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65277-42-1 Usage

Uses

It is antifungal drug for being used to treat athlete's foot and excessive dandruff.

Pharmacokinetics

This product can be dissolved and absorbed in gastric acid. Upon the reduction of the acidity of gastric acid, its absorption can be reduced. Administration after meals can increase its absorption with the bioavailability of administration after meal being as high as 75%. After the single-dose oral administration of 200mg and 400mg, the peak plasma concentrations were 3.6 ± 1.65mg/L and 6.5 ± 1.44mg/L, respectively with the time for reaching peak being 1-4 hours. After the absorption, this product is widely distributed in the body and can reach the synovial fluid of inflammation, saliva, bile, urine, tendons, skin and soft tissue, feces and so on. It has a poor penetrating capability through the blood-brain barrier. In most cases, the drug concentration in the cerebrospinal fluid is less than 1mg/L. This product can also penetrate through the blood placental barrier. The binding rate of serum protein is about 90% or more with the elimination half-life being 6.5 to 9 hours. Some part of the drugs is subjected to metabolism in the liver through degradation into inactive imidazole ring and piperazine ring. The metabolites and prototype drug is mainly excreted through the bile. The drug excreted through the kidneys only accounts 13% of the administered dose, of which about 2% to 4% for drug prototype. The product can also be secreted into milk.

Chemical Properties

White Powder

Category

Toxic substances

Biological Activity

Antifungal agent; potent inhibitor of cytochrome P450c17.

Uses

An inhibitor of CYP proteins, thromboxane synthetase, and 5-LO

Flammability and hazardous characteristics

It is combustible with burning releasing toxic chloride fumes and nitrogen oxides.

Acute toxicity

Oral-rat LD50: 166 mg/kg; Oral-Mouse LD50: 618 mg/kg.

Uses

antifungal, PXR/SRC1 & CAR/SRC1 inhibitor

Indications

Ketoconazole is suitable for treating the following systemic fungal infections:
1. Candidiasis, chronic mucocutaneous candidiasis, oral candidiasis infection, Candida urinary tract infections as well as chronic, recurrent vaginal candidiasis which can be cured by topical therapy.
2. Dermatitis blastomycosis.
3. Coccidioidomycosis.
4. Histoplasmosis.
5. Chromomycosis.
6. Paracoccidioidomycosis.
It can be used for treating fungal skin diseases, hair ringworm and tinea versicolor caused by fungi and yeasts. When local therapy or oral administration of griseofulvin is invalid, or griseofulvin is unacceptable in the treatment of severe refractory fungal skin infection, we can choose the treatment of this drug.
The above information is edited by the chemicalbook of Dai Xiongfeng.

Chemical Properties

It is white crystalline powder with the melting point being 146 ℃ and insoluble in water.

Side effects

External administration
1. Common erythema, burning, itching, stinging or other irritation, folliculitis, skin atrophy and thinning as well as telangiectasia.
2. It can be observed of dry skin, hirsutism, striae atrophicae and increased susceptibility to infection.
3. Long-term medication may cause cortex hyperthyroidism, manifested as hirsutism, acne, moon face, osteoporosis and other symptoms.
4. It can be occasionally observed of allergic contact dermatitis.
Side effects of oral administration
1. Hepatotoxicity: ketoconazole can cause increased serum aminotransferase (AST, ALT) level and is reversible. It can be occasionally observed of severe liver toxicity, primarily being liver cell type with the incidence being about 0.01%. The clinical manifestations include jaundice, dark urine, white-color faeces and abnormal fatigue, etc., these effects can usually resume after the withdrawal of the drug, but there are also cases of deaths; there are also cases of hepatitis in children.
2. Gastrointestinal reaction: nausea, vomiting and anorexia are common cases.
3. Gynecomastia and lack of semen; this is related to the effect of this product on suppression of the biosynthesis of testosterone and adrenal cortical hormone.

Uses

For the treatment of the following systemic fungal infections: candidiasis, chronic mucocutaneous candidiasis, oral thrush, candiduria, blastomycosis, coccidioidomycosis, histoplasmosis, chromomycosis, and paracoccidioidomycosis.

Antifungal drug

Ketoconazole is a broad-spectrum antifungal imidazole with commercially available product being under the trade name of Jindakening, Meikangling and keNing. It interferes with the activity of fungal cytochrome P-450 with a high selectivity, thus inhibiting the biosynthesis of ergosterol in fungal cell membrane. It is effective in treating both shallow, deep fungal infections and can inhibit both fungal growth and the transition from spores to mycelium to prevent the further infection. It has antifungal effect on Candida genus, Fonsecaea, Coccidioides, Histoplasma, Sporothrix spp and Trichophyton. Clinically, it is suitable for the treatment of ringworm, athlete's foot, and skin ringworm, tinea, jock itch, and thrush, tinea versicolor as well as cutaneous candidiasis.
Ketoconazole lotion, as a skin external use, is mainly used for clinical treatment and prevention of various kinds of infections caused by Malassezia such as tinea versicolor, seborrheic dermatitis and scalp pityriasis (dandruff), and can quickly alleviate the desquamation and itching caused by seborrheic dermatitis and scalp pityriasis.

Precautions

1. Take it with caution upon the following cases:
lack of gastric acid (may cause the reduction of the absorption of the product).
Alcoholism or liver damage (it can cause liver toxicity).
2.Before or during the treatment, the patients should be regularly subject to monitoring of liver function. Elevated serum aminotransferase may not be accompanied by symptoms of hepatitis, however, if the serum aminotransferase value continues to rise or increase, or associated with liver toxicity symptoms, we should discontinue ketoconazole treatment.
3. For simultaneous administration of cimetidine or furan thiamine, take them at least 2 hours after taking this drug.
4. This product can cause photosensitivity reactions. Therefore, during the medication, we should avoid prolonged exposure to bright light and can wear colored glasses. 5. It is not allowed to take alcoholic beverages while taking the drug. Pay attention if dizziness or drowsiness occurs.
5. Patients of renal dysfunction don’t need to be subject to reduced dose upon taking it.
6. Ketoconazole has a very poor capability of penetrating blood-brain barrier and is not suitable for the treatment of fungal meningitis. This product also has poor efficacy in treating Aspergillus, Mucor or maduromycosis and thus is also not suitable.
7. Interfere with the diagnosis: can cause elevated serum aminotransferase, can also cause increased level of hemobilirubin.

Extinguishing agent

Dry powder, foam, sand, carbon dioxide, water mist.

Pharmacological effects

1. Pharmacology: ketoconazole belongs to azole-class antifungal drugs and has antifungal activity against various kinds of genus of deep fungal infections such as Candida, Fonsecaea, Coccidioides, Histoplasma, Sporothrix spp as well as Trichophyton. However, this product has a relative weak activity against Aspergillus, Sporothrix schenckii as well as some species of Dermateaceae and Mucor. This product, through actively interfering with the activity of cytochrome P-450, is capable of inhibiting the biosynthesis of the major steroids-ergosterol of the fungal cell membrane. Therefore, it destroys the fungal cell membrane and changes its permeability, resulting in the leakage of important intracellular material. Ketoconazole can also inhibit the biosynthesis of fungal triglyceride and phospholipid biosynthesis, inhibit the activity of oxidase and peroxidase, causing accumulation of intracellular hydrogen peroxide which further leads to cell submicroscopic structural degeneration and necrosis. For candida albicans, it can also suppress the transition process from spores to aggressive mycelium.
2. Toxicology: Long-term animal toxicity experiments have showed that ketoconazole can significantly increase the level of alkaline phosphatase and cause liver cell degeneration.

Brand name

Ketozole (Taro); Nizoral (Janssen); Nizoral (McNeil).

Pregnant and lactating women

The product can penetrate through the blood placental barrier. Animal experiments have shown that the product can be teratogenic such as syndactylia, lack of finger (toe) and dystocia in rats. US FDA data has shown that the application of this drug in pregnant women should be classified into Class C, namely being toxic in animal studies but is lack of adequate information in human studies. Therefore, pregnant women should be avoided for using it. Ketoconazole can be secreted into breast milk. The administration of it for humans has not found any issues, but the product can increase the likelihood of the occurrence of neonatal kernicterus, lactating women should weigh both advantages and disadvantages for using it.

Toxicity grading

Highly toxic

Production method

Put the mixture containing 2.4 parts of 1-acetyl-4-(4-hydroxyphenyl) piperazine, 0.4 part of 78% sodium hydride, 75 parts of dimethyl sulfate, 22.5 parts of benzene at 40 ℃ for stirring of 1 hour, followed by addition of 4.2 parts of 2-(2,4-dichlorobenzyl-2-(1H-imidazol-1-yl-methyl)-1,3-dioxolane-4-ylmethyl methanesulfonate. Stir at 100 °C overnight with the reaction product resulting in 3.2 parts ketoconazole after treatment.

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

Storage characteristics

Treasury: ventilation, low-temperature and dry; store it separately from food raw materials.
InChI:InChI=1/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

65277-42-1 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Sigma (UC280)  Ketoconazole   65277-42-1 UC280-10MG 4,151.16CNY Detail
Sigma (UC280)  Ketoconazole   65277-42-1 UC280-5MG 2,403.18CNY Detail
USP (1356508)  Ketoconazole  United States Pharmacopeia (USP) Reference Standard 65277-42-1 1356508-200MG 4,662.45CNY Detail
Sigma-Aldrich (K0600000)  Ketoconazole  European Pharmacopoeia (EP) Reference Standard 65277-42-1 K0600000 1,880.19CNY Detail
TCI America (K0045)  Ketoconazole  >98.0%(HPLC)(T) 65277-42-1 5g 396.00CNY Detail
TCI America (K0045)  Ketoconazole  >98.0%(HPLC)(T) 65277-42-1 1g 155.00CNY Detail

65277-42-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Ketoconazole

1.2 Other means of identification

Product number -
Other names fungoral

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:65277-42-1 SDS

65277-42-1Synthetic route

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone
46503-52-0

1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone

(+/-)-1-acetyl-4-<4-(2,3-dihydroxypropoxy)phenyl>piperazine

(+/-)-1-acetyl-4-<4-(2,3-dihydroxypropoxy)phenyl>piperazine

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
With trifluoroacetic acid In dimethyl sulfoxide; toluene for 16h; Reagent/catalyst; Temperature; Reflux;80%
1H-imidazole
288-32-4

1H-imidazole

(2R,4S)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane
142128-67-4

(2R,4S)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane

A

ketoconazole
65277-42-1

ketoconazole

B

(2R,4S)-cis-2-(hydroxymethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane
142004-25-9

(2R,4S)-cis-2-(hydroxymethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl acetamide for 4h; Heating;A 53%
B 10%
(2R,4R)-(+)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl methanesulfonate
170210-43-2

(2R,4R)-(+)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl methanesulfonate

N-acetyl-N'-(4-hydroxyphenyl)piperazine
67914-60-7, 89929-31-7

N-acetyl-N'-(4-hydroxyphenyl)piperazine

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
With sodium hydride 1.) DMSO, RT, 1 h, 2.) DMSO, 80 deg C, 4 h; Yield given. Multistep reaction;
[cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl] 4-methyl-benzenesulfonate

[cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl] 4-methyl-benzenesulfonate

N-acetyl-N'-(4-hydroxyphenyl)piperazine
67914-60-7, 89929-31-7

N-acetyl-N'-(4-hydroxyphenyl)piperazine

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 0 - 80℃;
1-(4-hydroxyphenyl)piperazine
56621-48-8

1-(4-hydroxyphenyl)piperazine

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: pyridine / CH2Cl2
2: K2CO3 / methanol / 20 °C
3: NaH / dimethylsulfoxide / 0 - 80 °C
View Scheme
1-(4-Acetoxyphenyl)-4-acetylpiperazine
133345-21-8

1-(4-Acetoxyphenyl)-4-acetylpiperazine

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: K2CO3 / methanol / 20 °C
2: NaH / dimethylsulfoxide / 0 - 80 °C
View Scheme
(2R,4R)-(+)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl benzoate
70894-66-5, 134071-29-7, 138866-89-4

(2R,4R)-(+)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl benzoate

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NaOH / dioxane / Heating
2: pyridine
3: NaH / dimethylsulfoxide / 0 - 80 °C
View Scheme
(2R,4S)-(+)-2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolane-4-methanol
170210-42-1

(2R,4S)-(+)-2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolane-4-methanol

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: pyridine
2: NaH / dimethylsulfoxide / 0 - 80 °C
View Scheme
Multi-step reaction with 2 steps
1: 81 percent / pyridine / 16 h / 0 °C
2: 1.) NaH / 1.) DMSO, RT, 1 h, 2.) DMSO, 80 deg C, 4 h
View Scheme
(2R,4R)-(+)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl benzoate nitrate

(2R,4R)-(+)-<2-(2,4-dichlorophenyl)-2-<(1H-imidazol-1-yl)methyl>-1,3-dioxolan-4-yl>methyl benzoate nitrate

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 89 percent / 50percent aq. NaOH / dioxane / 0.5 h / Heating
2: 81 percent / pyridine / 16 h / 0 °C
3: 1.) NaH / 1.) DMSO, RT, 1 h, 2.) DMSO, 80 deg C, 4 h
View Scheme
1-(4-{4-[2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-ethanone
79156-75-5

1-(4-{4-[2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-ethanone

A

ketoconazole
65277-42-1

ketoconazole

B

(2R,4R)-Ketoconazole
142128-58-3

(2R,4R)-Ketoconazole

D

(2S,4S)-Ketoconazole
142128-60-7

(2S,4S)-Ketoconazole

Conditions
ConditionsYield
With methanol; sodium dodecyl-sulfate; 2,3,6-trimethyl-beta-cyclodextrin; sodium hydroxide In aq. phosphate buffer at 25℃; pH=2.5; pH-value; Reagent/catalyst; Temperature; Resolution of racemate;
Conditions
ConditionsYield
With Beckman P/ACE MDQ Capillary Electrophoresis System equipped fused-silica capillaries (Polymicro Technologies, Phoenix, Arizona) of 50-μm ID cut with sulfobutyl ether β-cyclodextrin as chiral selector In aq. buffer at 25℃; pH=2.5; Concentration; pH-value; Reagent/catalyst; Resolution of racemate;
N-acetyl-N'-(4-hydroxyphenyl)piperazine
67914-60-7, 89929-31-7

N-acetyl-N'-(4-hydroxyphenyl)piperazine

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide; tetrabutylammomium bromide / water; toluene / 16 h / 25 °C
2: trifluoroacetic acid / toluene; dimethyl sulfoxide / 16 h / Reflux
View Scheme
1,3-Dichlorobenzene
541-73-1

1,3-Dichlorobenzene

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 25 °C
1.2: 16 h / Reflux
2.1: triethylamine / dichloromethane / 10 °C
3.1: trifluoroacetic acid / toluene; dimethyl sulfoxide / 16 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: aluminum (III) chloride / dichloromethane / 0.5 h / 25 °C
1.2: 16 h / Reflux
2.1: triethylamine / dichloromethane / 10 °C
3.1: trifluoroacetic acid / toluene; dimethyl sulfoxide / 16 h / Reflux
View Scheme
2,4-dichlorophenacyl bromide
2631-72-3

2,4-dichlorophenacyl bromide

ketoconazole
65277-42-1

ketoconazole

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine / dichloromethane / 10 °C
2: trifluoroacetic acid / toluene; dimethyl sulfoxide / 16 h / Reflux
View Scheme
Conditions
ConditionsYield
With cellulose (3,5-dimethylphenylcarbamate) coated reduced graphene oxide(at)silica gel In hexane at 25℃; Resolution of racemate; enantioselective reaction;
copper(II) acetate monohydrate
6046-93-1

copper(II) acetate monohydrate

ketoconazole
65277-42-1

ketoconazole

[Cu(ketoconazole)2(Ac)2]*H2O

[Cu(ketoconazole)2(Ac)2]*H2O

Conditions
ConditionsYield
In methanol at 25℃; for 24h;94%
copper(II) nitrate trihydrate

copper(II) nitrate trihydrate

ketoconazole
65277-42-1

ketoconazole

[Cu(ketoconazole)2(NO3)(H2O)](NO3)*H2O

[Cu(ketoconazole)2(NO3)(H2O)](NO3)*H2O

Conditions
ConditionsYield
In methanol at 25℃; for 36h;89%
zinc(II) nitrate hexahydrate

zinc(II) nitrate hexahydrate

ketoconazole
65277-42-1

ketoconazole

[Zn(ketoconazole)2(NO3)(H2O)](NO3)

[Zn(ketoconazole)2(NO3)(H2O)](NO3)

Conditions
ConditionsYield
In methanol at 25℃; for 24h;86%
bis(triphenylphosphino)copper(I) nitrate
14494-93-0, 23751-62-4, 106678-35-7

bis(triphenylphosphino)copper(I) nitrate

ketoconazole
65277-42-1

ketoconazole

[Cu(PPh3)2(cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine)2]NO3

[Cu(PPh3)2(cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine)2]NO3

Conditions
ConditionsYield
In acetonitrile for 24h;83%
potassium tetrachloroplatinate(II)
10025-99-7

potassium tetrachloroplatinate(II)

ketoconazole
65277-42-1

ketoconazole

trans-Pt(cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine)2Cl2

trans-Pt(cis-1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazine)2Cl2

Conditions
ConditionsYield
In ethanol; water at 100℃; for 2h;78%
methanol
67-56-1

methanol

ketoconazole
65277-42-1

ketoconazole

zinc(II) chloride
7646-85-7

zinc(II) chloride

[Zn(ketoconazole)2Cl2]*0.4CH3OH

[Zn(ketoconazole)2Cl2]*0.4CH3OH

Conditions
ConditionsYield
at 25℃; for 24h;78%
(tetrahydrothiophene)gold(I) chloride
39929-21-0

(tetrahydrothiophene)gold(I) chloride

ketoconazole
65277-42-1

ketoconazole

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

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

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h;65%
zinc(II) acetate dihydrate
5970-45-6

zinc(II) acetate dihydrate

ketoconazole
65277-42-1

ketoconazole

[Zn(ketoconazole)2(Ac)2]*H2O

[Zn(ketoconazole)2(Ac)2]*H2O

Conditions
ConditionsYield
In methanol at 25℃; for 24h;65%
Ethyl bromodifluoroacetate
667-27-6

Ethyl bromodifluoroacetate

ketoconazole
65277-42-1

ketoconazole

1-(4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-((3-(difluoromethyl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)methyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one

1-(4-(4-(((2R,4S)-2-(2,4-dichlorophenyl)-2-((3-(difluoromethyl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)methyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazin-1-yl)ethan-1-one

Conditions
ConditionsYield
With rongalite; sulfur In N,N-dimethyl acetamide at 100℃; for 24h; Sealed tube;43%
With sulfur; rongalite In N,N-dimethyl acetamide at 100℃; for 24h; Sealed tube;43%
ketoconazole
65277-42-1

ketoconazole

copper dichloride

copper dichloride

[Cu(ketoconazole)2Cl2]*3.2H2O

[Cu(ketoconazole)2Cl2]*3.2H2O

Conditions
ConditionsYield
In methanol at 25℃; for 0.5h;38%
ethyl bromofluoroacetate
401-55-8

ethyl bromofluoroacetate

ketoconazole
65277-42-1

ketoconazole

2-(3-(((2R,4S)-4-((4-(4-acetylpiperazin-1-yl)phenoxy)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl)methyl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-2-fluoroacetic acid ethyl ester

2-(3-(((2R,4S)-4-((4-(4-acetylpiperazin-1-yl)phenoxy)methyl)-2-(2,4-dichlorophenyl)-1,3-dioxolan-2-yl)methyl)-2-thioxo-2,3-dihydro-1H-imidazol-1-yl)-2-fluoroacetic acid ethyl ester

Conditions
ConditionsYield
With sulfur; sodium dithionite In 1,2-dichloro-ethane at 80℃; for 24h; Sealed tube;37%
With sulfur; sodium dithionite In 1,2-dichloro-ethane at 100℃; for 24h; Sealed tube;37%
ketoconazole
65277-42-1

ketoconazole

(+/-)-Deacylketoconazole

(+/-)-Deacylketoconazole

Conditions
ConditionsYield
With potassium hydroxide In isopropyl alcohol
With sodium hydroxide In methanol Reflux;700 mg
ketoconazole
65277-42-1

ketoconazole

ketoconazole-iodine

ketoconazole-iodine

Conditions
ConditionsYield
With iodine In 1,4-dioxane at 24.84 - 39.84℃; Kinetics; Equilibrium constant; Thermodynamic data; Solvent;
ketoconazole
65277-42-1

ketoconazole

2,4-diamino-6-piperidinopyrimidine 3-oxide
38304-91-5

2,4-diamino-6-piperidinopyrimidine 3-oxide

65277-42-1Downstream Products

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