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Terfenadine
Identification
- Name
- Terfenadine
- Accession Number
- DB00342
- 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In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Terfenadine (DB00342)
- Weight
- Average: 471.6734
Monoisotopic: 471.313729561 - Chemical Formula
- C32H41NO2
- Synonyms
- (RS)-1-(4-tert-butylphenyl)-4-{4-[hydroxy(diphenyl)methyl]piperidin-1-yl}-butan-1-ol
- Terfenadin
- Terfenadina
- Terfénadine
- Terfenadine
- Terfenadinum
- External IDs
- RMI 9918
Pharmacology
- Indication
For the treatment of allergic rhinitis, hay fever, and allergic skin disorders.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Terfenadine, an H1-receptor antagonist antihistamine, is similar in structure to astemizole and haloperidol, a butyrophenone antipsychotic. The active metabolite of terfenadine is fexofenadine.
- Mechanism of action
Terfenadine competes with histamine for binding at H1-receptor sites in the GI tract, uterus, large blood vessels, and bronchial muscle. This reversible binding of terfenadine to H1-receptors suppresses the formation of edema, flare, and pruritus resulting from histaminic activity. As the drug does not readily cross the blood-brain barrier, CNS depression is minimal.
Target Actions Organism AHistamine H1 receptor antagonistHumans UPotassium voltage-gated channel subfamily H member 2 inhibitorHumans UMuscarinic acetylcholine receptor M3 antagonistHumans UMuscarinic acetylcholine receptor M1 binderHumans UMuscarinic acetylcholine receptor M5 binderHumans UMuscarinic acetylcholine receptor M4 binderHumans UMuscarinic acetylcholine receptor M2 binderHumans - Absorption
On the basis of a mass balance study using 14C labeled terfenadine the oral absorption of terfenadine was estimated to be at least 70%
- Volume of distribution
- Not Available
- Protein binding
70%
- Metabolism
Hepatic
Hover over products below to view reaction partners
- Route of elimination
- Not Available
- Half-life
3.5 hours
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Mild (e.g., headache, nausea, confusion), but adverse cardiac events including cardiac arrest, ventricular arrhythmias including torsades de pointes and QT prolongation have been reported. LD50=mg/kg (orally in mice)
- Affected organisms
- Humans and other mammals
- Pathways
Pathway Category Terfenadine H1-Antihistamine Action Drug action - Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Terfenadine can be increased when it is combined with Abametapir. Abatacept The metabolism of Terfenadine can be increased when combined with Abatacept. Abemaciclib The metabolism of Terfenadine can be decreased when combined with Abemaciclib. Abiraterone The metabolism of Terfenadine can be decreased when combined with Abiraterone. Acalabrutinib The metabolism of Terfenadine can be decreased when combined with Acalabrutinib. Acebutolol The metabolism of Terfenadine can be decreased when combined with Acebutolol. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Terfenadine. Acetaminophen The metabolism of Terfenadine can be decreased when combined with Acetaminophen. Acetazolamide The metabolism of Terfenadine can be decreased when combined with Acetazolamide. Acetophenazine Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Terfenadine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Exercise caution with grapefruit products. Grapefruit is a CYP3A4 inhibitor, and terfenadine is metabolized by CYP3A4. Co-administration may increase terfenadine concentrations and the risk of QT prolongation.
- Exercise caution with St. John's Wort. This herb induces CYP3A4 and terfenadine is a substrate of CYP3A4.
Products
- International/Other Brands
- Bronal (Galenika) / Daylert (Micro Labs) / Seldane / Servinin (Novartis ) / Teldane / Terfed (Cipla) / Terfenadin AL (Aliud) / Terfenadine FLX (Accord Healthcare) / Terfin (Interbat) / Ternadin (Dunar) / Trexyl (Ranbaxy) / Triludan
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataAllergy Relief Tablet 60 mg Oral Jcp Laboratories Inc. 1994-12-31 1998-08-12 Canada 
Allergy Relief Once A Day Allergy Caplet 120mg Tablet Oral Jcp Laboratories Inc. 1991-12-31 1998-08-12 Canada Seldane - Sus 30mg/5ml Suspension Oral Hoechst Marion Roussel 1995-12-31 1998-08-12 Canada Seldane - Tab 60mg Tablet Oral Hoechst Marion Roussel 1996-10-07 1998-08-12 Canada Seldane 120mg Once-A-day Caplets Tablet Oral Hoechst Marion Roussel 1995-12-31 1998-08-12 Canada Seldane Sus 6mg/ml Suspension Oral Merrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc 1985-12-31 1996-09-09 Canada Seldane Tab 120mg Tablet Oral Merrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc 1988-12-31 1997-08-05 Canada Seldane Tab 60mg Tablet Oral Merrell Pharms Inc., Division Of Merrell Dow (Can) 1983-12-31 1997-08-05 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataApo-terfenadine Tab 120mg Tablet Oral Apotex Corporation 1993-12-31 1999-12-08 Canada Apo-terfenadine Tablets 60mg Tablet Oral Apotex Corporation 1993-12-31 1999-12-08 Canada Novo-terfenadine Tab 60mg Tablet Oral Novopharm Limited 1993-12-31 1999-11-15 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- R06AX12 — Terfenadine
- Drug Categories
- Anticholinergic Agents
- Antihistamines for Systemic Use
- Benzene Derivatives
- Benzhydryl Compounds
- BSEP/ABCB11 Substrates
- 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 Inducers
- Cytochrome P-450 CYP3A4 Inducers (strength unknown)
- 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 CYP3A4 Substrates with a Narrow Therapeutic Index
- 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
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Phenylbutylamines / Phenylpropanes / Aralkylamines / Piperidines / Tertiary alcohols / Trialkylamines / Secondary alcohols / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives show 1 more
- Substituents
- Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Diphenylmethane / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound show 11 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- diarylmethane (CHEBI:9453)
Chemical Identifiers
- UNII
- 7BA5G9Y06Q
- CAS number
- 50679-08-8
- InChI Key
- GUGOEEXESWIERI-UHFFFAOYSA-N
- InChI
- InChI=1S/C32H41NO2/c1-31(2,3)26-18-16-25(17-19-26)30(34)15-10-22-33-23-20-29(21-24-33)32(35,27-11-6-4-7-12-27)28-13-8-5-9-14-28/h4-9,11-14,16-19,29-30,34-35H,10,15,20-24H2,1-3H3
- IUPAC Name
- 1-(4-tert-butylphenyl)-4-[4-(hydroxydiphenylmethyl)piperidin-1-yl]butan-1-ol
- SMILES
- CC(C)(C)C1=CC=C(C=C1)C(O)CCCN1CCC(CC1)C(O)(C1=CC=CC=C1)C1=CC=CC=C1
References
- Synthesis Reference
Timothy G. Fawcett, Christian T. Goralski, David W. Ziettlow, "Preparation of polymorphically pure terfenadine." U.S. Patent US4742175, issued April, 1975.
US4742175- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014486
- KEGG Drug
- D00521
- KEGG Compound
- C07463
- PubChem Compound
- 5405
- PubChem Substance
- 46507007
- ChemSpider
- 5212
- BindingDB
- 50017376
- 42330
- ChEBI
- 9453
- ChEMBL
- CHEMBL17157
- Therapeutic Targets Database
- DAP000102
- PharmGKB
- PA451619
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Terfenadine
- MSDS
- Download (72.9 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmedix
- Veratex Corp.
- Dosage Forms
Form Route Strength Tablet Oral 60 mg Tablet Oral Suspension Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 147 °C PhysProp water solubility 0.0963 mg/L (at 25 °C) MCFARLAND,JW ET AL. (2001) logP 7.1 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000458 mg/mL ALOGPS logP 5.89 ALOGPS logP 6.48 ChemAxon logS -6 ALOGPS pKa (Strongest Acidic) 13.2 ChemAxon pKa (Strongest Basic) 9.02 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 3 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 43.7 Å2 ChemAxon Rotatable Bond Count 9 ChemAxon Refractivity 146.27 m3·mol-1 ChemAxon Polarizability 56.45 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9535 Blood Brain Barrier + 0.5319 Caco-2 permeable + 0.6691 P-glycoprotein substrate Substrate 0.8338 P-glycoprotein inhibitor I Inhibitor 0.7145 P-glycoprotein inhibitor II Inhibitor 0.5515 Renal organic cation transporter Inhibitor 0.5731 CYP450 2C9 substrate Non-substrate 0.8286 CYP450 2D6 substrate Substrate 0.7689 CYP450 3A4 substrate Substrate 0.6664 CYP450 1A2 substrate Inhibitor 0.5553 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Inhibitor 0.5229 CYP450 3A4 inhibitor Non-inhibitor 0.8309 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9627 Ames test Non AMES toxic 0.8907 Carcinogenicity Non-carcinogens 0.8443 Biodegradation Not ready biodegradable 0.9683 Rat acute toxicity 2.0063 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.5556 hERG inhibition (predictor II) Inhibitor 0.8014
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Histamine receptor activity
- Specific Function
- In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamin...
- Gene Name
- HRH1
- Uniprot ID
- P35367
- Uniprot Name
- Histamine H1 receptor
- Molecular Weight
- 55783.61 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [PubMed:9485522]
- Salata JJ, Jurkiewicz NK, Wallace AA, Stupienski RF 3rd, Guinosso PJ Jr, Lynch JJ Jr: Cardiac electrophysiological actions of the histamine H1-receptor antagonists astemizole and terfenadine compared with chlorpheniramine and pyrilamine. Circ Res. 1995 Jan;76(1):110-9. [PubMed:8001268]
- Wood-Baker R, Smith R, Holgate ST: A double-blind, placebo controlled study of the effect of the specific histamine H1-receptor antagonist, terfenadine, in chronic severe asthma. Br J Clin Pharmacol. 1995 Jun;39(6):671-5. [PubMed:7654486]
- Phillips GD, Polosa R, Holgate ST: The effect of histamine-H1 receptor antagonism with terfenadine on concentration-related AMP-induced bronchoconstriction in asthma. Clin Exp Allergy. 1989 Jul;19(4):405-9. [PubMed:2569356]
- Rafferty P, Holgate ST: Terfenadine (Seldane) is a potent and selective histamine H1 receptor antagonist in asthmatic airways. Am Rev Respir Dis. 1987 Jan;135(1):181-4. [PubMed:2879489]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Voltage-gated potassium channel activity involved in ventricular cardiac muscle cell action potential repolarization
- Specific Function
- Pore-forming (alpha) subunit of voltage-gated inwardly rectifying potassium channel. Channel properties are modulated by cAMP and subunit assembly. Mediates the rapidly activating component of the ...
- Gene Name
- KCNH2
- Uniprot ID
- Q12809
- Uniprot Name
- Potassium voltage-gated channel subfamily H member 2
- Molecular Weight
- 126653.52 Da
References
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
- Gessner G, Zacharias M, Bechstedt S, Schonherr R, Heinemann SH: Molecular determinants for high-affinity block of human EAG potassium channels by antiarrhythmic agents. Mol Pharmacol. 2004 May;65(5):1120-9. [PubMed:15102940]
- Testai L, Cecchetti V, Sabatini S, Martelli A, Breschi MC, Calderone V: Effects of K openers on the QT prolongation induced by HERG-blocking drugs in guinea-pigs. J Pharm Pharmacol. 2010 Jul;62(7):924-30. doi: 10.1211/jpp.62.06.0014. [PubMed:20636881]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Antagonist
- General Function
- Receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM3
- Uniprot ID
- P20309
- Uniprot Name
- Muscarinic acetylcholine receptor M3
- Molecular Weight
- 66127.445 Da
References
- Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [PubMed:10212017]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM1
- Uniprot ID
- P11229
- Uniprot Name
- Muscarinic acetylcholine receptor M1
- Molecular Weight
- 51420.375 Da
References
- Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [PubMed:10212017]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Phosphatidylinositol phospholipase c activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM5
- Uniprot ID
- P08912
- Uniprot Name
- Muscarinic acetylcholine receptor M5
- Molecular Weight
- 60073.205 Da
References
- Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [PubMed:10212017]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Guanyl-nucleotide exchange factor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM4
- Uniprot ID
- P08173
- Uniprot Name
- Muscarinic acetylcholine receptor M4
- Molecular Weight
- 53048.65 Da
References
- Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [PubMed:10212017]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- G-protein coupled acetylcholine receptor activity
- Specific Function
- The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
- Gene Name
- CHRM2
- Uniprot ID
- P08172
- Uniprot Name
- Muscarinic acetylcholine receptor M2
- Molecular Weight
- 51714.605 Da
References
- Yasuda SU, Yasuda RP: Affinities of brompheniramine, chlorpheniramine, and terfenadine at the five human muscarinic cholinergic receptor subtypes. Pharmacotherapy. 1999 Apr;19(4):447-51. [PubMed:10212017]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitorInducer
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Wang RW, Newton DJ, Liu N, Atkins WM, Lu AY: Human cytochrome P-450 3A4: in vitro drug-drug interaction patterns are substrate-dependent. Drug Metab Dispos. 2000 Mar;28(3):360-6. [PubMed:10681383]
- Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [PubMed:9485522]
- Nemeroff CB, DeVane CL, Pollock BG: Newer antidepressants and the cytochrome P450 system. Am J Psychiatry. 1996 Mar;153(3):311-20. [PubMed:8610817]
- Flockhart Table of Drug Interactions [Link]
- WHO: PHARMACEUTICALS: RESTRICTIONS IN USE AND AVAILABILITY [File]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Kishimoto W, Hiroi T, Sakai K, Funae Y, Igarashi T: Metabolism of epinastine, a histamine H1 receptor antagonist, in human liver microsomes in comparison with that of terfenadine. Res Commun Mol Pathol Pharmacol. 1997 Dec;98(3):273-92. [PubMed:9485522]
- Cvetkovic RS, Goa KL: Lopinavir/ritonavir: a review of its use in the management of HIV infection. Drugs. 2003;63(8):769-802. [PubMed:12662125]
- Kortunay S, Bozkurt A, Basci NE, Kayaalp SO: Effects of terfenadine and diphenhydramine on the CYP2D6 activity in healthy volunteers. Eur J Drug Metab Pharmacokinet. 2002 Jul-Sep;27(3):171-4. doi: 10.1007/BF03190453. [PubMed:12365197]
- Jones BC, Hyland R, Ackland M, Tyman CA, Smith DA: Interaction of terfenadine and its primary metabolites with cytochrome P450 2D6. Drug Metab Dispos. 1998 Sep;26(9):875-82. [PubMed:9733666]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Flockhart Table of Drug Interactions [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- Molecular Weight
- 55824.275 Da
References
- Ong CE, Coulter S, Birkett DJ, Bhasker CR, Miners JO: The xenobiotic inhibitor profile of cytochrome P4502C8. Br J Clin Pharmacol. 2000 Dec;50(6):573-80. doi: 10.1046/j.1365-2125.2000.00316.x. [PubMed:11136296]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- This enzyme metabolizes arachidonic acid predominantly via a NADPH-dependent olefin epoxidation to all four regioisomeric cis-epoxyeicosatrienoic acids. One of the predominant enzymes responsible f...
- Gene Name
- CYP2J2
- Uniprot ID
- P51589
- Uniprot Name
- Cytochrome P450 2J2
- Molecular Weight
- 57610.165 Da
References
- Chen C, Li G, Liao W, Wu J, Liu L, Ma D, Zhou J, Elbekai RH, Edin ML, Zeldin DC, Wang DW: Selective inhibitors of CYP2J2 related to terfenadine exhibit strong activity against human cancers in vitro and in vivo. J Pharmacol Exp Ther. 2009 Jun;329(3):908-18. doi: 10.1124/jpet.109.152017. Epub 2009 Mar 16. [PubMed:19289568]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
- Gene Name
- ABCB1
- Uniprot ID
- P08183
- Uniprot Name
- Multidrug resistance protein 1
- Molecular Weight
- 141477.255 Da
References
- Wang EJ, Casciano CN, Clement RP, Johnson WW: Active transport of fluorescent P-glycoprotein substrates: evaluation as markers and interaction with inhibitors. Biochem Biophys Res Commun. 2001 Nov 30;289(2):580-5. [PubMed:11716514]
- Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389]
- Hait WN, Gesmonde JF, Murren JR, Yang JM, Chen HX, Reiss M: Terfenadine (Seldane): a new drug for restoring sensitivity to multidrug resistant cancer cells. Biochem Pharmacol. 1993 Jan 26;45(2):401-6. [PubMed:8094615]
- Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Substrate
- General Function
- Transporter activity
- Specific Function
- Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
- Gene Name
- ABCB11
- Uniprot ID
- O95342
- Uniprot Name
- Bile salt export pump
- Molecular Weight
- 146405.83 Da
References
- Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]
Drug created on June 13, 2005 07:24 / Updated on July 02, 2020 00:36
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