KTN

CIS-1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE

Created:	2001-09-20
Last modified:	2021-03-01

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2 entries where KTN is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	64
Chiral Atom Count	2
Bond Count	68
Aromatic Bond Count	17

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Chemical Component Summary
Name	CIS-1-ACETYL-4-(4-((2-(2,4-DICHLOROPHENYL)-2-(1H-IMIDAZOL-1-YLMETHYL)-1,3-DIOXOLAN-4-YL)METHOXY)PHENYL)PIPERAZINE
Synonyms	KETOCONAZOLE
Systematic Name (OpenEye OEToolkits)	1-[4-[4-[[(4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone
Formula	C₂₆ H₂₈ Cl₂ N₄ O₄
Molecular Weight	531.431
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(N5CCN(c4ccc(OCC1OC(OC1)(c2ccc(Cl)cc2Cl)Cn3cncc3)cc4)CC5)C
SMILES	CACTVS	3.341	CC(=O)N1CCN(CC1)c2ccc(OC[CH]3CO[C](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
SMILES	OpenEye OEToolkits	1.5.0	CC(=O)N1CCN(CC1)c2ccc(cc2)OCC3COC(O3)(Cn4ccnc4)c5ccc(cc5Cl)Cl
Canonical SMILES	CACTVS	3.341	CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2
Canonical SMILES	OpenEye OEToolkits	1.5.0	CC(=O)N1CCN(CC1)c2ccc(cc2)OC[C@H]3COC(O3)(Cn4ccnc4)c5ccc(cc5Cl)Cl
InChI	InChI	1.03	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	InChI	1.03	XMAYWYJOQHXEEK-JYFHCDHNSA-N

Drug Info: DrugBank

DrugBank ID	DB01026
Name	Ketoconazole
Groups	approved investigational
Description	Ketoconazole is an imidazole antifungal agent used in the prevention and treatment of a variety of fungal infections.[FDA Label] It functions by preventing the synthesis of ergosterol, the fungal equivalent of cholesterol, thereby increasing membrane fluidity and preventing growth of the fungus.[A181802,T116] Ketoconazole was first approved in an oral formulation for systemic use by the FDA in 1981.[A188054] At this time it was considered a significant improvement over previous antifungals, [miconazole] and [clotrimazole], due to its broad spectrum and good absorption. However, it was discovered that ketoconazole produces frequent gastrointestinal side effects and dose-related hepatitis.[A188054,A188057] These effects combined with waning efficacy led to its eventual replacement by triazole agents, [fluconazole], [itraconazole], [voriconazole], and [posaconazole]. Ketoconazole and its predecessor [clotrimazole] continue to be used in topical formulations.
Synonyms	Ketoconazolum Ketoconazole Ketoconazol Ketozole
Brand Names	Pureskin Seborrheic Dermatitis Eczema Cream Nizoral Extina Ketoconazole Cream, 2% Ketoconazole 2% / Salicylic Acid 2% Ketocon Nizoral Oral Suspension 20mg/ml PedizolPAK Teva-ketoconazole Ketoconazole Hydrocortisone 2.5% / Ketoconazole 2% Ketoconazole 2% / Niacinamide 4% Ketoderm Cream 2% Nizoral Tablets 200mg Apo-ketoconazole Podiatrole Ketaconazole Nizoral A-D Ketodan Nizoral Cream 2% Ketoconazole Cream Dermetazole Nizoral Shp 2% Hydrocortisone 2.5% / Iodoquinol 1% / Ketoconazole 2% Xolegel Ketoconazole Hra
Indication	Ketoconazole is used in the treatment or prevention of fungal infections including blastomycosis, candidiasis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.[FDA Label] In Europe, it is also used in the treatment of endogenous Cushing's syndrome.[L7736]
Categories	14-alpha Demethylase Inhibitors Agents causing hyperkalemia Anti-Infective Agents Antiadrenal Preparations Anticorticosteroids Antifungal Agents Antifungals for Dermatological Use Antifungals for Topical Use Antiinfectives for Systemic Use Antimycotics for Systemic Use Azole Antifungals BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates Cytochrome P-450 CYP1A2 Inhibitors Cytochrome P-450 CYP1A2 Inhibitors (moderate) Cytochrome P-450 CYP2A6 Inhibitors Cytochrome P-450 CYP2A6 Inhibitors (moderate) Cytochrome P-450 CYP2B6 Inhibitors Cytochrome P-450 CYP2B6 Inhibitors (moderate) Cytochrome P-450 CYP2C19 Inhibitors Cytochrome P-450 CYP2C19 inhibitors (strength unknown) Cytochrome P-450 CYP2C8 Inhibitors Cytochrome P-450 CYP2C8 Inhibitors (moderate) Cytochrome P-450 CYP2C8 Inhibitors (strong) Cytochrome P-450 CYP2C9 Inhibitors Cytochrome P-450 CYP2C9 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors Cytochrome P-450 CYP2D6 Inhibitors (moderate) Cytochrome P-450 CYP2D6 Inhibitors (strength unknown) Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (strong) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A5 Inhibitors Cytochrome P-450 CYP3A5 Inhibitors (strong) Cytochrome P-450 CYP3A7 Inhibitors Cytochrome P-450 CYP3A7 Inhibitors (strong) Cytochrome P-450 Enzyme Inhibitors Cytochrome P-450 Substrates Dermatologicals Drugs causing inadvertant photosensitivity Enzyme Inhibitors Gynecological Antiinfectives and Antiseptics Hepatotoxic Agents Imidazole and Triazole Derivatives Imidazole Derivatives OATP1B1/SLCO1B1 Inhibitors P-glycoprotein inhibitors P-glycoprotein substrates Photosensitizing Agents Piperazines Potential QTc-Prolonging Agents QTc Prolonging Agents Steroid Synthesis Inhibitors Systemic Hormonal Preparations, Excl. Sex Hormones and Insulins UGT1A1 Inhibitors UGT2B7 Inhibitors
ATC-Code	G01AF11 G01AF20 J02AB02 H02CA03 D01AC08
CAS number	65277-42-1

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Lanosterol 14-alpha demethylase	MSTENTSLVVELLEYVKLGLSYFQALPLAQRVSIMVALPFVYTITWQLLY...	unknown	inhibitor
Steroid 17-alpha-hydroxylase/17,20 lyase	MWELVALLLLTLAYLFWPKRRCPGAKYPKSLLSLPLVGSLPFLPRHGHMH...	unknown	inhibitor
Androgen receptor	MEVQLGLGRVYPRPPSKTYRGAFQNLFQSVREVIQNPGPRHPEAASAAPP...	unknown	binder
Steroid 21-hydroxylase	MLLLGLLLLPLLAGARLLWNWWKLRSLHLPPLAPGFLHLLQPDLPIYLLG...	unknown	inhibitor
Potassium voltage-gated channel subfamily H member 2	MPVRRGHVAPQNTFLDTIIRKFEGQSRKFIIANARVENCAVIYCNDGFCE...	unknown	inhibitor
Nuclear receptor subfamily 1 group I member 2	MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...	unknown	antagonist
Nuclear receptor subfamily 1 group I member 3	MASREDELRNCVVCGDQATGYHFNALTCEGCKGFFRRTVSKSIGPTCPFA...	unknown
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	inhibitor
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	inhibitor
Cytochrome P450 1A1	MLFPISMSATEFLLASVIFCLVFWVIRASRPQVPKGLKNPPGPWGWPLIG...	unknown	inhibitor,inducer
Cytochrome P450 1A2	MALSQSVPFSATELLLASAIFCLVFWVLKGLRPRVPKGLKSPPEPWGWPL...	unknown	inhibitor
Cytochrome P450 2A6	MLASGMLLVALLVCLTVMVLMSVWQQRKSKGKLPPGPTPLPFIGNYLQLN...	unknown	inhibitor
Cytochrome P450 1B1	MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...	unknown	inhibitor
Cytochrome P450 2B6	MELSVLLFLALLTGLLLLLVQRHPNTHDRLPPGPRPLPLLGNLLQMDRRG...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	inhibitor
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	inhibitor
Cytochrome P450 2D6	MGLEALVPLAVIVAIFLLLVDLMHRRQRWAARYPPGPLPLPGLGNLLHVD...	unknown	inhibitor
Cytochrome P450 11B1, mitochondrial	MALRAKAEVCMAVPWLSLQRAQALGTRAARVPRTVLPFEAMPRRPGNRWL...	unknown	inhibitor
UDP-glucuronosyltransferase 1-1	MAVESQGGRPLVLGLLLCVLGPVVSHAGKILLIPVDGSHWLSMLGAIQQL...	unknown	inhibitor
UDP-glucuronosyltransferase 1-7	MARAGWTGLLPLYVCLLLTCGFAKAGKLLVVPMDGSHWFTMQSVVEKLIL...	unknown	inhibitor
UDP-glucuronosyltransferase 2B7	MSVKWTSVILLIQLSFCFSSGNCGKVLVWAAEYSHWMNIKTILDELIQRG...	unknown	inhibitor
Cytochrome P450 4F12	MSLLSLPWLGLRPVATSPWLLLLLVVGSWLLARILAWTYAFYNNCRRLQC...	unknown	inhibitor
Cytochrome P450 19A1	MVLEMLNPIHYNITSIVPEAMPAATMPVLLLTGLFLLVWNYEGTSSIPGP...	unknown	inhibitor
Leukotriene-B(4) omega-hydroxylase 1	MSQLSLSWLGLWPVAASPWLLLLLVGASWLLAHVLAWTYAFYDNCRRLRC...	unknown	inhibitor
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown	ligand
Sex hormone-binding globulin	MESRGPLATSRLLLLLLLLLLRHTRQGWALRPVLPTQSAHDPPAVHLSNG...	unknown	ligand
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	inhibitor
Solute carrier organic anion transporter family member 1B1	MDQNQHLNKTAEAQPSENKKTRYCNGLKMFLAALSLSFIAKTLGAIIMKS...	unknown	inhibitor
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	inhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682