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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-containing small molecule inhibitor of cytochrome P-450. It is an inhibitor of CYP17A1, CYP3A4 and CYP3A5. Ketoconazole inhibits cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively. Ketoconazole also inhibits TXA Synthase (thromboxane synthetase) and 5-LO (5-lipoxygenase) activity. Ketoconazole induces a decrease of the number of cells in S phase and a corresponding increase of the percentage of cells in Go-G1 in HT29-S-B6 cells. Ketoconazole (25 mg/kg, i.p.) significantly decreased plasma corticosterone and reduced low dose cocaine self-administration without affecting food-reinforced responding. Ketoconazole is currently in a phase 2 clinical trial with Prostate Cancer. ......by AbMole BioScience
As an antifungal, ketoconazole is structurally similar to imidazole, and interferes with the fungal synthesis of ergosterol, a constituent of fungal cell membranes, as well as certain enzymes. ......by AdooQ BioScience, LLC
(+)-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. ......by BOC Sciences
Ketoconazole is a synthetic imidazole antifungal drug used primarily to treat fungal infections. It is sold commercially as a tablet for oral administration (although this use has been discontinued in a number of countries), and in a variety of formulations for topical administration, such as creams (used to treat tinea; cutaneous candidiasis, including candidal paronychia; and pityriasis versicolor) and shampoos (used primarily to treat dandruff—seborrhoeic dermatitis of the scalp). ......by MedKoo Biosciences, Inc.
Ketoconazole inhibits cyclosporine oxidase and testosterone 6 beta-hydroxylase with IC50 of 0.19 mM and 0.22 mM, respectively. ......by Selleck Chemicals LLC
Antifungal agent; potent inhibitor of cytochrome P450c17. ......by Tocris Bioscience Inc.
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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
AA Blocks LLC
AbMole BioScience USA
AdooQ BioScience, LLC USA
Ark Pharm, Inc. USA
BOC Sciences
CHEMSCENE, LLC 10mg/USD100();50mg/USD350() USA
Cayman Chemical Company USA
MedChemexpress Co., Ltd. 10mg/USD100();50mg/USD350() USA
MedKoo Biosciences, Inc. USA
Selleck Chemicals LLC USA
Shanghai Haoyuan Chemexpress Co., Ltd. 10mg/USD100();50mg/USD350() China
Tocris Bioscience Inc. USA
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Related Products

Other Forms of 142128-59-4

Name CAS No Formula MW
(+)-Ketoconazole 142128-59-4 C26H28Cl2N4O4 531.4309

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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