Ketoconazole (65277-42-1),Ketoconazole (65277-42-1) Manufacturers & Suppliers,Synthesis,MSDS

Basic information

Name:
Ketoconazole
CAS No.:
65277-42-1
Molecular Structure:
Formula:
C₂₆H₂₈Cl₂H₄O₄
Molecular Weight:
531.44 .
Deleted CAS:
72093-26-6
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
Appearance:
White powder
Hazard Symbols:
T
Risk Codes:
25-36/37/38-23/24/25
Safety Description:
36-45-36/37/39-26 Details
Transport Information:
UN 2811 6.1/PG 3

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Chemistry

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

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: 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.

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 .