Emetine

Summary

Emetine (CHEMBL50588) is an approved small-molecule antiprotozoal drug (ATC P01AX52); indicated across 1 condition including amebiasis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: P01AX52 (+1 more)
• Indications: 1 condition
• Clinical trials: 1
• Chemistry: 480.6 Da · C29H40N2O4

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL50588
Name	Emetine
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	10219
ChEBI	CHEBI:4781
ATC	P01AX52, P01AX02
Molecular formula	C29H40N2O4
Molecular weight	480.6
InChIKey	AUVVAXYIELKVAI-CKBKHPSWSA-N

SMILES: CC[C@H]1CN2CCC3=CC(=C(C=C3[C@@H]2C[C@@H]1C[C@@H]4C5=CC(=C(C=C5CCN4)OC)OC)OC)OC

IUPAC name: (2S,3R,11bS)-2-[[(1R)-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl]-3-ethyl-9,10-dimethoxy-2,3,4,6,7,11b-hexahydro-1H-benzo[a]quinolizine

ChEBI definition: A pyridoisoquinoline comprising emetam having methoxy substituents at the 6’-, 7’-, 10- and 11-positions. It is an antiprotozoal agent and emetic. It inhibits SARS-CoV2, Zika and Ebola virus replication and displays antimalarial, antineoplastic and antiamoebic properties.

Pharmacological roles (ChEBI): antiprotozoal drug, antiviral agent, emetic, protein synthesis inhibitor, antimalarial, antineoplastic agent, autophagy inhibitor, antiinfective agent, expectorant, anticoronaviral agent, antiamoebic agent.

Other ChEBI roles (chemical / environmental): plant metabolite.

Also known as: (-)-emetine, Cephaeline methyl ether, Emetin, Emetine, Emetinum, GNF-Pf-196, NSC-33669, TCMDC-125531, emetine, SID90341404, SID50104287, SID50104288

Parent form; salt/anhydrous children: CHEMBL493439, CHEMBL513000, CHEMBL1255782

Patent coverage: 5,696 distinct patent families (22,457 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 22,210 (99%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 18 (assay-derived). Sample: Serine hydrolase RBBP9, G-protein coupled receptor 35, NPC intracellular cholesterol transporter 1, Ras-related protein Rab-9A, Alpha-2A adrenergic receptor, Alpha-2C adrenergic receptor, D(1A) dopamine receptor, 5-hydroxytryptamine receptor 1A, D(2) dopamine receptor, Hypoxia inducible factors; HIF-1-alpha, HIF-2-alpha.

Bioactivity

ChEMBL activities: 25 potent at pChembl ≥ 5 of 32 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
ADRA2A	7.85	Ki	14	nM	CHEMBL_ACT_7658404
ADRA2C	7.58	Ki	26	nM	CHEMBL_ACT_7658408
ADRA2A	7.42	IC50	38	nM	CHEMBL_ACT_7658403
HIF1A	7.08	IC50	83	nM	CHEMBL_ACT_2543413
ADRA2A	7.05	AC50	90	nM	CHEMBL_ACT_25156475
SLC2A1	6.97	IC50	108	nM	CHEMBL_ACT_15345841
HIF1A	6.96	IC50	110	nM	CHEMBL_ACT_2540621
ADRA2C	6.74	IC50	182	nM	CHEMBL_ACT_7658407
ADRA2C	6.64	AC50	230	nM	CHEMBL_ACT_25147762
GPR35	6.45	IC50	352.5	nM	CHEMBL_ACT_25751455
P15823	5.97	Ki	1071	nM	CHEMBL_ACT_7658400
ADRA2A	5.92	AC50	1196	nM	CHEMBL_ACT_25219785
MTOR	5.73	Potency	1849	nM	CHEMBL_ACT_4783734
P15823	5.71	IC50	1934	nM	CHEMBL_ACT_7658399
ABCB1	5.62	IC50	2400	nM	CHEMBL_ACT_11001314
ADRA1A	5.6	AC50	2510	nM	CHEMBL_ACT_25234659
P43140	5.58	Ki	2642	nM	CHEMBL_ACT_7658398
MTOR	5.28	Potency	5212	nM	CHEMBL_ACT_4522072
ADRA1A	5.22	AC50	6000	nM	CHEMBL_ACT_25137867
OPRM1	5.22	AC50	5990	nM	CHEMBL_ACT_25158221
P43140	5.18	IC50	6527	nM	CHEMBL_ACT_7658397
RBBP9	5.11	IC50	7800	nM	CHEMBL_ACT_3244657
ABCB1	5.04	IC50	9200	nM	CHEMBL_ACT_11001898
KCNH2	5.04	AC50	9100	nM	CHEMBL_ACT_25117710
ABCB1	5.02	IC50	9600	nM	CHEMBL_ACT_11001900

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

1 indication (1 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
amebiasis	4	MONDO:0005644	EFO:0007144

Clinical trials

Total trials: 1.

Phase distribution

Phase	Trials
PHASE2/PHASE3	1

Top trials by phase / activity

NCT	Phase	Status	Title
NCT07016321	PHASE2/PHASE3	NOT_YET_RECRUITING	Emetine for Viral Outbreaks (a.k.a. EVOLVE Antiviral Initiative)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No PharmGKB pharmacogenomic data curated for this drug.

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).