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...

General Information

Structure

Molecular Formula

C₁₃H₁₂F₂N₆O

Molecular Mass

306.2707864

Exact Mass

306.10406547

Charge

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

Calculated Properties

JChem

Acid pKa

12.707209

H Acceptors

H Donor

LogD (pH = 5.5)

0.5604975

LogD (pH = 7.4)

0.56095034

Log P

0.56095827

Molar Refractivity

97.1995

Polarizability

26.91871

Polar Surface Area

81.65

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

0.58

LOG S

-2.34

Solubility (Water)

1.39e+00 g/l

Data Source

Names and Identifiers

IUPAC name

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

Brand Name

TriflucanElazorBiocanolFlucostatFlucazolDiflucanFlunizolBiozoleneFlusolPritenzolFlukezol

IUPAC Traditional name

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

Synonyms

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-olFlumyconZoltecFlunazolUK 49858FluconalDifluconazoleElazorFlusolFlucostatα-(2,4-Difluorophenyl)-α-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazol-1-ethanolFluzon1-(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-olFluconazole2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-olFungata

Names and Identifiers

Registration numbers

CAS Number

86386-73-4

PubChem CID

3365

PubChem SID

1609635444650573524724485

MDL Number

MFCD00274549

Registration numbers

Properties

Pharmacology Properties

P450

human ... CYP1A2(1544)

Inhibitor of fungal cytochrome P450 enzyme 14alpha-demethylase

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

• 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)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

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

Brand Name

TriflucanElazorBiocanolFlucostatFlucazolDiflucanFlunizolBiozoleneFlusolPritenzolFlukezol

IUPAC Traditional name

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

Synonyms

Registration numbers

CAS Number

86386-73-4

PubChem CID

3365

PubChem SID

1609635444650573524724485

MDL Number

MFCD00274549

References

PubChem Literature

From Data Sources

• 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)

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

P450

human ... CYP1A2(1544)

Inhibitor of fungal cytochrome P450 enzyme 14alpha-demethylase

Molecule Details

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

PHR1160

TRC

F421000

Used as an antifungal.

Molecule

ID:81