SPORANOX
Itraconazole
CAS: 84625-61-6
Molecular Formula: C35H38Cl2N8O4
SPORANOX - Names and Identifiers
| Name | Itraconazole |
| Synonyms | R51211 sporanox SPORANOX TRIASPORIN ORICONAZOLE oriconazole Itraconazole ITRACONAZOLE ITRACONAZOLE-D3 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-dihyd 2-butan-2-yl-4-[4-[4-[4-[[2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-yl methyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]phenyl]-1,2,4-triazol-3-one |
| CAS | 84625-61-6 |
| EINECS | 617-596-9 |
| 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 |
| InChIKey | VHVPQPYKVGDNFY-UHFFFAOYSA-N |
SPORANOX - Physico-chemical Properties
| Molecular Formula | C35H38Cl2N8O4 |
| Molar Mass | 705.63 |
| Density | 1.27 g/cm3 |
| Melting Point | 166°C |
| Boling Point | 850.0±75.0 °C(Predicted) |
| Specific Rotation(α) | -0.1～+0.1°(D/20℃)(c=10,CH2Cl2) |
| Flash Point | >110°(230°F) |
| Water Solubility | Insoluble in water. Solube in chloroform at 50 mg/ml. Slightly soluble in ethanol or methanol |
| Solubility | DMSO 4 mg/mL;Water <1 mg/mL;Ethanol <1 mg/mL. Almost insoluble in water and dilute acid solutions. |
| Appearance | Solid |
| Color | white |
| Merck | 14,5245 |
| pKa | 3.7(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents. |
| Sensitive | Sensitive to heat |
| MDL | MFCD00870168 |
| Physical and Chemical Properties | Melting Point: 166°C |
| Use | Azole broad-spectrum antifungal agents for systemic infections caused by deep fungi, as well as for candidiasis and Aspergillosis |
SPORANOX - Risk and Safety
| Risk Codes | R36/37/38 - Irritating to eyes, respiratory system and skin. R36/38 - Irritating to eyes and skin. R22 - Harmful if swallowed R39/23/24/25 - R23/24/25 - Toxic by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | 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. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. |
| UN IDs | UN 3286 8(6.1)(3) / PGII |
| WGK Germany | 3 |
| RTECS | XZ5481000 |
| HS Code | 2934990002 |
| Toxicity | LD50 (14 day) in mice, rats, dogs (mg/kg): >320, >320, >200 orally (Van Cauteren) |
SPORANOX - Upstream Downstream Industry
| Raw Materials | 2',4'-Dichloroacetophenone 2-Bromobutane |
SPORANOX - Reference
| Reference Show more | 1. Wang, Wenping, et al. "Itraconazole exerts anti-liver cancer potential through the Wnt, PI3K/AKT/mTOR, and ROS pathways." Biomedicine & Pharmacotherapy 131 (2020): 110661.https://doi.org/10.1016/j.biopha.2020.110661 2. [IF=6.529] Wenping Wang et al."Itraconazole exerts anti-liver cancer potential through the Wnt, PI3K/AKT/mTOR, and ROS pathways."Biomed Pharmacother. 2020 Nov;131:110661 |
SPORANOX - Nature
Open Data Verified Data
crystallization from toluene, melting point 166.2 °c. pK. 3.7. Almost insoluble in water and dilute acid solution.
Last Update：2024-01-02 23:10:35
SPORANOX - Preparation Method
Open Data Verified Data
from M-dichlorobenzene, by and ketoconazole completely similar reaction can be obtained 2-(2, 4-= chlorophenyl) a 2 (1H 1.2, 4-triazol-1-ylmethyl) -1.3-methanesulfonate of dioxolane-4-ylmethanol. And 1-acetyl -4-(4-hydroxyphenyl) piperazine condensation, followed by hydrolysis to remove acetyl, and p-nitrochlorobenzene condensation, hydrogenation reduction, chloroformate acylation, it is then reacted with hydrazine hydrate and then cyclized to obtain itraconazole.
Last Update：2022-01-01 09:08:37
SPORANOX - Standard
Authoritative Data Verified Data
This product is (±)-l-SEC-butyl -4-[4-[4-[(2R,4S)2-(2, 4-dichlorophenyl)] -2-(lH-l,2, 4-triazolyl -1-methyl)-l, 3-dioxol-4-yl] methoxy] phenyl]-1-piperazinyl] phenyl -1, 2, 4-triazol-5-one. Calculated as dried product, containing no less than 98.5% of C35H38C12N804.
Last Update：2024-01-02 23:10:35
SPORANOX - Trait
Authoritative Data Verified Data
- This product is white or off-white powder; Odorless.
- This product is soluble in methylene chloride, slightly soluble in Tetrahydrofuran, and almost insoluble in water, methanol or ethanol.
melting point
The melting point of this product (General 0612) is 165~169°C.
Last Update：2022-01-01 11:53:23
SPORANOX - Use
Open Data Verified Data
Janssen Belgium was developed in 1984 and was first launched in Mexico in 1988. It is a triazole drug, similar to ketoconazole, but has a more extensive antibacterial spectrum and fewer side effects. In addition to candidiasis, sporotrichosis, histoplasmosis, dermatophytosis, and toxiasis, it also treats aspergillosis and cryptococcosis. Triazole ring of imidazole antifungal drugs. By preventing the activation of cytochrome P-450, including oxidase and peroxidase, the 14. A- methyl sterol cannot be dehydrogenated and cannot be converted into ergosterol, thus inhibiting the growth and proliferation of fungi and having strong lipophilicity, can cross the biofilm, inhibit the binding of the membrane and fungi. It is effective for Superficial mycosis, dermatomycoses and the like, and is expected to be an efficient and safe drug for deep fungal infections such as cryptococcal encephalitis (AIDS patients). Clinical application is mainly used in systemic infections caused by deep fungi, such as fungal keratitis, oral candidiasis, finger and toe mycosis.
Last Update：2022-01-01 09:08:38
SPORANOX - Differential diagnosis
Authoritative Data Verified Data
- add methanol-tetrahydrofuran (4:1) to dissolve and dilute the product and itraconazole in appropriate amounts to prepare a solution containing about 0.2mg per 1 ml, as test solution and control solution. The retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution according to the chromatographic conditions under the relevant substances.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
- take about 30mg of this product, place it in a crucible, add 0.3g of anhydrous sodium carbonate, heat it for 10 minutes, let it cool, take the residue, add 5ml of dilute nitric acid, shake well, filter, add 1ml of filtrate and 1ml of water, shake well, and identify the reaction of (1) (General rule 0301).
Last Update：2022-01-01 11:53:23
SPORANOX - Safety
Open Data Verified Data
mouse, rat, dog oral (14 days) LD50 (mg/kg):>320,> 320,> 200.
Last Update：2022-01-01 09:08:38
SPORANOX - Exam
Authoritative Data Verified Data
optical rotation
take this product, precision weighing, plus dichloromethane dissolved and quantitative dilution made per lml containing 0.lg of the solution, measured according to the law (General rule 0621), the optical rotation is 0.10 ° to +0.10 °.
clarity and color of dichloromethane solution
take this product l. Add 10ml of dichloromethane to dissolve, the solution should be clear and colorless; If it is turbid, it should not be more concentrated compared with No. 1 turbidity standard solution (General rule 0902 method 1); If it is colored, no deeper color shall be compared with the orange-yellow or brown-red standard colorimetric solution No. 4 (general rule 0901 method 1).
Related substances
take an appropriate amount of this product, add methanol-tetrahydrofuran (4:1) to dissolve and dilute to prepare a solution containing about 2mg per 1ml as a test solution; Take 1ml for precision measurement, in a 200ml measuring flask, dilute to the mark with methanol-tetrahydrofuran (4:1) and shake to a control solution. An appropriate amount of the control solution was accurately measured and diluted with methanol-tetrahydrofuran (4:1) to prepare a solution containing about 1 ug per 1ml as a sensitivity solution. According to the high performance liquid chromatography (General 0512) test, using eighteen alkyl silane bonded silica gel (BDS3um or performance equivalent column) as filler; using 0.02mol/L tetrabutylammonium hydrogen sulfate solution as mobile phase A and acetonitrile as mobile Phase B, gradient elution was carried out according to the following procedure; The flow rate was 1.5ml per minute; The detection wavelength was 225mn. Take about 20mg of itraconazole reference, add 1ml of formic acid to dissolve, heat in 60°C water bath for 3 hours, dilute to 10ml with methanol-tetrahydrofuran (4:1), and shake well, at room temperature for 24 hours, as the system applicable solution, 10ul was injected into the liquid chromatograph, and the chromatogram was recorded. The retention time of itraconazole peak was about 23 minutes, the separation degree between itraconazole peak and impurity peak with relative retention time of about 0.97 and 1.05 shall meet the requirements (impurities with relative retention time of about 0.97 and 1.05 shall be calculated by area normalization method, the chromatographic peak content is about 0.1% and 0.4%, respectively). Take the sensitivity solution 10 u1, inject into the liquid chromatograph, record the chromatogram, the signal to noise ratio of the main component peak height should be greater than 10. 10ul of the test solution and the control solution were respectively injected into the liquid chromatograph, and the chromatograms were recorded. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.5% ) , and the sum of each impurity peak area shall not be greater than 2.5 times (1.25%) of the area of the main peak of the control solution.. The peaks in the chromatogram of the test solution which are smaller than the main peak area of the sensitivity solution are ignored.
residual solvent
methanol, ethanol, dichloromethane, N-butanol and ethyl acetate take this product about 0.1kg, precision weighing, precision plus internal standard solution (take the right amount of N-propanol, use N,N-dimethylformamide was diluted to prepare 5ml of a solution containing about 20ug per 1 ml), which was sufficiently shaken to dissolve, and used as a test solution. Accurately weigh the appropriate amount of methanol, ethanol, dichloromethane, n-butanol and ethyl acetate, and quantitatively dilute with internal standard solution to make methanol 60ug, ethanol 100ug, dichloromethane 12ug per lml, A solution of n-butanol lOOug and ethyl acetate 100ug as a control solution. According to the test for determination of residual solvent (General Principle 0861 third method), 6% cyanopropylphenyl-94% dimethylpolysiloxane is used as the fixing solution (or similar to the polarity); The initial temperature is 50°C, and the retention time is 5 minutes, the temperature was increased to 150°C at a rate of 10°C per minute for 10 minutes. Take the reference solution 2u1, inject the human gas chromatograph, record the chromatogram, and the separation degree between the chromatographic peaks shall meet the requirements. 2 u1 of the test solution and the reference solution were respectively injected into the gas chromatograph, and the chromatograms were recorded. According to the internal standard method to calculate the peak area, methanol, ethanol, dichloromethane, n-butanol and ethyl acetate residues should be in accordance with the provisions.
toluene and dimethylformamide
take about 0.5g of this product, precision weighing, precision plus internal standard solution (take butyl acetate 80mg, put in 1000ml measuring flask, add dichloromethane to dilute to the scale, shake well) 5ml, fully shake to dissolve, as a test solution; Accurately weigh toluene 89mg, N,N-dimethylformamide 88mg, put in the same 100ml measuring flask, dilute to the scale with internal standard solution, shake well, take 5ml accurately, put it in a 50ml measuring flask, dilute it to the scale with internal standard solution, shake well, and use it as a reference solution. According to the residual solvent determination method (General 0861 third method) test, 6% cyanopropylphenyl-94% dimethyl polysiloxane was used as the stationary liquid (or polar similar); The column temperature was 90°C. Take the reference solution 2u1, inject the human gas chromatograph, record the chromatogram, and the separation degree between the chromatographic peaks shall meet the requirements. 2 u1 of the test solution and the reference solution were respectively injected into the gas chromatograph, and the chromatograms were recorded. According to the internal standard method, the residual amount of toluene and N ,N-dimethylformamide should be calculated by the peak area.
2-methoxyethanol
take this product about lg, precision weighing, precision plus dichloromethane 5ml, fully shake to dissolve, as a test solution; Take the appropriate amount of 2-methoxyethanol, precision weighing, A solution containing 10ug per 1 ml was prepared as a control solution by quantitative dilution with dichloromethane. According to the test of residual solvent determination method (General 0861 third method), the Nitro terephthalic acid modified polyethylene glycol (or polar similar) was used as the stationary liquid; The column temperature was 60°C. 2ul of the test solution and the reference solution were accurately measured and injected into the human gas chromatograph respectively, and the chromatograms were recorded. According to the external standard method to calculate the peak area, 2-methoxyethanol residues should comply with the provisions.
chloroform
take this product about 0.1g, precision weighing, precision plus N,N-dimethylformamide 5ml, fully shake to dissolve, as a test solution; Take the appropriate amount of chloroform, precision weighing, A solution containing 1.2ug per 1 ml was prepared as a control solution by quantitative dilution with N,N-dimethylformamide. According to the test for determination of residual solvent (General Principle 0861 third method), 6% cyanopropylphenyl-94% dimethylpolysiloxane is used as the fixing solution (or similar to the polarity); The initial temperature is 50°C, and the retention time is 5 minutes, the temperature was raised to 150°C at a rate of 10°C per minute for 10 minutes; The detector was an electron capture detector (ECD). The sample solution and the reference solution are respectively injected into the gas chromatograph, and the chromatogram is recorded. The peak area is calculated according to the external standard method, and the residual amount of chloroform should be in accordance with the regulations.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall be inspected according to law (General Principles 0821, second law) and shall not contain more than 20 parts per million of heavy metals.
Last Update：2022-01-01 11:53:24
SPORANOX - Content determination
Authoritative Data Verified Data
take this product about 0.3g, precision weighing, add butanone-glacial acetic acid (7:l)70ml to dissolve, according to the potential titration method (General 0701), with perchloric acid titration solution (0.1 mol/L) titration, the second burst point as the titration end point. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 35.28mg of C35H38Cl2N8O4.
Last Update：2022-01-01 11:53:25
SPORANOX - Category
Authoritative Data Verified Data
antifungal drugs.
Last Update：2022-01-01 11:53:25
SPORANOX - Storage
Authoritative Data Verified Data
sealed, stored in a cool, dry place.
Last Update：2022-01-01 11:53:25
SPORANOX - Itraconazole Capsules
Authoritative Data Verified Data
itraconazole (C35H38C12N804) should be 95.0% ~ 105.0% of the labeled amount.
trait
The content of this product is white to light yellow pill-like granules.
identification
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- appropriate amount of the contents of the product was taken, and the same results were shown according to the identification (3) test under the item of itraconazole.
examination
- contents under the item of difference in loading amount of related substances, mix well, weigh appropriate amount, add methanol-tetrahydrofuran (4:1) dissolve and dilute to make a solution containing 2mg of itraconazole per 1ml, filter, and take the filtrate as the test solution; Take 1ml of precision measurement and put it in a 200ml measuring flask, as a control solution, it was diluted to the scale with methanol-tetrahydrofuran (4:1) and shaken. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than the area of the main peak of the control solution (0.5% ) , the sum of each impurity peak area shall not be greater than 3 times (1.5%) of the main peak area of the control solution.
- the content of this product is about 0.1 μg in dichloromethane, which is accurately weighed and placed in a top-empty bottle, and 5ml of precision plus internal standard solution (a proper amount of chloroform is taken and diluted with water to make a solution containing about 24ug per lml), seal the mouth of the bottle, shake at room temperature to make a uniform suspension, as a test solution; Take dichloromethane for children, precision weighing, quantitative dilution with internal standard solution to prepare a solution containing 12ug per 1 ml,
- 5ml was accurately measured, placed in a top empty bottle, sealed, and used as a reference solution. According to the residual solvent determination method (General 0861 first method) test, 6% cyanopropylphenyl-94% dimethyl polysiloxane (or polar similar) was used as the stationary liquid; The column temperature was 60°C. The Headspace bottle equilibration temperature was 60°C and the equilibration time was 40 minutes. Take the reference solution into the headspace, the separation degree between the dichloromethane peak and the trichloromethane peak should meet the requirements. The test solution and the reference solution were injected by Headspace, and the chromatograms were recorded. According to the internal standard method to calculate the peak area, the residual amount of dichloromethane should comply with the provisions.
- dissolution the dissolution of this product was determined according to the dissolution and release determination method (General rule 0931 second method), with hydrochloric acid solution (9-1000) 1000ml as the dissolution medium, and the rotation speed was 75 rpm, operate in accordance with the law, after 45 minutes, take the appropriate amount of solution, filter, take the filtrate 5ml, put it in a 25ml measuring flask, dilute it to the scale with methanol-dissolution medium (5:95), shake well, as a test solution; Another itraconazole reference about 20mg, precision weighing, 200ml flask, add 40ml of fermentation, 40°C water bath, heat and shake to dissolve, cool, dilute to scale with dissolution medium, shake well, take 5 m l precisely, put it in a 25m l volumetric flask, dilute to scale with dissolution medium, shake well, as a control solution. The test solution and the reference solution were taken, and the absorbance at the wavelength of 0401 NM was measured by ultraviolet-visible spectrophotometry (general rule), and the dissolution amount of each particle was calculated. The limit is 80% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
- measured by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test with eighteen alkyl silane bonded silica gel (BDS3um or performance equivalent column) as the filler; the mobile phase was acetonitrile -0.02mol / L tetrabutylammonium hydrogen sulfate solution (40:60), and the detection wavelength was 225nm. The number of theoretical plates is not less than 3000 calculated by the itraconazole peak, and the separation degree between the itraconazole peak and the adjacent impurity peak should meet the requirements.
- determine the contents under the item of loading difference, mix evenly, weigh an appropriate amount (about 50mg equivalent to itraconazole) accurately, and put it in a 250ml measuring flask, add methanol-tetrahydrofuran (4:1) Ultrasonic to dissolve itraconazole and dilute to the scale, shake well, filter, take the continued filtrate as the test solution, take 10 u1 accurately, note human liquid chromatograph, record chromatogram; Take appropriate amount of itraconazole reference substance, precise weighing, add appropriate amount of methanol-tetrahydrofuran (4:1), ultrasonic dissolution and quantitative dilution of the solution containing 0.2mg per 1 ml, the same method. According to the external standard method to calculate the peak area, that is.
category
Same as itraconazole.
specification
O.lg
storage
sealed, stored in a cool, dry place.
Last Update：2022-01-01 11:53:26
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View History
SPORANOX
2-(3-CARBOXYPROPYL)-3-AMINO-6-(4 METHOXYPHENYL)PYRIDAZINIUM BROMIDE
3-Dimethylphenyl)ethyl chloride
1-ALLYL-3-ISOPROPYL-6,6-DIMETHYL-1,5,6,8-TETRAHYDRO-2H-PYRANO[4',3':4,5]THIENO[2,3-D]PYRIMIDINE-2,4(3H)-DIONE
Poly(11-aminoundecanoicacid)
4-{[4-(trifluoromethoxy)phenyl]carbamoyl}phenyl N,N-dimethylsulfamate
8-phenylbenzo[e]acephenanthrylene
2-Chlor-1,3-dimethyl-imidazolidinium-hexafluorophosphat
2-Boc-6-oxo-2-azaspiro[3.4]octane - X7231
103527-34-0
2-(3-CARBOXYPROPYL)-3-AMINO-6-(4 METHOXYPHENYL)PYRIDAZINIUM BROMIDE
3-Dimethylphenyl)ethyl chloride
1-ALLYL-3-ISOPROPYL-6,6-DIMETHYL-1,5,6,8-TETRAHYDRO-2H-PYRANO[4',3':4,5]THIENO[2,3-D]PYRIMIDINE-2,4(3H)-DIONE
Poly(11-aminoundecanoicacid)
4-{[4-(trifluoromethoxy)phenyl]carbamoyl}phenyl N,N-dimethylsulfamate
8-phenylbenzo[e]acephenanthrylene
2-Chlor-1,3-dimethyl-imidazolidinium-hexafluorophosphat
2-Boc-6-oxo-2-azaspiro[3.4]octane - X7231
103527-34-0
Raw Materials for SPORANOX