Drug Information

General Information
Drug ID
DR00594
Drug Name
Ketoconazole
Synonyms
(+)-Ketoconazole; (+-)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine; (+/-)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine; (+/-)-cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; 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; CIS-1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE; Cis-1-Acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine; Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-piperazine; Fungarest; Fungoral; K 1003; KCZ; KS-1205; KTZ; KW-1414; Ketoconazol; Ketoconazole [USAN:INN:BAN:JAN]; Ketoderm; Nizoral (TN); Nizoral, Extina, Xolegel, Kuric, Ketoconazole; Perkhotal (TN); R 41,400; R 41400; R-41400; R41,400; R41400
Drug Type
Small molecular drug
Indication Fungal infections [ICD11:1F20-1F2Z] Approved [1]
Therapeutic Class
Antifungal Agents
Structure
3D MOL 2D MOL
Formula
C26H28Cl2N4O4
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
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
InChIKey
XMAYWYJOQHXEEK-UHFFFAOYSA-N
CAS Number
CAS 65277-42-1
Pharmaceutical Properties Molecular Weight 531.4 Topological Polar Surface Area 69.1
Heavy Atom Count 36 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
XLogP
4.3
PubChem CID
3823
PubChem SID
103845251 ,104014719 ,104304628 ,11407121 ,117361105 ,117571495 ,118836543 ,125355519 ,125357821 ,125433866 ,125544749 ,126685446 ,126728346 ,127316656 ,127316657 ,127316658 ,127316659 ,127316660 ,129708236 ,135650454 ,137100792 ,142426911 ,143837446 ,152057681 ,162022954 ,162092001 ,162914824 ,163315720 ,164811453 ,164830408 ,172824381 ,179116748 ,223677862 ,223726587 ,226399613 ,252825836 ,29222942 ,456469 ,46506746 ,46530753 ,47261387 ,51021382 ,5316931 ,57322009 ,8152421 ,85087144 ,85174349 ,85787593 ,93620728
ChEBI ID
ChEBI:47519
TTD Drug ID
D0B4IF
DT(s) Transporting This Drug P-GP Transporter Info P-glycoprotein 1 Substrate [2]
References
1 Ketoconazole was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.

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