Name: Itraconazole
SKU: 84625-61-6

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Basic Information

Molecular Structure:
CAS No.:	84625-61-6
Name:	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:	Xi,Xn
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

Conditions	Yield
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

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

: C39H38Cl2O4Si

: 84625-61-6
itraconazole

Conditions

Yield

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

Yield

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

Conditions	Yield
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

Conditions	Yield
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

Yield

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

Conditions	Yield
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

Conditions	Yield
In chloroform; acetonitrile

: 84625-61-6
itraconazole

: C35H37ClN8O4

: C35H39ClN8O4

Conditions

Conditions	Yield
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/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

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: Irritant Xi, Harmful Xn
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.

84625-61-6

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Chemistry

History

Uses

Toxicity Data With Reference

Safety Profile

Specification