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Ketoconazole

Ketoconazole structure

CAS No:
65277-42-1
Formula:
C26H28Cl2N4O4
Chemical Name:
Ketoconazole
Synonyms:
Ethanone,1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]-,rel-;Piperazine,1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-,cis-;Piperazine,1-acetyl-4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-,rel-;rel-1-[4-[4-[[(2R,4S)-2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-piperazinyl]ethanone;Ketoconazole;R 41400;Nizoral;(±)-Ketoconazole;Fungoral;Nizral;Orifungal M;Ketoderm;Panfungol;Ketoisdin;Fungarest;Brizoral;Onofin K;Ketozoral;Phytorol;Tocon;Nizaral;Micosin;72093-26-6
Categories:
Active Pharmaceutical Ingredients > Inhibitor Drugs

Description

Ketoconazole is an imidazole anti-fungal agent, a CYP3A4 and CYP24A1 inhibitor.Target: CYP3A4 CYP24A1Ketoconazole, 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

Ketoconazole Basic Attributes

Molecular Weight：

531.43100

Exact Mass：

531.43

HScode：

2933990090

Characteristics

PSA：

69.06000

XLogP3：

4.20870

Appearance：

white to off white crystalline powder

Density：

1.38g/cm3

Melting Point：

146 °C

Boiling Point：

753.4ºC at 760 mmHg

Flash Point：

409.4ºC

Refractive Index：

1.642

Water Solubility：

Soluble in DMSO, ethanol, chloroform, water, and methanol.

Storage Conditions：

2-8ºC

Toxicity：

LD50 in mice, rats, guinea pigs, dogs (mg/kg): 44, 86, 28, 49 i.v.; 702, 227, 202, 780 orally (Heel)

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

UN 2811

wgk germany：

hazard class code：

R25

safety instructions：

S36-S45

RTECS Number：

TK7912300

Marks：

Stability/Shelf Life：

Stable at room temperature in closed containers under normal storage and handling conditions.

Precautionary statement(s)：

P201-P273-P301 + P310-P308 + P313-P501

Hazard Statements：

H301-H360F-H373-H410

Ketoconazole Use and Manufacturing

Methods of Manufacturing

(0.4 mmol) was added to an oven-dried 15 mL sealed tube equipped with a magnetic stir bar with a magnetic stirrer.Sulfur powder (S8) (0.8 mmol), ethyl bromodifluoroacetate (1.0 mmol) in sodium hydroxymethanesulfinate (HOCH2SO2Na) (0.8 mmol) as a solventThe reaction was stirred at 100 C for 24 hours in a solution of N, N-dimethylacetamide (DMA) (2.0 mL).After the reaction is completed, the reaction mixture is cooled to room temperature. The mixture is saturated with brine and ethyl acetate.Ester solvent extraction, The combined organic layers were dried over anhydrous Na 2SO Flash column chromatography was performed using 300-400 mesh silica gel, and the crude mixture was purified by preparative TLC monitoring spotting.The product (I-32) was obtained as a yellow oil, yield 43%.Adding

Uses

Inhibits cytochrome P-450 dependent steps in the biosynthesis of steroid hormones in vivo. Antimetastatic and antineoplastic activity. Orally active 5-lipoxygenase and thromboxane synthase inhibitor

Computed Properties

Molecular Weight:531.4
XLogP3:4.3
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:7
Exact Mass:530.1487608
Monoisotopic Mass:530.1487608
Topological Polar Surface Area:69.1
Heavy Atom Count:36
Complexity:735
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Diethanolamine

Triethylamine

p-Toluenesulfonamide

Drug Function and Efficacy

Ketoconazole is an antifungal drug that has inhibitory effects on dermatophytes such as Trichophyton, Epidermophyton, Microsporum, and yeasts such as Candida. It is hardly absorbed through the skin when applied topically.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Ketoconazole cream
Ingredients	This product contains ketoconazole as the main ingredient and stearic acid, white vaseline, glyceryl monostearate and preservative (ethyl hydroxybenzoate) as auxiliary materials.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	10g:0.2g

Compound Ketoconazole Hair Wash
Ingredients	This product is a compound preparation, containing 15 mg of ketoconazole and 0.25 mg of clobetasol propionate per gram.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	Each gram contains 15mg of ketoconazole and 0.25mg of clobetasol propionate
Manufacturer	Baolong Pharmaceutical Co., Ltd.

Compound Ketoconazole Hair Wash
Ingredients	This product is a compound preparation, containing 15 mg of ketoconazole and 0.25 mg of clobetasol propionate per gram.
Indication	Drug interactions may occur if used with other drugs. Please consult your doctor or pharmacist for details.
Specifications	Each gram contains 15mg of ketoconazole and 0.25mg of clobetasol propionate
Manufacturer	Baolong Pharmaceutical Co., Ltd.

See More Related Drugs

Registered Holders

PIRAMAL PHARMA LTD

United States
Active
UNION QUIMICO FARMACEUTICA SA (UQUIFA SA)

United States
Active
Uquifa Mexico, S.A. de C.V.

Japan
Active

See More Registered Holders

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