Chloroquine Phosphate
Basic information
- CAS
50-63-5- Standard SMILES
CCN(CC)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=P(O)(O)O.O=P(O)(O)O- InChIKey
QKICWELGRMTQCR-UHFFFAOYSA-N- Molecular formula
- C18H32ClN3O8P2
- Average molar mass
- 515.9 g/mol
- Monoisotopic mass
- 515.1353167
Overview
Chloroquine Phosphate is the phosphate salt of chloroquine, a quinoline compound with antimalarial and anti-inflammatory properties. Chloroquine is the most widely used drug against malaria, except for those cases caused by chloroquine resistant Plasmodium falciparum. Although the mechanism of action is not fully understood, chloroquine is shown to inhibit the parasitic enzyme heme polymerase that converts the toxic heme into non-toxic hemazoin, thereby resulting in the accumulation of toxic heme within the parasite. Chloroquine may also interfere with the biosynthesis of nucleic acids.
Names & identifiers
- Preferred name
- Chloroquine Phosphate
- IUPAC
- 4-N-(7-chloroquinolin-4-yl)-1-N,1-N-diethylpentane-1,4-diamine;phosphoric acid
- English name
- Chloroquine diphosphate
- Molecular formula
- C18H32ClN3O8P2
- Molecular weight
- 515.86
Names & synonyms
Chloroquine diphosphateChloroquine phosphateAralen phosphateArechinAvloclorResochinChingamin phosphateDelagilChloroquini phosphasNSC-140506E17K3343PSN-7618
Show more names
CHLOROQUIN PHOSPHATECHLOROQUINE DIPHOSPHATE SALTwr1522alermineh-stadurkhingaminMelatonine2klorokinfosfatChloropicrin 1
WR-15227-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline phosphate (1:2)1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2)N(4)-(7-Chloro-4-quinolinyl)-N(1),N(1)-diethyl-1,4-pentanediamine, phosphate (1:2)khingamin phosphateNSC14050MalarivonChloroquinum Phos.
Database identifiers
- CAS
50-63-5- PubChem CID
- 64927
- DTXSID
DTXSID7044681
Properties
Computed structural properties
- Topological polar surface area
- 184 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 8
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 358
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Anti-infective Agents; Antiparasitic Agents; Antimalarials; Antirheumatic Agents; Antiprotozoal Agents
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Animal DrugsFDA approved animal drugs -> Active ingredient
Collision Cross Section175.6 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 200 °C · 200 °C (dec.) (lit.)
- vapor pressure
- 1e-7 kPa · <0.0000001 kPa ( 25 °C)
- storage temp.
- protect from light
- solubility
- 2 O: · H2O: 50 mg/mL, clear
- form
- solid
- pka
- 8.1 · pKa 8.10(H2O t = 20 c = 0.0025) (Uncertain)
- color
- White
- PH
- pH(100g/l, 25℃) : 3.8～4.3
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Hazard information
Other Safety InformationIMAP assessments - 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-, phosphate (1:2): Environment tier I assessment
Toxicology
Treatment
Treatment is symptomatic and must be prompt with immediate evacuation of the stomach by emesis (at home, before transportation to the hospital) or gastric lavage until the stomach is completely emptied. If finely powdered, activated charcoal is introduced by stomach tube, after lavage, and within 30 minutes after ingestion of the antimalarial, it may inhibit further intestinal absorption of the drug. To be effective, the dose of activated charcoal should be at least five times the estimated dose of chloroquine ingested. Convulsions, if present, should be controlled before attempting gastric lavage. (L1712)
Health Effects
Possible heath effects include an irreversible retinal damage, visual disturbances, nyctalopia; scotomatous vision with field defects of paracentral, pericentral ring types, and typically temporal scotomas, nerve type deafness; tinnitus, reduced hearing in patients with preexisting auditory damage. Other effects include pleomorphic skin eruptions, skeletal muscle myopathy, hypotension, electrocardiographic change as well as neuropsychiatric changes including psychosis, delirium, personality changes and depression (RxList, A308).
Exposure RoutesInhalation
Completely absorbed from gastrointestinal tract
Toxicity Summary
The mechanism of plasmodicidal action of chloroquine is not completely certain. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites. nside red blood cells, the malarial parasite must degrade hemoglobin to acquire essential amino acids, which the parasite requires to construct its own protein and for energy metabolism. Digestion is carried out in a vacuole of the parasite cell. During this process, the parasite produces the toxic and soluble molecule heme. The heme moiety consists of a porphyrin ring called Fe(II)-protoporphyrin IX (FP). To avoid destruction by this molecule, the parasite biocrystallizes heme to form hemozoin, a non-toxic molecule. Hemozoin collects in the digestive vacuole as insoluble crystals. Chloroquine enters the red blood cell, inhabiting parasite cell, and digestive vacuole by simple diffusion. Chloroquine then becomes protonated (to CQ2+), as the digestive vacuole is known to be acidic (pH 4.7); chloroquine then cannot leave by diffusion. Chloroquine caps hemozoin molecules to prevent further biocrystallization of heme, thus leading to heme buildup. Chloroquine binds to heme (or FP) to form what is known as the FP-Chloroquine complex; this complex is highly toxic to the cell and disrupts membrane function. Action of the toxic FP-Chloroquine and FP results in cell lysis and ultimately parasite cell autodigestion. In essence, the parasite cell drowns in its own metabolic products.
Chemistry & industry
Pharmacology
Metabolism/Metabolites
Completely absorbed from gastrointestinal tract. Chloroquine is partially metabolized; the major metabolite is desethylchloroquine. Desethylchloroquine also has antiplasmodial activity, but is slightly less active than chloroquine. Bisdesethylchloroquine, which is a carboxylic acid derivative, and several other unidentified metabolites are also formed in small amounts (A625). Route of Elimination: Excretion of chloroquine is quite slow, but is increased by acidification of the urine. Half Life: 1-2 months
FDA Pharmacological Classification
CHLOROQUINE PHOSPHATE
Antimalarial [EPC]
CHLOROQUINUM PHOS.
Antimalarial [EPC]
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Agents used in the treatment of malaria. They are usually classified on the basis of their action against plasmodia at different stages in their life cycle in the human. (From AMA, Drug Evaluations Annual, 1992, p1585)
Pharmacological agents destructive to nematodes in the superfamily Filarioidea.
Uses & manufacturing
UsesFor the suppressive treatment and for acute attacks of malaria due to P. vivax, P.malariae, P. ovale, and susceptible strains of P. falciparum, Second-line agent in treatment of Rheumatoid Arthritis (A308).
Household ProductsInformation on 1 consumer products that contain Chloroquine phosphate in the following categories is provided:
Related reactions
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Compound notes
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