CAS 86386-73-4|2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol|Triflucan|fluconazole|Elazor|Biocanol|Flucostat|Flucazol|Diflucan|Flunizol|Biozolene|Flusol|Fluconazole|Pritenzol|Fluk...

基本信息

化学结构

分子式

C₁₃H₁₂F₂N₆O

分子量

306.2707864

精确质量

306.10406547

电荷

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

Canonic Smiles

Fc1ccc(c(c1)F)C(Cn1cncn1)(Cn1cncn1)O

Isomeric Smiles

Fc1c(C(O)(Cn2ncnc2)Cn2ncnc2)ccc(F)c1

计算属性

JChem

Acid pKa

12.707209

质子受体

质子供体

LogD (pH = 5.5)

0.5604975

LogD (pH = 7.4)

0.56095034

Log P

0.56095827

摩尔折射率

97.1995

极化性

26.91871

极化表面积

81.65

可自由旋转的化学键

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

数据来源

名称和标识

商标名

ElazorBiocanolTriflucanDiflucanFlukezolPritenzolFlusolBiozoleneFlucazolFlunizolFlucostat

IUPAC传统名

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

IUPAC标准名

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

别名

FluconazoleTricanAlfumetDiflucan2,4-difluoro-,1-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol2-(2,4-difluorophenyl)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-olElazorFlunazolDifluconazoleFlusolZoltecUK 49858FluconalFlumyconFluzonα-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazol-1-ethanolFlucostat1-(2,4-Difluorophenyl)-1,1-bis[(1H-1,2,4-triazol-1-yl)methyl]methanolBiozoleneTriflucan2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-olFluconazoleFungata

名称和标识

数据登录号

CAS号

86386-73-4

PubChem SID

1609635444650573524724485

PubChem CID

3365

MDL号

MFCD00274549

数据登录号

化合物性质

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

化合物性质

分子相关蛋白质

暂无数据

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分子图谱

暂无数据

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描述信息

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]

MP Biomedicals

02198986

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

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.

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.

TRC

F421000

Used as an antifungal.

描述信息

参考文献

PubChem文献

数据源提供

• http://en.wikipedia.org/wiki/Fluconazole

• R.P. Warrell, Jr. and E. Berman, Evaluation of therapeutic efficacy and CNS toxicity in acute refractory leukemia: J. Clin Oncol., 4: 74 (1986).

• Richard, K. et al.: Antimicrob. Ag. Chemother., 27, 832 (1985)

• Cobos Garcia, F.J. et al., Farm. Clin., 1991, 8, 423, (rev)

• U.K. Pat., 1982, Pfizer, 2 099 818; CA, 99, 38467q, (synth, pharmacol)

• Urbak, S.F. et al., Ophthalmologica, 1994, 208, 147, (use, rev)

• Pat. Coop. Treaty (WIPO), 1997, Pfizer, 97 28 169; CA, 127, 220800s, (fosfluconazole, synth, pharmacol)

• Fluconazole, (Eds., Powderly, W.G. et al), Marius Press, 1992, (book)

• Morck, H., Pharm. Ztg., 1991, 136, 56; 60, (rev)

• Morita, K. et al., Chem. Pharm. Bull., 1992, 40, 1247, (pharmacol)

• Grant, S.M. et al., Drugs, 1990, 39, 877, (rev)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 378

• 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)

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

商标名

ElazorBiocanolTriflucanDiflucanFlukezolPritenzolFlusolBiozoleneFlucazolFlunizolFlucostat

IUPAC传统名

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

IUPAC标准名

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

别名

数据登录号

CAS号

86386-73-4

PubChem SID

1609635444650573524724485

PubChem CID

3365

MDL号

MFCD00274549

描述信息

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

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

External Links

• [Wikipedia]

• [RxList]

• [Drugs.com]

Selleck Chemicals

S1331

MP Biomedicals

02198986

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

Sigma Aldrich

F8929