| XLogP | 2,9 |
|---|---|
| Polarare Oberfläche (TPSA) | 34,1 |
| H-Brücken-Donoren | 0 |
| H-Brücken-Akzeptoren | 2 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 17 |
| Formalladung | 0 |
| Komplexität | 304 |
| Arzneimittel | Pharmaceuticals -> Listed in ZINC15 |
| pH | 4.5 IN SATURATED SOLN @ 25 °C |
| SpringerMaterials Properties | Chemical shift |
| LogP (Verteilungskoeffizient) | 2.6 |
| Geruch | ALMOST ODORLESS |
| Color/Form | LEAFLETS FROM ALCOHOLCREAMY WHITE TO PALE YELLOW CRYSTALS OR CRYSTALLINE POWDER |
| Löslichkeit | PRACTICALLY INSOL IN COLD WATERSOL IN CHLOROFORMSLIGHTLY SOL IN WARM WATERREADILY SOL IN ALKALINE SOLNSOL IN METHANOL, ETHANOL, ETHER, ACETONE, BENZENE2.30e-02 g/LVery slightly soluble in waterslightly soluble in ethanol (96%) and in ether. Solutions are yellow to red. |
| Human Drugs | FDA approved drugs -> Active ingredientPharmaceuticals |
| Schmelzpunkt | 149-151 °C148 - 151 °C144-148 °C(lit.) |
| Physical Description | Solid |
| Collision Cross Section | 160.15 Ų [M+K]+ [CCS Type: TWMethod: calibrated with polyalanine and drug standards]145.9 Ų [M+H]+ [CCS Type: TW |
| Other Experimental Properties | SOLN IN ALKALIES ARE RED, IN CONCN H2SO4 BLUE |
| Siedepunkt | 243.3 °C (0.3 mmHg) |
| Dichte | 1.1404 (rough estimate) |
| Brechungsindex | 1.6600 (estimate) |
| Flammpunkt | 208 °C |
| Lagerbedingungen | Inert atmosphere,Room Temperature |
| Aggregatzustand | powder to crystal |
| pKa (Säurekonstante) | pKa 4.09(H2O,t =25,I=0.1) (Uncertain) |
| Farbe | White to Light yellow |
| Merck | 14,7234 |
| InChI | InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H |
| InChIKey | NFBAXHOPROOJAW-UHFFFAOYSA-N |
| SMILES | C1(=O)C2=C(C=CC=C2)C(=O)C1C1=CC=CC=C1 |
| CAS Datenbank | 83-12-5(CAS DataBase Reference) |
Sicherheit & Vorschriften
| GHS-Einstufung | DangerH301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]P261, P264, P270, P272, P280, P301+P316, P302+P352, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 43 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Hazard Classes and Categories | Acute Tox. 3 (100%) |
| Treatment | The primary antidote to phenindione poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin timethen 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses phenindione can affect the body for many months, and the antidote must be administered regularly for a long period of time. (L1257) |
| Wechselwirkungen | HALOPERIDOL WAS FOUND TO REDUCE PROTHROMBIN TIME NORMALLY PRODUCED BY PHENINDIONE.ACTIVITY OF...INDANDIONE ANTICOAGULANT PHENINDIONE HAVE ALSO BEEN ENHANCED BY C-17-ALKYLATED ANDROGENS.CORTICOTROPIN & ADRENOCORTICOSTEROIDS HAVE BEEN REPORTED TO CAUSE SEVERE HEMORRHAGE WHEN GIVEN WITH ORAL ANTICOAGULANTS... /ANTICOAGULANTS/ANTIPYRINE (IN VIVO) & SULFINPYRAZONE (IN VITRO) HAVE BEEN REPORTED TO INTERACT WITH WARFARIN & SHOULD BE USED CAUTIOUSLY IN PT RECEIVING ANTICOAGULANTS. /ANTICOAGULANTS/For more Interactions (Complete) data for PHENINDIONE (12 total), please visit the HSDB record page. |
| Gesundheitliche Auswirkungen | Phenindione is an anticoagulant and may cause internal bleeding, leading to shock, loss of consciousness, and eventually death. (L1257) |
| Expositionspfade | Ingestion (L1817)dermal (L1817). Absorbed slowly from the gastrointestinal tract. |
| Toxizitätsübersicht | Phenindione inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots. (A308) |
| Signs and Symptoms | Phenindione may cause bleeding complications. (L1257) |
| Human Toxicity Excerpts | ...COLORS URINE RED-ORANGE. ...REPORTS OF SENSITIVITY REACTIONS... MOST COMMON OF THESE ARE RASH, PYREXIA, & LEUKOPENIAOCCASIONALLY LEUKOCYTOSIS OCCURS. THESE...ARE ACCOMPANIED BY FEVER, MALAISE, & HEADACHE. RASH IS...ERYTHEMATOUS & MACULAR...OCCASIONALLY PAPULAR &...WITH SCALING & ITCHING.RARELY...EXFOLIATIVE DERMATITIS. SERIOUS RENAL DAMAGE WITH EXTENSIVE TUBULAR NECROSIS HAS BEEN REPORTED. ALBUMINURIA & MASSIVE EDEMA HAVE ALSO BEEN OBSERVED. OTHER...TOXIC EFFECTS INCL DIARRHEA, PARALYSIS OF ACCOMMODATION, & BLURRED VISION. ...REPORTS OF HEPATITIS & AGRANULOCYTOSIS. ...DEATHS HAVE OCCURRED...UNTOWARD EFFECTS...INCL JAUNDICE...NEPHROPATHY... URINARY DISCOLORATION MAY MASK IMPORTANT SIGN... FOR THIS REASON, MORE SERIOUS HEMORRHAGIC EPISODES OCCUR WITH THIS DRUG THAN WITH ANY OTHER PROTHROMBOPENIC DRUG....HAS ANTITHYROID ACTION &...IMPAIR URATE REABSORPTION BY RENAL TUBULES & THUS INCR AMT OF URIC ACID IN URINE. |
| Carcinogen Classification | No indication of carcinogenicity to humans (not listed by IARC). |
| Toxicity Data | Oral, mouse: LD50 = 175 mg/kgOral, rat: LD50 = 163 mg/kg. |
| Wassergefährdungsklasse (WGK) | 3 |
| UN-Transportnummer | UN 2811 6.1/PG 3 |
| Zollcode | 2914.39.9000 |
| RTECS-Nr. | NK6125000 |
| R-Sätze (R) | 25-43 |
| Gefahrensymbole | T |
| Sicherheitshinweise (S) | 36/37/39-45 |
| Gefahrenklasse | 6.1(b) |
| Verpackungsgruppe | III |
| Gefahrstoffdaten | 83-12-5(Hazardous Substances Data) |
Anwendungen & Verwendung
Beschreibung
Phenindione is an anticoagulant and vitamin K antagonist. It inhibits the reduction of vitamin K1 epoxide to vitamin K1 by vitamin K1 epoxide reductase in rat liver homogenates in a concentration-dependent manner. In vivo, phenindione (500 mg/kg) inhibits prothrombin synthesis and conversion of vitamin K1 epoxide to vitamin K1 in rats by 50 and 57%, respectively. Dietary administration of phenindione (4 mg/kg per day) inhibits aortic atherosclerosis or intracardial thrombosis in rat models of diet-induced atherosclerosis or intravascular thrombosis, respectively.
Verwenden
Oral anticoagulant (indanedione).