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Substance Name: Chloroquine [USP:INN:BAN]
RN: 54-05-7
UNII: 886U3H6UFF
InChIKey: WHTVZRBIWZFKQO-UHFFFAOYSA-N
Note
- The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.
Molecular Formula
- C18-H26-Cl-N3
Molecular Weight
- 319.8774
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Amebicides
- Anti-Amebic
- Anti-Infective Agents
- Antimalarial
- Antimalarials
- Antiparasitic Agents
- Antiprotozoal Agents
- Antirheumatic Agents
- Antiviral (COVID-19)
- Drug / Therapeutic Agent
- Human Data
- Mutation Data
- Reproductive Effect
- Tumor Data
Superlist Classification Code
- Overall Carcinogenic Evaluation: Group 3
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
Names and Synonyms
Name of Substance
- Chloroquine
- Chloroquine [USP:INN:BAN]
MeSH Heading
- Chloroquine
Synonyms
- (+-)-Chloroquine
- 1,4-Pentanediamine, N(4)-(7-chloro-4-quinolinyl)-N(1),N(1)-diethyl-
- 7-Chloro-4-((4-(diethylamino)-1-methylbutyl)amino)quinoline
- Amokin
- Aralen
- Arthrochin
- Artrichin
- Bemaco
- Bemasulph
- Benaquin
- Bipiquin
- BRN 0482809
- Capquin
- CCRIS 3439
- Chemochin
- Chloraquine
- Chlorochin
- Chlorochinum
- Chloroquina
- Chloroquine
- Chloroquine (VAN)
- Chloroquinium
- Chloroquinum
- Chloroquinum [INN-Latin]
- Chlorquin
- Cidanchin
- Clorochina
- Clorochina [DCIT]
- Cloroquina
- Cloroquina [INN-Spanish]
- Cocartrit
- CQ
- Dichinalex
- EINECS 200-191-2
- Elestol
- Gontochin
- Heliopar
- HSDB 3029
- Imagon
- Iroquine
- Khingamin
- Klorokin
- Lapaquin
- Malaquin
- Malaren
- Malarex
- Mesylith
- N(sup 4)-(7-Chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-1,4-pentanediamine
- N4-(7-Chloro-4-quinolinyl)-N1,N1-diethyl-1,4-pentanediamine
- Neochin
- Nivaquine
- NSC 187208
- Pfizerquine
- Quinachlor
- Quinercyl
- Quinilon
- Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-
- Quinoscan
- Reumachlor
- Ronaquine
- Roquine
- RP 3377
- Silbesan
- Siragan
- Solprina
- Sopaquin
- ST 21
- ST 21 (pharmaceutical)
- Tresochin
- Trochin
- UNII-886U3H6UFF
- W 7618
- WIN 244
Systematic Names
- 1,4-Pentanediamine, N(sup 4)-(7-chloro-4-quinolinyl)-N(sup 1),N(sup 1)-diethyl-
- 1,4-Pentanediamine, N4-(7-chloro-4-quinolinyl)-N1,N1-diethyl-
- Chloroquine
- Quinoline, 7-chloro-4-((4-(diethylamino)-1-methylbutyl)amino)-
Superlist Name
- Chloroquine
Registry Numbers
CAS Registry Number
- 54-05-7
FDA UNII
- 886U3H6UFF
Other Registry Number
- 56598-66-4
System Generated Number
- 0000054057
Structure Descriptors
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-NSmiles
CCN(CC)Toxicity
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
child | LDLo | oral | 37593ug/kg (37.593mg/kg) | BRAIN AND COVERINGS: OTHER DEGENERATIVE CHANGES CARDIAC: CHANGE IN RATE BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Annals of Emergency Medicine. Vol. 19, Pg. 47, 1990. |
human | LDLo | oral | 20mg/kg (20mg/kg) | VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE BEHAVIORAL: COMA | Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973. |
man | LDLo | oral | 86mg/kg (86mg/kg) | CARDIAC: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING CARDIAC: CHANGE IN RATE | New England Journal of Medicine. Vol. 318, Pg. 1, 1988. |
mouse | LD50 | intramuscular | 71mg/kg (71mg/kg) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 4, Pg. 69, 1983. | |
mouse | LD50 | intraperitoneal | 66mg/kg (66mg/kg) | Arzneimittel-Forschung. Drug Research. Vol. 32, Pg. 1219, 1982. | |
mouse | LD50 | intravenous | 21600ug/kg (21.6mg/kg) | Zhongguo Yaoli Xuebao. Acta Pharmacologica Sinica. Chinese Journal of Pharmacology. Vol. 4, Pg. 69, 1983. | |
mouse | LD50 | oral | 311mg/kg (311mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION BEHAVIORAL: TREMOR | Oyo Yakuri. Pharmacometrics. Vol. 7, Pg. 753, 1973. |
mouse | LD50 | subcutaneous | 150mg/kg (150mg/kg) | Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973. | |
rabbit | LD50 | intravenous | 8mg/kg (8mg/kg) | Therapie. Vol. 25, Pg. 823, 1970. | |
rabbit | LD50 | subcutaneous | 75mg/kg (75mg/kg) | Journal Europeen de Toxicologie. Vol. 6, Pg. 86, 1973. | |
rabbit | LDLo | intramuscular | 20mg/kg (20mg/kg) | Yaoxue Xuebao. Acta Pharmaceutica Sinica. Pharmaceutical Journal. Vol. 15, Pg. 630, 1980. | |
rat | LD50 | intraperitoneal | 102mg/kg (102mg/kg) | GASTROINTESTINAL: OTHER CHANGES | Pharmacology: International Journal of Experimental and Clinical Pharmacology. Vol. 13, Pg. 401, 1975. |
rat | LD50 | intravenous | 60mg/kg (60mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 38, 1966. | |
rat | LD50 | oral | 330mg/kg (330mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD LUNGS, THORAX, OR RESPIRATION: DYSPNEA BEHAVIORAL: ATAXIA | Journal of Toxicology, Clinical Toxicology. Vol. 20, Pg. 271, 1983. |
rat | LD50 | subcutaneous | 190mg/kg (190mg/kg) | Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 38, 1966. | |
women | LDLo | oral | 110mg/kg (110mg/kg) | CARDIAC: CHANGE IN RATE CARDIAC: OTHER CHANGES GASTROINTESTINAL: NAUSEA OR VOMITING | New England Journal of Medicine. Vol. 318, Pg. 1, 1988. |
women | LDLo | oral | 180mg/kg (180mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP VASCULAR: BP LOWERING NOT CHARACTERIZED IN AUTONOMIC SECTION BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD | Medical Journal of Australia. Vol. 160, Pg. 231, 1994. |
women | TDLo | oral | 24mg/kg/12D-I (24mg/kg) | BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY) BRAIN AND COVERINGS: CHANGES IN SURFACE EEG | Annals of Internal Medicine. Vol. 123, Pg. 76, 1995. |
women | TDLo | oral | 3600mg/kg/3Y (3600mg/kg) | SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE GASTROINTESTINAL: OTHER CHANGES | Tropical and Geographical Medicine. Vol. 32, Pg. 216, 1980. |
Physical Properties
Physical Property | Value | Units | Temp (deg C) | Source |
---|---|---|---|---|
Melting Point | 289 dec | deg C | EXP | |
pKa Dissociation Constant | 10.1 | (none) | EXP | |
log P (octanol-water) | 4.63 | (none) | EXP | |
Water Solubility | 10.6 | mg/L | 25 | EST |
Vapor Pressure | 1.92E-07 | mm Hg | 25 | EST |
Henry's Law Constant | 1.07E-12 | atm-m3/mole | 25 | EST |
Atmospheric OH Rate Constant | 1.59E-10 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.