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

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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

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Achieving Therapeutic Synergy

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Representative Experiment Reporting the Effect of This Combination

[2]

Detail(s)

Combination Info

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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.

Drug Details

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Correspondence

Prof. Feng ZHU (zhufeng@zju.edu.cn)

Prof. Xinbing SUI (hzzju@hznu.edu.cn)