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Sigma-Aldrich

Ketoconazole

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Synonym(s):
(±)-cis-1-Acetyl-4-(4-[(2-[2,4-dichlorophenyl]-2-[1H-imidazol-1-ylmethyl]-1,3-dioxolan-4-yl)-methoxy]phenyl)piperazine
Empirical Formula (Hill Notation):
C26H28Cl2N4O4
CAS Number:
65277-42-1
Molecular Weight:
531.43
EC Number:
265-667-4
MDL number:
MFCD00058579
UNSPSC Code:
12161501
PubChem Substance ID:
24724652
NACRES:
NA.77

Assay

≥99% (HPLC)

form

solid

color

white to light yellow

solubility

DMSO: soluble

antibiotic activity spectrum

fungi
yeast

Mode of action

enzyme | inhibits

originator

Johnson & Johnson

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)

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Application

Ketoconazole has been used as a cytochrome P450 (CYP) inhibitor to study its functions in embryonic testes of rats. Ketoconazole has also been used for the screening of antimicrobial agents against nonreplicating M. tuberculosis. Furthermore, studies have used ketoconazole for antifungal susceptibility testing and also as a standard antifungal agent.
CYP3A4 inhibitor

Biochem/physiol Actions

Ketoconazole is an imidazole derivative. It plays an important role in inhibiting the conversion of lanosterol to ergosterol in the cell wall of fungi. Ketoconazole has therapeutic effects against dermatophytosis, superficial candidiasis, and paracoccidioidomycosis.
Antifungal agent

Features and Benefits

This compound is a featured product for ADME Tox research. Click here to discover more featured ADME Tox products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound was developed by Johnson & Johnson. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Preparation Note

Ketoconazole is soluble in DMSO.

Signal Word

Danger

Hazard Statements

H301,H360F,H373,H410

Hazard Classifications

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

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ketoconazole.
Hay, R.
British Medical Journal (Clinical Research ed.), 285(6342), 584-584 (1982)
Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis.
D Feldman
Endocrine reviews, 7(4), 409-420 (1986-11-01)
Bhaskar Das et al.
Frontiers in pharmacology, 13, 990926-990926 (2023-01-24)
Mollugo oppositifolia Linn. is traditionally used in neurological complications. The study aimed to investigate in-vitro neuroprotective effect of the plant extracts through testing against acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and β-secretase linked to Alzheimer's disease (AD). To understand the safety aspects
Ketoconazole and other imidazole derivatives as inhibitors of steroidogenesis
Feldman, David
Endocrine Reviews, 7(4), 409-420 (1986)
Po-Ren Hsueh et al.
Antimicrobial agents and chemotherapy, 49(2), 512-517 (2005-01-28)
The susceptibilities of nonduplicate isolates to six antifungal agents were determined for 391 blood isolates of seven Candida species, 70 clinical isolates (from blood or cerebrospinal fluid) of Cryptococcus neoformans, and 96 clinical isolates of four Aspergillus species, which were
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