HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
Chloroquin
Diphenylhydramine · Cloroquine · Chloroquin · Aralen · (7-chloro-4-(4-diethylamino-1-methylbutylamino)-quinoline · w7618 · Imagon · win244
Identifikatoren & physikalische Daten
| CAS No. | 54-05-7 |
|---|---|
| Summenformel | C18H26ClN3 |
| Durchschnittliche Molmasse | 319,9 g/mol |
| Monoisotopische Masse | 319,18152551 g/mol |
| SMILES | CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12 |
| InChIKey | WHTVZRBIWZFKQO-UHFFFAOYSA-N |
| PubChem CID | 2719 |
| ChEMBL | CHEMBL76 |
| ChEBI | CHEBI:3638 |
| EC No. | 200-191-2 |
| DTXSID | DTXSID2040446 |
| Lokaler Name | Chloroquin |
Chemische & physikalische Eigenschaften
| XLogP | 4,6 |
|---|---|
| Polarare Oberfläche (TPSA) | 28,2 |
| H-Brücken-Donoren | 1 |
| H-Brücken-Akzeptoren | 3 |
| Frei drehbare Bindungen | 8 |
| Schwere Atome | 22 |
| Formalladung | 0 |
| Komplexität | 309 |
| Arzneimittel | Pharmaceuticals |
| LogP (Verteilungskoeffizient) | log Kow = 4.634.34.61 |
| Geruch | ODORLESS |
| Geschmack | Bitter taste |
| Color/Form | WHITE TO SLIGHTLY YELLOW, CRYSTALLINE POWDERColorless crystals |
| Löslichkeit | Bitter colorless crystals, dimorphic. Freely soluble in water, less sol in neutral or alkaline pH. Stable to heat in soln pH4 to 6.5. Practically in soluble in alcohol, benzene and chloroform /Diphosphate/WHITE CRYSTALLINE POWDERODORLESSBITTER TASTEFREELY SOL IN WATERPRACTICALLY INSOL IN ALCOHOL, CHLOROFORM, ETHERAQ SOLN HAS PH OF ABOUT 4.5PKA1= 7PKA2= 9.2 /PHOSPHATE/VERY SLIGHTLY SOL IN WATERSOL IN DIL ACIDS, CHLOROFORM, ETHERInsoluble in alcohol, benzene, chloroform, ether.1.75e-02 g/LChloroform (Slightly), Methanol (Slightly) |
| Human Drugs | Breast FeedingLactationMilk, HumanAnti-infective AgentsAntiparasitic AgentsAntimalarialsAntirheumatic AgentsAntiprotozoal AgentsPharmaceuticalsAntimalarial medicines > For chemoprevention |
| Schmelzpunkt | 87-89.587 °C289 °C87° |
| Physical Description | Solid |
| Stability/Shelf Life | Stable to heat in solutions of pH 4.0 to 6.5 /Chloroquine Diphosphate/SENSITIVE TO LIGHT. /PHOSPHATE/SENSITIVE TO LIGHT. /SULFATE/ |
| Dissociation Constants | 10.1pKa = 10.1 |
| Collision Cross Section | 176.8 Ų [M+H]+ [CCS Type: TWMethod: Major Mix IMS/Tof Calibration Kit (Waters)] |
| Siedepunkt | 475.41°C (rough estimate) |
| Dichte | 1.0500 (rough estimate) |
| Brechungsindex | 1.6010 (estimate) |
| Lagerbedingungen | 2-8°C(protect from light) |
| Aggregatzustand | Solid |
| pKa (Säurekonstante) | pKa 8.4(H2O t = 20) (Uncertain) |
| Farbe | White to Light Brown |
| Geruch | Odorless |
| Stabilität | Stable, but light sensitive. Incompatible with strong oxidizing agents. |
| InChI | InChI=1S/C18H26ClN3/c1-4-22(5-2)12-6-7-14(3)21-17-10-11-20-18-13-15(19)8-9-16(17)18/h8-11,13-14H,4-7,12H2,1-3H3,(H,20,21) |
| InChIKey | WHTVZRBIWZFKQO-UHFFFAOYSA-N |
| SMILES | C(N(CC)CC)CCC(NC1C2C(N=CC=1)=CC(Cl)=CC=2)C |
| EPA chemische Informationen | 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl- (54-05-7) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH302 (100%): 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 41 reports by companies from 2 notifications to the ECHA C&L Inventory. |
|---|---|
| Weitere Sicherheitsinformationen | IMAP assessments - 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-: Human health tier I assessment |
| FDA-Anforderungen | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl chloroquine phosphate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Chloroquine phosphate/ |
| Special Reports | Fitch CDFerriprotoporphyrin IX: role in chloroquine susceptibility and resistance in malaria.Prog Clin Biol Res 313: 45-52 (1989). A review of all available evidence supports the hypothesis that ferriprotoporphyrin is the receptor for chloroquine and mediator of its antimalarial activity.Ochsendorf FR, Runne UChloroquine and hydroxychloroquine: side effect profile of important therapeutic drugsHautarzt 42 (3): 140-6 (1991). Precise knowledge of the undesirable effects of chloroquine and hydroxychloroquine allows better exploitation of their therapeutic effects. |
| Hazard Classes and Categories | Acute Tox. 4 (100%) |
| Skin, Eye, and Respiratory Irritations | Eleven cases of macular degeneration occurring between the ages of 22 yr and 40 yr are presented. All the patients gave positive history of chloroquine intake and outdoor activity. In 4 of the 11 cases, pterygium was an associated ocular finding. The female to male ratio was 3 to 1. The macular lesions were bilateral and symmetrical in all the cases. It is postulated that the effect of chronic chloroquine ingestion exacerbated by chronic light toxicity might be responsible for this type of macular degeneration presenting in adults. |
| Entsorgungsverfahren | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
Anwendungen & Verwendung
Beschreibung
Chloroquine is the most effective of the hundreds of 4-aminoquinolines synthesized and tested during World War II as potential antimalarials. Structure–activity relationships demonstrated that the chloro at the 8-position increased activity, whereas alkylation at C-3 and C-8 diminished activity. The replacement of one of its N-ethyl groups with an hydroxyethyl produced hydroxychloroquine, a compound with reduced toxicity that is rarely used today except in cases of rheumatoid arthritis.
Verwenden
Chloroquine used in the treatment of malaria and MDR-strains. It is a COVID19-related research product.