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65277-42-1

Basic Information
CAS No.: 65277-42-1
Name: Ketoconazole
Molecular Structure:
Molecular Structure of 65277-42-1 (Ketoconazole)
Formula: C26H28Cl2H4O4
Molecular Weight: 531.44 .
Synonyms: Ketoconazole [USAN:BAN:INN:JAN];Ketoconazol [INN-Spanish];1-acetyl-4-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine;Ketoconazole (JAN/USP);Nizoral (TN);KW-1414;(+-)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine;Nizoral;cis-1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1h-imidazol-1-ylmethyl)-1,3-diox olan- 4-yl)methoxy)phenyl)-piperazine;Prestwick_744;Fungarest;1-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone;Fungoral;Ketoconazol;Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, cis-;Ketoderm;cis-1-Acetyl-4-[4-[2-(2,4-dichlorophenyl)-2-(1H-cmidazol-1-ylmethyl)-1,3-dioxolan-4-ylmethoxy]phenyl]pipenazine;
EINECS: 265-667-4
Density: 1.38 cm3
Melting Point: 146 °C
Boiling Point: 753.4 °C at 760 mmHg
Flash Point: 409.4 °C
Solubility: Soluble in DMSO, ethanol, chloroform, water, and methanol.
Appearance: White powder
Hazard Symbols: ToxicT
Risk Codes: 25-36/37/38-23/24/25
Safety: 36-45-36/37/39-26
Transport Information: UN 2811 6.1/PG 3
PSA: 69.06000
LogP: 4.20870
Synthetic route
46503-52-0

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

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

65277-42-1

ketoconazole

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

1H-imidazole

142128-67-4

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

A

65277-42-1

ketoconazole

B

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%
170210-43-2

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

67914-60-7, 89929-31-7

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

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

67914-60-7, 89929-31-7

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

65277-42-1

ketoconazole

Conditions
ConditionsYield
With sodium hydride In dimethyl sulfoxide at 0 - 80℃;
56621-48-8

1-(4-hydroxyphenyl)piperazine

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
133345-21-8

1-(4-Acetoxyphenyl)-4-acetylpiperazine

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
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

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
170210-42-1

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

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

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
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

65277-42-1

ketoconazole

B

142128-58-3

(2R,4R)-Ketoconazole

D

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;
67914-60-7, 89929-31-7

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

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
541-73-1

1,3-Dichlorobenzene

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
2631-72-3

2,4-dichlorophenacyl bromide

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;
6046-93-1

copper(II) acetate monohydrate

65277-42-1

ketoconazole

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

Conditions
ConditionsYield
In methanol at 25℃; for 24h;94%

copper(II) nitrate trihydrate

65277-42-1

ketoconazole

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

Conditions
ConditionsYield
In methanol at 25℃; for 36h;89%

zinc(II) nitrate hexahydrate

65277-42-1

ketoconazole

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

Conditions
ConditionsYield
In methanol at 25℃; for 24h;86%
14494-93-0, 23751-62-4, 106678-35-7

bis(triphenylphosphino)copper(I) nitrate

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

Conditions
ConditionsYield
In acetonitrile for 24h;83%
10025-99-7

potassium tetrachloroplatinate(II)

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

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

methanol

65277-42-1

ketoconazole

7646-85-7

zinc(II) chloride

[Zn(ketoconazole)2Cl2]*0.4CH3OH

Conditions
ConditionsYield
at 25℃; for 24h;78%
39929-21-0

(tetrahydrothiophene)gold(I) chloride

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

Conditions
ConditionsYield
In dichloromethane at 0℃; for 2h;65%
5970-45-6

zinc(II) acetate dihydrate

65277-42-1

ketoconazole

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

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

Ethyl bromodifluoroacetate

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

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%
65277-42-1

ketoconazole

copper dichloride

[Cu(ketoconazole)2Cl2]*3.2H2O

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

ethyl bromofluoroacetate

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

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%
65277-42-1

ketoconazole

(+/-)-Deacylketoconazole

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

ketoconazole

ketoconazole-iodine

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

ketoconazole

38304-91-5

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

Downstream Products
38304-91-5
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Chemistry

Structure of Ketoconazole (CAS NO.65277-42-1):
 
Molecular Formula:C26H28Cl2N4O4
Molecular Weight:531.44
EINECS:265-667-4 
Index of Refraction: 1.642
Molar Refractivity: 139.11 cm3
Molar Volume: 384.9 cm3
Polarizability: 55.15×10-24cm3
Surface Tension: 52.1 dyne/cm
Density: 1.38 g/cm3
Flash Point: 409.4 °C
Enthalpy of Vaporization: 109.78 kJ/mol
Melting point: 146 oC
Boiling Point: 753.4 °C at 760 mmHg
Vapour Pressure: 1.39E-22 mmHg at 25 °C
Physical Appearance: White Powder
Product Categories: Active Pharmaceutical Ingredients;Organics;Antifungals for Research and Experimental Use;Antitumors for Research and Experimental Use;Biochemistry;Antibiotic Explorer;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;API;API's;Antifungal

History

 Ketoconazole was discovered in 1976 and released in 1981. It followed griseofulvin as one of the first available oral treatments for fungal infections.
 

Uses

Usage of Ketoconazole (CAS NO.65277-42-1):
1.Inhibits cytochrome P-450 dependent steps in the biosynthesis of steroid hormones in vivo.
2.Antimetastatic and antineoplastic activity.
3.Orally active 5-lipoxygenase and thromboxane synthase inhibitor.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 450mg/kg/90D- (450mg/kg) ENDOCRINE: EVIDENCE OF THYROID HYPOFUNCTION British Medical Journal. Vol. 293, Pg. 993, 1986.
dog LD50 intravenous 23300ug/kg (23.3mg/kg)   Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981.
dog LD50 oral 178mg/kg (178mg/kg)   Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981.
guinea pig LD50 intravenous 23300ug/kg (23.3mg/kg)   Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981.
guinea pig LD50 oral 178mg/kg (178mg/kg)   Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981.
man LDLo oral 45mg/kg/17D-I (45mg/kg) BEHAVIORAL: COMA

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Gut. Vol. 26, Pg. 636, 1986.
man TDLo oral 49mg/kg/17D-I (49mg/kg) LIVER: OTHER CHANGES Gastroenterology. Vol. 86, Pg. 503, 1984.
mouse LD50 intraperitoneal 2937mg/kg (2937mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987.
mouse LD50 intravenous 32mg/kg (32mg/kg)   Antimicrobial Agents and Chemotherapy. Vol. 33, Pg. 895, 1989.
mouse LD50 oral 618mg/kg (618mg/kg)   Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981.
mouse LD50 subcutaneous > 4gm/kg (4000mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987.
rat LD50 intraperitoneal 1474mg/kg (1474mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987.
rat LD50 intravenous 86mg/kg (86mg/kg)   Drugs. International Journal of Current Therapeutics and Applied Pharmacology Reviews. Vol. 23, Pg. 1, 1982.
rat LD50 oral 166mg/kg (166mg/kg)   Medicamentos de Actualidad. Vol. 17, Pg. 373, 1981.
rat LD50 subcutaneous > 2400mg/kg (2400mg/kg)   Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 18, Pg. 474, 1987.
women LDLo oral 264mg/kg/66D- (264mg/kg) LIVER: OTHER CHANGES Gastroenterology. Vol. 86, Pg. 503, 1984.
women LDLo oral 412mg/kg/15W- (412mg/kg) BEHAVIORAL: COMA

LIVER: "HEPATITIS (HEPATOCELLULAR NECROSIS), DIFFUSE"

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"
Gut. Vol. 26, Pg. 636, 1986.
women TDLo oral 60mg/kg (60mg/kg) LIVER: OTHER CHANGES Gastroenterology. Vol. 86, Pg. 503, 1984.
 

Safety Profile

Hazard Codes: ToxicT
Risk Statements: 25-36/37/38-23/24/25 
R25 :Toxic if swallowed. 
R36/37/38:Irritating to eyes, respiratory system and skin. 
R23/24/25:Toxic by inhalation, in contact with skin and if swallowed.
Safety Statements: 36-45-36/37/39-26 
S36:Wear suitable protective clothing. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: TK7912300
HazardClass: 6.1(b)
PackingGroup: III
Poison by ingestion and intravenous routes. Experimental reproductive effects. Human systemic effects: liver changes, evidence of thyroid hypofunction. Human mutation data reported. Note: May be associated with hepatic toxicity. When heated to decomposition it emits toxic fumes of Cl and NOx.

Specification

  Ketoconazole (CAS NO.65277-42-1), its Synonyms are (+-)-cis-1-Acetyl-4-(p-((2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine ; Ketoconazolum ; Ketoderm ; Ketoisdin ; Ketozole ; Kuric ; Onofin K ; Orifungal M ; Panfungol .

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