Molecule Details
| InChIKey | GUGOEEXESWIERI-UHFFFAOYSA-N |
|---|---|
| Compound Name | Terfenadine |
| Canonical SMILES | CC(C)(C)c1ccc(C(O)CCCN2CCC(C(O)(c3ccccc3)c3ccccc3)CC2)cc1 |
| Clinical Status | Clinical Multi-Target |
| Targets (Human+Pathogen) | 18 |
| Pfam Stratification | Cross-Family |
| Avg pChEMBL | 6.53 |
| Source | ChEMBL;BindingDB;TTD_MultiTarget |
2D Structure
Activity Profile
DrugBank Annotations
| DrugBank ID | DB00342 |
|---|---|
| Drug Name | Terfenadine |
| CAS Number | 50679-08-8 |
| Groups | approved withdrawn |
| ATC Codes | R06AX12 |
| Description | In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation. |
Categories: Anticholinergic Agents Antihistamines for Systemic Use BSEP/ABCB11 Substrates Benzene Derivatives Benzhydryl Compounds Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (strength unknown) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors (weak) Cytochrome P-450 CYP2D6 Substrates Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates (strength unknown) Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Highest Risk QTc-Prolonging Agents Histamine Agents Histamine Antagonists Histamine H1 Antagonists Histamine H1 Antagonists, Non-Sedating Muscarinic Antagonists Neurotransmitter Agents P-glycoprotein inhibitors P-glycoprotein substrates Piperidines QTc Prolonging Agents
Cross-references: BindingDB: 50017376 ChEBI: 9453 CHEMBL17157 ChemSpider: 5212 Drugs Product Database (DPD): 1918 Guide to Pharmacology: 2608 IUPHAR: 2608 C07463 D00521 PharmGKB: PA451619 PubChem:5405 PubChem:46507007 RxCUI: 42330 Therapeutic Targets Database: DAP000102 Wikipedia: Terfenadine
Target Activities (18)
| Target | Gene | Organism | Category | Pfam | pChEMBL | Type | Source |
|---|---|---|---|---|---|---|---|
| P35348 | ADRA1A | Homo sapiens | Human | PF00001 | 8.6 | pIC50 | TTD_MultiTarget |
| P41595 | HTR2B | Homo sapiens | Human | PF00001 | 7.4 | IC50 | ChEMBL |
| P35367 | HRH1 | Homo sapiens | Human | PF00001 | 7.4 | IC50 | ChEMBL;BindingDB |
| Q12809 | KCNH2 | Homo sapiens | Human | PF00027 PF00520 PF13426 | 6.9 | IC50 | ChEMBL;BindingDB |
| P28223 | HTR2A | Homo sapiens | Human | PF00001 | 6.9 | IC50 | ChEMBL |
| Q01959 | SLC6A3 | Homo sapiens | Human | PF00209 | 6.6 | IC50 | ChEMBL |
| P08684 | CYP3A4 | Homo sapiens | Human | PF00067 | 6.5 | IC50 | ChEMBL;BindingDB |
| P35462 | DRD3 | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
| P18825 | ADRA2C | Homo sapiens | Human | PF00001 | 6.3 | Ki | ChEMBL |
| P50406 | HTR6 | Homo sapiens | Human | PF00001 | 6.2 | Ki | ChEMBL |
| P28335 | HTR2C | Homo sapiens | Human | PF00001 | 6.2 | Ki | ChEMBL |
| P51681 | CCR5 | Homo sapiens | Human | PF00001 | 6.1 | Ki | ChEMBL |
| P21452 | TACR2 | Homo sapiens | Human | PF00001 | 6.0 | Ki | ChEMBL |
| O60840 | CACNA1F | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.0 | IC50 | ChEMBL |
| Q01668 | CACNA1D | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.0 | IC50 | ChEMBL |
| Q13698 | CACNA1S | Homo sapiens | Human | PF08763 PF16905 PF00520 | 6.0 | IC50 | ChEMBL |
| Q13936 | CACNA1C | Homo sapiens | Human | PF08763 PF16885 PF16905 PF00520 | 6.0 | IC50 | ChEMBL;BindingDB |
| Q14524 | SCN5A | Homo sapiens | Human | PF00520 PF24609 PF06512 PF11933 | 6.0 | IC50 | ChEMBL;BindingDB |
DrugBank Target Actions (21)
| Target | Gene | Target Name | Action | Type |
|---|---|---|---|---|
| P02763 | P02763 | alpha1-acid glycoprotein | binder | carriers |
| P02768 | ALB | Albumin | binder | carriers |
| P02763 | P02763 | alpha1-acid glycoprotein | regulator | carriers |
| P02768 | ALB | Albumin | regulator | carriers |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | inhibitor | enzymes |
| P10632 | CYP2C8 | Cytochrome P450 2C8 | inhibitor | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | inhibitor | enzymes |
| P51589 | CYP2J2 | Cytochrome P450 2J2 | inhibitor | enzymes |
| P08684 | CYP3A4 | Cytochrome P450 3A4 | substrate | enzymes |
| P10635 | CYP2D6 | Cytochrome P450 2D6 | substrate | enzymes |
| P20815 | CYP3A5 | Cytochrome P450 3A5 | substrate | enzymes |
| P24462 | CYP3A7 | Cytochrome P450 3A7 | substrate | enzymes |
| P20309 | CHRM3 | Muscarinic acetylcholine receptor M3 | antagonist | targets |
| P35367 | HRH1 | Histamine H1 receptor | antagonist | targets |
| P08172 | CHRM2 | Muscarinic acetylcholine receptor M2 | binder | targets |
| P08173 | CHRM4 | Muscarinic acetylcholine receptor M4 | binder | targets |
| P08912 | CHRM5 | Muscarinic acetylcholine receptor M5 | binder | targets |
| P11229 | CHRM1 | Muscarinic acetylcholine receptor M1 | binder | targets |
| Q12809 | KCNH2 | Voltage-gated inwardly rectifying potassium channel KCNH2 | inhibitor | targets |
| P08183 | ABCB1 | ATP-dependent translocase ABCB1 | inhibitor | transporters |
| O95342 | ABCB11 | Bile salt export pump | substrate | transporters |