hydroxychloroquine

CHEBI:5801 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

An aminoquinoline that is chloroquine in which one of the N-ethyl groups is hydroxylated at position 2. An antimalarial with properties similar to chloroquine that acts against erythrocytic forms of malarial parasites, it is mainly used as the sulfate salt for the treatment of lupus erythematosus, rheumatoid arthritis, and light-sensitive skin eruptions. — ChEBI

Machine-generated and unreviewed. Identity, structure and cross-references come straight from ChEBI's and CARD's own data; no curator has signed off on this record yet.

Classification

Strictly broader compounds or drug classes this molecule belongs to.

CHEBI:15734 CHEBI:15734
CHEBI:36683 CHEBI:36683
CHEBI:36709 CHEBI:36709
CHEBI:50995 CHEBI:50995
CHEBI:50996 CHEBI:50996

Chemical structure

Computed structure properties
Molecular formula	C18H26ClN3O
Charge	0
Average mass	335.879 Da
Monoisotopic mass	335.17644 Da
Source	ChEBI
InChIKey	XXSMGPRMXLTPCZ-UHFFFAOYSA-N

SMILES

CCN(CCO)CCCC(C)Nc1ccnc2cc(Cl)ccc12

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)

Also called

Polirreumin (BRAND_NAME)— chebi
hidroxicloroquina (INN)— chebi
hydroxychloroquinum (INN)— chebi
2-[{4-[(7-chloroquinolin-4-yl)amino]pentyl}(ethyl)amino]ethanol (EXACT_SYNONYM)— chebi
(±)-hydroxychloroquine (EXACT_SYNONYM)— chebi
2-((4-((7-chloro-4-quinolyl)amino)pentyl)ethylamino)ethanol (EXACT_SYNONYM)— chebi
2-(N-(4-(7-chlor-4-chinolylamino)-4-methylbutyl)ethylamino)ethanol (EXACT_SYNONYM)— chebi
7-chloro-4-(4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino)quinoline (EXACT_SYNONYM)— chebi
7-chloro-4-(4-(ethyl(2-hydroxyethyl)amino)-1-methylbutylamino)quinoline (EXACT_SYNONYM)— chebi
7-chloro-4-[4-(N-ethyl-N-β-hydroxyethylamino)-1-methylbutylamino]quinoline (EXACT_SYNONYM)— chebi
7-chloro-4-[5-(N-ethyl-N-2-hydroxyethylamino)-2-pentyl]aminoquinoline (EXACT_SYNONYM)— chebi
NSC4375 (EXACT_SYNONYM)— chebi
oxichlorochine (EXACT_SYNONYM)— chebi
oxichloroquine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:118-42-3
drugbank:DB01611
drugcentral:1395
hmdb:HMDB0015549
kegg.compound:C07043
kegg.drug:D08050
lincs.smallmolecule:LSM-5193
patent:US2546658
reaxys:253894
wikipedia.en:Hydroxychloroquine

Activity roles

Every antimicrobial role a source asserts for this compound — the unreduced evidence behind its antimicrobial_class.

CHEBI:149553 CHEBI:149553
CHEBI:38068 CHEBI:38068

Source concepts

Every upstream concept that resolved to this record. The merge is the product: this is what shows ChEBI and CARD are describing the same structure.

Upstream concepts merged into this record
Source	Native ID	Label	Minted CURIE	Version
CHEBI	`CHEBI:5801`	hydroxychloroquine	`antibioticmech:chebi-a04a1e3f85`	2026-08-30

Molecular targets

The molecular entity or process this compound acts on. Each target carries evidence — this is a mechanistic claim, not a classification.

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

BindingDB quantitative measurement in the named target organism; source assay descriptions and identifiers are retained per measurement. Evidence status: PRIMARY_EVIDENCE. Source: BINDINGDB 2026-09 (retrieved 2026-08-31).

Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	3584000 nM	Various Assay This is a review article. Please point to the original journal.	`RSID 1074394` `assay 10079_1` `monomer 50467780`	`PMID:34798775`

Organism-specific examples
Protein	Gene	Organism	Entry
Replicase polyprotein 1ab `UniProtKB:P0DTD1`	—	Severe acute respiratory syndrome coronavirus 2	REVIEWED

PMID:34798775 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Curation history

SEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Seeded from data/raw/ inventories (CHEBI)
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-30 · seed_from_sources
Re-seeded from updated data/raw/ inventories
RESEEDED_FROM_SOURCES 2026-08-31 · seed_from_sources
Re-seeded from updated data/raw/ inventories

Provenance

Seeded by scripts/seed_from_sources.py from the committed inventories in data/raw/. View the record.