2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol

• ChemBase编号: 81
• 分子式: C13H12F2N6O
• 平均质量: 306.2707864
• 单一同位素质量: 306.10406547
• SMILES: Fc1c(C(O)(Cn2ncnc2)Cn2ncnc2)ccc(F)c1
• Canonical SMILES: Fc1ccc(c(c1)F)C(Cn1cncn1)(Cn1cncn1)O
• InChI: InChI=1S/C13H12F2N6O/c14-10-1-2-11(12(15)3-10)13(22,4-20-8-16-6-18-20)5-21-9-17-7-19-21/h1-3,6-9,22H,4-5H2
• InChIKey: RFHAOTPXVQNOHP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
• IUPAC传统名: fluconazole; 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
• 商标名: Biocanol; Biozolene; Diflucan; Elazor; Flucazol; Flucostat; Flukezol; Flunizol; Flusol; Pritenzol; Triflucan
• 别名: α-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazol-1-ethanol; 1-(2,4-Difluorophenyl)-1,1-bis[(1H-1,2,4-triazol-1-yl)methyl]methanol; Biozolene; Difluconazole; Elazor; Fluconal; Flucostat; Flumycon; Flunazol; Flusol; Fluzon; Triflucan; UK 49858; Zoltec; 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol; Fluconazole; 2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol; 2,4-difluoro-,1-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol; Fluconazole; Diflucan; Trican; Alfumet; 2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol; Fungata

登记号

• CAS号: 86386-73-4
• MDL号: MFCD00274549
• PubChem SID: 160963544; 24724485; 46505735
• PubChem CID: 3365

理论计算性质

JChem

• Acid pKa: 12.707209
• 质子受体: 5
• 质子供体: 1
• LogD (pH = 5.5): 0.5604975
• LogD (pH = 7.4): 0.56095034
• Log P: 0.56095827
• 摩尔折射率: 97.1995 cm^3
• 极化性: 26.91871 Å^3
• 极化表面积: 81.65 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 0.58
• LOG S: -2.34
• 溶解度: 1.39e+00 g/l

分子性质

理化性质

• 溶解度: 1 mg/L; DMSO: soluble5 mg/mL; Ethyl Acetate; Methanol
• 外观: powder; White to Off-White Solid
• 熔点: 138-140°C
• 疏水性(logP): 0.4; -0.44

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: XZ4810000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22-36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302-H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: room temp

药理学性质

• 作用靶点: P450
• 相关基因信息: human ... CYP1A2(1544)
• 生物活性机理: Inhibitor of fungal cytochrome P450 enzyme 14alpha-demethylase

产品相关信息

• 纯度: ≥98% (HPLC); 95%
• 级别: certified reference material
• 成盐信息: Free Base
• 包装: pkg of 1 g
• 应用领域: Antifungal agent; Effective in single oral dose against vaginal candidiasis; Not active against Aspergillus; Prophylactic treatment for AIDS patients
• Pharmacopeia Traceability: traceable to USP 1271700
• Empirical Formula (Hill Notation): C13H12F2N6O

详细说明

MP Biomedicals - 02198986

A highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethylation.

DrugBank - DB00196

• Drug Groups: approved
• Description: Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. [PubChem]
• Indication: For the treatment of fungal infections.
• Pharmacology: Fluconazole, a synthetic antifungal agent of the imidazole class, is used to treat vaginal candidiasis. It inhibits the fungal lanosterol 14 alpha-demethylase which thereby prevents the formation of ergosterol which is an essential component in the fungal cell membrane.
• Toxicity: Symptoms of overdose include hallucinations and paranoid behavior.
• Affected Organisms: Fungi
• Biotransformation: Hepatic
• Absorption: 90%
• Half Life: 30 hours (range 20-50 hours)
• Protein Binding: 11 to 12%
• Elimination: In normal volunteers, fluconazole is cleared primarily by renal excretion, with approximately 80% of the administered dose appearing in the urine as unchanged drug.
• Clearance: * 0.23 mL/min/Kg [adults]; * 0.18 mL/min/Kg [In premature newborns within 36 hours of birth]; * 0.22 mL/min/Kg [In premature newborns 6 days old]; * 0.33 mL/min/Kg [In premature newborns 12 days old]; * 0.4 mL/min/kg [9 Months-13 yearsreceiving single-oral 2 mg/kg]; * 0.51 mL/min/Kg [9 Months-13 yearsreceiving single-oral 8 mg/kg]; * 0.49 mL/min/Kg [5-15 yearsreceiving multiple IV 2 mg/kg]; * 0.59 mL/min/Kg [5-15 yearsreceiving multiple IV 4 mg/kg]; * 0.66 mL/min/Kg [5-15 yearsreceiving multiple IV 8 mg/kg]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1331

Research Area: Immunology , Infection
Biological Activity:
Fluconazole is used to treat serious fungal or yeast infections, such as vaginal candidiasis, oropharyngeal candidiasis, esophageal candidiasis, other candida infections, or fungal meningitis. This medicine works by killing the fungus or yeast, or preventing its growth. [1]Fluconazole is also used to prevent candidiasis in patients having bone marrow transplants, who receive cancer or radiation treatment.[1]

Sigma Aldrich - F8929

Biochem/physiol Actions
Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. F8929.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - PHR1160

General description
This certified reference material (CRM) is produced and certified in accordance with ISO/IEC 17025 and ISO Guide 34.
Other Notes
Values of analytes vary lot to lot.
Biochem/physiol Actions
Fluconazole is an antifungal agent. It is highly selective inhibitor of fungal cytochrome P-450 sterol C-14 α-demethyllation. Fluconazole is a potent inhibitor of CYP2C9. Fluconazole interferes with fungal ergosterol synthesis and downregulates the metallothionein gene.

Toronto Research Chemicals - F421000

Used as an antifungal.

参考文献

• R.P. Warrell, Jr. and E. Berman, Evaluation of therapeutic efficacy and CNS toxicity in acute refractory leukemia: J. Clin Oncol., 4: 74 (1986).
• http://en.wikipedia.org/wiki/Fluconazole
• Richard, K. et al.: Antimicrob. Ag. Chemother., 27, 832 (1985)
• U.K. Pat., 1982, Pfizer, 2 099 818; CA, 99, 38467q, (synth, pharmacol)
• Grant, S.M. et al., Drugs, 1990, 39, 877, (rev)
• Cobos Garcia, F.J. et al., Farm. Clin., 1991, 8, 423, (rev)
• Morck, H., Pharm. Ztg., 1991, 136, 56; 60, (rev)
• Morita, K. et al., Chem. Pharm. Bull., 1992, 40, 1247, (pharmacol)
• Fluconazole, (Eds., Powderly, W.G. et al), Marius Press, 1992, (book)
• Urbak, S.F. et al., Ophthalmologica, 1994, 208, 147, (use, rev)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 3349, (synonyms)
• Goa, K.L. et al., Drugs, 1995, 50, 658, (rev, pharmacokinet)
• Pat. Coop. Treaty (WIPO), 1997, Pfizer, 97 28 169; CA, 127, 220800s, (fosfluconazole, synth, pharmacol)
• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 378