File:Hydroxychloroquine.svg · Wikimedia Commons · See Wikimedia Commons
hydroxychloroquine
Sign in to saveAlso known as NSC4375, (+-)-hydroxychloroquine, 7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline, 7-chloro-4-[4-(N-ethyl-N-beta-hydroxyethylamino)-1-methylbutylamino]quinoline, (±)-hydroxychloroquine, oxychlorochine, 2-({4-[(7-chloro-4-quinolyl)amino]pentyl}ethylamino)ethanol, 7-chloro-4-{4-[ethyl(2-hydroxyethyl)amino]-1-methylbutylamino}quinoline
OverviewAI-generated
Hydroxychloroquine is a chemical compound with the formula C₁₈H₂₆ClN₃O. Its IUPAC name is 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol. The substance has a molecular mass of 335.17644 and a weight of 335.9. It carries a charge of 0 and features an xlogp value of 3.6.
The compound possesses 2 hydrogen bond donors and 4 hydrogen bond acceptors, with a topological polar surface area of 48.4. Its defined daily dose is 0.516. Hydroxychloroquine is referenced by 355 other encyclopedia articles and has been the subject of 12447 PubMed entries.
Synthesized by Vinony from 18 facts across 4 sources: Wikidata, PubChem, PubMed, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.ATC_suffix
- BA02
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 443862546
- Drug.image
- Hydroxychloroquine.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.caption
- Skeletal formula of hydroxychloroquine
- Drug.image2
- Hydroxychloroquine-based-on-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
- Drug.width2
- 200
- Drug.caption2
- Ball-and-stick model of the hydroxychloroquine freebase molecule
- Drug.tradename
- Plaquenil, others
- Drug.MedlinePlus
- a601240
- Drug.DailyMedID
- Hydroxychloroquine
- Drug.pregnancy_AU
- D
- Drug.routes_of_administration
- By mouth (tablets)
- Drug.ATC_prefix
- P01
via Wikipedia infobox
Chemical data
- Formula
- C18H26ClN3O
- Molecular weight
- 335.9 g/mol
- IUPAC name
- 2-[4-[(7-chloroquinolin-4-yl)amino]pentyl-ethylamino]ethanol
- SMILES
- CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO
- InChIKey
- XXSMGPRMXLTPCZ-UHFFFAOYSA-N
- XLogP
- 3.6
- Polar surface area
- 48.4 Ų
- H-bond donors
- 2
- H-bond acceptors
- 4
- Formal charge
- 0
via PubChem
Research
12,447 papers- Hydroxychloroquine: A double‑edged sword (Review).ReviewMolecular medicine reports · 2025Huo R, Wei C, Yang Y et al.DOI: 10.3892/mmr.2025.13467
- Hydroxychloroquine and COVID-19: a Rheumatologist's Take on the Lessons Learned.ReviewCurrent allergy and asthma reports · 2021Udupa A, Leverenz D, Balevic SJ et al.DOI: 10.1007/s11882-020-00983-9
- Hydroxychloroquine as an Adjunct Therapy for Diabetes in Pregnancy.ReviewInternational journal of molecular sciences · 2024Basri NI, Murthi P, Abd Rahman RDOI: 10.3390/ijms25179681
- Will Hydroxychloroquine Still Be a Game-Changer for COVID-19 by Combining Azithromycin?ReviewFrontiers in immunology · 2020Li C, Cheng GDOI: 10.3389/fimmu.2020.01969
- Hydroxychloroquine as prophylaxis or treatment for COVID-19: What does the evidence say?ReviewIndian journal of public health · 2020Nina PB, Dash APDOI: 10.4103/ijph.IJPH_496_20
- Hydroxychloroquine Ocular Toxicity: A Comprehensive Review.ReviewThe Journal of rheumatology · 2026Sit M, Mason RH, Kaplan AJDOI: 10.3899/jrheum.2025-0127
- Hydroxychloroquine-related hyperpigmentation.Rheumatology (Oxford, England) · 2022Muller R, Jarrot PA, Kaplanski GDOI: 10.1093/rheumatology/keab352
- Taking hydroxychloroquine to heart.Journal of the American Academy of Dermatology · 2024Heymann WRDOI: 10.1016/j.jaad.2024.07.1477
via PubMed
Wikidata facts
- Mass
- 335.17644
- Has use
- medication
Show 9 more facts
- medical condition treated
- systemic lupus erythematosus
- chemical formula
- C₁₈H₂₆ClN₃O
- Commons category
- Hydroxychloroquine
- World Health Organisation international non-proprietary name
- hydroxychloroquine
- canonical SMILES
- CCN(CCCC(C)NC1=C2C=CC(=CC2=NC=C1)Cl)CCO
- defined daily dose
- 0.516
- subject has role
- bactericide
- different from
- chloroquine
- on focus list of Wikimedia project
- WikiProject COVID-19
Sources (11)
via Wikidata · CC0
~6 min read
Encyclopedic overview
17 sectionsContents
- Medical uses
- Contraindications
- Adverse effects
- Eyes
- Overdose
- Detection
- Interactions
- Pharmacology
- Pharmacokinetics
- Pharmacodynamics
- Mechanism of action
- History
- Chemical synthesis
- Manufacturing
- COVID-19
- References
- External links
{{Infobox drug | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 443862546 | image = Hydroxychloroquine.svg | image_class = skin-invert-image | width = 250 | alt = | caption = Skeletal formula of hydroxychloroquine | image2 = Hydroxychloroquine-based-on-xtal-3D-bs-17.png | image_class2 = bg-transparent | width2 = 200 | alt2 = | caption2 = Ball-and-stick model of the hydroxychloroquine freebase molecule
| pronounce = | tradename = Plaquenil, others | Drugs.com = | MedlinePlus = a601240 | DailyMedID = Hydroxychloroquine | pregnancy_AU = D | pregnancy_AU_comment = | pregnancy_category = | routes_of_administration = By mouth (tablets) | class = | ATCvet = | ATC_prefix = P01 | ATC_suffix = BA02 | ATC_supplemental =
Excerpted from Wikipedia’s “hydroxychloroquine” article, available under the CC BY-SA 4.0 licence.