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	antagonist	Humans
UPotassium voltage-gated channel subfamily H member 2	inhibitor	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

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

Terfenadine
- fexofenadine

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)

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
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Abametapir	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 Acalabrutinib can be decreased when combined with Terfenadine.
Acebutolol	The metabolism of Terfenadine can be decreased when combined with Acebutolol.
Acenocoumarol	The serum concentration of Acenocoumarol can be increased when it is combined with Terfenadine.
Acetaminophen	The metabolism of Terfenadine can be decreased when combined with Acetaminophen.
Acetazolamide	Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Terfenadine.
Acetophenazine	Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Terfenadine.

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Allergy Relief	Tablet	60 mg	Oral	Jcp Laboratories Inc.	1994-12-31	1998-08-12
Allergy Relief Once A Day Allergy Caplet 120mg	Tablet		Oral	Jcp Laboratories Inc.	1991-12-31	1998-08-12
Seldane - Sus 30mg/5ml	Suspension		Oral	Hoechst Marion Roussel	1995-12-31	1998-08-12
Seldane - Tab 60mg	Tablet		Oral	Hoechst Marion Roussel	1996-10-07	1998-08-12
Seldane 120mg Once-A-day Caplets	Tablet		Oral	Hoechst Marion Roussel	1995-12-31	1998-08-12
Seldane Sus 6mg/ml	Suspension		Oral	Merrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc	1985-12-31	1996-09-09
Seldane Tab 120mg	Tablet		Oral	Merrell Dow Pharmaceuticals (Canada) Inc., Division Of Mmdc	1988-12-31	1997-08-05
Seldane Tab 60mg	Tablet		Oral	Merrell Pharms Inc., Division Of Merrell Dow (Can)	1983-12-31	1997-08-05

Generic Prescription Products

Name	Dosage	Route	Labeller	Marketing Start	Marketing End
Apo-terfenadine Tab 120mg	Tablet	Oral	Apotex Corporation	1993-12-31	1999-12-08
Apo-terfenadine Tablets 60mg	Tablet	Oral	Apotex Corporation	1993-12-31	1999-12-08
Novo-terfenadine Tab 60mg	Tablet	Oral	Novopharm Limited	1993-12-31	1999-11-15

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
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

Phase	Status	Purpose	Conditions	Count

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Pharmaceutical Utilization Management Program VA Inc.
Pharmedix
Veratex Corp.

Dosage Forms

Form	Route	Strength
Tablet	Oral	60 mg
Suspension	Oral	30 MG/5ML
Syrup
Suspension	Oral
Tablet	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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Mass Spectrum (Electron Ionization)	MS	splash10-001i-8890000000-2c6ad1195e498f463cbf
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0000900000-577805b6e639de28dd59
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-00di-0000900000-6ee8ace68773688ab606
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-0000900000-8d9a4ec2424b97bb3b80
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-000i-6770900000-9830d37d285444cff791
LC-MS/MS Spectrum - LC-ESI-QTOF , positive	LC-MS/MS	splash10-0a4i-5920000000-909f0029205fa0a7663f
MS/MS Spectrum - , positive	LC-MS/MS	splash10-000i-2541900000-f3da0c526b0e748b9567

Targets

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Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	295	N/A	N/A	2562852
IC 50 (nM)	94	N/A	N/A	7562938
Kd (nM)	35.48	N/A	N/A	7608912
Ki (nM)	2	N/A	N/A	11809864
Ki (nM)	3.16	N/A	N/A	8903934
Ki (nM)	40	N/A	N/A	19660947
Ki (nM)	58	N/A	N/A	12747773

Details1. 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

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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	128.82	N/A	N/A	19110341
IC 50 (nM)	129	N/A	N/A	15745831
IC 50 (nM)	200	N/A	N/A	12873512 / 15911273 / 18448342
IC 50 (nM)	204	N/A	N/A	12190308
IC 50 (nM)	213	N/A	N/A	19534531
IC 50 (nM)	213.8	N/A	N/A	21185626
IC 50 (nM)	30	N/A	N/A	19260734
IC 50 (nM)	312	N/A	N/A	19660947
IC 50 (nM)	50	N/A	N/A	15324906
IC 50 (nM)	56	N/A	N/A	12729675 / 12747773 / 22542010
IC 50 (nM)	56000	N/A	N/A	16931010
Ki (nM)	320	N/A	N/A	15771419

Details2. Potassium voltage-gated channel subfamily H member 2

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]

Details3. Muscarinic acetylcholine receptor M3

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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	2900	N/A	N/A	7562938

Details4. Muscarinic acetylcholine receptor M1

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]

Details5. Muscarinic acetylcholine receptor M5

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]

Details6. Muscarinic acetylcholine receptor M4

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]

Details7. Muscarinic acetylcholine receptor M2

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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	320	N/A	N/A	12699389

Details1. 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

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]

Details2. Cytochrome P450 3A7

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]

Details3. Cytochrome P450 2D6

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

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]

Details4. Cytochrome P450 3A5

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]

Details5. Cytochrome P450 2C8

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]

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	8100	N/A	N/A	16495056

Details6. 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

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

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	1100	N/A	N/A	12699389
IC 50 (nM)	1400	N/A	N/A	12699389
IC 50 (nM)	1800	N/A	N/A	11716514
IC 50 (nM)	2500	N/A	N/A	11716514
IC 50 (nM)	2700	N/A	N/A	11716514

Details1. 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

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]

Details2. Bile salt export pump

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 13:24 / Updated on February 21, 2021 18:50

Terfenadine

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Structure for Terfenadine (DB00342)

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Transporters

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