Product Name

  • Name

    Itraconazole

  • EINECS 617-596-9
  • CAS No. 84625-61-6
  • Article Data5
  • CAS DataBase
  • Density 1.4 g/cm3
  • Solubility chloroform: 50 mg/mL, clear, colorless
  • Melting Point 166 ºC
  • Formula C35H38Cl2N8O4
  • Boiling Point 850 ºC at 760 mmHg
  • Molecular Weight 705.644
  • Flash Point 467.9 ºC
  • Transport Information
  • Appearance off-white crystalline solid
  • Safety 22-26-36
  • Risk Codes 36/37/38
  • Molecular Structure Molecular Structure of 84625-61-6 (Itraconazole)
  • Hazard Symbols IrritantXi,HarmfulXn
  • 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;
  • PSA 104.70000
  • LogP 5.70730

Synthetic route

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

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

itraconazole
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%
s-butyl bromide
78-76-2, 5787-31-5

s-butyl bromide

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
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

itraconazole
84625-61-6

itraconazole

Conditions
ConditionsYield
With potassium hydroxide In dimethyl sulfoxide for 14h;46%
C39H38Cl2O4Si

C39H38Cl2O4Si

itraconazole
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

C18H18Cl2O3

itraconazole
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

C18H17Cl2IO3

itraconazole
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

C20H19Cl2N3O3

itraconazole
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

C36H30Cl2O4

itraconazole
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
itraconazole
84625-61-6

itraconazole

chloromethyl octanoate
61413-70-5

chloromethyl octanoate

C44H55Cl2N8O6(1+)*I(1-)

C44H55Cl2N8O6(1+)*I(1-)

Conditions
ConditionsYield
With sodium iodide In acetonitrile for 4h; Inert atmosphere; Reflux;60%
3,5-dimethyl-4-hydroxybenzyl bromide
45952-56-5

3,5-dimethyl-4-hydroxybenzyl bromide

itraconazole
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

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
itraconazole
84625-61-6

itraconazole

C35H37ClN8O4

C35H37ClN8O4

C35H39ClN8O4

C35H39ClN8O4

Conditions
ConditionsYield
In ethanol UV-irradiation; Microbiological reaction;
itraconazole
84625-61-6

itraconazole

C35H37ClN8O4

C35H37ClN8O4

C35H39ClN8O4

C35H39ClN8O4

C35H39ClN8O4

C35H39ClN8O4

Conditions
ConditionsYield
In acetonitrile UV-irradiation;
...Expand

Itraconazole Chemical Properties


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/cm3 
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

Itraconazole History

It was  invented in 1984.

Itraconazole 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.

Itraconazole 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.

Itraconazole 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

Itraconazole 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.

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