2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol

• ChemBase ID: 1388
• Molecular Formular: C18H26ClN3O
• Molecular Mass: 335.87154
• Monoisotopic Mass: 335.17644015
• SMILES: Clc1cc2nccc(NC(CCCN(CCO)CC)C)c2cc1
• Canonical SMILES: OCCN(CCCC(Nc1ccnc2c1ccc(c2)Cl)C)CC
• InChI: InChI=1S/C18H26ClN3O/c1-3-22(11-12-23)10-4-5-14(2)21-17-8-9-20-18-13-15(19)6-7-16(17)18/h6-9,13-14,23H,3-5,10-12H2,1-2H3,(H,20,21)
• InChIKey: XXSMGPRMXLTPCZ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-({4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino)ethan-1-ol
• IUPAC Traditional name: hydroxychloroquine
• Brand Name: Ercoquin; Quensyl; Plaquenil
• Synonyms: 2-((4-((7-Chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol; Gen-Hydroxychloroquine 200mg Tablets; HCQ; Hidroxicloroquina [inn-spanish]; Hydroxychloroguine; Hydroxychloroquine sulfate; Hydroxychloroquinum [inn-latin]; Idrossiclorochina [dcit]; Oxichlorochinum; Oxichloroquine; Oxychlorochin; Oxychloroquine; Hydroxychloroquine

Database IDs

• CAS Number: 118-42-3
• PubChem SID: 160964848; 46508459
• PubChem CID: 3652
• ATC CODE: P01BA02
• CHEMBL: 1535
• Chemspider ID: 3526
• DrugBank ID: DB01611
• KEGG ID: D08050
• Unique Ingredient Identifier: 4QWG6N8QKH
• Wikipedia Title: Hydroxychloroquine
• Medline Plus: a601240

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.59329
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -1.7593226
• LogD (pH = 7.4): 0.3267855
• Log P: 2.8869712
• Molar Refractivity: 97.9667 cm^3
• Polarizability: 38.672028 Å^3
• Polar Surface Area: 48.39 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.87
• LOG S: -4.11
• Solubility (Water): 2.61e-02 g/l

PROPERTIES

Pharmacology Properties

• Admin Routes: Oral
• Excretion: Renal
• Half Life: 1–2 months
• Legal Status: POM (UK), ?-only (U.S.)
• Pregnancy Category: D (Au), C (U.S.)

DETAILS

DrugBank - DB01611

• Drug Groups: approved
• Description: A chemotherapeutic agent that acts against erythrocytic forms of malarial parasites.
• Indication: For the suppressive treatment and treatment of acute attacks of malaria due to Plasmodium vivax, P. malariae, P. ovale, and susceptible strains of P. falciparum. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis.
• Pharmacology: Hydroxychloroquine possesses antimalarial properties and also exerts a beneficial effect in lupus erythematosus (chronic discoid or systemic) and acute or chronic rheumatoid arthritis. The precise mechanism of action is not known.
• Toxicity: Symptoms of overdose include headache, drowsiness, visual disturbances, cardiovascular collapse, and convulsions, followed by sudden and early respiratory and cardiac arrest. The electrocardiogram may reveal atrial standstill, nodal rhythm, prolonged intraventricular conduction time, and progressive bradycardia leading to ventricular fibrillation and/or arrest.
• Affected Organisms: Plasmodium
• Biotransformation: Partially hepatic, to active de-ethylated metabolites.
• Absorption: Very rapidly and completely absorbed following oral administration.
• Half Life: Terminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.
• Protein Binding: Approximately 45%.
• External Links: Wikipedia; RxList; Drugs.com