3,3',4',5-TETRACHLOROSALICYLANILIDE
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Also known as Irgasan bs200SID144212390
Summary
3,3’,4’,5-Tetrachlorosalicylanilide (CHEMBL291338) is an approved small molecule targeting HTR6, HTR7, and HTR1A.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- Targets: 8 (HTR6, HTR7, HTR1A…)
- Chemistry: 351 Da · C13H7Cl4NO2
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL291338 |
| Name | 3,3’,4’,5-TETRACHLOROSALICYLANILIDE |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | no |
| PubChem CID | 14385 |
| ChEBI | CHEBI:188648 |
| Molecular formula | C13H7Cl4NO2 |
| Molecular weight | 351 |
| InChIKey | SJQBHPJLLIJASD-UHFFFAOYSA-N |
SMILES: C1=CC(=C(C=C1NC(=O)C2=C(C(=CC(=C2)Cl)Cl)O)Cl)Cl
IUPAC name: 3,5-dichloro-N-(3,4-dichlorophenyl)-2-hydroxybenzamide
ChEBI definition: A salicylanilide derivative with chloride substituents at C-3 and C-5 of the salicylate moiety and at C-3 and C-4 of the anilide moiety.
Pharmacological roles (ChEBI): drug allergen.
Also known as: Irgasan bs200, SID144212390
Patent coverage: 595 distinct patent families (721 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 604 (84%) 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 |
|---|---|---|---|---|---|
| HTR6 | 5-HT6 receptor | Full agonist | 7 | 0.2% | P50406 |
| HTR7 | 5-HT7 receptor | Full agonist | 7.1 | 0.8% | P34969 |
| HTR1A | 5-HT1A receptor | Full agonist | 8 | 0% | P08908 |
| HTR1B | 5-HT1B receptor | Full agonist | 7.9 | 0.2% | P28222 |
| HTR1D | 5-HT1D receptor | Full agonist | 8.2 | 0% | P28221 |
| HTR1E | 5-ht1e receptor | Antagonist | 7 | 0% | P28566 |
| HTR1F | 5-HT1F receptor | Antagonist | 7.3 | 0.1% | P30939 |
| HTR2B | 5-HT2B receptor | Antagonist | 9 | 0.4% | P41595 |
Broader ChEMBL bioactivity targets: 6 (assay-derived). Sample: Thromboxane-A synthase, KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F), Prostaglandin G/H synthase 1, Prostaglandin G/H synthase 2, Mitogen-activated protein kinase 14, Mitogen-activated protein kinase 1.
Bioactivity
ChEMBL activities: 5 potent at pChembl ≥ 5 of 8 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| PTGS2 | 6.27 | IC50 | 542 | nM | CHEMBL_ACT_7632889 |
| PTGS1 | 6.18 | IC50 | 666 | nM | CHEMBL_ACT_7632887 |
| MAPK1 | 6.05 | IC50 | 886 | nM | CHEMBL_ACT_7634267 |
| MAPK14 | 5.66 | IC50 | 2176 | nM | CHEMBL_ACT_7634269 |
| TBXAS1 | 5.31 | IC50 | 4927 | nM | CHEMBL_ACT_7635536 |
Target pathways
Aggregated over 8 target gene(s): HTR6, HTR7, HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B.
Top Reactome pathways
11 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Signal Transduction | 8 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| Signaling by GPCR | 8 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| Class A/1 (Rhodopsin-like receptors) | 8 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| Amine ligand-binding receptors | 8 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| Serotonin receptors | 8 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| GPCR ligand binding | 8 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| GPCR downstream signalling | 7 | HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| G alpha (i) signalling events | 4 | HTR1B, HTR1D, HTR1E, HTR1F |
| G alpha (s) signalling events | 2 | HTR6, HTR7 |
| G alpha (q) signalling events | 1 | HTR2B |
| RHOBTB3 ATPase cycle | 1 | HTR7 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger | 8 |
| chemical synaptic transmission | 8 |
| signal transduction | 8 |
| G protein-coupled receptor signaling pathway | 8 |
| adenylate cyclase-inhibiting serotonin receptor signaling pathway | 5 |
| G protein-coupled serotonin receptor signaling pathway | 4 |
| vasoconstriction | 4 |
| regulation of behavior | 4 |
| adenylate cyclase-activating G protein-coupled receptor signaling pathway | 4 |
| adenylate cyclase-inhibiting G protein-coupled receptor signaling pathway | 4 |
| smooth muscle contraction | 3 |
| adenylate cyclase-activating serotonin receptor signaling pathway | 2 |
| serotonin receptor signaling pathway | 2 |
| positive regulation of cell population proliferation | 2 |
| phospholipase C-activating serotonin receptor signaling pathway | 2 |
Indications & clinical
Indications
0 indications (0 at ChEMBL trial phase 4).
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.
618 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| IMIPRAMINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| RISPERIDONE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| SEROTONIN | ChEMBL + PubChem | Phase 3 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| MEBUFOTENIN | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| BREXPIPRAZOLE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR2B, HTR6, HTR7 |
| CLOZAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| ERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6 |
| OLANZAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| SUMATRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR7 |
| YOHIMBINE | ChEMBL + PubChem | Phase 3 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B, HTR6 |
| PSILOCIN | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D, HTR1E, HTR2B, HTR6, HTR7 |
| CYPROHEPTADINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| QUETIAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| RIZATRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B |
| SORAFENIB | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F, HTR2B, HTR6, HTR7 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR6, HTR7 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | HTR1B, HTR1D, HTR1E, HTR2B, HTR6, HTR7 |
| CARIPRAZINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR6, HTR7 |
| KETANSERIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR6, HTR7 |
| NEFAZODONE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR6, HTR7 |
| VILAZODONE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR6, HTR7 |
| LYSERGIDE | ChEMBL | Phase 2 | HTR1A, HTR1D, HTR1E, HTR2B, HTR6, HTR7 |
| LASMIDITAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1D, HTR1E, HTR1F, HTR2B, HTR7 |
| METHYLERGONOVINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR1F, HTR2B, HTR6 |
| NARATRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| PRAMIPEXOLE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR2B, HTR7 |
| ZIPRASIDONE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR2B, HTR6, HTR7 |
| ZOLMITRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR1F |
| CINACALCET | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D, HTR2B, HTR6, HTR7 |
| FROVATRIPTAN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR1E, HTR7 |
| MIANSERIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D, HTR2B, HTR6, HTR7 |
| OXYMETAZOLINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR6 |
| SALMETEROL | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR7 |
| SILODOSIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B, HTR7 |
| TEGASEROD | ChEMBL | Phase 4 (approved) | HTR1A, HTR1D, HTR2B, HTR6, HTR7 |
| LATREPIRDINE | ChEMBL | Phase 3 | HTR1D, HTR1E, HTR2B, HTR6, HTR7 |
| GSK163090 | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1D, HTR2B, HTR7 |
| PENFLURIDOL | ChEMBL | Phase 2 | HTR1A, HTR1D, HTR2B, HTR6, HTR7 |
| RITANSERIN | ChEMBL | Phase 2 | HTR1A, HTR1B, HTR1E, HTR6, HTR7 |
| SPIRAMIDE | ChEMBL | Phase 2 | HTR1A, HTR1D, HTR2B, HTR6, HTR7 |
| ASENAPINE | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1E, HTR2B, HTR6 |
| ELETRIPTAN | ChEMBL + PubChem | Phase 4 (approved) | HTR1A, HTR1B, HTR1E, HTR1F |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| CARVEDILOL | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| CHLORPROMAZINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| DOXEPIN | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| FLUPHENAZINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| HALOPERIDOL | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| KETOTIFEN | ChEMBL | Phase 4 (approved) | HTR1B, HTR2B, HTR6, HTR7 |
| LOXAPINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| METHYSERGIDE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| PROMAZINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| SERTINDOLE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR2B, HTR6 |
| THIORIDAZINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| THIOTHIXENE | ChEMBL | Phase 4 (approved) | HTR1A, HTR2B, HTR6, HTR7 |
| XYLOMETAZOLINE | ChEMBL | Phase 4 (approved) | HTR1A, HTR1B, HTR1D, HTR2B |
| BRILAROXAZINE | ChEMBL | Phase 3 | HTR1A, HTR2B, HTR6, HTR7 |
| CHLOROPHENYLPIPERAZINE | ChEMBL | Phase 2 | HTR1A, HTR2B, HTR6, HTR7 |
Related Atlas pages
- Genes: HTR6, HTR7, HTR1A, HTR1B, HTR1D, HTR1E, HTR1F, HTR2B
- Drugs: Dihydroergotamine, Imipramine, Risperidone, Serotonin, Brexpiprazole, Clozapine, Ergotamine, Olanzapine, Sumatriptan, Yohimbine, Cyproheptadine, Quetiapine, Rizatriptan, Sorafenib, Aripiprazole, Azelastine, Cariprazine, Ketanserin, Nefazodone, Vilazodone, Lasmiditan, Methylergonovine, Naratriptan, Pramipexole, Ziprasidone, Zolmitriptan, Cinacalcet, Frovatriptan, Mianserin, Oxymetazoline, Salmeterol, Silodosin, Tegaserod, Latrepirdine, Asenapine, Eletriptan, Amoxapine, Astemizole, Carvedilol, Chlorpromazine, Doxepin, Fluphenazine, Haloperidol, Ketotifen, Loxapine, Methysergide, Promazine, Sertindole, Thioridazine, Thiothixene, Xylometazoline, Brilaroxazine