Disopyramide
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Also known as (rs)-disopyramideDicorantilDisopiramidaDl-disopyramideH-3292IsorythmLispineRitmilenRythmodan pSC-7031Searle-703SID50106174SID85231006SID90340571SID90341382SID85148360SID174006632SID144204278SID170464947
Summary
Disopyramide (CHEMBL517) is an approved small-molecule anti-arrhythmia drug (ATC C01BA03) targeting KCNH2; indicated across 3 conditions including atrial fibrillation and heart failure.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C01BA03
- Targets: 1 (KCNH2)
- Indications: 3 conditions
- Clinical trials: 2
- Chemistry: 339.5 Da · C21H29N3O
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL517 |
| Name | Disopyramide |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 3114 |
| ChEBI | CHEBI:4657 |
| ATC | C01BA03 |
| Molecular formula | C21H29N3O |
| Molecular weight | 339.5 |
| InChIKey | UVTNFZQICZKOEM-UHFFFAOYSA-N |
SMILES: CC(C)N(CCC(C1=CC=CC=C1)(C2=CC=CC=N2)C(=O)N)C(C)C
IUPAC name: 4-[di(propan-2-yl)amino]-2-phenyl-2-pyridin-2-ylbutanamide
ChEBI definition: A monocarboxylic acid amide that is butanamide substituted by a diisopropylamino group at position 4, a phenyl group at position 2 and a pyridin-2-yl group at position 2. It is used as a anti-arrhythmia drug.
Pharmacological roles (ChEBI): anti-arrhythmia drug.
Also known as: (rs)-disopyramide, Dicorantil, Disopiramida, Disopyramide, Dl-disopyramide, H-3292, Isorythm, Lispine, Ritmilen, Rythmodan p, SC-7031, Searle-703
Parent form; salt/anhydrous children: CHEMBL1201020
Patent coverage: 3,172 distinct patent families (11,140 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 11,139 (100%) 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 |
|---|---|---|---|---|---|
| KCNH2 | Kv11.1 | Inhibition | 4.04 | 0.3% | Q12809 |
Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: RecQ-like DNA helicase BLM, Peripheral myelin protein 22, Solute carrier family 22 member 2, Multidrug and toxin extrusion protein 1, Solute carrier family 22 member 2, Thyroid hormone receptor beta, Solute carrier family 22 member 1, Progesterone receptor, Kappa-type opioid receptor, Voltage-gated inwardly rectifying potassium channel KCNH2.
Bioactivity
ChEMBL activities: 7 potent at pChembl ≥ 5 of 21 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| BLM | 6.25 | Potency | 562.3 | nM | CHEMBL_ACT_4749910 |
| BLM | 6.25 | Potency | 562.3 | nM | CHEMBL_ACT_4933856 |
| SLC22A2 | 5.54 | IC50 | 2900 | nM | CHEMBL_ACT_12064059 |
| THRB | 5.5 | Potency | 3162 | nM | CHEMBL_ACT_4020966 |
| PDE3A | 5.27 | AC50 | 5400 | nM | CHEMBL_ACT_25190873 |
| OPRK1 | 5.17 | AC50 | 6731 | nM | CHEMBL_ACT_25129593 |
| ADRB3 | 5.08 | AC50 | 8370 | nM | CHEMBL_ACT_25153353 |
Target pathways
Aggregated over 1 target gene(s): KCNH2.
Top Reactome pathways
6 total, by targets touching each:
| Pathway | Targets | Genes |
|---|---|---|
| Neuronal System | 1 | KCNH2 |
| Potassium Channels | 1 | KCNH2 |
| Voltage gated Potassium channels | 1 | KCNH2 |
| Muscle contraction | 1 | KCNH2 |
| Phase 3 - rapid repolarisation | 1 | KCNH2 |
| Cardiac conduction | 1 | KCNH2 |
Dominant GO biological processes
| GO term | Targets |
|---|---|
| regulation of heart rate by hormone | 1 |
| potassium ion transport | 1 |
| regulation of membrane potential | 1 |
| positive regulation of DNA-templated transcription | 1 |
| potassium ion homeostasis | 1 |
| cardiac muscle contraction | 1 |
| regulation of membrane repolarization | 1 |
| regulation of ventricular cardiac muscle cell membrane repolarization | 1 |
| cellular response to xenobiotic stimulus | 1 |
| potassium ion transmembrane transport | 1 |
| ventricular cardiac muscle cell action potential | 1 |
| membrane repolarization | 1 |
| membrane depolarization during action potential | 1 |
| membrane repolarization during action potential | 1 |
| membrane repolarization during cardiac muscle cell action potential | 1 |
Indications & clinical
Indications
3 indications (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 |
|---|---|---|---|
| atrial fibrillation | 3 | MONDO:0004981 | EFO:0000275 |
| heart failure | 3 | MONDO:0005252 | EFO:0003144 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 2.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE3 | 1 |
| Not specified | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT00000556 | PHASE3 | COMPLETED | Atrial Fibrillation Follow-up Investigation of Rhythm Management (AFFIRM) |
| NCT02294955 | Not specified | UNKNOWN | Catheter Ablation Compared With Pharmacological Therapy for Atrial Fibrillation (CAPTAF Trial) |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
PharmGKB dosing guidelines (1) — CPIC / DPWG genotype-guided dosing for this drug (drug × pharmacogene):
| Guideline | Source | Gene(s) | Dosing | Recommendation |
|---|---|---|---|---|
| Annotation of DPWG Guideline for disopyramide and CYP2D6 | DPWG | CYP2D6 |
PharmGKB also curates 1 clinical and 2 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
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.
617 molecules share ≥1 primary target. Top 60 by shared-target count:
| Molecule | Source | Status | Shared targets |
|---|---|---|---|
| AFATINIB | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| DIHYDROERGOTAMINE | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| GENTIAN VIOLET | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| MAVORIXAFOR | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| PIMAVANSERIN | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| PROPOXYPHENE | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| RELUGOLIX | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| RIOCIGUAT | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| VORAPAXAR | ChEMBL + PubChem | Phase 4 (approved) | KCNH2 |
| ABEMACICLIB | ChEMBL | Phase 4 (approved) | KCNH2 |
| ACENOCOUMAROL | ChEMBL | Phase 4 (approved) | KCNH2 |
| ACETOPHENAZINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ACLIDINIUM BROMIDE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ALBENDAZOLE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ALMOTRIPTAN | ChEMBL | Phase 4 (approved) | KCNH2 |
| ALOSETRON | ChEMBL | Phase 4 (approved) | KCNH2 |
| ALPIDEM | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMBENONIUM | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMCINONIDE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMIODARONE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMISULPRIDE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMITRIPTYLINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMLODIPINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMODIAQUINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMOROLFINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMOXAPINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| AMSACRINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ANISOTROPINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ANTAZOLINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| APOMORPHINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ARIPIPRAZOLE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ASCIMINIB | ChEMBL | Phase 4 (approved) | KCNH2 |
| ASENAPINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ASTEMIZOLE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ATOMOXETINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| ATRACURIUM | ChEMBL | Phase 4 (approved) | KCNH2 |
| AVATROMBOPAG | ChEMBL | Phase 4 (approved) | KCNH2 |
| AZELASTINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BAZEDOXIFENE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BEDAQUILINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BENFLUOREX | ChEMBL | Phase 4 (approved) | KCNH2 |
| BENOXINATE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BENPERIDOL | ChEMBL | Phase 4 (approved) | KCNH2 |
| BENZPHETAMINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BENZTROPINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BENZYDAMINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BEPRIDIL | ChEMBL | Phase 4 (approved) | KCNH2 |
| BERBERINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BETRIXABAN | ChEMBL | Phase 4 (approved) | KCNH2 |
| BEXAROTENE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BIFONAZOLE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BIPERIDEN | ChEMBL | Phase 4 (approved) | KCNH2 |
| BITHIONOL | ChEMBL | Phase 4 (approved) | KCNH2 |
| BOSUTINIB | ChEMBL | Phase 4 (approved) | KCNH2 |
| BROMHEXINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BROMPERIDOL | ChEMBL | Phase 4 (approved) | KCNH2 |
| BUCLIZINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BUFLOMEDIL | ChEMBL | Phase 4 (approved) | KCNH2 |
| BUPIVACAINE | ChEMBL | Phase 4 (approved) | KCNH2 |
| BUPRENORPHINE | ChEMBL | Phase 4 (approved) | KCNH2 |
Related Atlas pages
- Genes: KCNH2
- Diseases: atrial fibrillation, heart failure
- Drugs: Afatinib, Dihydroergotamine, Mavorixafor, Pimavanserin, Propoxyphene, Relugolix, Riociguat, Vorapaxar, Abemaciclib, Acenocoumarol, Acetophenazine, Aclidinium Bromide, Albendazole, Almotriptan, Alosetron, Alpidem, Ambenonium, Amcinonide, Amiodarone, Amisulpride, Amitriptyline, Amlodipine, Amodiaquine, Amorolfine, Amoxapine, Amsacrine, Anisotropine, Antazoline, Apomorphine, Aripiprazole, Asciminib, Asenapine, Astemizole, Atomoxetine, Atracurium, Avatrombopag, Azelastine, Bazedoxifene, Bedaquiline, Benfluorex, Benoxinate, Benperidol, Benzphetamine, Benztropine, Benzydamine, Bepridil, Berberine, Betrixaban, Bexarotene, Bifonazole, Biperiden, Bithionol, Bosutinib, Bromhexine, Bromperidol, Buclizine, Buflomedil, Bupivacaine, Buprenorphine