Ketoconazole supplier | CasNO.65277-42-1

Name
Ketoconazole
EINECS 265-667-4
CAS No. 65277-42-1
Article Data12
CAS DataBase
Density 1.38 cm³
Solubility Soluble in DMSO, ethanol, chloroform, water, and methanol.
Melting Point 146 °C
Formula C₂₆H₂₈Cl₂H₄O₄
Boiling Point 753.4 °C at 760 mmHg
Molecular Weight 531.439
Flash Point 409.4 °C
Transport Information UN 2811 6.1/PG 3
Appearance White powder
Safety 36-45-36/37/39-26
Risk Codes 25-36/37/38-23/24/25
Molecular Structure
Hazard Symbols T
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;
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

Conditions	Yield
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

Conditions	Yield
With potassium carbonate In N,N-dimethyl acetamide for 4h; Heating;	A 53% B 10%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
With sodium hydride In dimethyl sulfoxide at 0 - 80℃;

: 56621-48-8
1-(4-hydroxyphenyl)piperazine

: 65277-42-1
ketoconazole

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

C: 65277-42-1, 72093-26-6, 79156-75-5, 83374-59-8, 142128-57-2, 142128-58-3, 142128-59-4, 142128-60-7
ketoconazole

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

Conditions

Conditions	Yield
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;

...Expand

: ketokonazole

A: 65277-42-1
ketoconazole

B: 65277-42-1, 72093-26-6, 79156-75-5, 83374-59-8, 142128-57-2, 142128-58-3, 142128-59-4, 142128-60-7
ketoconazole

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 10 °C 2: trifluoroacetic acid / toluene; dimethyl sulfoxide / 16 h / Reflux View Scheme

: 65277-42-1
ketoconazole

A: 65277-42-1
ketoconazole

B: 65277-42-1, 72093-26-6, 79156-75-5, 83374-59-8, 142128-57-2, 142128-58-3, 142128-59-4, 142128-60-7
ketoconazole

Conditions

Conditions	Yield
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

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

: copper(II) nitrate trihydrate

: 65277-42-1
ketoconazole

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

Conditions

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

: zinc(II) nitrate hexahydrate

: 65277-42-1
ketoconazole

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

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
at 25℃; for 24h;	78%

...Expand

: 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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide In isopropyl alcohol
With sodium hydroxide In methanol Reflux;	700 mg

: 65277-42-1
ketoconazole

: ketoconazole-iodine

Conditions

Conditions	Yield
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

Ketoconazole Chemical Properties

Structure of Ketoconazole (CAS NO.65277-42-1):

Molecular Formula:C₂₆H₂₈C_l2N₄O₄
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

Ketoconazole History

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

Ketoconazole 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.

Ketoconazole 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.

Ketoconazole Safety Profile

Hazard Codes: Toxic T
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 NO_x.

Ketoconazole 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 .

Product Name

Ketoconazole

Synthetic route

Ketoconazole Chemical Properties

Ketoconazole History

Ketoconazole Uses

Ketoconazole Toxicity Data With Reference

Ketoconazole Safety Profile

Ketoconazole Specification

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