Drug Details

General Information of the Drug (ID: DR4974)
Name
Ketoconazole
Synonyms
ketoconazole; 65277-42-1; (+)-Ketoconazole; (2R,4S)-ketoconazole; Kuric; Ketocanazole; CPD000058460; CHEMBL75; MFCD00058579; C26H28Cl2N4O4; SMR000058460; MLS000069784; MLS001146934; 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone; 1-acetyl-4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine; 142128-59-4; CHEBI:48336; DSSTox_CID_9879; DSSTox_RID_78829; DSSTox_GSID_29879; 1-(4-(4-(((2R,4S)-2-((1H-IMIDAZOL-1-YL)METHYL)-2-(2,4-DICHLOROPHENYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZIN-1-YL)ETHANONE; R-41400; rac-trans-Ketoconazole; KTZ; SR-01000075626; SR-01000597381; Ketoconazole (k); Ketoconazole,(S); NCGC00016907-01; 83374-59-8; Prestwick_744; CAS-65277-42-1; Tocris-1103; Opera_ID_397; Prestwick0_000389; Prestwick1_000389; Prestwick2_000389; Prestwick3_000389; R 41,400; UPCMLD-DP138; SCHEMBL8407; Lopac0_000666; BSPBio_000577; MLS000758224; MLS001423987; MLS002207053; MLS002222255; BIDD:GT0696; US9150527, Ketoconazole; SPBio_002498; AMY917; BDBM8610; BPBio1_000635; DTXSID7029879; UPCMLD-DP138:001; BDBM60666; HY-B0105A; Ketoconazole, >=98% (HPLC); HMS1569M19; HMS2051A19; HMS2089N05; HMS2096M19; HMS2234H17; HMS3262E13; HMS3414J19; HMS3678J17; HMS3713M19; ZINC643138; BCP28528; Piperazine, (+/-)-1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel-; Ketoconazole 2.0 mg/ml in Methanol; Tox21_110676; Tox21_300267; Tox21_500666; EI-107; s1353; AKOS007930650; AB02344; CCG-100815; CS-1846; KS-1205; LP00666; MCULE-2726394491; NC00065; SDCCGSBI-0050645.P002; MRF-0000100; 24F2-1,25(OH)D3; NCGC00025000-01; NCGC00025000-02; NCGC00025000-03; NCGC00025000-04; NCGC00025000-05; NCGC00025000-06; NCGC00025000-07; NCGC00025000-08; NCGC00025000-09; NCGC00025000-10; NCGC00025000-14; NCGC00025000-16; NCGC00025000-28; NCGC00253967-01; NCGC00261351-01; (+/-)-cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; AC-15957; cis-1-Acetyl-4-[4-[[2-(2,4-; AB0090681; Ketoconazole 100 microg/mL in Acetonitrile; EU-0100666; K0045; SW196888-4; BIM-0050645.0001; J10202; K 1003; W-2941; 277K421; Ketoconazole, Antibiotic for Culture Media Use Only; Q-201267; SR-01000075626-1; SR-01000075626-4; SR-01000597381-1; SR-01000597381-6; BRD-K29113274-001-03-6; BRD-K29113274-001-11-9; BRD-K29113274-001-21-8; Q27121163; Ketoconazole, British Pharmacopoeia (BP) Reference Standard; UNII-R9400W927I component XMAYWYJOQHXEEK-OZXSUGGESA-N; Ketoconazole, European Pharmacopoeia (EP) Reference Standard; Ketoconazole, United States Pharmacopeia (USP) Reference Standard; dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-piperazine; Ketoconazole, Pharmaceutical Secondary Standard; Certified Reference Material; (+/-)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine; (2R,4S)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine; 1-(4-(4-(((2R,4S)-2-((1H-imidazol-1-yl)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one; 1-[4-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one; cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl] methoxy]phenyl]piperazine; Ethanone, 1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-; KZ; Piperazine, (+)-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-
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Molecular Type
Small molecule
Disease Fungal infection [ICD-11: 1F29-1F2F] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 2.5-3 mg/L
Absorption Tmax
The time to maximum plasma concentration (Tmax) is 1-4 h
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Bioavailability
75% of drug becomes completely available to its intended biological destination(s)
Clearance
The clearance of drug is 8.66 L/h
Elimination
Only 2-4% of the ketoconazole dose is eliminated unchanged in the urine, and over 95% is eliminated through hepatic metabolism
Half-life
The concentration or amount of drug in body reduced by one-half in 2 hours
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 10.7525 micromolar/kg/day
Vd
The volume of distribution (Vd) of drug is 25.41 L or 0.36 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 0.0069 mg/mL
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Formula
C26H28Cl2N4O4
PubChem CID
456201
Canonical SMILES
CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
InChI
1S/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-/m0/s1
InChIKey
XMAYWYJOQHXEEK-OZXSUGGESA-N
CAS Number
CAS 65277-42-1
ChEBI ID
CHEBI:48336
TTD Drug ID
D0B4IF
DrugBank ID
DB01026
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Xanthotoxin      Cullen corylifolium     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model Candida albicans ATCC 22972 Microorganism model Candida albicans
Candida glabrata ATCC 90525 Microorganism model Candida glabrata
Candida guilliermondii ATCC 20216 Microorganism model Candida guilliermondii
Candida krusei ATCC 6258 Microorganism model Candida krusei
Candida parapsilosis ATCC 7330 Microorganism model Candida parapsilosis
Candida tropicalis ATCC 42678 Microorganism model Candida tropicalis
                    Experimental
                    Result(s)		 1/2 MIC dose of xanthorrhizol in combination with 1/2 MIC dose of ketoconazole or 1/2 MIC dose of amphotericin B exhibited growth inhibition of all Candida species tested and reduced viable cells by several logs within 4 h.
Target and Pathway
Target(s) Candida Cytochrome P450 51 (Candi ERG11)  Molecule Info  [3]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2568).
Reference 2 Synergistic anticandidal activity of xanthorrhizol in combination with ketoconazole or amphotericin B. FEMS Yeast Res. 2009 Dec;9(8):1302-11.
Reference 3 Clinical pharmacokinetics and pharmacodynamics of solifenacin. Clin Pharmacokinet. 2009;48(5):281-302.
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