Identification

Name
Bifonazole
Accession Number
DB04794
Type
Small Molecule
Groups
Approved, Investigational
Description

Bifonazole is an azole antifungal drug. [Wikipedia]

Structure
Thumb
Synonyms
  • (+-)-1-(p,alpha-Diphenylbenzyl)imidazole
  • (+-)1-([1,1'-Biphenyl]-4-ylphenylmethyl)-1H-imidazole
  • 1-((4-Biphenylyl)phenylmethyl)-1H-imidazole
  • 1-(alpha-(4-Biphenylyl)benzyl)imidazole
  • 1-(p,alpha-Diphenylbenzyl)imidazole
  • Bay h 4502
  • Bifonazol
  • Bifonazolum
  • Mycospor
  • Trifonazole
International/Other Brands
Amycor (Merck) / Azolmen (Menarini) / Bayclear Plus (Bayer) / Bifonol (Mayado Seiyaku) / Canespor (Bayer) / Canesten (Bayer) / Mycospor (Bayer)
Categories
UNII
QYJ305Z91O
CAS number
60628-96-8
Weight
Average: 310.3917
Monoisotopic: 310.146998586
Chemical Formula
C22H18N2
InChI Key
OCAPBUJLXMYKEJ-UHFFFAOYSA-N
InChI
InChI=1S/C22H18N2/c1-3-7-18(8-4-1)19-11-13-21(14-12-19)22(24-16-15-23-17-24)20-9-5-2-6-10-20/h1-17,22H
IUPAC Name
1-[phenyl(4-phenylphenyl)methyl]-1H-imidazole
SMILES
C1=CN(C=N1)C(C1=CC=CC=C1)C1=CC=C(C=C1)C1=CC=CC=C1

Pharmacology

Indication

Used for the treatment of various topical fungal infections, including athlete's foot (tinea pedis).

Pharmacodynamics

Bifonazole is a type of antifungal medicine known as an imidazole. It kills fungi and yeasts by interfering with their cell membranes.

Mechanism of action

Bifonazole works by inhibiting the production of a substance called ergosterol, which is an essential component of fungal cell membranes.It acts to destabilize the fungal cyctochrome p450 51 enzyme (also known as Lanosterol 14-alpha demethylase). This is vital in the cell membrance structure of the fungus. Its inhibition leads to cell lysis. The disruption in production of ergosterol disrupts the cell membrane and causes holes to appear. The cell membranes of fungi are vital for their survival. They keep unwanted substances from entering the cells and stop the contents of the cells from leaking out. As bifonazole causes holes to appear in the cell membranes, essential constituents of the fungal cells can leak out. This kills the fungi.

TargetActionsOrganism
ALanosterol 14-alpha demethylase
inhibitor
Yeast
UCytochrome P450 2B6Not AvailableHuman
Absorption

Very low absorption following topical administration (0.6% of an applied dose). In cases of skin lesions absorption is increased (2.5%).

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination
Not Available
Half life

1-2 hours

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

Interactions

Drug Interactions
DrugInteractionDrug group
AgmatineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Agmatine.Experimental, Investigational
AmiodaroneThe therapeutic efficacy of Bifonazole can be increased when used in combination with Amiodarone.Approved, Investigational
AmlodipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Amlodipine.Approved
Amphotericin BThe therapeutic efficacy of Amphotericin B can be decreased when used in combination with Bifonazole.Approved, Investigational
AmrinoneThe therapeutic efficacy of Bifonazole can be increased when used in combination with Amrinone.Approved
AranidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Aranidipine.Approved, Investigational
AsunaprevirThe serum concentration of Asunaprevir can be increased when it is combined with Bifonazole.Approved, Investigational, Withdrawn
AtorvastatinThe risk or severity of adverse effects can be increased when Bifonazole is combined with Atorvastatin.Approved
AzelnidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Azelnidipine.Approved, Investigational
AzimilideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Azimilide.Investigational
BarnidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Barnidipine.Approved
BencyclaneThe therapeutic efficacy of Bifonazole can be increased when used in combination with Bencyclane.Experimental
BenidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Benidipine.Approved, Investigational
BepridilThe therapeutic efficacy of Bifonazole can be increased when used in combination with Bepridil.Approved, Withdrawn
BioallethrinThe therapeutic efficacy of Bifonazole can be increased when used in combination with Bioallethrin.Approved, Experimental
BosutinibThe serum concentration of Bosutinib can be increased when it is combined with Bifonazole.Approved
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Bifonazole.Approved, Investigational
BuspironeThe metabolism of Buspirone can be decreased when combined with Bifonazole.Approved, Investigational
BusulfanThe serum concentration of Busulfan can be increased when it is combined with Bifonazole.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Bifonazole.Approved
CarboxyamidotriazoleThe therapeutic efficacy of Bifonazole can be increased when used in combination with Carboxyamidotriazole.Investigational
CaroverineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Caroverine.Experimental
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Bifonazole.Approved, Withdrawn
CilnidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Cilnidipine.Approved, Investigational
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Bifonazole.Approved, Investigational
CinnarizineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Cinnarizine.Approved, Investigational
CisaprideThe serum concentration of Cisapride can be increased when it is combined with Bifonazole.Approved, Investigational, Withdrawn
ClevidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Clevidipine.Approved, Investigational
CyclandelateThe therapeutic efficacy of Bifonazole can be increased when used in combination with Cyclandelate.Approved
CyclosporineThe metabolism of Cyclosporine can be decreased when combined with Bifonazole.Approved, Investigational, Vet Approved
DarodipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Darodipine.Experimental
DidanosineDidanosine can cause a decrease in the absorption of Bifonazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Bifonazole.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Bifonazole.Approved, Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Bifonazole.Experimental
DihydroergotamineThe risk or severity of adverse effects can be increased when Dihydroergotamine is combined with Bifonazole.Approved, Investigational
DiltiazemThe therapeutic efficacy of Bifonazole can be increased when used in combination with Diltiazem.Approved, Investigational
DocetaxelThe metabolism of Docetaxel can be decreased when combined with Bifonazole.Approved, Investigational
DofetilideThe serum concentration of Dofetilide can be increased when it is combined with Bifonazole.Approved, Investigational
DotarizineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Dotarizine.Investigational
EfonidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Efonidipine.Approved, Investigational
EperisoneThe therapeutic efficacy of Bifonazole can be increased when used in combination with Eperisone.Approved, Investigational
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Bifonazole.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Bifonazole.Approved
EthosuximideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Ethosuximide.Approved
EtravirineThe serum concentration of Etravirine can be increased when it is combined with Bifonazole.Approved
FelodipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Felodipine.Approved, Investigational
FendilineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Fendiline.Withdrawn
Fish oilThe therapeutic efficacy of Bifonazole can be increased when used in combination with Fish oil.Approved, Nutraceutical
FlunarizineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Flunarizine.Approved
FluspirileneThe therapeutic efficacy of Bifonazole can be increased when used in combination with Fluspirilene.Approved, Investigational
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Bifonazole.Approved
FosphenytoinThe serum concentration of Bifonazole can be decreased when it is combined with Fosphenytoin.Approved, Investigational
GabapentinThe therapeutic efficacy of Bifonazole can be increased when used in combination with Gabapentin.Approved, Investigational
GallopamilThe therapeutic efficacy of Bifonazole can be increased when used in combination with Gallopamil.Investigational
IbrutinibThe serum concentration of Ibrutinib can be increased when it is combined with Bifonazole.Approved
IsradipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Isradipine.Approved, Investigational
LacidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Lacidipine.Approved, Investigational
LamotrigineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Lamotrigine.Approved, Investigational
LercanidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Lercanidipine.Approved, Investigational
LevetiracetamThe therapeutic efficacy of Bifonazole can be increased when used in combination with Levetiracetam.Approved, Investigational
LidoflazineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Lidoflazine.Experimental
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Bifonazole.Approved, Investigational
LoperamideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Loperamide.Approved
LosartanThe metabolism of Losartan can be decreased when combined with Bifonazole.Approved
LovastatinThe serum concentration of Lovastatin can be increased when it is combined with Bifonazole.Approved, Investigational
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Bifonazole.Illicit, Investigational, Withdrawn
Magnesium sulfateThe therapeutic efficacy of Bifonazole can be increased when used in combination with Magnesium sulfate.Approved, Investigational, Vet Approved
ManidipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Manidipine.Approved, Investigational
MentholThe therapeutic efficacy of Bifonazole can be increased when used in combination with Menthol.Approved
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Bifonazole.Experimental
MethsuximideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Methsuximide.Approved
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Bifonazole.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Bifonazole.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Bifonazole.Experimental
MibefradilThe therapeutic efficacy of Bifonazole can be increased when used in combination with Mibefradil.Investigational, Withdrawn
NaftopidilThe therapeutic efficacy of Bifonazole can be increased when used in combination with Naftopidil.Investigational
NicardipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nicardipine.Approved, Investigational
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Bifonazole.Approved, Investigational
NifedipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nifedipine.Approved
NiguldipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Niguldipine.Experimental
NiludipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Niludipine.Experimental
NilvadipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nilvadipine.Approved, Investigational
NimesulideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nimesulide.Approved, Investigational, Withdrawn
NimodipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nimodipine.Approved, Investigational
NisoldipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nisoldipine.Approved
NitrendipineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nitrendipine.Approved, Investigational
NylidrinThe therapeutic efficacy of Bifonazole can be increased when used in combination with Nylidrin.Approved
OtiloniumThe therapeutic efficacy of Bifonazole can be increased when used in combination with Otilonium.Experimental, Investigational
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Bifonazole.Approved, Investigational, Vet Approved, Withdrawn
PhenytoinThe serum concentration of Phenytoin can be increased when it is combined with Bifonazole.Approved, Vet Approved
PinaveriumThe therapeutic efficacy of Bifonazole can be increased when used in combination with Pinaverium.Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Bifonazole.Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Bifonazole.Approved
PrenylamineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Prenylamine.Withdrawn
ProgesteroneThe absorption of Progesterone can be decreased when combined with Bifonazole.Approved, Vet Approved
QuinidineThe serum concentration of Quinidine can be increased when it is combined with Bifonazole.Approved, Investigational
RanolazineThe serum concentration of Ranolazine can be increased when it is combined with Bifonazole.Approved, Investigational
RifabutinThe serum concentration of Rifabutin can be increased when it is combined with Bifonazole.Approved, Investigational
RifampicinThe serum concentration of Rifampicin can be increased when it is combined with Bifonazole.Approved
RifapentineThe serum concentration of Rifapentine can be increased when it is combined with Bifonazole.Approved, Investigational
RifaximinThe serum concentration of Rifaximin can be increased when it is combined with Bifonazole.Approved, Investigational
RilpivirineThe serum concentration of Rilpivirine can be increased when it is combined with Bifonazole.Approved
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Bifonazole.Approved
SeletracetamThe therapeutic efficacy of Bifonazole can be increased when used in combination with Seletracetam.Investigational
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Bifonazole.Approved
SolifenacinThe metabolism of Solifenacin can be decreased when combined with Bifonazole.Approved
SucralfateSucralfate can cause a decrease in the absorption of Bifonazole resulting in a reduced serum concentration and potentially a decrease in efficacy.Approved
SunitinibThe metabolism of Sunitinib can be decreased when combined with Bifonazole.Approved, Investigational
TacrolimusThe metabolism of Tacrolimus can be decreased when combined with Bifonazole.Approved, Investigational
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Bifonazole.Experimental
TerodilineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Terodiline.Experimental
TetrahydropalmatineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Tetrahydropalmatine.Investigational
Tolfenamic AcidThe therapeutic efficacy of Bifonazole can be increased when used in combination with Tolfenamic Acid.Approved, Investigational
TolvaptanThe serum concentration of Tolvaptan can be increased when it is combined with Bifonazole.Approved
TranilastThe therapeutic efficacy of Bifonazole can be increased when used in combination with Tranilast.Approved, Investigational
TrimebutineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Trimebutine.Approved
TrimethadioneThe therapeutic efficacy of Bifonazole can be increased when used in combination with Trimethadione.Approved
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Bifonazole.Approved
VerapamilThe therapeutic efficacy of Bifonazole can be increased when used in combination with Verapamil.Approved
VinpocetineThe therapeutic efficacy of Bifonazole can be increased when used in combination with Vinpocetine.Investigational
WIN 55212-2The therapeutic efficacy of Bifonazole can be increased when used in combination with WIN 55212-2.Experimental
ZiconotideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Ziconotide.Approved
ZolpidemThe serum concentration of Zolpidem can be increased when it is combined with Bifonazole.Approved
ZonisamideThe therapeutic efficacy of Bifonazole can be increased when used in combination with Zonisamide.Approved, Investigational
Food Interactions
Not Available

References

Synthesis Reference

Regal, E., Draber, W., Buchel, K.H.and Plempel, M.; U.S. Patent 4,118,487; October 3,1978; assigned to Bayer A.G.

US4118487
General References
  1. Watanabe S, Takahashi H, Nishikawa T, Takiuchi I, Higashi N, Nishimoto K, Kagawa S, Yamaguchi H, Ogawa H: A comparative clinical study between 2 weeks of luliconazole 1% cream treatment and 4 weeks of bifonazole 1% cream treatment for tinea pedis. Mycoses. 2006 May;49(3):236-41. [PubMed:16681817]
  2. Cho KJ, Su W, Chen WC, Law YP, Fang HC, Liu CP, Cheng JS, Lee KC, Lo YK, Chang HT, Huang JK, Jan CR: Mechanism of bifonazole-induced [Ca2+]i increases in MDCK renal tubular cells. Chin J Physiol. 2001 Sep 30;44(3):97-101. [PubMed:11767287]
  3. Tanuma H, Doi M, Sato N, Nishiyama S, Abe M, Kume H, Katsuoka K: Bifonazole (Mycospor cream) in the treatment of moccasin-type tinea pedis. Comparison between combination therapy of bifonazole cream + 10% urea ointment (Urepearl) and occlusive dressing therapy with the same agents. Mycoses. 2000;43(3-4):129-37. [PubMed:10907343]
  4. Berg D, Regel E, Harenberg HE, Plempel M: Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. [PubMed:6372801]
External Links
Human Metabolome Database
HMDB0015583
PubChem Compound
2378
PubChem Substance
46507284
ChemSpider
2287
BindingDB
50128548
ChEBI
78692
ChEMBL
CHEMBL277535
Therapeutic Targets Database
DAP000877
PharmGKB
PA164746464
HET
TMI
Wikipedia
Bifonazole
ATC Codes
D01AC60 — Bifonazole, combinationsD01AC10 — Bifonazole

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentClotrimazole / Ovulen / Vulvovaginal Candidiasis1
3CompletedTreatmentOnychomycosis1
4CompletedTreatmentFoot Dermatoses1
4CompletedTreatmentVulvovaginal Candidiasis1
4Unknown StatusTreatmentMelasma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)142Regal, E., Draber, W., Buchel, K.H.and Plempel, M.; U.S. Patent 4,118,487; October 3,1978; assigned to Bayer A.G.
logP4.77BIOBYTE (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00245 mg/mLALOGPS
logP4.92ALOGPS
logP5.23ChemAxon
logS-5.1ALOGPS
pKa (Strongest Basic)6.69ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.82 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity97.94 m3·mol-1ChemAxon
Polarizability35.41 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9934
Blood Brain Barrier+0.9828
Caco-2 permeable+0.6357
P-glycoprotein substrateNon-substrate0.7794
P-glycoprotein inhibitor INon-inhibitor0.8037
P-glycoprotein inhibitor IINon-inhibitor0.8724
Renal organic cation transporterNon-inhibitor0.6194
CYP450 2C9 substrateNon-substrate0.7897
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateNon-substrate0.7693
CYP450 1A2 substrateInhibitor0.7884
CYP450 2C9 inhibitorNon-inhibitor0.6395
CYP450 2D6 inhibitorInhibitor0.6381
CYP450 2C19 inhibitorInhibitor0.8503
CYP450 3A4 inhibitorInhibitor0.578
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9523
Ames testAMES toxic0.5674
CarcinogenicityNon-carcinogens0.9066
BiodegradationNot ready biodegradable0.9521
Rat acute toxicity2.3581 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.967
hERG inhibition (predictor II)Non-inhibitor0.6458
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/MSsplash10-0006-1390000000-1be085eadfe1ca8da91f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0006-0290000000-77357a487121e6eca52c
MS/MS Spectrum - , positiveLC-MS/MSsplash10-00kf-2690000000-8eaa22839544d8c21308
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0190000000-e6d6c0b5fe503dddd253

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
Biphenyls and derivatives / N-substituted imidazoles / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Hydrocarbon derivatives
Substituents
Diphenylmethane / Biphenyl / N-substituted imidazole / Heteroaromatic compound / Imidazole / Azole / Azacycle / Organoheterocyclic compound / Organic nitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
imidazoles, biphenyls (CHEBI:78692)

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name
ERG11
Uniprot ID
P10613
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
60674.965 Da
References
  1. Carrillo-Munoz AJ, Giusiano G, Ezkurra PA, Quindos G: Antifungal agents: mode of action in yeast cells. Rev Esp Quimioter. 2006 Jun;19(2):130-9. [PubMed:16964330]
  2. Rossello A, Bertini S, Lapucci A, Macchia M, Martinelli A, Rapposelli S, Herreros E, Macchia B: Synthesis, antifungal activity, and molecular modeling studies of new inverted oxime ethers of oxiconazole. J Med Chem. 2002 Oct 24;45(22):4903-12. [PubMed:12383016]
  3. Berg D, Plempel M: Bifonazole, a biochemist's view. Dermatologica. 1984;169 Suppl 1:3-9. [PubMed:6396116]
  4. Berg D, Regel E, Harenberg HE, Plempel M: Bifonazole and clotrimazole. Their mode of action and the possible reason for the fungicidal behaviour of bifonazole. Arzneimittelforschung. 1984;34(2):139-46. [PubMed:6372801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
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. 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
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 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
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. 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 September 11, 2007 11:49 / Updated on July 02, 2018 18:22