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Cas Database |
| Name |
Ketoconazole |
EINECS | 265-667-4 |
| CAS No. | 65277-42-1 | Density | 1.38 cm3 |
| PSA | 69.06000 | LogP | 4.20870 |
| 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; |
Article Data | 12 |
Ketoconazole Synthetic route
- 46503-52-0
1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone
- 65277-42-1
ketoconazole
| 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 | Yield |
|---|---|
| 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 | 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℃; |
- 56621-48-8
1-(4-hydroxyphenyl)piperazine
- 65277-42-1
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 |
- 133345-21-8
1-(4-Acetoxyphenyl)-4-acetylpiperazine
- 65277-42-1
ketoconazole
| 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 | 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 | 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 |
- 65277-42-1
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 |
- 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 | 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; |
Ketoconazole Chemical Properties
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 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: 
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 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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