amodiaquine

CHEBI:2674 ·resolve ·ANTIPROTOZOAL ·EXACT SEEDED

A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position. — 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:33853 CHEBI:33853
CHEBI:36683 CHEBI:36683
CHEBI:36709 CHEBI:36709
CHEBI:50995 CHEBI:50995
CHEBI:50996 CHEBI:50996

Chemical structure

Computed structure properties
Molecular formula	C20H22ClN3O
Charge	0
Average mass	355.869 Da
Monoisotopic mass	355.14514 Da
Source	ChEBI
InChIKey	OVCDSSHSILBFBN-UHFFFAOYSA-N

SMILES

CCN(CC)Cc1cc(Nc2ccnc3cc(Cl)ccc23)ccc1O

InChI

InChI=1S/C20H22ClN3O/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19/h5-12,25H,3-4,13H2,1-2H3,(H,22,23)

Also called

amodiaquina (INN)— chebi
amodiaquinum (INN)— chebi
4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol (EXACT_SYNONYM)— chebi
Amodiaquine (EXACT_SYNONYM)— chebi

Cross-references

Equivalent identifiers for this same structure in other resources.

cas:86-42-0
drugbank:DB00613
drugcentral:186
kegg.compound:C07626
kegg.drug:D02922
lincs.smallmolecule:LSM-4042
patent:US2474821
pdb-ccd:CQA
reaxys:300962
wikipedia.en:Amodiaquine

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:2674`	amodiaquine	`antibioticmech:chebi-6a126cf0f9`	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.

Orf1a protein 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).

Middle East respiratory syndrome-related coronavirus NCBITaxon:1335626

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
EC50	2100 nM	No assay is provided This is a review article.	`RSID 868965` `assay 8918_1` `monomer 586429`	`PMID:32852058`
EC50	6210 nM	No assay is provided This is a review article.	`RSID 868979` `assay 8918_1` `monomer 586429`	`PMID:32852058`

Organism-specific examples
Protein	Gene	Organism	Entry
Orf1a protein `UniProtKB:A0A1L2E0X0`	—	Middle East respiratory syndrome-related coronavirus	UNREVIEWED

PMID:32852058 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Severe acute respiratory syndrome coronavirus 2 NCBITaxon:2697049

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
IC50	5150 nM	DRC analysis by immunofluorescence Ten-point DRCs were generated for each drug. Vero cells were seeded at 1.2 × 104 cells per well in DMEM, supplemented with 2% FBS and 1× antibiotic-antimycotic solution (Gibco), in black, 384-well μClear plates (Greiner Bio-One) 24 h prior to the experiment. Ten-point DRCs were generated, with compound concentrations ranging from 0.1 to 50 μM. For the viral infections, plates were transferred into the BSL3 containment facility and SARS-CoV-2 was added at a multiplicity of infection (MOI) of 0.0125. The cells were fixed at 24 hours postinfection (hpi) with 4% PFA and analyzed by immunofluorescence. The acquired images were analyzed using in-house software to quantify cell numbers and infection ratios, and antiviral activity was normalized to positive (mock) and negative (0.5% DMSO) controls in each assay plate. DRCs were fitted by sigmoidal dose-response models, with the following equation: Y = bottom + (top − bottom)/[1 + (IC50/X)Hillslope], using XLfit 4 software or Prism7. IC50 values were calculated from the normalized activity data set-fitted curves. All IC50 and 50% cytotoxic concentration (CC50) values were measured in duplicate, and the quality of each assay was controlled by Z -factor and the coefficient of variation in percent (%CV).	`RSID 874405` `assay 8945_1` `monomer 586429`	`PMID:32366720`

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

PMID:32366720 (BindingDB literature-curated quantitative target measurement; source value, assay text, reaction-set ID, and target organism retained.)

Replicase polyprotein 1ab VIRAL_PROTEIN MEASURED_TARGET_ASSOCIATION

Severe acute respiratory syndrome coronavirus NCBITaxon:2901879

Quantitative measurements
Type	Reported value	Assay	BindingDB IDs	Reference
EC50	1270 nM	No assay is provided This is a review article.	`RSID 868980` `assay 8918_1` `monomer 586429`	`PMID:32852058`

Organism-specific examples
Protein	Gene	Organism	Entry
Replicase polyprotein 1ab `UniProtKB:P0C6X7`	—	Severe acute respiratory syndrome coronavirus	REVIEWED

PMID:32852058 (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.