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| CAS No.: | 84625-61-6 |
|---|---|
| Name: | Itraconazole |
| Article Data: | 5 |
| Molecular Structure: | |
|
|
|
| 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 |
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- 911112-05-55-Iodo-3-(trifluoromethyl)-2-pyridinamine
- 106461-41-0
(-)-(R)-2,4dihydro-4-[4-[4-(4-hydroxyphenyl)-1-piperazinyl]phenyl]-2-(1-methylpropyl)-3H-1,2,4-triazol 3-one
- 84625-61-6
itraconazole
| 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 | Yield |
|---|---|
| With potassium hydroxide In dimethyl sulfoxide for 14h; | 46% |
- 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 |
- 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 |
- 84625-61-6
itraconazole
| 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 |
- 84625-61-6
itraconazole
| 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 |
- 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 |
| 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
| Conditions | Yield |
|---|---|
| In chloroform; acetonitrile |
| Conditions | Yield |
|---|---|
| In ethanol UV-irradiation; Microbiological reaction; |
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Chemistry
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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: 
Xi,
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.