Basic information
- CAS
747-36-4- Standard SMILES
CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12.O=S(=O)(O)O- InChIKey
JCBIVZZPXRZKTI-UHFFFAOYSA-N- Molecular formula
- C18H28ClN3O5S
- Average molar mass
- 434 g/mol
- Monoisotopic mass
- 433.1438199
Overview
Hydroxychloroquine Sulfate is a synthetic derivative of quinolyl with chemotherapeutic and antibiotic properties, Hydroxychloroquine Sulfate acts against erythrocytic malarial parasites (Plasmodium vivax, ovale, and malariae) by concentrating in food vacuoles. It inhibits plasmodial heme polymerase and acts through other unknown mechanisms. Hydroxychloroquine also has anti-inflammatory properties and is used in the treatment of rheumatoid arthritis and lupus erythematosus. (NCI04)
Names & identifiers
- Preferred name
- Hydroxychloroquine Sulfate
- IUPAC
- 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol;sulfuric acid
- English name
- Hydroxychloroquine sulfate
- Molecular formula
- C18H28ClN3O5S
- Molecular weight
- 433.95
Names & synonyms
HYDROXYCHLOROQUINE SULFATE747-36-4Hydroxychloroquine sulphateErcoquinOxiklorinPlaquenil sulfateQuensylQuinoricDTXSID1047811NSC-4375SOVUNA8Q2869CNVH
Show more names
HydroxychloroquinHydrochloroquine sulfateHydroxycloroquine sulfateHydroxychloroquine sulfate tablets2-((4-((7-Chloro-4-quinolinyl)amino)pentyl)ethylamino)ethanol sulfate (1:1) (salt)7-Chloro-4-[4-(N-ethyl-N-b-hydroxyethylamino)-1-methylbutylamino]quinoline sulfatePlaquinol
DTXCID9027788Hydroxychloroquine Sulfate (1:1) SaltHydroxychloroquinesulfateRefChem:56573212-019-32-((4-((7-Chloroquinolin-4-yl)amino)pentyl)(ethyl)amino)ethanol sulfateC18H28ClN3O5SMFCD00078203
Database identifiers
- CAS
747-36-4- PubChem CID
- 12947
- DTXSID
DTXSID1047811- ChEMBL
Properties
Computed structural properties
- Topological polar surface area
- 131 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 8
- Rotatable bonds
- 9
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 413
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section178.4 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 240 °C · 240 °C
- storage temp.
- protect from light
- solubility
- 2 O: · H2O: >20mg/mL
- form
- Crystalline Powder
- color
- white to off-white
- PH
- 3.5 · 3.5-5.5 (1% in aqueous solution, pH <6.0)
- biological source
- synthetic
- Water Solubility
- FREELY SOLUBLE
- Merck
- 14 · 14,4818
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in water may be stored at -20°C for up to 3 months.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (92.9%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P272, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P333+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 56 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (92.9%)
Toxicology
Exposure RoutesVery rapidly and completely absorbed following oral administration.
Toxicity Summary
Although the exact mechanism of action is unknown, it may be based on ability of hydroxychloroquine to bind to and alter DNA. Hydroxychloroquine has also has been found to be taken up into the acidic food vacuoles of the parasite in the erythrocyte. This increases the pH of the acid vesicles, interfering with vesicle functions and possibly inhibiting phospholipid metabolism. In suppressive treatment, hydroxychloroquine inhibits the erythrocytic stage of development of plasmodia. In acute attacks of malaria, it interrupts erythrocytic schizogony of the parasite. Its ability to concentrate in parasitized erythrocytes may account for their selective toxicity against the erythrocytic stages of plasmodial infection. As an antirheumatic, hydroxychloroquine is thought to act as a mild immunosuppressant, inhibiting the production of rheumatoid factor and acute phase reactants. It also accumulates in white blood cells, stabilizing lysosomal membranes and inhibiting the activity of many enzymes, including collagenase and the proteases that cause cartilage breakdown.
Chemistry & industry
Pharmacology
Metabolism/MetabolitesPartially hepatic, to active de-ethylated metabolites.
Half Life: Terminal elimination half-life In blood is approximately 50 days. In plasma it is approximately 32 days.
FDA Pharmacological Classification
HYDROXYCHLOROQUINE SULFATE
Antirheumatic Agent [EPC]; Antimalarial [EPC]
MeSH Pharmacological Classification
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)
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction.
Drugs that are used to treat RHEUMATOID ARTHRITIS.
Uses & manufacturing
Uses
For the suppressive treatment and treatment of acute attacks of malaria due to <i>Plasmodium vivax</i>, <i>P. malariae</i>, <i>P. ovale</i>, and susceptible strains of <i>P. falciparum</i>. It is also indicated for the treatment of discoid and systemic lupus erythematosus, and rheumatoid arthritis.
Applications
DescriptionHydroxychloroquine is an aminoquinoline with antimalarial, anti-inflammatory, and antiviral activities. It is active against the chloroquine-sensitive NF54 and D6 strains of P. falciparum (IC50s = 16.3 and 15 nM, respectively) but has decreased activity against chloroquine-resistant P. falciparum strains (IC50s = 422.7-1,735.3 nM). Hydroxychloroquine inhibits production of IL-22, IL-17A, and IL-6 induced by phorbol 12-myristate 13-acetate (TPA; ) and ionomycin in peripheral blood mononuclear cells (PBMCs) isolated from healthy individuals or patients with systemic lupus erythematosus (SLE) or rheumatoid arthritis (RA). It inhibits accumulation of sequestosome-1 (SQSTM1) puncta, a marker of autophagy, in mouse embryonic fibroblasts (MEFs) in a concentration-dependent manner. Hydroxychloroquine reduces viral titers of severe acute respiratory syndrome coronavirus 2 (SARS-CoV-2) in the culture supernatant of infected Vero E6 cells but does not reduce SARS-CoV-2 viral titers in an in vitro human airway epithelium model or the respiratory tract of infected cynomolgus macaques. Formulations containing hydroxychloroquine have been used in the prevention or treatment of malaria, as well as in the treatment of RA and SLE.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…