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| CAS No.: | 65277-42-1 |
|---|---|
| Name: | Ketoconazole |
| Molecular Structure: | |
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|
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| Formula: | C26H28Cl2H4O4 |
| Molecular Weight: | 531.439 |
| 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: |
 T
|
| 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 |
1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone
ketoconazole
| Conditions | Yield |
|---|---|
| With trifluoroacetic acid In dimethyl sulfoxide; toluene for 16h; Reagent/catalyst; Temperature; Reflux; | 80% |
1H-imidazole
(2R,4S)-cis-2-(bromomethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane
A
ketoconazole
B
(2R,4S)-cis-2-(hydroxymethyl)-2-(2,4-dichlorophenyl)-4-<<4-(4-acetylpiperazin-1-yl)phenoxy>methyl>-1,3-dioxolane
| Conditions | Yield |
|---|---|
| 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
N-acetyl-N'-(4-hydroxyphenyl)piperazine
ketoconazole
| Conditions | Yield |
|---|---|
| With sodium hydride 1.) DMSO, RT, 1 h, 2.) DMSO, 80 deg C, 4 h; Yield given. Multistep reaction; |
| Conditions | Yield |
|---|---|
| With sodium hydride In dimethyl sulfoxide at 0 - 80℃; |
1-(4-hydroxyphenyl)piperazine
ketoconazole
| Conditions | Yield |
|---|---|
| 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
ketoconazole
| Conditions | Yield |
|---|---|
| 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
ketoconazole
| Conditions | Yield |
|---|---|
| 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
ketoconazole
| 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 |
ketoconazole
| 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 |
1-(4-{4-[2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-ethanone
A
ketoconazole
B
(2R,4R)-Ketoconazole
D
(2S,4S)-Ketoconazole
| 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; |
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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
Ketoconazole was discovered in 1976 and released in 1981. It followed griseofulvin as one of the first available oral treatments for fungal infections.
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.
| 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. |
Hazard Codes: 
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 NOx.
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 .
