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142128-59-4 ((+)-Ketoconazole)

1

Identification

(+)-Ketoconazole (+)-Ketoconazole
Name (+)-Ketoconazole
Formula C26H28Cl2N4O4
MW 531.43
CAS No. 142128-59-4
EINECS
Smiles ClC(C=C1)=CC(Cl)=C1[[email protected]@]2(CN3C=CN=C3)OC[[email protected]](COC4=CC=C(N5CCN(C(C)=O)CC5)C=C4)O2
Synonyms 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
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/t23-,26-/m0/s1
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Introduction

(+)-Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor. Target: CYP3A4 (+)-Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1].

Background Information

(+)-Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 inhibitor. Target: CYP3A4 (+)-Ketoconazole, an imidazole anti-fungal agent, has often produced features of androgen deficiency including decreased libido, gynecomastia, impotence, oligospermia, and decreased testosterone levels, in men being treated for chronic mycotic infections [1]. (+)-Ketoconazole also is a cytochrome P450 inhibitor [2]. (+)-Ketoconazole (KTZ), on the antischistosomal potential of these quinolines against Schistosoma mansoni infection by evaluating parasitological, histopathological, and biochemical parameters. Mice were classified into 7 groups: uninfected untreated (I), infected untreated (II), infected treated orally with PZQ (1,000 mg/kg) (III), QN (400 mg/kg) (IV), KTZ (10 mg/kg)+QN as group IV (V), HF (400 mg/kg) (VI), and KTZ (as group V)+HF (as group VI) (VII). KTZ plus QN or HF produced more inhibition (P<0.05) in hepatic CYP450 (85.7% and 83.8%) and CYT b5 (75.5% and 73.5%) activities, respectively, than in groups treated with QN or HF alone. This was accompanied with more reduction in female (89.0% and 79.3%), total worms (81.4% and 70.3%), and eggs burden (hepatic; 83.8%, 66.0% and intestinal; 68%, 64.5%), respectively, and encountering the granulomatous reaction to parasite eggs trapped in the liver [3]. Clinical indications: Candida infection; Dermatophytosis; Folliculitis FDA Approved Date: Toxicity: teratogenesis; liver injuries; adrenal gland problems ......by MedChemexpress Co., Ltd.
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Protocol(Only for Reference)

Cell Experiment

Animal Experiment

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Physical and Chemical Properties

Appearance: EBNumber:EB000013173

Storage condition

Solubility

DMSO 3 mg/mL; Water <1 mg/mL by MedChemexpress Co., Ltd.
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Mechanism and Indication

Signaling Pathways Metabolic Enzyme/Protease Anti-infection
Target Fungal Cytochrome P450
Research Area Infection
Indications
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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
(+)-Ketoconazole - Launched
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Safety Data of (+)-Ketoconazole

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Spectral Information

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Suppliers List

Company Price and Availability Country/Region
CHEMSCENE, LLC USA
MedChemexpress Co., Ltd. 1g/USD99(Get quote);5g/USD338(Get quote) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 500mg/USD120(Get quote);1g/USD200(Get quote) China
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Related Products

Other Forms of 142128-59-4

Name CAS No Formula MW
Ketoconazole 65277-42-1 C26H28Cl2N4O4 531.43

Recommended Compounds in Fungal Cytochrome P450

Name CAS No Formula MW
Micafungin 235114-32-6 C56H71N9O23S 1270.27
Pneumocandin B0 135575-42-7 C50H80N8O17 1065.21
UM729 1448723-60-1 C20H25N5O2 367.44
Sertaconazole (nitrate) 99592-39-9 C20H16Cl3N3O4S 500.78
Miconazole (nitrate) 22832-87-7 C18H15Cl4N3O4 479.14
Naftifine (hydrochloride) 65473-14-5 C21H22ClN 323.86
Hygromycin B 31282-04-9 C20H37N3O13 527.52
Miconazole 22916-47-8 C18H14Cl4N2O 416.13
Econazole (nitrate) 24169-02-6 C18H16Cl3N3O4 444.7
Ciclopirox 29342-05-0 C12H17NO2 207.27
Methasulfocarb 66952-49-6 C9H11NO4S2 261.32
Flumorph 211867-47-9 C21H22FNO4 371.4
Itraconazole 84625-61-6 C35H38Cl2N8O4 705.63
Tolnaftate 2398-96-1 C19H17NOS 307.41
Fenticonazole (Nitrate) 73151-29-8 C24H21Cl2N3O4S 518.41
Liranaftate 88678-31-3 C18H20N2O2S 328.43
Tioconazole 65899-73-2 C16H13Cl3N2OS 387.71
Bifonazole 60628-96-8 C22H18N2 310.39
Butoconazole (nitrate) 64872-77-1 C19H18Cl3N3O3S 474.79
Amphotericin B 1397-89-3 C47H73NO17 924.08

Recommended Compounds in Same Indication

Name CAS No Formula MW
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Route of Synthesis

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References

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More Information

(+)-Ketoconazole

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