Terfenadine

Identification

Summary

Terfenadine is an antihistamine for the treatment of allergy symptoms.

Generic Name
Terfenadine
DrugBank Accession Number
DB00342
Background

In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.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Approved, Withdrawn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
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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofAllergic rhinitis (ar)••••••••••••••••••
Treatment ofAllergies••••••••••••••••••••••
Treatment ofPollen allergy••••••••••••••••••
Treatment ofSkin allergy••••••••••••••••••
Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AHistamine H1 receptor
antagonist
Humans
UMuscarinic acetylcholine receptor M3
antagonist
Humans
UMuscarinic acetylcholine receptor M1
binder
Humans
UMuscarinic acetylcholine receptor M5
binder
Humans
UMuscarinic acetylcholine receptor M4
binder
Humans
UMuscarinic acetylcholine receptor M2
binder
Humans
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Humans
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
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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)

Pathways
PathwayCategory
Terfenadine H1-Antihistamine ActionDrug 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.
DrugInteraction
1,2-BenzodiazepineThe metabolism of 1,2-Benzodiazepine can be decreased when combined with Terfenadine.
AbametapirThe serum concentration of Terfenadine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Terfenadine can be increased when combined with Abatacept.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Terfenadine.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Terfenadine.
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

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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
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Allergy ReliefTablet60 mg / tabOralJcp Laboratories Inc.1994-12-311998-08-12Canada flag
Allergy Relief Once A Day Allergy Caplet 120mgTablet120 mgOralJcp Laboratories Inc.1991-12-311998-08-12Canada flag
Seldane - Sus 30mg/5mlSuspension30 mg / 5 mLOralHoechst Marion Roussel1995-12-311998-08-12Canada flag
Seldane - Tab 60mgTablet60 mg / tabOralHoechst Marion Roussel1996-10-071998-08-12Canada flag
Seldane 120mg Once-A-day CapletsTablet120 mg / tabOralHoechst Marion Roussel1995-12-311998-08-12Canada flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-terfenadine Tab 120mgTablet120 mg / tabOralApotex Corporation1993-12-311999-12-08Canada flag
Apo-terfenadine Tablets 60mgTablet60 mg / tabOralApotex Corporation1993-12-311999-12-08Canada flag
Novo-terfenadine Tab 60mgTablet60 mg / tabOralNovopharm Limited1993-12-311999-11-15Canada flag

Categories

ATC Codes
R06AX12 — Terfenadine
Drug Categories
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)
Affected organisms
  • Humans and other mammals

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
Human Metabolome Database
HMDB0014486
KEGG Drug
D00521
KEGG Compound
C07463
PubChem Compound
5405
PubChem Substance
46507007
ChemSpider
5212
BindingDB
50017376
RxNav
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

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Veratex Corp.
Dosage Forms
FormRouteStrength
TabletOral120 mg
SuspensionOral
TabletOral120 mg / tab
TabletOral60 mg / tab
SuspensionOral30 MG/5ML
TabletOral
SuspensionOral30 mg / 5 mL
SuspensionOral6 mg / mL
Syrup
SuspensionOral0.612 g
TabletOral60 mg
SuspensionOral0.6487 g
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)147 °CPhysProp
water solubility0.0963 mg/L (at 25 °C)MCFARLAND,JW ET AL. (2001)
logP7.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000458 mg/mLALOGPS
logP5.89ALOGPS
logP6.48Chemaxon
logS-6ALOGPS
pKa (Strongest Acidic)13.2Chemaxon
pKa (Strongest Basic)9.02Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area43.7 Å2Chemaxon
Rotatable Bond Count9Chemaxon
Refractivity146.27 m3·mol-1Chemaxon
Polarizability56.45 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9535
Blood Brain Barrier+0.5319
Caco-2 permeable+0.6691
P-glycoprotein substrateSubstrate0.8338
P-glycoprotein inhibitor IInhibitor0.7145
P-glycoprotein inhibitor IIInhibitor0.5515
Renal organic cation transporterInhibitor0.5731
CYP450 2C9 substrateNon-substrate0.8286
CYP450 2D6 substrateSubstrate0.7689
CYP450 3A4 substrateSubstrate0.6664
CYP450 1A2 substrateInhibitor0.5553
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.5229
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9627
Ames testNon AMES toxic0.8907
CarcinogenicityNon-carcinogens0.8443
BiodegradationNot ready biodegradable0.9683
Rat acute toxicity2.0063 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5556
hERG inhibition (predictor II)Inhibitor0.8014
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-001i-0922300000-f2ebf7861ae9f28463f9
Mass Spectrum (Electron Ionization)MSsplash10-001i-8890000000-2c6ad1195e498f463cbf
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0573-2592100000-35fee494c6fb22cf9279
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0000900000-577805b6e639de28dd59
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0000900000-6ee8ace68773688ab606
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0000900000-8d9a4ec2424b97bb3b80
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-6770900000-9830d37d285444cff791
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-5920000000-909f0029205fa0a7663f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-2541900000-f3da0c526b0e748b9567
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f79-0000900000-6fa4462833830121560a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0000900000-ef665023b01a82d39e10
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0f7a-1006900000-6fcb3edc85fd628079df
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0fk9-0103900000-9037119314945c4bcf96
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00di-2916700000-00858b0e1b5edbe04bbd
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-05fr-0459400000-f090406e40178c9094aa
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-244.8578083
predicted
DarkChem Lite v0.1.0
[M-H]-207.60046
predicted
DeepCCS 1.0 (2019)
[M+H]+243.6098083
predicted
DarkChem Lite v0.1.0
[M+H]+209.98558
predicted
DeepCCS 1.0 (2019)
[M+Na]+244.1497083
predicted
DarkChem Lite v0.1.0
[M+Na]+216.48138
predicted
DeepCCS 1.0 (2019)

Targets

Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock new
insights and accelerate drug research.
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Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
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Details
1. Histamine H1 receptor
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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
  5. 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. [Article]
  6. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. 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. [Article]
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
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. 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. [Article]
  3. 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. [Article]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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. [Article]
  2. 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. [Article]
  3. Nemeroff CB, DeVane CL, Pollock BG: Newer antidepressants and the cytochrome P450 system. Am J Psychiatry. 1996 Mar;153(3):311-20. [Article]
  4. Zhou S, Yung Chan S, Cher Goh B, Chan E, Duan W, Huang M, McLeod HL: Mechanism-based inhibition of cytochrome P450 3A4 by therapeutic drugs. Clin Pharmacokinet. 2005;44(3):279-304. doi: 10.2165/00003088-200544030-00005. [Article]
  5. Flockhart Table of Drug Interactions [Link]
  6. 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
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
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
  1. 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. [Article]
  2. Cvetkovic RS, Goa KL: Lopinavir/ritonavir: a review of its use in the management of HIV infection. Drugs. 2003;63(8):769-802. [Article]
  3. 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. [Article]
  4. 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. [Article]
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
  1. 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
  1. 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. [Article]
Details
6. Cytochrome P450 2J2
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
  1. 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. [Article]

Carriers

Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Regulator
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...

Components:
References
  1. Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
Regulator
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Martinez-Gomez MA, Carril-Aviles MM, Sagrado S, Villanueva-Camanas RM, Medina-Hernandez MJ: Characterization of antihistamine-human serum protein interactions by capillary electrophoresis. J Chromatogr A. 2007 Apr 20;1147(2):261-9. doi: 10.1016/j.chroma.2007.02.054. Epub 2007 Feb 22. [Article]

Transporters

Details
1. P-glycoprotein 1
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
  1. 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. [Article]
  2. 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. [Article]
  3. 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. [Article]
  4. 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. [Article]
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
  1. 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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 03, 2024 02:24