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K1003

Ketoconazole

99.0-101.0% (EP, titration), meets EP testing specifications

Synonym(s):

(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine

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About This Item

Empirical Formula (Hill Notation):
C26H28Cl2N4O4
CAS Number:
65277-42-1
Molecular Weight:
531.43
NACRES:
NA.85
PubChem Substance ID:
24278176
UNSPSC Code:
51101500
EC Number:
265-667-4
MDL number:
MFCD00058579
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Quality Level

200

agency

meets EP testing specifications

description

Specific Optical Rotation (EP): (−0.10) ∼ +0.10 °

assay

99.0-101.0% (EP, titration)

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-positive bacteria, fungi, yeast

mode of action

enzyme | inhibits

storage temp.

2-8°C

SMILES string

CC(=O)N1CCN(CC1)c2ccc(OC[C@H]3CO[C@@](Cn4ccnc4)(O3)c5ccc(Cl)cc5Cl)cc2

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

InChI key

XMAYWYJOQHXEEK-OZXSUGGESA-N

Gene Information

human ... ABCB1(5243), CYP11B1(1584), CYP11B2(1585), CYP17A1(1586), CYP19A1(1588), CYP1A2(1544), CYP24A1(1591), CYP26A1(1592), CYP3A4(1576), CYP51A1(1595), KCNH1(3756)
mouse ... Abcb1a(18671), Abcb1b(18669)
rat ... Alox5(25290), Cyp17a1(25146), Cyp51(25427), Cyp7a1(25428)

General description

Chemical structure: imidazole

Application

CYP3A4 inhibitor
Ketoconazole is a broad spectrum antifungal agent used to treat candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis. It is used to identify p-glycoprotein/CYP3A-limited bioavailability in the monkey model, to study interleukin 1 mediated antitumor effects, and drug interactions in vivo

Biochem/physiol Actions

Antifungal agent
Ketoconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme that is necessary for the conversion of lanosterol to ergosterol. This interaction inhibits ergosterol synthesis and results in increased fungal cellular permeability. Other possible mechanisms of action are 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 inhibits the synthesis of thromboxane and sterols such as aldosterone, cortisol, and testosterone .

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Danger

Hazard Classifications

Acute Tox. 3 Oral - Aquatic Acute 1 - Aquatic Chronic 1 - Repr. 1B - STOT RE 2

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
SLCC4160
SLBR1290V
SLBK7327V
SLBG3774V
SLBB5223V

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Wendy W J van de Sande et al.
Antimicrobial agents and chemotherapy, 54(6), 2738-2740 (2010-03-31)
Eumycetoma caused by Madurella mycetomatis is treated surgically and with high doses of ketoconazole. Therapeutic responses are poor, and recurrent infections are common. In search of therapeutic alternatives in the treatment of mycetoma, we determined the in vitro susceptibilities of
Francisco M Garibotto et al.
Bioorganic & medicinal chemistry, 18(1), 158-167 (2009-12-05)
The synthesis, in vitro evaluation, and conformational study of a new series of small-size peptides acting as antifungal agents are reported. In a first step of our study we performed a conformational analysis using Molecular Mechanics calculations. The electronic study
L L von Moltke et al.
The Journal of pharmacology and experimental therapeutics, 268(3), 1278-1283 (1994-03-01)
Biotransformation of the tricyclic antidepressant desipramine (DMI) to its metabolite 2-hydroxy-desipramine (2-OH-DMI) was studied in vitro using microsomal preparations from human, monkey, mouse and rat liver. In all species 2-OH-DMI was the principal identified metabolite. Mean (+/- S.E.) reaction parameters
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Global Trade Item Number

SKUGTIN
K1003-100MG04061833867877