Bithionol

Summary

Bithionol (CHEMBL290106) is an approved small-molecule antiplatyhelmintic drug (ATC D10AB01) targeting NAPEPLD and KCNT1; indicated across 2 conditions including acne and helminthiasis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: D10AB01 (+1 more)
• Targets: 2 (NAPEPLD, KCNT1)
• Indications: 2 conditions
• Chemistry: 356 Da · C12H6Cl4O2S

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL290106
Name	Bithionol
Type	Small molecule
Max phase	4
FDA approved	no
PubChem CID	2406
ChEBI	CHEBI:3131
ATC	D10AB01, P02BX01
Molecular formula	C12H6Cl4O2S
Molecular weight	356
InChIKey	JFIOVJDNOJYLKP-UHFFFAOYSA-N

SMILES: C1=C(C=C(C(=C1SC2=C(C(=CC(=C2)Cl)Cl)O)O)Cl)Cl

IUPAC name: 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol

ChEBI definition: An aryl sulfide that is diphenyl sulfide in which each phenyl group is substituted at position 2 by hydroxy and at positions 3 and 5 by chlorine. A fungicide and anthelmintic, it was used in various topical drug products for the treatment of liver flukes, but withdrawn after being shown to be a potent photosensitizer with the potential to cause serious skin disorders.

Pharmacological roles (ChEBI): antiplatyhelmintic drug, antifungal agrochemical.

Also known as: Bithin, Bithionol, Bitionol, Lorothidol, NSC-47129, SID17389712, SID26751444, SID855531, SID99234233, SID104171365, SID50100878, SID50123605

Parent form; salt/anhydrous children: CHEMBL1447476

Patent coverage: 1,944 distinct patent families (6,439 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 6,217 (97%) 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

Primary targets (GtoPdb curated mechanism): the Cancer dependency column is the DepMap CRISPR fitness signal (% of screened cell lines dependent on the target).

Gene	Target	Action	pAffinity	Cancer dependency	UniProt
NAPEPLD	N-Acylphosphatidylethanolamine-phospholipase D	Inhibition	4.97	0%	Q6IQ20
KCNT1	KNa1.1	Agonist	6	1.2%	Q5JUK3

Broader ChEMBL bioactivity targets: 67 (assay-derived). Sample: Microtubule-associated protein tau, Lysine-specific demethylase 4E, Nuclear receptor ROR-gamma, Survival motor neuron protein, Prelamin-A/C, ATP-dependent DNA helicase Q1, RecQ-like DNA helicase BLM, Ferritin light chain, 15-hydroxyprostaglandin dehydrogenase [NAD(+)], Solute carrier family 22 member 2.

Bioactivity

ChEMBL activities: 63 potent at pChembl ≥ 5 of 110 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
TTR	7.21	Kd	62	nM	CHEMBL_ACT_23263059
MAPK14	6.5	IC50	318	nM	CHEMBL_ACT_7615257
MAPK1	6.42	IC50	385	nM	CHEMBL_ACT_7615255
ADORA3	6.33	Ki	468	nM	CHEMBL_ACT_7613721
ADRA2B	6.25	Ki	560	nM	CHEMBL_ACT_7613733
PGR	6.22	AC50	607.8	nM	CHEMBL_ACT_25204100
EGFR	6.21	IC50	614	nM	CHEMBL_ACT_7615261
ADRA2C	6.2	Ki	638	nM	CHEMBL_ACT_7613735
ADORA2A	6.18	Ki	655	nM	CHEMBL_ACT_7613719
ALOX12	6.15	Potency	707.9	nM	CHEMBL_ACT_4533141
ADORA3	6.08	IC50	829	nM	CHEMBL_ACT_7613720
NR1I2	6	EC50	1000	nM	CHEMBL_ACT_15465467
TTR	5.96	Kd	1100	nM	CHEMBL_ACT_23262936
ADORA2A	5.93	IC50	1167	nM	CHEMBL_ACT_7613718
ADRA2B	5.91	IC50	1226	nM	CHEMBL_ACT_7613732
SLC6A2	5.91	IC50	1235	nM	CHEMBL_ACT_7613742
SLC6A2	5.91	Ki	1225	nM	CHEMBL_ACT_7613743
ADRA2A	5.84	Ki	1434	nM	CHEMBL_ACT_7613731
DRD3	5.84	Ki	1433	nM	CHEMBL_ACT_7613803
TACR2	5.81	Ki	1553	nM	CHEMBL_ACT_7615300
SLC6A3	5.76	Ki	1733	nM	CHEMBL_ACT_7613807
TBXAS1	5.74	IC50	1840	nM	CHEMBL_ACT_7615303
SLC22A2	5.72	IC50	1900	nM	CHEMBL_ACT_12636202
MCL1	5.72	IC50	1899	nM	CHEMBL_ACT_4734101
ALOX12	5.7	Potency	1995	nM	CHEMBL_ACT_4532918
ERBB2	5.67	IC50	2147	nM	CHEMBL_ACT_7615265
SLC6A3	5.66	IC50	2181	nM	CHEMBL_ACT_7613806
SLC22A1	5.65	IC50	2230	nM	CHEMBL_ACT_18040338
OPRM1	5.65	Ki	2236	nM	CHEMBL_ACT_7615220
LCK	5.65	IC50	2255	nM	CHEMBL_ACT_7615267

Target pathways

Aggregated over 2 target gene(s): NAPEPLD, KCNT1.

Top Reactome pathways

5 total, by targets touching each:

Pathway	Targets	Genes
Disease	1	NAPEPLD
Retinoid cycle disease events	1	NAPEPLD
Biosynthesis of A2E, implicated in retinal degradation	1	NAPEPLD
Diseases associated with visual transduction	1	NAPEPLD
Diseases of the neuronal system	1	NAPEPLD

Dominant GO biological processes

GO term	Targets
temperature homeostasis	1
phospholipid catabolic process	1
response to isolation stress	1
host-mediated modulation of intestinal microbiota composition	1
positive regulation of inflammatory response	1
N-acylethanolamine metabolic process	1
N-acylphosphatidylethanolamine metabolic process	1
positive regulation of brown fat cell differentiation	1
negative regulation of eating behavior	1
lipid metabolic process	1
phospholipid metabolic process	1
lipid catabolic process	1
protein homotetramerization	1
potassium ion transmembrane transport	1
monoatomic ion transport	1

Indications & clinical

Indications

2 indications (2 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
acne	4	MONDO:0011438	EFO:0003894
helminthiasis	4	MONDO:0004664	EFO:1001342

Clinical trials

Total trials: 0.

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

Molecules sharing ≥1 of this drug’s curated primary targets, merged from two biobtree sources and ranked by shared-target count, then clinical phase: ChEMBL clinical-stage candidates (development phase ≥2) and PubChem drug-class bioactivity (approved / known drugs acting on the target). Deduplicated by drug name; the drug’s own salt forms are excluded. Note: for a drug with few primary targets a shared-target match can reflect off-target / promiscuous binding rather than the same therapeutic mechanism — the phase ordering surfaces bona-fide therapeutics first.

5 molecules share ≥1 primary target. Top 5 by shared-target count:

Molecule	Source	Status	Shared targets
QUINIDINE	ChEMBL + PubChem	Phase 4 (approved)	KCNT1
BEPRIDIL	ChEMBL	Phase 4 (approved)	KCNT1
HEXACHLOROPHENE	ChEMBL	Phase 4 (approved)	NAPEPLD
Loxapine	PubChem	Approved	KCNT1
Orlistat	PubChem	Approved	NAPEPLD