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Voriconazole

Voriconazole Structure
CAS No.
137234-62-9
Chemical Name:
Voriconazole
Synonyms
Isopropyl 4-hydroxybutane-1-sulfonate;Voriconzole;(2R,3S)-2-(2,4-DIFLUOROPHENYL)-3-(5-FLUOROPYRIMIDIN-4-YL)-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL;2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol;(2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol;(2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-((1H)-1,2,4-triazol-1-yl)-butan-2-;(2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-((1H)-1,2,4-triazol-1-yl)-butan-2-ol;UK-10949;UK-109496;Voricozole
CBNumber:
CB1160110
Molecular Formula:
C16H14F3N5O
Molecular Weight:
349.31
MOL File:
137234-62-9.mol
Modify Date:
2024/10/11 15:07:33
Request For Quotation

Voriconazole Properties

Melting point 127-130°C
alpha D25 -62° (c = 1 in methanol)
Boiling point 508.6±60.0 °C(Predicted)
Density 1.42±0.1 g/cm3(Predicted)
Flash point 9℃
storage temp. 2-8°C
solubility DMSO: >20mg/mL
form white powder
pka 11.54±0.29(Predicted)
color White to Almost white
Merck 14,10033
InChI InChI=1/C16H14F3N5O/c1-10(15-14(19)5-20-7-22-15)16(25,6-24-9-21-8-23-24)12-3-2-11(17)4-13(12)18/h2-5,7-10,25H,6H2,1H3/t10-,16+/s3
InChIKey BCEHBSKCWLPMDN-MGPLVRAMSA-N
SMILES [C@@](C1C=CC(F)=CC=1F)(O)(CN1N=CN=C1)[C@H](C1=NC=NC=C1F)C |&1:0,16,r|
CAS DataBase Reference 137234-62-9(CAS DataBase Reference)

SAFETY

Risk and Safety Statements

Symbol(GHS) 
GHS06,GHS08
Signal word  Danger
Hazard statements  H301-H341-H351-H361-H371-H372-H373-H412
Precautionary statements  P201-P202-P260-P264-P273-P301+P310
Hazard Codes  Xn,T,F
Risk Statements  22-36/38-52/53-48/22-40-25-61-39/23/24/25-23/24/25-11
Safety Statements  26-36-45-36/37-22-53-16
RIDADR  UN1230 - class 3 - PG 2 - Methanol, solution
WGK Germany  3
RTECS  UV9145000
HazardClass  6.1
PackingGroup  III
HS Code  29335990
NFPA 704
0
2 0

Voriconazole price More Price(7)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich(India) V-032 Voriconazole solution 2.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 137234-62-9 1ML ₹15374.8 2022-06-14 Buy
Sigma-Aldrich(India) PZ0005 Voriconazole ≥98% (HPLC) 137234-62-9 5MG ₹15891.1 2022-06-14 Buy
Sigma-Aldrich(India) PZ0005 Voriconazole ≥98% (HPLC) 137234-62-9 25MG ₹63477.8 2022-06-14 Buy
Sigma-Aldrich(India) PHR1892 Voriconazole Pharmaceutical Secondary Standard: Certified Reference Material 137234-62-9 1G ₹22743.33 2022-06-14 Buy
Sigma-Aldrich(India) 32483 Voriconazole VETRANAL?, analytical standard 137234-62-9 25MG ₹10716.75 2022-06-14 Buy
Product number Packaging Price Buy
V-032 1ML ₹15374.8 Buy
PZ0005 5MG ₹15891.1 Buy
PZ0005 25MG ₹63477.8 Buy
PHR1892 1G ₹22743.33 Buy
32483 25MG ₹10716.75 Buy

Voriconazole Chemical Properties,Uses,Production

Description

Voriconazole is a broad-spectrum triazole antifungal ,it is primarily used for the treatment of progressive, possibly life-threatening infections in immune deficiency patients. Indications include: immunosuppressed patients with severe fungal infections, acute invasive aspergillosis (the most common pathogen is Aspergillus fumigatus, followed by A. flavus, Aspergillus niger and Aspergillus soil), severe invasive infections caused by fluconazole-resistant Candida (including C. krusei) severe infection caused by Foot actinomycetes bacteria genus and Fusarium bacteria genus . Moderate to severe renal insufficiency is administered intravenously paying caution.

Chemical Properties

Cyrstalline Solid

Uses

Voriconazole is an antifungal (systemic) that belong to an ergosterol biosynthesis inhibitor. It is used to treat serious fungal or yeast infections, such as aspergillosis (fungal infection in the lungs), candidemia (fungal infection in the blood), esophageal candidiasis (candida esophagitis), or other fungal infections (infections in the skin, stomach, kidney, bladder, or wounds).

Definition

ChEBI: Voriconazole is a triazole-based antifungal agent used for the treatment of esophageal candidiasis, invasive pulmonary aspergillosis, and serious fungal infections caused by Scedosporium apiospermum and Fusarium spp. It is an inhibitor of cytochrome P450 2C9 (CYP2C9) and CYP3A4. It has a role as a P450 inhibitor. It is a member of pyrimidines, a difluorobenzene, a tertiary alcohol, a triazole antifungal drug and a conazole antifungal drug.

Indications

Voriconazole (Vfend), a derivative of fluconazole, is a second-generation triazole that has improved antifungal activity against Aspergillus and Fusarium spp., P. boydii, Penicillium marneffei, and fluconazole-resistant Candida spp. Like fluconazole, voriconazole has high oral bioavailability and good cerebrospinal fluid penetration, but unlike fluconazole, it undergoes extensive hepatic metabolism and is highly protein bound. No significant amount of bioactive drug is excreted into the urine. Dosage reduction is necessary with severe hepatic insufficiency but not with renal insufficiency.

Antimicrobial activity

The spectrum includes most fungi that cause human disease: dimorphic fungi (Blast. dermatitidis, Coccidioides spp., Hist. capsulatum, Paracocc. brasiliensis, Pen. marneffei and Spor. schenckii), molds (Aspergillus spp., Fusarium spp. and Scedosporium spp.), dematiaceous fungi and yeasts (Candida spp., Cryptococcus spp. and Trichosporon spp.).

Acquired resistance

Some fluconazole- and itraconazole-resistant strains of Candida and Aspergillus spp. show reduced susceptibility to voriconazole.

General Description

Voriconazole is a synthetically prepared, broad-spectrum triazole derivative of fluconazole, which shows in vitro activity against many yeasts and a broad-spectrum of mold and dermatophyte isolates. Its mode of action involves the inhibition of cytochrome P450 (CYP)-dependent enzyme, 14-α-sterol demethylase, and hence it is involved in disrupting the cell membrane and terminate the fungal growth.

Pharmaceutical Applications

Voriconazole is a triazole, antifungal agent that inhibits a broad range of pathogenic yeasts, including Candida (MIC = 0.03-8 μg/ml), and filamentous fungi such as Aspergillus, Scedosporium, and Fusarium. Its inhibitory action results from its ability to inhibit the synthesis of ergosterol, the major sterol of the fungal cell membrane.

Biological Activity

Voriconazole is an triazole antifungal agent used to treat serious fungal infections. It inhibits ergosterol synthesis by inhibiting CYP450-dependent 14-α sterol demethylase resulting in a depletion of ergosterol in fungal cell membranes. Displays potent activity against Candida , Cryptococcus and Aspergillus species.

Pharmacokinetics

Oral absorption: 96%
Cmax 400 mg oral: c. 2 mg/L after 2 h
Plasma half-life: c. 6 h
Volume of distribution: 4.6 L/kg
Plasma protein binding: 58%
Absorption
Oral absorption is rapid and almost complete, and is unaffected by intragastric pH. In adults, there is a disproportionate increase in blood concentrations with increasing oral and parenteral dosage, due to partial saturation of first-pass metabolism. In children given low dosages of the drug, proportional changes in drug levels are seen.
Distribution
It is widely distributed into body tissues and fluids, including brain and CSF.
Metabolism and excretion
It is extensively metabolized by the liver. More than 80% of a dose appears in the urine, but less than 2% is excreted in unchanged form. It is metabolized by several different hepatic cytochrome P450 enzymes. Some people with point mutations in the genes encoding these enzymes are poor metabolizers while others are extensive metabolizers. Drug levels are as much as four-fold lower in individuals who metabolize the drug more extensively.

Clinical Use

Acute and chronic invasive aspergillosis
Serious invasive Candida infections
Serious infections caused by Scedosporium and Fusarium spp.

Side effects

Unwanted effects include mild to moderate visual disturbance, rashes, and transient abnormalities of liver enzymes. Rare side effects include life-threatening hepatitis.

Mode of action

Voriconazole is structurally related to fluconazole (Pfizer, diflucan) and acts by inhibiting the cytochrome P450- dependant enzyme 14a-sterol demethylase of ergosterol synthesis (thereby resulting in the formation of a cell membrane with abnormal characteristics and accumulation of toxic sterol intermediates). Voriconazole was more active than itraconazole and fluconazole against Cryptococcus neoformans and a variety of Candidas species such as C. albicans, C. glabrata C. krusei. It also exhibits similar or superior activity compared to amphotericin B and itraconazole against filamentous fungi such as Aspergillus, an important pathogen which is not susceptible to fluconazole.

Precautions

Significant drug interactions include cyclosporins(increased cyclosporine levels), phenytoin, rifampin,and rifabutin (decreased voriconazole levels). Becauseof its low toxicity profile, this drug may gain importancein the chronic treatment of infections with invasive dimorphicfungi and resistant Candida spp.

Voriconazole Preparation Products And Raw materials

Raw materials

Hydrogen Palladium hydroxide Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S,4R)-, compd. with (αR,βS)-α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol (1:1) Pyrimidine, 4-ethenyl-5-fluoro- 2,4-Difluoro-alpha-(1H-1,2,4-triazolyl)acetophenone
Voriconazole Impurity 19 3-(6-Chloro-5-fluoropyrimidin-4-yl)-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol hydrochloride (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride (1R)-(-)-10-Camphorsulfonic acid
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Preparation Products

Voriconazole Suppliers

Global( 676)Suppliers
Supplier Tel Country ProdList Advantage Inquiry
Navone Specialties (OPC) Pvt Ltd +91-9323789882 +91-9323789882 Maharashtra, India 151 58 Inquiry
Jigs Chemical ltd +919099003427 Gujarat, India 239 58 Inquiry
HEMA PHARMACEUTICALS PVT LTD +91-9537936912 +91-9537936912 Gujarat, India 48 58 Inquiry
Suntril Pharmaceuticals Pvt Ltd +91-9041049907 +91-8591010191 Haryana, India 6 58 Inquiry
Apicore Pharmaceuticals Pvt Ltd +91-2662267177 +91-2662267166 Gujarat, India 181 58 Inquiry
Apionex Pharma Pvt Ltd +91-9773830459 +91-9819236256 Maharashtra, India 26 58 Inquiry
Sibram Pharmaceutical +91-8655777550 +91-8655777550 Maharashtra, India 244 58 Inquiry
Aspen Biopharma Labs Pvt Ltd +91-9248058660 +91-9248058662 Telangana, India 234 58 Inquiry
Prajna generics pvt ltd +91-9441174873 +91-9441174873 Hyderabad, India 24 58 Inquiry
SURYA LIFE SCIENCES LIMITED +91-2646226290 +91-9428511112 Gujarat, India 62 58 Inquiry
Supplier Advantage
Navone Specialties (OPC) Pvt Ltd 58
Jigs Chemical ltd 58
HEMA PHARMACEUTICALS PVT LTD 58
Suntril Pharmaceuticals Pvt Ltd 58
Apicore Pharmaceuticals Pvt Ltd 58
Apionex Pharma Pvt Ltd 58
Sibram Pharmaceutical 58
Aspen Biopharma Labs Pvt Ltd 58
Prajna generics pvt ltd 58
SURYA LIFE SCIENCES LIMITED 58

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Voriconazole Spectrum

Voriconazole(137234-62-9)1HNMR

137234-62-9(Voriconazole)Related Search:

(2R,3S/2S,3R)-2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol (2R,3S/2S,3R)-3-(4-Chloro-5-fluoro-6-pyrimidinyl)-2-(2,4-difluorophenyl)butan-2-ol hydrochloride Candesartan Ravuconazole Ambroxol
Itraconazole Human serum albumin Fluconazole Dexmedetomidine Linezolid
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Clindamycin (2RS, 3RS)-2-(2,4-Difluorophenyl)-3-(5-fluoropyriMidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol) 6-(1-Bromoethyl)-4-chloro-5-fluoropyrimidine
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Voriconazole 2-(2,4-Difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1H-1,2,4-triazol-1-yl)butan-2-ol Voriconazole solution (2R,3S)-2-(2,4-Difluorophenyl)-3 2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1,2,4-triazol-1-yl)butan-2-ol 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol Voriconazole, >=98.5% (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol Voriconazole(UK 109496) Voriconazole, 98%, a potent and broad-spectrum anti-fungal agent Voriconazole USP Voriconazole tab Voriconazole - Vfend | UK 109496 (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-((1H)-1,2,4-triazol-1-yl)-butan-2- Voriconazole≥ 99.9% (HPLC, Dried basis) Voricozole 2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1h-1,2,4-triazol-1-yl)butan-2-ol VORICONAZOLE (2R,3S/2S,3R)-3-(5-FLUORO-4-PYRIMIDINYL)-2-(2,4-DIFLUOROPHENYL)-1-(1H-1,2,4-TRIA (aR,bS)-a-(2,4-Difluorophenyl)-5-fluoro-b-methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol UK-10949 (2R,3S)-2-(2,4-DIFLUOROPHENYL)-3-(5-FLUOROPYRIMIDIN-4-YL)-1-(1H-1,2,4-TRIAZOL-1-YL)BUTAN-2-OL (aR,S)-a-(2,4-Difluorophenyl)-5-fluoro--methyl-a-(1H-1,2,4-triazol-1-ylmethyl)-4-pyrimidineethanol UK-109496 Vorionazole (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoropyrimidin-4-yl)-1-(1,2,4-triazol-1-yl)butan-2-ol (2R,3S)-2-(2,4-Difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-((1H)-1,2,4-triazol-1-yl)-butan-2-ol (R*,S*)-α-(2,4-Difluorophenyl)-5-fluoro-β-Methyl-α-(1H- 1,2,4-triazol-1-ylMethyl)-4-pyriMidineethanol (αR,βS)-α-(2,4-Difluorophenyl)-5-fluoro-β-Methyl-α-(1H-1,2,4-triazol-1-ylMethyl)-4-pyriMidineethanol Voriconazole RS Voriconazole CRS (αR,βS)-Voriconazole Voriconzole 4-Pyrimidineethanol, α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-, (αR,βS)- Isopropyl 4-hydroxybutane-1-sulfonate Voriconazole USP/EP/BP Voriconazole DISCONTINUED Voriconsrole VoriconazoleQ: What is Voriconazole Q: What is the CAS Number of Voriconazole Q: What is the storage condition of Voriconazole Q: What are the applications of Voriconazole Voriconazole (1718008) 4-Pyrimidineethanol, α-(2,4-difluorophenyl)-5-fluoro-β-methyl-α-(1H-1,2,4-triazol-1-ylmethyl)-, (αR,βS)- voriconazole base 137234-62-9 137234-63-9 C16H14N5OF3 C16H14F3N5O 1 Inhibitor Fine Chemical ZINACEF antifungal API Antifungal (Systemic) Aromatics Heterocycles Pfizer compounds Inhibitors Intermediates & Fine Chemicals Pharmaceuticals