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84625-61-6

Basic Information
CAS No.: 84625-61-6
Name: Itraconazole
Article Data: 5
Molecular Structure:
Molecular Structure of 84625-61-6 (Itraconazole)
Formula: C35H38Cl2N8O4
Molecular Weight: 705.644
Synonyms: ITCZ;ITR;3H-1,2,4-Triazol-3-one, 4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-1-pipera-zinyl]phenyl]-2,4-dihydro-2-(1-methylpropyl);ITZ;Itraconazolum [Latin];R 51211;Itrizole;Itraconazole [USAN:BAN:INN:JAN];Itraconazole (JAN/USAN);Itrizole (TN);Itraconazol [Spanish];3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)-;Sporanox (TN);Oriconazole;Sporanox;
EINECS: 617-596-9
Density: 1.4 g/cm3
Melting Point: 166 ºC
Boiling Point: 850 ºC at 760 mmHg
Flash Point: 467.9 ºC
Solubility: chloroform: 50 mg/mL, clear, colorless
Appearance: off-white crystalline solid
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 36/37/38
Safety: 22-26-36
PSA: 104.70000
LogP: 5.70730
Synthetic route
106461-41-0

(-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one

Toluene-4-sulfonic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester

84625-61-6

itraconazole

Conditions
ConditionsYield
Stage #1: (-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one With hydrazine hydrate; sodium hydroxide In N,N-dimethyl-formamide at 40℃; for 0.666667h; Inert atmosphere;
Stage #2: Toluene-4-sulfonic acid (2R,4R)-2-(2,4-dichloro-phenyl)-2-[1,2,4]triazol-1-ylmethyl-[1,3]dioxolan-4-ylmethyl ester In N,N-dimethyl-formamide at 60℃; for 1.5h;
90.5%
78-76-2, 5787-31-5

s-butyl bromide

89848-41-9

cis-4-<4-<4-<4-<<2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl>methoxy>phenyl>-1-piperazinyl>phenyl>-2,4-dihydro-3H-1,2,4-triazol-3-one

84625-61-6

itraconazole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 14h;46%

C39H38Cl2O4Si

84625-61-6

itraconazole

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: sulfuric acid / tert-butyl methyl ether / 3.5 h / 25 - 60 °C
2.1: iodine; sodium hydrogencarbonate / ethanol / -15 - -10 °C
3.1: dimethyl sulfoxide / 25 h / 20 - 100 °C
4.1: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol; water / 18 h / 20 °C / 1500.15 Torr
5.1: triethylamine / dichloromethane / 24.33 h / 20 °C / Reflux
6.1: sodium hydroxide; hydrazine hydrate / N,N-dimethyl-formamide / 0.67 h / 40 °C / Inert atmosphere
6.2: 1.5 h / 60 °C
View Scheme

C18H18Cl2O3

84625-61-6

itraconazole

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: iodine; sodium hydrogencarbonate / ethanol / -15 - -10 °C
2.1: dimethyl sulfoxide / 25 h / 20 - 100 °C
3.1: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol; water / 18 h / 20 °C / 1500.15 Torr
4.1: triethylamine / dichloromethane / 24.33 h / 20 °C / Reflux
5.1: sodium hydroxide; hydrazine hydrate / N,N-dimethyl-formamide / 0.67 h / 40 °C / Inert atmosphere
5.2: 1.5 h / 60 °C
View Scheme

C18H17Cl2IO3

84625-61-6

itraconazole

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: dimethyl sulfoxide / 25 h / 20 - 100 °C
2.1: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol; water / 18 h / 20 °C / 1500.15 Torr
3.1: triethylamine / dichloromethane / 24.33 h / 20 °C / Reflux
4.1: sodium hydroxide; hydrazine hydrate / N,N-dimethyl-formamide / 0.67 h / 40 °C / Inert atmosphere
4.2: 1.5 h / 60 °C
View Scheme

C20H19Cl2N3O3

84625-61-6

itraconazole

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol; water / 18 h / 20 °C / 1500.15 Torr
2.1: triethylamine / dichloromethane / 24.33 h / 20 °C / Reflux
3.1: sodium hydroxide; hydrazine hydrate / N,N-dimethyl-formamide / 0.67 h / 40 °C / Inert atmosphere
3.2: 1.5 h / 60 °C
View Scheme

C36H30Cl2O4

84625-61-6

itraconazole

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: magnesium; iodine / tert-butyl methyl ether / 2 h / 0 - 56 °C / Inert atmosphere; Reflux
1.2: 5 h / -10 - 30 °C
2.1: sulfuric acid / tert-butyl methyl ether / 3.5 h / 25 - 60 °C
3.1: iodine; sodium hydrogencarbonate / ethanol / -15 - -10 °C
4.1: dimethyl sulfoxide / 25 h / 20 - 100 °C
5.1: hydrogenchloride; palladium on activated charcoal; hydrogen / methanol; water / 18 h / 20 °C / 1500.15 Torr
6.1: triethylamine / dichloromethane / 24.33 h / 20 °C / Reflux
7.1: sodium hydroxide; hydrazine hydrate / N,N-dimethyl-formamide / 0.67 h / 40 °C / Inert atmosphere
7.2: 1.5 h / 60 °C
View Scheme
84625-61-6

itraconazole

61413-70-5

chloromethyl octanoate

C44H55Cl2N8O6(1+)*I(1-)

Conditions
ConditionsYield
With sodium iodide In acetonitrile for 4h; Inert atmosphere; Reflux;60%
45952-56-5

3,5-dimethyl-4-hydroxybenzyl bromide

84625-61-6

itraconazole

1-[4-(4-{4-[4-(1-sec-butyl-5-oxo-1,5-dihydro-[1,2,4]triazol-4-yl)-phenyl]-piperazin-1-yl}-phenoxymethyl)-2-(2,4-dichloro-phenyl)-[1,3]dioxolan-2-ylmethyl]-4-(4-hydroxy-3,5-dimethyl-benzyl)-1H-[1,2,4]triazol-4-ium; bromide

Conditions
ConditionsYield
In chloroform; acetonitrile
84625-61-6

itraconazole

C35H37ClN8O4

C35H39ClN8O4

Conditions
ConditionsYield
In ethanol UV-irradiation; Microbiological reaction;
Raw Materials
78-76-2
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Chemistry


IUPAC Name: 2-butan-2-yl-4-[4-[4-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1, 3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one
Molecular Formula: C35H38Cl2N8O4
Molecular Weight: 705.63 g/mol
Canonical SMILES: c1(cc(ccc1[C@]1(Cn2cncn2)O[C@H](CO1)COc1ccc(cc1)N1CCN(CC1)c1ccc(cc1)n1c(n(nc1)[C@@H](C)CC)=O)Cl)Cl
InChI: InChI=1/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
Classification Code: Anti-Infective Agents; Antifungal ; Antifungal agents; Antiparasitic Agents; Antiprotozoal Agents; Drug / Therapeutic Agent; Human Data; Reproductive Effect
Product Categories: Active Pharmaceutical Ingredients; Antibiotic Explorer; Chiral Reagents; Heterocycles; Intermediates & Fine Chemicals; Pharmaceuticals; Antifungal
Index of Refraction: 1.678 
Molar Refractivity: 189.33 cm3 
Molar Volume: 502 cm3 
Polarizability: 75.05×10-24 cm3 
Surface Tension: 55.9 dyne/cm 
Density: 1.4 g/cm
Flash Point: 467.9 °C 
Enthalpy of Vaporization: 123.51 kJ/mol 
Boiling Point: 850 °C at 760 mmHg 
Melting Point: 166 °C
Storage temperature: 2-8 °C
Solubility:  chloroform: 50 mg/mL, clear, colorless
Stability: Stable. Incompatible with strong oxidizing agents
Vapour Pressure of Itraconazole (CAS NO.84625-61-6): 3.53E-29 mmHg at 25 °C

History

It was  invented in 1984.

Uses

  Itraconazole (CAS NO.84625-61-6) is a triazole antifungal agent that is prescribed to patients with fungal infections. Itraconazole is available as capsules or as an oral solution. It is used as an orally active antimycotic structurally related to Ketoconazole.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD50 oral > 200mg/kg (200mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
guinea pig LD50 oral > 160mg/kg (160mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
man TDLo oral 240mg/kg/6W-I (240mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: LIVER FUNCTION TESTS IMPAIRED
Lancet. Vol. 340, Pg. 251, 1992.
mouse LD50 intravenous 46400ug/kg (46.4mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 381, 1991.
mouse LD50 oral > 320mg/kg (320mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
rat LD50 intravenous 40mg/kg (40mg/kg)   Kiso to Rinsho. Clinical Report. Vol. 25, Pg. 381, 1991.
rat LD50 oral > 320mg/kg (320mg/kg)   Reviews of Infectious Diseases. Vol. 9(Suppl,
women TDLo oral 32mg/kg/8D-I (32mg/kg) SKIN AND APPENDAGES (SKIN): HAIR: OTHER British Medical Journal. Vol. 293, Pg. 822, 1986.
women TDLo oral 140mg/kg/5W-I (140mg/kg) LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

LIVER: LIVER FUNCTION TESTS IMPAIRED

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
Lancet. Vol. 340, Pg. 251, 1992.

Safety Profile

Hazard Codes: IrritantXi,HarmfulXn
Risk Statements: 36/37/38-36/38-22 
R36/37/38: Irritating to eyes, respiratory system and skin. 
R36/38: Irritating to eyes and skin. 
R22: Harmful if swallowed.
Safety Statements: 22-26-36 
S22: Do not breathe dust. 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36: Wear suitable protective clothing.
WGK Germany: 3
RTECS Itraconazole (CAS NO.84625-61-6): XZ5481000

Specification

 Itraconazole (CAS NO.84625-61-6), its Synonyms are (+-)-1-sec-Butyl-4-(p-(4-(p-(((2R*,4S*)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-delta(sup 2)-1,2,4-triazolin-5-one ; Hyphanox ; Itraconazol ; Itraconazolum ; Oriconazole ; 3H-1,2,4-Triazol-3-one, 4-(4-(4-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-1-piperazinyl)phenyl)-2,4-dihydro-2-(1-methylpropyl)- . It is an off-white crystalline solid.