Ibutilide
drugOn this page
Also known as Ibutilida
Summary
Ibutilide (CHEMBL533) is an approved small molecule (ATC C01BD05) targeting KCNH2; indicated across 1 condition.
At a glance
- Status: Approved (max clinical phase 4)
- Modality: Small molecule
- ATC class: C01BD05
- Targets: 1 (KCNH2)
- Indications: 1 condition
- Clinical trials: 6
- Chemistry: 384.6 Da · C20H36N2O3S
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL533 |
| Name | Ibutilide |
| Type | Small molecule |
| Max phase | 4 |
| FDA approved | yes |
| PubChem CID | 60753 |
| ATC | C01BD05 |
| Molecular formula | C20H36N2O3S |
| Molecular weight | 384.6 |
| InChIKey | ALOBUEHUHMBRLE-UHFFFAOYSA-N |
SMILES: CCCCCCCN(CC)CCCC(C1=CC=C(C=C1)NS(=O)(=O)C)O
IUPAC name: N-[4-[4-[ethyl(heptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide
Also known as: Ibutilida, Ibutilide, ibutilide, IBUTILIDE
Parent form; salt/anhydrous children: CHEMBL2355456, CHEMBL3187455
Patent coverage: 27 distinct patent families (48 SureChEMBL compound mentions), from 1 matched compound structure(s). 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 | 8 | 0.3% | Q12809 |
Broader ChEMBL bioactivity targets: 9 (assay-derived). Sample: Alpha-2C adrenergic receptor, Alpha-2B adrenergic receptor, Voltage-gated L-type calcium channel, Muscarinic acetylcholine receptor M2, 5-hydroxytryptamine receptor 2A, Sodium-dependent serotonin transporter, D(3) dopamine receptor, Voltage-gated inwardly rectifying potassium channel KCNH2, Muscarinic acetylcholine receptor M3.
Bioactivity
ChEMBL activities: 9 potent at pChembl ≥ 5 of 14 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| KCNH2 | 8 | IC50 | 10 | nM | CHEMBL_ACT_1037289 |
| KCNH2 | 8 | IC50 | 10 | nM | CHEMBL_ACT_1523559 |
| KCNH2 | 8 | IC50 | 10 | nM | CHEMBL_ACT_2358301 |
| KCNH2 | 7.82 | IC50 | 15.14 | nM | CHEMBL_ACT_5219046 |
| KCNH2 | 7.7 | IC50 | 20 | nM | CHEMBL_ACT_1449222 |
| KCNH2 | 6.96 | AC50 | 110 | nM | CHEMBL_ACT_25118240 |
| SLC6A4 | 5.8 | AC50 | 1600 | nM | CHEMBL_ACT_25150588 |
| ADRA2C | 5.5 | AC50 | 3200 | nM | CHEMBL_ACT_25148142 |
| DRD3 | 5.37 | AC50 | 4300 | nM | CHEMBL_ACT_25193786 |
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
1 indication (1 at ChEMBL trial phase 4).
The 1 indication record carries no mapped disease name (EFO/MeSH-only); none shown.
Clinical trials
Total trials: 6.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE4 | 3 |
| Not specified | 2 |
| PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02513940 | PHASE4 | COMPLETED | Influence of Testosterone Administration on Drug-Induced QT Interval Prolongation and Torsades de Pointes |
| NCT03834883 | PHASE4 | COMPLETED | Reducing the Risk of Drug-Induced QT Interval Lengthening in Women |
| NCT04675788 | PHASE4 | COMPLETED | Novel Approaches for Minimizing Drug-Induced QT Interval Lengthening |
| NCT01929083 | PHASE2 | COMPLETED | Influence of Progesterone Administration on Drug-Induced QT Interval Lengthening |
| NCT01014741 | Not specified | COMPLETED | Modified Ablation Guided by Ibutilide Use in Chronic Atrial Fibrillation |
| NCT03370536 | Not specified | TERMINATED | ECGi Ibutilide: Effect of Ibutilide on AF Source Location and Organization |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 0 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
- 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