Identification

Name
Terbinafine
Accession Number
DB00857  (APRD00508)
Type
Small Molecule
Groups
Approved, Investigational, Vet approved
Description

Terbinafine hydrochloride (Lamisil) is a synthetic allylamine antifungal. It is highly lipophilic in nature and tends to accumulate in skin, nails, and fatty tissues. Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting the fungal squalene monooxygenase (squalene 2,3-epoxidase), an enzyme that is part of the fungal cell wall synthesis pathway.

Structure
Thumb
Synonyms
  • (e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalene methanamine
  • (e)-N-(6,6-Dimethyl-2-hepten-4-ynyl)-N-methyl-1-naphthalenemethylamine
  • Terbinafina
  • Terbinafinum
External IDs
SF-86-327 / TDT-067
Product Ingredients
IngredientUNIICASInChI Key
Terbinafine Hydrochloride012C11ZU6G78628-80-5BWMISRWJRUSYEX-SZKNIZGXSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act TerbinafineTablet250 mgOralActavis Pharma Company2005-02-11Not applicableCanada
LamisilGranule125 mg/1OralNovartis2007-09-28Not applicableUs
LamisilSpray1 %TopicalNovartis1999-01-05Not applicableCanada
LamisilGranule187.5 mg/1OralNovartis2007-09-28Not applicableUs
LamisilTablet250 mg/1OralNovartis1996-05-10Not applicableUs
Lamisil Crm 1%Cream1 %TopicalNovartis1993-12-31Not applicableCanada
Lamisil DermgelGel10 mgTopicalNovartisNot applicableNot applicableCanada
Lamisil Tab 250mgTablet250 mgOralNovartis1993-12-31Not applicableCanada
Q-terbinafineTablet250 mgOralQd Pharmaceuticals Ulc2012-02-032015-08-21Canada
TerbinafineTablet250 mgOralPrempharm Inc2003-09-032005-08-05Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-terbinafineTablet250 mgOralApotex Corporation2000-05-16Not applicableCanada
Auro-terbinafineTablet250 mgOralAuro Pharma Inc2011-05-30Not applicableCanada
Auro-terbinafineTablet125 mgOralAuro Pharma IncNot applicableNot applicableCanada
Dom-terbinafineTablet250 mgOralDominion Pharmacal2011-03-03Not applicableCanada
Jamp-terbinafineTablet250 mgOralJamp Pharma Corporation2010-10-24Not applicableCanada
Mylan-terbinafineTablet250 mgOralMylan Pharmaceuticals2000-11-202017-01-09Canada
Nu-terbinafineTablet250 mgOralNu Pharm Inc2004-07-242012-09-04Canada
PHL-terbinafineTablet250 mgOralPharmel Inc2007-10-202016-10-25Canada
PMS-terbinafineTablet250 mgOralPharmascience Inc2009-06-19Not applicableCanada
PMS-terbinafineTablet250 mgOralPharmascience Inc2000-02-14Not applicableCanada
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AntifungalCream1 g/100gTopicalMeijer Distribution2007-07-02Not applicableUs
Antifungal FootCream1 g/100gTopicalAmerican Sales Company2007-07-02Not applicableUs
Athletes FootCream1 g/100gTopicalTarget Corporation.2007-07-02Not applicableUs
Athletes FootCream1 g/100gTopicalChain Drug Marketing Association2007-07-02Not applicableUs
Athletes FootCream1 g/100gTopicalSafeway2007-07-02Not applicableUs
Athletes FootCream1 g/100gTopicalSupervalu2007-07-02Not applicableUs
Athletes FootCream1 g/100gTopicalPublix Supermarkets, Inc.2007-07-02Not applicableUs
Athletes FootCream10 mg/1gTopicalTarget Corporation.2009-08-31Not applicableUs
Athletes FootCream1 g/100gTopicalTopco Associates2007-07-02Not applicableUs
Athletes FootCream1 g/100gTopicalH.E.B.2007-07-02Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Terbinafine HCl Chlortimazole and TolnaftateTerbinafine Hydrochloride (1 g/100mL) + Clotrimazole (1 g/100mL) + Tolnaftate (1 g/100mL)SolutionTopicalDr Marc's Manufacturing And Sales2018-01-302018-04-18Us
Terbinafine HCl CiclopiroxTerbinafine Hydrochloride (4 g/100mL) + Ciclopirox (4 g/100mL)SolutionTopicalDr Marc's Manufacturing And Sales2018-01-302018-04-18Us
International/Other Brands
Lamasil / Terbinex
Categories
UNII
G7RIW8S0XP
CAS number
91161-71-6
Weight
Average: 291.4299
Monoisotopic: 291.198699805
Chemical Formula
C21H25N
InChI Key
DOMXUEMWDBAQBQ-WEVVVXLNSA-N
InChI
InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+
IUPAC Name
[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
SMILES
CN(C\C=C\C#CC(C)(C)C)CC1=CC=CC2=CC=CC=C12

Pharmacology

Indication

For the treatment of dermatophyte infections of the toenail or fingernail caused by susceptible fungi. Also for the treatment of tinea capitis (scalp ringworm) and tinea corporis (body ringworm) or tinea cruris (jock itch).

Associated Conditions
Pharmacodynamics

Terbinafine is an allylamine antifungal agent and acts by inhibiting squalene epoxidase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. In vitro, mammalian squalene monooxygenase (squalene 2,3-epoxidase) is only inhibited at higher (4000 fold) concentrations than is needed for inhibition of the dermatophyte enzyme. Depending on the concentration of the drug and the fungal species test in vitro, Terbinafine may be fungicidal. However, the clinical significance of in vitro data is unknown.

Mechanism of action

Terbinafine is hypothesized to act by inhibiting squalene monooxygenase, thus blocking the biosynthesis of ergosterol, an essential component of fungal cell membranes. This inhibition also results in an accumulation of squalene, which is a substrate catalyzed to 2,3-oxydo squalene by squalene monooxygenase. The resultant high concentration of squalene and decreased amount of ergosterol are both thought to contribute to terbinafine's antifungal activity.

TargetActionsOrganism
ASqualene monooxygenase
inhibitor
Human
Absorption

Readily absorbed from gastrointestinal tract.

Volume of distribution
Not Available
Protein binding

>99%

Metabolism

Hepatic

Route of elimination

Prior to excretion, terbinafine is extensively metabolized.

Half life

36 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Fungi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Terbinafine.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Terbinafine.
3-isobutyl-1-methyl-7H-xanthineThe serum concentration of 3-isobutyl-1-methyl-7H-xanthine can be increased when it is combined with Terbinafine.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Terbinafine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Terbinafine.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Terbinafine.
5-androstenedioneThe metabolism of 5-androstenedione can be increased when combined with Terbinafine.
6-Deoxyerythronolide BThe metabolism of Terbinafine can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe serum concentration of 6-O-benzylguanine can be increased when it is combined with Terbinafine.
7-DeazaguanineThe serum concentration of 7-Deazaguanine can be increased when it is combined with Terbinafine.
Food Interactions
Not Available

References

Synthesis Reference

Graziano Castaldi, "Process for the preparation of terbinafine." U.S. Patent US20020123651, issued September 05, 2002.

US20020123651
General References
  1. Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65. [PubMed:12477372]
  2. Klobucnikova V, Kohut P, Leber R, Fuchsbichler S, Schweighofer N, Turnowsky F, Hapala I: Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene. Biochem Biophys Res Commun. 2003 Sep 26;309(3):666-71. [PubMed:12963042]
  3. Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [PubMed:1543672]
  4. Birnbaum JE: Pharmacology of the allylamines. J Am Acad Dermatol. 1990 Oct;23(4 Pt 2):782-5. [PubMed:2229523]
  5. McClellan KJ, Wiseman LR, Markham A: Terbinafine. An update of its use in superficial mycoses. Drugs. 1999 Jul;58(1):179-202. [PubMed:10439936]
  6. Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. doi: 10.1517/14656560903307462. [PubMed:19874252]
  7. Gianni C: Update on antifungal therapy with terbinafine. G Ital Dermatol Venereol. 2010 Jun;145(3):415-24. [PubMed:20461049]
  8. Korting HC, Kiencke P, Nelles S, Rychlik R: Comparable efficacy and safety of various topical formulations of terbinafine in tinea pedis irrespective of the treatment regimen: results of a meta-analysis. Am J Clin Dermatol. 2007;8(6):357-64. [PubMed:18039018]
External Links
Human Metabolome Database
HMDB0014995
KEGG Drug
D02375
KEGG Compound
C08079
PubChem Compound
1549008
PubChem Substance
46508519
ChemSpider
1266005
BindingDB
50018518
ChEBI
9448
ChEMBL
CHEMBL822
Therapeutic Targets Database
DAP000753
PharmGKB
PA451614
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Terbinafine
ATC Codes
D01BA02 — TerbinafineD01AE15 — Terbinafine
AHFS Codes
  • 08:14.04 — Allylamines
  • 84:04.08.04 — Allylamines
FDA label
Download (137 KB)
MSDS
Download (73.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers4
1CompletedOtherMycoses1
1CompletedTreatmentAutoimmune Diseases / Disseminated or Multiple Sclerosis Nos / Disseminated Sclerosis / Multiple Sclerosis, Acute Relapsing / Multiple Sclerosis, Chronic Progressive / Multiple Sclerosis, Primary Progressive1
1CompletedTreatmentFasting1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentOnychomycosis/Onycholysis and Tinea Pedis1
1Unknown StatusTreatmentOnychomycosis1
2CompletedScreeningOnychomycosis1
2CompletedTreatmentOnychomycosis3
2CompletedTreatmentTinea Pedis1
2Not Yet RecruitingTreatmentTinea infections1
2RecruitingTreatmentUlcerative Colitis (UC)1
2, 3Not Yet RecruitingTreatmentCandidiasis infection1
3Active Not RecruitingTreatmentDistal Subungual Onychomycosis1
3CompletedTreatmentOnychomycosis3
3CompletedTreatmentTinea Capitis2
3CompletedTreatmentTinea Pedis1
3Not Yet RecruitingTreatmentAntifungal Drugs in Onychomycosis1
3Not Yet RecruitingTreatmentICU Yeast Intra-abdominal Infection1
3WithdrawnTreatmentOnychomycosis of Toenail1
4CompletedTreatmentOnychomycosis1
4RecruitingTreatmentBacterial Vaginosis (BV) / Candidiasis infection1
4Unknown StatusTreatmentOnychomycosis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
Not AvailableCompletedTreatmentOnychomycosis2
Not AvailableNo Longer AvailableNot AvailableDiabetes, Diabetes Mellitus Type 11
Not AvailableNot Yet RecruitingTreatmentOnychomycosis / Type 2 Diabetes Mellitus1
Not AvailableUnknown StatusTreatmentOnychomycosis1

Pharmacoeconomics

Manufacturers
  • Novartis consumer health inc
  • Novartis pharmaceuticals corp
  • Taro pharmaceuticals usa inc
  • Apotex corp
  • Aurobindo pharma ltd
  • Breckenridge pharmaceutical inc
  • Dr reddys laboratories inc
  • Gedeon richter usa inc
  • Genpharm inc
  • Glenmark generics ltd
  • Harris pharmaceutical inc
  • Invagen pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Orchid healthcare
  • Roxane laboratories inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wockhardt ltd
Packagers
  • Actavis Group
  • Apotex Inc.
  • A-S Medication Solutions LLC
  • Aurobindo Pharma Ltd.
  • Blu Pharmaceuticals LLC
  • Bryant Ranch Prepack
  • Camber Pharmaceuticals Inc.
  • Cipla Ltd.
  • CVS Pharmacy
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Glenmark Generics Ltd.
  • Harris Pharmaceutical Inc.
  • InvaGen Pharmaceuticals Inc.
  • JSJ Pharmaceuticals Inc.
  • Kaiser Foundation Hospital
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Novartis AG
  • Orchid Healthcare
  • Patheon Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Rebel Distributors Corp.
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sandoz
  • Southwood Pharmaceuticals
  • Sunmark
  • Target Corp.
  • Teva Pharmaceutical Industries Ltd.
  • The Jay Group Inc.
  • Wockhardt Ltd.
Dosage forms
FormRouteStrength
TabletOral125 mg
CreamTopical1 g/100g
GranuleOral125 mg/1
GranuleOral187.5 mg/1
SprayTopical1.25 mL/125mL
Aerosol, sprayTopical0.84 g/125mL
CreamTopical10 mg/1g
SprayTopical1 mL/100mL
GelTopical10 mg/1g
LiquidTopical0.84 g/125mL
CreamTopical1 %
GelTopical10 mg
TabletOral250 mg
SprayTopical1 %
SolutionTopical
TabletOral250 1/1
TabletOral250 mg/1
Prices
Unit descriptionCostUnit
LamISIL 14 187.5 mg Packets Packet202.16USD packet
LamISIL 1% Solution 30ml Bottle88.18USD bottle
Terbinafine hcl powder42.84USD g
Terbinafine HCl 1% Cream 24 gm Tube17.99USD tube
Lamisil 250 mg tablet14.22USD tablet
Terbinafine hcl 250 mg tablet13.19USD tablet
Lamisil 250 mg Tablet4.79USD tablet
Apo-Terbinafine 250 mg Tablet2.64USD tablet
Co Terbinafine 250 mg Tablet2.64USD tablet
Mylan-Terbinafine 250 mg Tablet2.64USD tablet
Novo-Terbinafine 250 mg Tablet2.64USD tablet
Pms-Terbinafine 250 mg Tablet2.64USD tablet
Sandoz Terbinafine 250 mg Tablet2.64USD tablet
Lamisil 1% cream2.13USD g
Lamisil 1 % Solution0.58USD g
Lamisil 1 % Cream0.57USD g
Sm athlete's 1% foot cream0.53USD g
Lamisil at 1% cream0.51USD g
CVS Pharmacy jock itch 1% cream0.49USD g
CVS Pharmacy athlete's foot 1% cream0.4USD g
Athlete's 1% foot cream0.27USD g
Lamisil af defense crm to powd0.2USD g
Lamisil antifungal 1% spray0.07USD ml
Lamisil af defense 1% powder0.05USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5681849No1997-10-282015-04-28Us
US5856355No1999-01-052012-05-18Us
CA2062341No2004-05-112012-03-05Canada
CA2068957No2002-12-172012-05-19Canada

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)195-198 °CNot Available
water solubilitySlightly solubleNot Available
logP5.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000738 mg/mLALOGPS
logP5.51ALOGPS
logP5.53ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity98.08 m3·mol-1ChemAxon
Polarizability35.83 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9876
Blood Brain Barrier+0.9381
Caco-2 permeable+0.7436
P-glycoprotein substrateSubstrate0.6026
P-glycoprotein inhibitor INon-inhibitor0.7495
P-glycoprotein inhibitor IIInhibitor0.8205
Renal organic cation transporterNon-inhibitor0.581
CYP450 2C9 substrateNon-substrate0.7806
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6461
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 inhibitorNon-inhibitor0.8951
CYP450 2D6 inhibitorInhibitor0.6772
CYP450 2C19 inhibitorNon-inhibitor0.6194
CYP450 3A4 inhibitorNon-inhibitor0.6314
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5884
Ames testNon AMES toxic0.8736
CarcinogenicityCarcinogens 0.5109
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8932 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8785
hERG inhibition (predictor II)Non-inhibitor0.5566
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
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-3940000000-70d0c46dfa6b0976b000
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-1920000000-a7ec8e83df0d61d1f6b5

Taxonomy

Description
This compound belongs to the class of organic compounds known as naphthalenes. These are compounds containing a naphthalene moiety, which consists of two fused benzene rings.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Naphthalenes
Sub Class
Not Available
Direct Parent
Naphthalenes
Alternative Parents
Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Naphthalene / Aralkylamine / Tertiary aliphatic amine / Tertiary amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine / Aromatic homopolycyclic compound
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
allylamine antifungal drug, tertiary amine, naphthalenes, acetylenic compound, enyne (CHEBI:9448)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
General Function
Squalene monooxygenase activity
Specific Function
Catalyzes the first oxygenation step in sterol biosynthesis and is suggested to be one of the rate-limiting enzymes in this pathway.
Gene Name
SQLE
Uniprot ID
Q14534
Uniprot Name
Squalene monooxygenase
Molecular Weight
63922.505 Da
References
  1. Sander CS, Hipler UC, Wollina U, Elsner P: Inhibitory effect of terbinafine on reactive oxygen species (ROS) generation by Candida albicans. Mycoses. 2002 Jun;45(5-6):152-5. [PubMed:12100530]
  2. Wentzinger LF, Bach TJ, Hartmann MA: Inhibition of squalene synthase and squalene epoxidase in tobacco cells triggers an up-regulation of 3-hydroxy-3-methylglutaryl coenzyme a reductase. Plant Physiol. 2002 Sep;130(1):334-46. [PubMed:12226513]
  3. Darkes MJ, Scott LJ, Goa KL: Terbinafine: a review of its use in onychomycosis in adults. Am J Clin Dermatol. 2003;4(1):39-65. [PubMed:12477372]
  4. Klobucnikova V, Kohut P, Leber R, Fuchsbichler S, Schweighofer N, Turnowsky F, Hapala I: Terbinafine resistance in a pleiotropic yeast mutant is caused by a single point mutation in the ERG1 gene. Biochem Biophys Res Commun. 2003 Sep 26;309(3):666-71. [PubMed:12963042]
  5. Leber R, Fuchsbichler S, Klobucnikova V, Schweighofer N, Pitters E, Wohlfarter K, Lederer M, Landl K, Ruckenstuhl C, Hapala I, Turnowsky F: Molecular mechanism of terbinafine resistance in Saccharomyces cerevisiae. Antimicrob Agents Chemother. 2003 Dec;47(12):3890-900. [PubMed:14638499]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  7. Ryder NS: Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J Dermatol. 1992 Feb;126 Suppl 39:2-7. [PubMed:1543672]
  8. Krishnan-Natesan S: Terbinafine: a pharmacological and clinical review. Expert Opin Pharmacother. 2009 Nov;10(16):2723-33. doi: 10.1517/14656560903307462. [PubMed:19874252]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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. Vickers AE, Sinclair JR, Zollinger M, Heitz F, Glanzel U, Johanson L, Fischer V: Multiple cytochrome P-450s involved in the metabolism of terbinafine suggest a limited potential for drug-drug interactions. Drug Metab Dispos. 1999 Sep;27(9):1029-38. [PubMed:10460803]
  4. Lamisil FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
  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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
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. Abdel-Rahman SM, Marcucci K, Boge T, Gotschall RR, Kearns GL, Leeder JS: Potent inhibition of cytochrome P-450 2D6-mediated dextromethorphan O-demethylation by terbinafine. Drug Metab Dispos. 1999 Jul;27(7):770-5. [PubMed:10383919]
  2. Madani S, Barilla D, Cramer J, Wang Y, Paul C: Effect of terbinafine on the pharmacokinetics and pharmacodynamics of desipramine in healthy volunteers identified as cytochrome P450 2D6 (CYP2D6) extensive metabolizers. J Clin Pharmacol. 2002 Nov;42(11):1211-8. [PubMed:12412819]
  3. Debruyne D, Coquerel A: Pharmacokinetics of antifungal agents in onychomycoses. Clin Pharmacokinet. 2001;40(6):441-72. [PubMed:11475469]
  4. Abdel-Rahman SM, Gotschall RR, Kauffman RE, Leeder JS, Kearns GL: Investigation of terbinafine as a CYP2D6 inhibitor in vivo. Clin Pharmacol Ther. 1999 May;65(5):465-72. [PubMed:10340911]
  5. 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]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [PubMed:19515014]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 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]

Drug created on June 13, 2005 07:24 / Updated on November 21, 2018 07:14