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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:33
Primary Accession Number DB01026
Secondary Accession Number
  • APRD00401
Name Ketoconazole
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Broad spectrum antifungal agent used for long periods at high doses, especially in immunosuppressed patients. [PubChem]
Synonyms
  1. 2%
  2. Ketocanazole
  3. Ketoconazol
  4. Ketoconazol [INN-Spanish]
  5. Ketoconazole [Usan:Ban:Inn:Jan]
  6. Ketoconazolum [INN-Latin]
  7. ketoconazole
Brand Names
  1. Extina
  2. Fungarest
  3. Fungoral
  4. Ketoderm
  5. Ketoisdin
  6. Ketozole
  7. Nizoral
  8. Nizoral Cream
  9. Nizoral Shampoo
  10. Nizoral a-D
  11. Nizoral a-D Shampoo
  12. Orifungal
  13. Orifungal M
  14. Panfungol
  15. Sebazole
Brand Mixtures Not Available
Chemical IUPAC Name 1-[4-[4-[[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
Chemical Formula C26H28Cl2N4O4
Chemical Structure Structure
CAS Registry Number 65277-42-1
InChI Identifier InChI=1/C26H28Cl2N4O4/c1-19(33)31-10-12-32(13-11-31)21-3-5-22(6-4-21)34-15-23-16-35-26(36-23,17-30-9-8-29-18-30)24-7-2-20(27)14-25(24)28/h2-9,14,18,23H,10-13,15-17H2,1H3/t23-,26-/m1/s1
InChI Key XMAYWYJOQHXEEK-ZEQKJWHPBO
KEGG Drug D00351 Link Image
KEGG Compound Not Available
PubChem Compound 47576 Link Image
PubChem Substance 186839 Link Image
ChEBI ID Not Available
PharmGKB ID PA450146 Link Image
HET ID KTN Link Image
GenBank ID Not Available
Drug ID Number [DIN] 02237235 Link Image
RxList Link http://www.rxlist.com/cgi/generic/ketocon.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/niz1297.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Ketoconazole Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference J. Heeres et al., U.S. Pat. 4,144,346 (1979)
Average Molecular Weight 531.4310
Monoisotopic Molecular Weight 530.1488
State Solid
Melting Point 146 oC
Experimental Water Solubility 0.0866 mg/L Source: PhysProp
Predicted Water Solubility 9.31e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 4 Source: PhysProp
Predicted LogP 4.31 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -4.76 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CC(=O)N1CCN(CC1)C1=CC=C(OC[C@@H]2CO[C@](CN3C=CN=C3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1
Canonical SMILES CC(=O)N1CCN(CC1)C1=CC=C(OCC2COC(CN3C=CN=C3)(O2)C2=C(Cl)C=C(Cl)C=C2)C=C1
Drug Category
  • Antifungal Agents
  • Antifungals
ATC Codes
AHFS Codes
  • 08:14.08
  • 84:04.08.08
Indication For the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.
Pharmacology Ketoconazole, like clotrimazole, fluconazole, itraconazole, and miconazole, is an imidazole antifungal agent.
Mechanism of Action Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary for the conversion of lanosterol to ergosterol. This results in inhibition of ergosterol synthesis and increased fungal cellular permeability. Other mechanisms may involve the inhibition of endogenous respiration, interaction with membrane phospholipids, inhibition of yeast transformation to mycelial forms, inhibition of purine uptake, and impairment of triglyceride and/or phospholipid biosynthesis. Ketoconazole can also inhibit the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone.
Absorption Moderate
Toxicity Hepatotoxicity, LD50=86 mg/kg (orally in rat)
Protein Binding 99% (in vitro, plasma protein binding)
Biotransformation Hepatic
Half Life 2 hours
Dosage Forms
Form Route
Cream Topical
Shampoo Topical
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
Acenocoumarol The imidazole increases the effect of the anticoagulant
Alfentanil The imidazole increases the effect and toxicity of alfentanil
Alfuzosin The antifungal increases the effect of alfuzosin
Almotriptan This potent CYP3A4 inhibitor increases the effect and toxicity of the triptan
Alprazolam The imidazole increases the effect of the benzodiazepine
Aluminium The antacid decreases the effect of the imidazole
Amitriptyline The imidazole increases the effect and toxicity of the tricyclic
Anisindione The imidazole increases the effect of the anticoagulant
Aprepitant This CYP3A4 inhibitor increases the effect and toxicity of aprepitant
Aripiprazole The imidazole increases the effect of aripiprazole
Astemizole Increased risk of cardiotoxicity and arrhythmias
Atorvastatin Increased risk of myopathy/rhabdomyolysis
Bismuth The antacid decreases the effect of the imidazole
Bosentan The imidazole increases the effect and toxicity of bosentan
Budesonide The imidazole increases levels/effect of budesonide
Buspirone The macrolide increases the effect and toxicity of buspirone
Calcium The antacid decreases the effect of the imidazole
Carbamazepine The imidazole increases the effect of carbamazepine
Cerivastatin Increased risk of myopathy/rhabdomyolysis
Chlordiazepoxide The imidazole increases the effect of the benzodiazepine
Ciclesonide Increased effects/toxicity of ciclesonide
Cilostazol The imidazole increases the effect of cilostazol
Cimetidine The anti-H2 decreases the absorption of the imidazole
Cinacalcet The imidazole increases the effect and toxicity of cinacalcet
Cisapride Increased risk of cardiotoxicity and arrhythmias
Clonazepam The imidazole increases the effect of the benzodiazepine
Clorazepate The imidazole increases the effect of the benzodiazepine
Cyclosporine The imidazole increases the effect of immunosuppressant
Darifenacin This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Diazepam The imidazole increases the effect of the benzodiazepine
Dicumarol The imidazole increases the effect of the anticoagulant
Dihydroergotamine Possible ergotism and sever ischemia with this combination
Docetaxel The agent increases the serum levels and toxicity of docetaxel
Dofetilide This strong CYP3A4 inhibitor increases the effect and toxicity of dofetilide
Eletriptan This potent CYP3A4 inhibitor increases the effect and toxicity of the triptan
Eplerenone The imidazole increases the effect and toxicity of eplerenone
Ergotamine Possible ergotism and sever ischemia with this combination
Erlotinib This CYP3A4 inhibitor increases levels/toxicity of erlotinib
Esomeprazole The proton pump inhibitor decreases the absorption of imidazole
Estazolam The imidazole increases the effect of the benzodiazepine
Ethinyl Estradiol This anti-infectious agent could decrease the effect of the oral contraceptive
Everolimus The imidazole increases everolimus levels/toxicity
Famotidine The anti-H2 decreases the absorption of the imidazole
Fentanyl The imidazole increases levels/toxicity of fentanyl
Flurazepam The imidazole increases the effect of the benzodiazepine
Galantamine Ketoconazole increases the effect and toxicity of galantamine
Gefitinib This CYP3A4 inhibitor increases levels/toxicity of gefitinib
Halazepam The imidazole increases the effect of the benzodiazepine
Haloperidol The imidazole increases the effect and toxicity of haloperidol
Imatinib The imidazole increases the levels of imatinib
Imipramine The imidazole increases the effect and toxicity of the tricyclic
Indinavir Ketoconazole increases the effect of indinavir
Irinotecan Ketoconazole increases the effect and toxicity of irinotecan
Isoniazid Isoniazid decreases the effect of ketoconazole
Lansoprazole The proton pump inhibitor decreases the absorption of imidazole
Lovastatin Increased risk of myopathy/rhabdomyolysis
Magnesium The antacid decreases the effect of the imidazole
Magnesium oxide The antacid decreases the effect of the imidazole
Mestranol This anti-infectious agent could decrease the effect of the oral contraceptive
Methylprednisolone The imidazole increases the effect and toxicity of the corticosteroid
Midazolam The imidazole increases the effect of the benzodiazepine
Nevirapine Nevirapine decreases the effect of ketoconazole
Nizatidine The anti-H2 decreases the absorption of the imidazole
Nortriptyline The imidazole increases the effect and toxicity of the tricyclic
Omeprazole The proton pump inhibitor decreases the absorption of imidazole
Pantoprazole The proton pump inhibitor decreases the absorption of imidazole
Pimozide Increased risk of cardiotoxicity and arrhythmias
Pioglitazone Ketoconazole increases the effect of pioglitazone
Prednisolone The imidazole increases the effect and toxicity of the corticosteroid
Prednisone The imidazole increases the effect and toxicity of the corticosteroid
Quazepam The imidazole increases the effect of the benzodiazepine
Quetiapine Ketoconazole increases the effect/toxicity of quetiapine
Quinidine The imidazole increases the effect and toxicity of quinidine
Quinidine barbiturate The imidazole increases the effect and toxicity of quinidine
Rabeprazole The proton pump inhibitor decreases the absorption of imidazole
Ramelteon The imidazole increases the levels/toxicity of ramelteon
Ranitidine The anti-H2 decreases the absorption of the imidazole
Ranolazine Increased levels of ranolazine - risk of toxicity
Rifampin Rifampin dereases the effect of the imidazole
Ritonavir The imidazole increases the effect and toxicity of ritonavir
Rosiglitazone Ketoconazole increases the effect of rosiglitazone
Saquinavir The imidazole increases the effect and toxicity of saquinavir
Sibutramine Ketoconazole increases the levels and toxicity of sibutramine
Sildenafil The imidazole increases the effect and toxicity of sildenafil
Simvastatin Increased risk of myopathy/rhabdomyolysis
Sirolimus The imidazole increases the effect and toxicity of sirolimus
Solifenacin This potent CYP3A4 inhibitor slows darifenacin/solifenacin metabolism
Sucralfate Sucralfate decreases the absorption of the imidazole
Sunitinib Possible increase in sunitinib levels
Tacrolimus The imidazole increases the effect of immunosuppressant
Tadalafil The imidazole increases tadalafil levels
Terfenadine Increased risk of cardiotoxicity and arrhythmias
Tolbutamide Ketoconazole increases the effect and toxicity of tolbutamide
Tolterodine The imidazole increases the effect and toxicity of tolterodine
Trazodone This strong CYP3A4 inhibitor increases the effect and toxicity of trazodone
Triazolam The imidazole increases the effect of the benzodiazepine
Valdecoxib The imidazole increases the effect and toxicity of valdecoxib
Vardenafil The imidazole increases the effect and toxicity of vardenafil
Vinblastine The imidazole increases the effect and toxicity of vinblastine
Vincristine The imidazole increases the effect and toxicity of the antineoplasic
Warfarin The imidazole increases the effect of the anticoagulant
Ziprasidone Ketoconazole increases the effect and toxicity of ziprasidone
Food Interactions
  • Avoid alcohol.
  • Avoid milk, calcium containing dairy products, iron, antacids, or aluminum salts 2 hours before or 6 hours after using antacids while on this medication.
  • Take with food.
Pathways Not Available
General References
  1. Berwaerts J, Verhelst J, Mahler C, Abs R: Cushing's syndrome in pregnancy treated by ketoconazole: case report and review of the literature. Gynecol Endocrinol. 1999 Jun;13(3):175-82. [PubMed Link Image]
  2. Goeders NE, Peltier RL, Guerin GF: Ketoconazole reduces low dose cocaine self-administration in rats. Drug Alcohol Depend. 1998 Dec 1;53(1):67-77. [PubMed Link Image]
  3. Pierard-Franchimont C, Goffin V, Decroix J, Pierard GE: A multicenter randomized trial of ketoconazole 2% and zinc pyrithione 1% shampoos in severe dandruff and seborrheic dermatitis. Skin Pharmacol Appl Skin Physiol. 2002 Nov-Dec;15(6):434-41. [PubMed Link Image]
  4. Kazy Z, Puho E, Czeizel AE: Population-based case-control study of oral ketoconazole treatment for birth outcomes. Congenit Anom (Kyoto). 2005 Mar;45(1):5-8. [PubMed Link Image]
  5. Drugs.com Link Image
  6. Wikipedia Link Image
  7. RxList Link Image
  8. PDRhealth Link Image
Organisms Affected
  • Fungi
Phase 1 Metabolizing Enzymes
  1. Cytochrome P450 3A5 (CYP3A5)
  2. Cytochrome P450 2C19 (CYP2C19)
  3. Cytochrome P450 3A4 (CYP3A4)
  4. Cytochrome P450 1A2 (CYP1A2)
  5. Cytochrome P450 2C8 (CYP2C8)
  6. Cytochrome P450 2C9 (CYP2C9)
  7. Cytochrome P450 2D6 (CYP2D6)
  8. Cytochrome P450 1A1 (CYP1A1)
Targets
  1. Cytochrome P450 51
  2. Cytochrome P450 51A1
Phase 1 Metabolizing Enzyme 1 [top]
Enzyme 1 Name Cytochrome P450 3A5 (CYP3A5)
Enzyme 1 Gene Name CYP3A5
Enzyme 1 SwissProt ID P20815 Link Image
Enzyme 1 SNPs SNPJam Report Link Image
Enzyme 1 Protein Sequence >sp|P20815|CP3A5_HUMAN Cytochrome P450 3A5 
MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNVLSYRQGLWKF
DTECYKKYGKMWGTYEGQLPVLAITDPDVIRTVLVKECYSVFTNRRSLGPVGFMKSAISL
AEDEEWKRIRSLLSPTFTSGKLKEMFPIIAQYGDVLVRNLRREAEKGKPVTLKDIFGAYS
MDVITGTSFGVNIDSLNNPQDPFVESTKKFLKFGFLDPLFLSIILFPFLTPVFEALNVSL
FPKDTINFLSKSVNRMKKSRLNDKQKHRLDFLQLMIDSQNSKETESHKALSDLELAAQSI
IFIFAGYETTSSVLSFTLYELATHPDVQQKLQKEIDAVLPNKAPPTYDAVVQMEYLDMVV
NETLRLFPVAIRLERTCKKDVEINGVFIPKGSMVVIPTYALHHDPKYWTEPEEFRPERFS
KKKDSIDPYIYTPFGTGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLDTQG
LLQPEKPIVLKVDSRDGTLSGE
Phase 1 Metabolizing Enzyme 2 [top]
Enzyme 2 Name Cytochrome P450 2C19 (CYP2C19)
Enzyme 2 Gene Name CYP2C19
Enzyme 2 SwissProt ID P33261 Link Image
Enzyme 2 SNPs SNPJam Report Link Image
Enzyme 2 Protein Sequence >sp|P33261|CP2CJ_HUMAN Cytochrome P450 2C19 (EC 1.14.13.80) 
MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDVSKSLTNLSKI
YGPVFTLYFGLERMVVLHGYEVVKEALIDLGEEFSGRGHFPLAERANRGFGIVFSNGKRW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFQKRFDYKDQQFLNLMEKLNENIRIVSTPWIQICNNFPTIIDYFPGTHNKLLKNLAFM
ESDILEKVKEHQESMDINNPRDFIDCFLIKMEKEKQNQQSEFTIENLVITAADLLGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVVGRNRSPCMQDRGHMPYTDAVVHEVQRYID
LIPTSLPHAVTCDVKFRNYLIPKGTTILTSLTSVLHDNKEFPNPEMFDPRHFLDEGGNFK
KSNYFMPFSAGKRICVGEGLARMELFLFLTFILQNFNLKSLIDPKDLDTTPVVNGFASVP
PFYQLCFIPV
Phase 1 Metabolizing Enzyme 3 [top]
Enzyme 3 Name Cytochrome P450 3A4 (CYP3A4)
Enzyme 3 Gene Name CYP3A4
Enzyme 3 SwissProt ID P08684 Link Image
Enzyme 3 SNPs SNPJam Report Link Image
Enzyme 3 Protein Sequence >sp|P08684|CP3A4_HUMAN Cytochrome P450 3A4 (EC 1.14.13.67) 
ALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNILSYHKGFCMFD
MECHKKYGKVWGFYDGQQPVLAITDPDMIKTVLVKECYSVFTNRRPFGPVGFMKSAISIA
EDEEWKRLRSLLSPTFTSGKLKEMVPIIAQYGDVLVRNLRREAETGKPVTLKDVFGAYSM
DVITSTSFGVNIDSLNNPQDPFVENTKKLLRFDFLDPFFLSITVFPFLIPILEVLNICVF
PREVTNFLRKSVKRMKESRLEDTQKHRVDFLQLMIDSQNSKETESHKALSDLELVAQSII
FIFAGYETTSSVLSFIMYELATHPDVQQKLQEEIDAVLPNKAPPTYDTVLQMEYLDMVVN
ETLRLFPIAMRLERVCKKDVEINGMFIPKGWVVMIPSYALHRDPKYWTEPEKFLPERFSK
KNKDNIDPYIYTPFGSGPRNCIGMRFALMNMKLALIRVLQNFSFKPCKETQIPLKLSLGG
LLQPEKPVVLKVESRDGTVSGA
Phase 1 Metabolizing Enzyme 4 [top]
Enzyme 4 Name Cytochrome P450 1A2 (CYP1A2)
Enzyme 4 Gene Name CYP1A2
Enzyme 4 SwissProt ID P05177 Link Image
Enzyme 4 SNPs SNPJam Report Link Image
Enzyme 4 Protein Sequence >P05177|CP1A2_HUMAN Cytochrome P450 1A2 - Homo sapiens (Human). 
MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPLLGHVLTLGKN
PHLALSRMSQRYGDVLQIRIGSTPVLVLSRLDTIRQALVRQGDDFKGRPDLYTSTLITDG
QSLTFSTDSGPVWAARRRLAQNALNTFSIASDPASSSSCYLEEHVSKEAKALISRLQELM
AGPGHFDPYNQVVVSVANVIGAMCFGQHFPESSDEMLSLVKNTHEFVETASSGNPLDFFP
ILRYLPNPALQRFKAFNQRFLWFLQKTVQEHYQDFDKNSVRDITGALFKHSKKGPRASGN
LIPQEKIVNLVNDIFGAGFDTVTTAISWSLMYLVTKPEIQRKIQKELDTVIGRERRPRLS
DRPQLPYLEAFILETFRHSSFLPFTIPHSTTRDTTLNGFYIPKKCCVFVNQWQVNHDPEL
WEDPSEFRPERFLTADGTAINKPLSEKMMLFGMGKRRCIGEVLAKWEIFLFLAILLQQLE
FSVPPGVKVDLTPIYGLTMKHARCEHVQARRFSIN
Phase 1 Metabolizing Enzyme 5 [top]
Enzyme 5 Name Cytochrome P450 2C8 (CYP2C8)
Enzyme 5 Gene Name CYP2C8
Enzyme 5 SwissProt ID P10632 Link Image
Enzyme 5 SNPs SNPJam Report Link Image
Enzyme 5 Protein Sequence >sp|P10632|CP2C8_HUMAN Cytochrome P450 2C8 (EC 1.14.14.1) 
MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDICKSFTNFSKV
YGPVFTVYFGMNPIVVFHGYEAVKEALIDNGEEFSGRGNSPISQRITKGLGIISSNGKRW
KEIRRFSLTTLRNFGMGKRSIEDRVQEEAHCLVEELRKTKASPCDPTFILGCAPCNVICS
VVFQKRFDYKDQNFLTLMKRFNENFRILNSPWIQVCNNFPLLIDCFPGTHNKVLKNVALT
RSYIREKVKEHQASLDVNNPRDFIDCFLIKMEQEKDNQKSEFNIENLVGTVADLFVAGTE
TTSTTLRYGLLLLLKHPEVTAKVQEEIDHVIGRHRSPCMQDRSHMPYTDAVVHEIQRYSD
LVPTGVPHAVTTDTKFRNYLIPKGTTIMALLTSVLHDDKEFPNPNIFDPGHFLDKNGNFK
KSDYFMPFSAGKRICAGEGLARMELFLFLTTILQNFNLKSVDDLKNLNTTAVTKGIVSLP
PSYQICFIPV
Phase 1 Metabolizing Enzyme 6 [top]
Enzyme 6 Name Cytochrome P450 2C9 (CYP2C9)
Enzyme 6 Gene Name CYP2C9
Enzyme 6 SwissProt ID P11712 Link Image
Enzyme 6 SNPs SNPJam Report Link Image
Enzyme 6 Protein Sequence >sp|P11712|CP2C9_HUMAN Cytochrome P450 2C9 (EC 1.14.13.80) 
MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDISKSLTNLSKV
YGPVFTLYFGLKPIVVLHGYEAVKEALIDLGEEFSGRGIFPLAERANRGFGIVFSNGKKW
KEIRRFSLMTLRNFGMGKRSIEDRVQEEARCLVEELRKTKASPCDPTFILGCAPCNVICS
IIFHKRFDYKDQQFLNLMEKLNENIKILSSPWIQICNNFSPIIDYFPGTHNKLLKNVAFM
KSYILEKVKEHQESMDMNNPQDFIDCFLMKMEKEKHNQPSEFTIESLENTAVDLFGAGTE
TTSTTLRYALLLLLKHPEVTAKVQEEIERVIGRNRSPCMQDRSHMPYTDAVVHEVQRYID
LLPTSLPHAVTCDIKFRNYLIPKGTTILISLTSVLHDNKEFPNPEMFDPHHFLDEGGNFK
KSKYFMPFSAGKRICVGEALAGMELFLFLTSILQNFNLKSLVDPKNLDTTPVVNGFASVP
PFYQLCFIPV
Phase 1 Metabolizing Enzyme 7 [top]
Enzyme 7 Name Cytochrome P450 2D6 (CYP2D6)
Enzyme 7 Gene Name CYP2D6
Enzyme 7 SwissProt ID P10635 Link Image
Enzyme 7 SNPs SNPJam Report Link Image
Enzyme 7 Protein Sequence >sp|P10635|CP2D6_HUMAN Cytochrome P450 2D6 (EC 1.14.14.1) 
MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVDFQNTPYCFDQ
LRRRFGDVFSLQLAWTPVVVLNGLAAVREALVTHGEDTADRPPVPITQILGFGPRSQGVF
LARYGPAWREQRRFSVSTLRNLGLGKKSLEQWVTEEAACLCAAFANHSGRPFRPNGLLDK
AVSNVIASLTCGRRFEYDDPRFLRLLDLAQEGLKEESGFLREVLNAVPVLLHIPALAGKV
LRFQKAFLTQLDELLTEHRMTWDPAQPPRDLTEAFLAEMEKAKGNPESSFNDENLRIVVA
DLFSAGMVTTSTTLAWGLLLMILHPDVQRRVQQEIDDVIGQVRRPEMGDQAHMPYTTAVI
HEVQRFGDIVPLGMTHMTSRDIEVQGFRIPKGTTLITNLSSVLKDEAVWEKPFRFHPEHF
LDAQGHFVKPEAFLPFSAGRRACLGEPLARMELFLFFTSLLQHFSFSVPTGQPRPSHHGV
FAFLVSPSPYELCAVPR
Phase 1 Metabolizing Enzyme 8 [top]
Enzyme 8 Name Cytochrome P450 1A1 (CYP1A1)
Enzyme 8 Gene Name CYP1A1
Enzyme 8 SwissProt ID P04798 Link Image
Enzyme 8 SNPs SNPJam Report Link Image
Enzyme 8 Protein Sequence >sp|P04798|CP1A1_HUMAN Cytochrome P450 1A1 (EC 1.14.14.1) 
MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIGHMLTLGKNPH
LALSRMSQQYGDVLQIRIGSTPVVVLSGLDTIRQALVRQGDDFKGRPDLYTFTLISNGQS
MSFSPDSGPVWAARRRLAQNGLKSFSIASDPASSTSCYLEEHVSKEAEVLISTLQELMAG
PGHFNPYRYVVVSVTNVICAICFGRRYDHNHQELLSLVNLNNNFGEVVGSGNPADFIPIL
RYLPNPSLNAFKDLNEKFYSFMQKMVKEHYKTFEKGHIRDITDSLIEHCQEKQLDENANV
QLSDEKIINIVLDLFGAGFDTVTTAISWSLMYLVMNPRVQRKIQEELDTVIGRSRRPRLS
DRSHLPYMEAFILETFRHSSFVPFTIPHSTTRDTSLKGFYIPKGRCVFVNQWQINHDQKL
WVNPSEFLPERFLTPDGAIDKVLSEKVIIFGMGKRKCIGETIARWEVFLFLAILLQRVEF
SVPLGVKVDMTPIYGLTMKHACCEHFQMQLRS
Drug Target 1 [top]
Target 1 ID 249
Target 1 Name Cytochrome P450 51
Target 1 Synonyms
  1. CYPLI
  2. EC 1.14.13.70
  3. Lanosterol 14-alpha demethylase
  4. P450-14DM
  5. P450-LIA1
  6. Sterol 14- alpha demethylase
Target 1 Gene Name ERG11
Target 1 Protein Sequence >Cytochrome P450 51 
MSATKSIVGEALEYVNIGLSHFLALPLAQRISLIIIIPFIYNIVWQLLYSLRKDRPPLVF
YWIPWVGSAVVYGMKPYEFFEECQKKYGDIFSFVLLGRVMTVYLGPKGHEFVFNAKLADV
SAEAAYAHLTTPVFGKGVIYDCPNSRLMEQKKFVKGALTKEAFKSYVPLIAEEVYKYFRD
SKNFRLNERTTGTIDVMVTQPEMTIFTASRSLLGKEMRAKLDTDFAYLYSDLDKGFTPIN
FVFPNLPLEHYRKRDHAQKAISGTYMSLIKERRKNNDIQDRDLIDSLMKNSTYKDGVKMT
DQEIANLLIGVLMGGQHTSAATSAWILLHLAERPDVQQELYEEQMRVLDGGKKELTYDLL
QEMPLLNQTIKETLRMHHPLHSLFRKVMKDMHVPNTSYVIPAGYHVLVSPGYTHLRDEYF
PNAHQFNIHRWNKDSASSYSVGEEVDYGFGAISKGVSSPYLPFGGGRHRCIGEHFAYCQL
GVLMSIFIRTLKWHYPEGKTVPPPDFTSMVTLPTGPAKIIWEKRNPEQKI
Target 1 Number of Residues 538
Target 1 Molecular Weight 60721
Target 1 Theoretical pI 8.95
Target 1 GO Classification
Function
tetrapyrrole binding
heme binding
binding
ion binding
cation binding
transition metal ion binding
iron ion binding
catalytic activity
oxidoreductase activity
monooxygenase activity
Process
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport
Component
Not Available
Target 1 General Function Secondary metabolites biosynthesis, transport and catabolism
Target 1 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
Target 1 Pathways Not Available
Target 1 Reactions
  • obtusifoliol + 3 O2 + 3 NADPH + 3 H+ = 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + 3 NADP+ + 4 H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 21-41
Target 1 Essentiality Essential
Target 1 GenBank ID Protein 170946 Link Image
Target 1 UniProtKB/Swiss-Prot ID P10614 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name CP51_YEAST Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1593 bp 
ATGTCTGCTACCAAGTCAATCGTTGGAGAGGCATTGGAATACGTAAACATTGGTTTAAGT
CATTTCTTGGCTTTACCATTGGCCCAAAGAATCTCTTTGATCATAATAATTCCTTTCATT
TACAATATTGTATGGCAATTACTATATTCTTTGAGAAAGGACCGTCCACCTCTAGTGTTT
TACTGGATTCCATGGGTCGGTAGTGCTGTTGTGTACGGTATGAAGCCATACGAGTTTTTC
GAAGAATGTCAAAAGAAATACGGTGATATTTTTTCATTCGTTTTGTTAGGAAGAGTCATG
ACTGTGTATTTAGGACCAAAGGGTCACGAATTTGTCTTCAACGCTAAGTTGGCAGATGTT
TCAGCAGAAGCTGCTTACGCTCATTTGACTACTCCAGTTTTCGGTAAAGGTGTTATTTAC
GATTGTCCAAATTCTAGATTGATGGAGCAAAAGAAGTTTGTTAAGGGTGCTCTAACCAAA
GAAGCCTTCAAGAGCTACGTTCCATTGATTGCTGAAGAAGTGTACAAGTACTTCAGAGAC
TCCAAAAACTTCCGTTTGAATGAAAGAACTACTGGTACTATTGACGTGATGGTTACTCAA
CCTGAAATGACTATTTTCACCGCTTCAAGATCATTATTGGGTAAGGAAATGAGAGCAAAA
TTGGATACCGATTTTGCTTACTTGTACAGTGATTTGGATAAGGGTTTCACTCCAATCAAC
TTCGTCTTCCCTAACTTACCATTGGAACACTATAGAAAGAGAGATCACGCTCAAAAGGCT
ATCTCCGGTACTTACATGTCTTTGATTAAGGAAAGAAGAAAGAACAACGACATTCAAGAC
AGAGATTTGATCGATTCCTTGATGAAGAACTCTACCTACAAGGATGGTGTGAAGATGACT
GATCAAGAAATCGCTAACTTGTTAATTGGTGTCTTAATGGGTGGTCAACATACTTCTGCT
GCCACTTCTGCTTGGATTTTGTTGCACTTGGCTGAAAGACCAGATGTCCAACAAGAATTG
TACGAAGAACAAATGCGTGTTTTGGATGGTGGTAAGAAGGAATTGACCTACGATTTATTA
CAAGAAATGCCATTGTTGAACCAAACTATTAAGGAAACTCTAAGAATGCACCATCCATTG
CACTCTTTGTTCCGTAAGGTTATGAAAGATATGCACGTTCCAAACACTTCTTATGTCATC
CCAGCAGGTTATCACGTTTTGGTTTCTCCAGGTTACACTCATTTAAGAGACGAATACTTC
CCTAATGCTCACCAATTCAACATTCACCGTTGGAACAAAGATTCTGCCTCCTCTTATTCC
GTCGGTGAAGAAGTCGATTACGGTTTCGGTGCCATTTCTAAGGGTGTCAGCTCTCCATAC
TTACCTTTCGGTGGTGGTAGACACAGATGTATCGGTGAACACTTTGCTTACTGTCAGCTA
GGTGTTCTAATGTCCATTTTTATCAGAACATTAAAATGGCATTACCCAGAGGGTAAGACC
GTTCCACCTCCTGACTTTACATCTATGGTTACTCTTCCAACCGGTCCAGCCAAGATCATC
TGGGAAAAGAGAAATCCAGAACAAAAGATCTAA
Target 1 GenBank Gene ID
Target 1 GeneCard ID Not Available
Target 1 GenAtlas ID Not Available
Target 1 HGNC ID Not Available
Target 1 Chromosome Location Not Available
Target 1 Locus Not Available
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Ghaemmaghami S, Huh WK, Bower K, Howson RW, Belle A, Dephoure N, O'Shea EK, Weissman JS: Global analysis of protein expression in yeast. Nature. 2003 Oct 16;425(6959):737-41. [PubMed Link Image]
  2. Ishida N, Aoyama Y, Hatanaka R, Oyama Y, Imajo S, Ishiguro M, Oshima T, Nakazato H, Noguchi T, Maitra US, et al.: A single amino acid substitution converts cytochrome P450(14DM) to an inactive form, cytochrome P450SG1: complete primary structures deduced from cloned DNAS. Biochem Biophys Res Commun. 1988 Aug 30;155(1):317-23. [PubMed Link Image]
  3. Kalb VF, Woods CW, Turi TG, Dey CR, Sutter TR, Loper JC: Primary structure of the P450 lanosterol demethylase gene from Saccharomyces cerevisiae. DNA. 1987 Dec;6(6):529-37. [PubMed Link Image]
  4. Kalb VF, Loper JC, Dey CR, Woods CW, Sutter TR: Isolation of a cytochrome P-450 structural gene from Saccharomyces cerevisiae. Gene. 1986;45(3):237-45. [PubMed Link Image]
  5. Johnston M, Andrews S, Brinkman R, Cooper J, Ding H, Dover J, Du Z, Favello A, Fulton L, Gattung S, et al.: Complete nucleotide sequence of Saccharomyces cerevisiae chromosome VIII. Science. 1994 Sep 30;265(5181):2077-82. [PubMed Link Image]
Target 1 Drug References
  1. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed Link Image]
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed Link Image]
  3. Raucy JL, Carpenter SJ, Trzaskos JM: Identification of lanosterol 14 alpha-methyl demethylase in human tissues. Biochem Biophys Res Commun. 1991 May 31;177(1):497-503. [PubMed Link Image]
  4. Kalb VF, Loper JC, Dey CR, Woods CW, Sutter TR: Isolation of a cytochrome P-450 structural gene from Saccharomyces cerevisiae. Gene. 1986;45(3):237-45. [PubMed Link Image]
  5. Gachotte D, Pierson CA, Lees ND, Barbuch R, Koegel C, Bard M: A yeast sterol auxotroph (erg25) is rescued by addition of azole antifungals and reduced levels of heme. Proc Natl Acad Sci U S A. 1997 Oct 14;94(21):11173-8. [PubMed Link Image]
Drug Target 2 [top]
Target 2 ID 1010
Target 2 Name Cytochrome P450 51A1
Target 2 Synonyms
  1. CYPLI
  2. EC 1.14.13.70
  3. LDM
  4. Lanosterol 14-alpha demethylase
  5. P450-14DM
  6. P45014DM
  7. P450LI
  8. Sterol 14-alpha demethylase
Target 2 Gene Name CYP51A1
Target 2 Protein Sequence >Cytochrome P450 51A1 
MLLLGLLQAGGSVLGQAMEKVTGGNLLSMLLIACAFTLSLVYLIRLAAGHLVQLPAGVKS
PPYIFSPIPFLGHAIAFGKSPIEFLENAYEKYGPVFSFTMVGKTFTYLLGSDAAALLFNS
KNEDLNAEDVYSRLTTPVFGKGVAYDVPNPVFLEQKKMLKSGLNIAHFKQHVSIIEKETK
EYFESWGESGEKNVFEALSELIILTASHCLHGKEIRSQLNEKVAQLYADLDGGFSHAAWL
LPGWLPLPSFRRRDRAHREIKDIFYKAIQKRRQSQEKIDDILQTLLDATYKDGRPLTDDE
VAGMLIGLLLAGQHTSSTTSAWMGFFLARDKTLQKKCYLEQKTVCGENLPPLTYDQLKDL
NLLDRCIKETLRLRPPIMIMMRMARTPQTVAGYTIPPGHQVCVSPTVNQRLKDSWVERLD
FNPDRYLQDNPASGEKFAYVPFGAGRHRCIGENFAYVQIKTIWSTMLRLYEFDLIDGYFP
TVNYTTMIHTPENPVIRYKRRSK
Target 2 Number of Residues 511
Target 2 Molecular Weight 56807
Target 2 Theoretical pI 8.72
Target 2 GO Classification
Function
tetrapyrrole binding
heme binding
binding
ion binding
cation binding
transition metal ion binding
iron ion binding
catalytic activity
oxidoreductase activity
monooxygenase activity
Process
physiological process
metabolism
cellular metabolism
generation of precursor metabolites and energy
electron transport
Component
Not Available
Target 2 General Function Secondary metabolites biosynthesis, transport and catabolism
Target 2 Specific Function Catalyzes C14-demethylation of lanosterol; it transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol
Target 2 Pathways Not Available
Target 2 Reactions
  • obtusifoliol + 3 O2 + 3 NADPH + 3 H+ = 4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + 3 NADP+ + 4 H2O
Target 2 Pfam Domain Function
Target 2 Signals
  • None
Target 2 Transmembrane Regions
  • 24-44
Target 2 Essentiality Non-Essential
Target 2 GenBank ID Protein 1698396 Link Image
Target 2 UniProtKB/Swiss-Prot ID Q16850 Link Image
Target 2 UniProtKB/Swiss-Prot Entry Name CP51A_HUMAN Link Image
Target 2 PDB ID Not Available
Target 2 Cellular Location
  • Microsome (Potential)
Target 2 Gene Sequence >1530 bp 
ATGGCGGCGGCGGCTGGGATGCTGCTGCTGGGCTTGCTGCAGGCGGGTGGGTCGGTGCTG
GGCCAGGCGATGGAGAAGGTGACAGGCGGCAACCTCTTGTCCATGCTGCTGATCGCCTGC
GCCTTCACCCTCAGCCTGGTCTACCTGATCCGTCTGGCCGCCGGCCACCTGGTCCAGCTG
CCCGCAGGGGTGAAAAGTCCTCCATACATTTTCTCCCCAATTCCATTCCTTGGGCATGCC
ATAGCATTTGGGAAAAGTCCAATTGAATTTCTAGAAAATGCATATGAGAAGTATGGACCT
GTATTTAGTTTTACCATGGTAGGCAAGACATTTACTTACCTTCTGGGGAGTGATGCTGCT
GCACTGCTTTTTAATAGTAAAAATGAAGACCTGAATGCAGAAGATGTCTACAGTCGCCTG
ACAACACCTGTGTTTGGGAAGGGAGTTGCATACGATGTGCCTAATCCAGTTTTCTTGGAG
CAGAAGAAAATGTTAAAAAGTGGCCTTAACATAGCCCACTTTAAACAGCATGTTTCTATA
ATTGAAAAAGAAACAAAGGAATACTTTGAGAGTTGGGGAGAAAGTGGAGAAAAAAATGTG
TTTGAAGCTCTTTCTGAGCTCATAATTTTAACAGCTAGCCATTGTTTGCATGGAAAGGAA
ATCAGAAGTCAACTCAATGAAAAGGTAGCACAGCTGTATGCAGATTTGGATGGAGGTTTC
AGCCATGCAGCCTGGCTCTTACCAGGTTGGCTGCCTTTGCCTAGTTTCAGACGCAGGGAC
AGAGCTCATCGGGAAATCAAGGATATTTTCTATAAGGCAATCCAGAAACGCAGACAGTCT
CAAGAAAAAATTGATGACATTCTCCAAACTTTACTAGATGCTACATACAAGGATGGGCGT
CCTTTGACTGATGATGAAGTAGCAGGGATGCTTATTGGATTACTCTTGGCAGGGCAGCAT
ACATCCTCAACTACTAGTGCTTGGATGGGCTTCTTTTTGGCCAGAGACAAAACACTTCAA
AAAAAATGTTATTTAGAACAGAAAACAGTCTGTGGAGAGAATCTGCCTCCTTTAACTTAT
GACCAGCTCAAGGATCTAAATTTACTTGATCGCTGTATAAAAGAAACATTAAGACTTAGA
CCTCCTATAATGATCATGATGAGAATGGCCAGAACTCCTCAGACTGTGGCAGGGTATACC
ATTCCTCCAGGACATCAGGTGTGTGTTTCTCCCACTGTCAATCAAAGACTTAAAGACTCA
TGGGTAGAACGCCTGGACTTTAATCCTGATCGCTACTTACAGGATAACCCAGCATCAGGG
GAAAAGTTTGCCTATGTGCCATTTGGAGCTGGGCGTCATCGTTGTATTGGGGAAAATTTT
GCCTATGTTCAAATTAAGACAATTTGGTCCACTATGCTTCGTTTATATGAATTTGATCTC
ATTGATGGATACTTTCCCACTGTGAATTATACAACTATGATTCACACCCCTGAGAACCCA
GTTATCCGTTACAAACGAAGATCAAAATGA
Target 2 GenBank Gene ID
Target 2 GeneCard ID CYP51A1 Link Image
Target 2 GenAtlas ID CYP51A1 Link Image
Target 2 HGNC ID HGNC:2649 Link Image
Target 2 Chromosome Location 7
Target 2 Locus 7q21.2-q21.3
Target 2 SNPs SNPJam Report Link Image
Target 2 General References
  1. Hillier LW, Fulton RS, Fulton LA, Graves TA, Pepin KH, Wagner-McPherson C, Layman D, Maas J, Jaeger S, Walker R, Wylie K, Sekhon M, Becker MC, O'Laughlin MD, Schaller ME, Fewell GA, Delehaunty KD, Miner TL, Nash WE, Cordes M, Du H, Sun H, Edwards J, Bradshaw-Cordum H, Ali J, Andrews S, Isak A, Vanbrunt A, Nguyen C, Du F, Lamar B, Courtney L, Kalicki J, Ozersky P, Bielicki L, Scott K, Holmes A, Harkins R, Harris A, Strong CM, Hou S, Tomlinson C, Dauphin-Kohlberg S, Kozlowicz-Reilly A, Leonard S, Rohlfing T, Rock SM, Tin-Wollam AM, Abbott A, Minx P, Maupin R, Strowmatt C, Latreille P, Miller N, Johnson D, Murray J, Woessner JP, Wendl MC, Yang SP, Schultz BR, Wallis JW, Spieth J, Bieri TA, Nelson JO, Berkowicz N, Wohldmann PE, Cook LL, Hickenbotham MT, Eldred J, Williams D, Bedell JA, Mardis ER, Clifton SW, Chissoe SL, Marra MA, Raymond C, Haugen E, Gillett W, Zhou Y, James R, Phelps K, Iadanoto S, Bubb K, Simms E, Levy R, Clendenning J, Kaul R, Kent WJ, Furey TS, Baertsch RA, Brent MR, Keibler E, Flicek P, Bork P, Suyama M, Bailey JA, Portnoy ME, Torrents D, Chinwalla AT, Gish WR, Eddy SR, McPherson JD, Olson MV, Eichler EE, Green ED, Waterston RH, Wilson RK: The DNA sequence of human chromosome 7. Nature. 2003 Jul 10;424(6945):157-64. [PubMed Link Image]
  2. Stromstedt M, Rozman D, Waterman MR: The ubiquitously expressed human CYP51 encodes lanosterol 14 alpha-demethylase, a cytochrome P450 whose expression is regulated by oxysterols. Arch Biochem Biophys. 1996 May 1;329(1):73-81. [PubMed Link Image]
  3. Rozman D, Stromstedt M, Waterman MR: The three human cytochrome P450 lanosterol 14 alpha-demethylase (CYP51) genes reside on chromosomes 3, 7, and 13: structure of the two retrotransposed pseudogenes, association with a line-1 element, and evolution of the human CYP51 family. Arch Biochem Biophys. 1996 Sep 15;333(2):466-74. [PubMed Link Image]
  4. Rozman D, Stromstedt M, Tsui LC, Scherer SW, Waterman MR: Structure and mapping of the human lanosterol 14alpha-demethylase gene (CYP51) encoding the cytochrome P450 involved in cholesterol biosynthesis; comparison of exon/intron organization with other mammalian and fungal CYP genes. Genomics. 1996 Dec 15;38(3):371-81. [PubMed Link Image]
Target 2 Drug References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.