Identification

Name
Terfenadine
Accession Number
DB00342  (APRD00606)
Type
Small Molecule
Groups
Approved, Withdrawn
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In the U.S., Terfenadine was superseded by fexofenadine in the 1990s due to the risk of cardiac arrhythmia caused by QT interval prolongation.

Structure
Thumb
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
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Allergy ReliefTablet60 mgOralJcp Laboratories Inc.1994-12-311998-08-12Canada
Pharmaplus Once A Day Allergy Caplet 120mgTablet120 mgOralJcp Laboratories Inc.1992-12-311997-01-13Canada
Seldane - Sus 30mg/5mlSuspension30 mgOralHoechst Marion Roussel1995-12-311998-08-12Canada
Seldane - Tab 60mgTablet60 mgOralHoechst Marion Roussel1996-10-071998-08-12Canada
Seldane 120mg Once-A-day CapletsTablet120 mgOralHoechst Marion Roussel1995-12-311998-08-12Canada
Seldane Sus 6mg/mlSuspension6 mgOralMerrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc1985-12-311996-09-09Canada
Seldane Tab 120mgTablet120 mgOralMerrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc1988-12-311997-08-05Canada
Seldane Tab 60mgTablet60 mgOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1983-12-311997-08-05Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-terfenadine Tab 120mgTablet120 mgOralApotex Corporation1993-12-311999-12-08Canada
Apo-terfenadine Tablets 60mgTablet60 mgOralApotex Corporation1993-12-311999-12-08Canada
Novo-terfenadine Tab 60mgTablet60 mgOralNovopharm Limited1993-12-311999-11-15Canada
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
Categories
UNII
7BA5G9Y06Q
CAS number
50679-08-8
Weight
Average: 471.6734
Monoisotopic: 471.313729561
Chemical Formula
C32H41NO2
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

Pharmacology

Indication

For the treatment of allergic rhinitis, hay fever, and allergic skin disorders.

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
Human
UPotassium voltage-gated channel subfamily H member 2
inhibitor
Human
UMuscarinic acetylcholine receptor M3
antagonist
Human
UMuscarinic acetylcholine receptor M1
binder
Human
UMuscarinic acetylcholine receptor M5
binder
Human
UMuscarinic acetylcholine receptor M4
binder
Human
UMuscarinic acetylcholine receptor M2
binder
Human
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

Route of elimination
Not Available
Half life

3.5 hours

Clearance
Not Available
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
PathwayCategory
Terfenadine H1-Antihistamine ActionDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Terfenadine can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Terfenadine can be decreased when combined with (S)-Warfarin.
1,10-PhenanthrolineThe therapeutic efficacy of Terfenadine can be decreased when used in combination with 1,10-Phenanthroline.
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative and stimulatory activities of Terfenadine.
2,5-Dimethoxy-4-ethylthioamphetamine2,5-Dimethoxy-4-ethylthioamphetamine may decrease the sedative and stimulatory activities of Terfenadine.
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative and stimulatory activities of Terfenadine.
3,5-diiodothyropropionic acidThe metabolism of Terfenadine can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative and stimulatory activities of Terfenadine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Terfenadine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Terfenadine.
Food Interactions
Not Available

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
ChEBI
9453
ChEMBL
CHEMBL17157
Therapeutic Targets Database
DAP000102
PharmGKB
PA451619
IUPHAR
2608
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Terfenadine
ATC Codes
R06AX12 — Terfenadine
MSDS
Download (72.9 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmedix
  • Veratex Corp.
Dosage forms
FormRouteStrength
TabletOral120 mg
TabletOral60 mg
SuspensionOral30 mg
SuspensionOral6 mg
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-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-001i-8890000000-2c6ad1195e498f463cbf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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

Taxonomy

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
Diphenylmethane / Phenylbutylamine / Phenylpropane / Aralkylamine / Piperidine / Tertiary alcohol / Tertiary aliphatic amine / Tertiary amine / Secondary alcohol / Organoheterocyclic compound
show 11 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
diarylmethane (CHEBI:9453)

Targets

Details
1. Histamine H1 receptor
Kind
Protein
Organism
Human
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. [PubMed:11752352]
  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. [PubMed:9485522]
  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. [PubMed:8001268]
  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. [PubMed:7654486]
  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. [PubMed:2569356]
  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. [PubMed:2879489]
Kind
Protein
Organism
Human
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. [PubMed:11752352]
  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. [PubMed:15102940]
  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. [PubMed:20636881]
Kind
Protein
Organism
Human
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. [PubMed:10212017]
Kind
Protein
Organism
Human
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. [PubMed:10212017]
Kind
Protein
Organism
Human
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. [PubMed:10212017]
Kind
Protein
Organism
Human
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. [PubMed:10212017]
Kind
Protein
Organism
Human
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. [PubMed:10212017]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
Inducer
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. [PubMed:10681383]
  2. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  3. 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]
  4. Nemeroff CB, DeVane CL, Pollock BG: Newer antidepressants and the cytochrome P450 system. Am J Psychiatry. 1996 Mar;153(3):311-20. [PubMed:8610817]
  5. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  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. [PubMed:9485522]
  3. 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]
Kind
Protein
Organism
Human
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. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Details
6. Cytochrome P450 2J2
Kind
Protein
Organism
Human
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:11716514]
  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. [PubMed:12699389]
  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. [PubMed:8094615]
  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. [PubMed:10213372]
Kind
Protein
Organism
Human
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. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 04:41