Difference between revisions of "Fluconazole"

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| CAS_number = 86386-73-4
 
| CAS_number = 86386-73-4
 
| ChemSpiderID = 3248
 
| ChemSpiderID = 3248
−
| CAS_supplemental =  
+
| CAS_supplemental =
 
| ATC_prefix = D01
 
| ATC_prefix = D01
 
| ATC_suffix = AC15
 
| ATC_suffix = AC15
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| routes_of_administration = Oral, [[intravenous|IV]], topical
 
| routes_of_administration = Oral, [[intravenous|IV]], topical
 
}}
 
}}
−
'''Fluconazole''' ({{pronEng|fluːˈkɒnəzoʊl}}) is a [[triazole]] [[antifungal drug]] used in the treatment and prevention of superficial and systemic fungal infections. In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol.<ref>MP Biomedicals[http://www.mpbio.com/product_info.php?products_id=198986]</ref> It is commonly marketed under the trade name '''Diflucan''' or '''Trican''' ([[Pfizer]]). In Mexico it is sold over the counter as '''Alfumet'''.
+
'''Fluconazole''' ({{pronEng|fluːˈkɒnəzoʊl}}) is a [[triazole]] [[antifungal drug]] used in the treatment and prevention of superficial and systemic fungal infections. In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol.<ref>[http://www.mpbio.com/product_info.php?products_id=198986 MP Biomedicals]</ref> It is commonly marketed under the trade name '''Diflucan''' or '''Trican''' ([[Pfizer]]). In Mexico it is sold over the counter as '''Alfumet'''. It is marketed under the brand name "candivast" in the Persian Gulf area.
  
 
==Pharmacology==
 
==Pharmacology==
 
===Mode of action===
 
===Mode of action===
−
Like other [[imidazole]]- and [[triazole]]-class antifungals, fluconazole inhibits the fungal [[cytochrome P450]] enzyme [[14α-demethylase]]. Mammalian demethylase activity is much less sensitive to fluconazole than fungal demethylase. This inhibition prevents the conversion of [[lanosterol]] to [[ergosterol]], an essential component of the fungal [[cytoplasmic membrane]], and subsequent accumulation of 14α-methyl sterols.<ref name="DiflucanPI">Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.</ref> Fluconazole is primarily [[fungistatic]], however may be [[fungicidal]] against certain organisms in a dose-dependent manner.{{fact}} It is interesting to note that, when fluconazole was in development at Pfizer, it was decided early in the process to avoid producing any [[Chirality (chemistry)|chiral]] centers in the drug so that subsequent synthesis and purification would not encounter difficulties with [[enantiomer]] separation and associated variations in biological effect.{{fact}} A number of related compounds were found to be extremely potent [[teratogens]], and were subsequently discarded.{{fact}}
+
Like other [[imidazole]]- and [[triazole]]-class antifungals, fluconazole inhibits the fungal [[cytochrome P450]] enzyme [[14α-demethylase]]. Mammalian demethylase activity is much less sensitive to fluconazole than fungal demethylase. This inhibition prevents the conversion of [[lanosterol]] to [[ergosterol]], an essential component of the fungal [[cytoplasmic membrane]], and subsequent accumulation of 14α-methyl sterols.<ref name="DiflucanPI">Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.</ref> Fluconazole is primarily [[fungistatic]], however may be [[fungicidal]] against certain organisms in a dose-dependent manner.{{Citation needed|date=July 2010}} It is interesting to note that, when fluconazole was in development at Pfizer, it was decided early in the process to avoid producing any [[Chirality (chemistry)|chiral]] centers in the drug so that subsequent synthesis and purification would not encounter difficulties with [[enantiomer]] separation and associated variations in biological effect.{{Citation needed|date=July 2010}} A number of related compounds were found to be extremely potent [[teratogens]], and were subsequently discarded.{{Citation needed|date=July 2010}}
  
 
===Microbiology===
 
===Microbiology===
Line 42: Line 42:
 
*''[[Trichophyton]]'' spp.
 
*''[[Trichophyton]]'' spp.
  
−
==Pharmacokinetics==
+
==Pharmacokinetics==
−
Following oral dosing, fluconazole is almost completely absorbed within two hours.{{fact}} [[Bioavailability]] is not significantly affected by the absence of stomach acid. Concentrations measured in the urine, tears, and skin are approximately 10 times the plasma concentration, whereas saliva, sputum, and vaginal fluid concentrations are approximately equal to the plasma concentration, following a standard dose range of between 100 mg and 400 mg per day.{{fact}} The [[elimination half-life]] of fluconazole follows zero order kinetics, and only 10% of elimination is due to [[metabolism]], the remainder is excreted in urine and sweat. Patients with impaired renal function will be at risk of overdose as well as patients taking drugs such as [[warfarin]].{{fact}}
+
Following oral dosing, fluconazole is almost completely absorbed within two hours.{{Citation needed|date=July 2010}} [[Bioavailability]] is not significantly affected by the absence of stomach acid. Concentrations measured in the urine, tears, and skin are approximately 10 times the plasma concentration, whereas saliva, sputum, and vaginal fluid concentrations are approximately equal to the plasma concentration, following a standard dose range of between 100&nbsp;mg and 400&nbsp;mg per day.{{Citation needed|date=July 2010}} The [[elimination half-life]] of fluconazole follows zero order kinetics, and only 10% of elimination is due to [[metabolism]], the remainder is excreted in urine and sweat. Patients with impaired renal function will be at risk of overdose as well as patients taking drugs such as [[warfarin]].{{Citation needed|date=July 2010}}
  
 
==Clinical use==
 
==Clinical use==
Line 53: Line 53:
 
*[[Meningitis|Cryptococcal meningitis]]
 
*[[Meningitis|Cryptococcal meningitis]]
  
−
Fluconazole can be used first-line for the following indications:<ref name="AMH2006">Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
+
Fluconazole can be used first-line for the following indications:<ref name="AMH2006"/>
 
*[[Coccidioidomycosis]]
 
*[[Coccidioidomycosis]]
 
*[[Cryptococcosis]]
 
*[[Cryptococcosis]]
Line 60: Line 60:
  
 
===Dosage===
 
===Dosage===
−
Dosage varies with indication and between patient groups, ranging from: a two-week course of 150 mg/day for vulvovaginal candidiasis, to 150–300 mg once weekly for resistant skin infections or some prophylactic indications. A dosage of 500–600 mg/day may be used for systemic or severe infections, and, in urgent infections such as meningitis caused by yeast, 800 mg/day have been used. Pediatric doses are measured at 6-12 mg/kg/d. A loading dose will be indicated when entering a daily dosage schedule; for example, a loading dose of 200 mg on the first day is commonly used with 150 mg/day following that.<ref name="AMH2006">Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
+
Dosage varies with indication and between patient groups, ranging from: a two-week course of 150&nbsp;mg/day for vulvovaginal candidiasis, to 150–300&nbsp;mg once weekly for resistant skin infections or some prophylactic indications. A dosage of 500–600&nbsp;mg/day may be used for systemic or severe infections, and, in urgent infections such as meningitis caused by yeast, 800&nbsp;mg/day have been used. Pediatric doses are measured at 6–12&nbsp;mg/kg/d. A loading dose will be indicated when entering a daily dosage schedule; for example, a loading dose of 200&nbsp;mg on the first day is commonly used with 150&nbsp;mg/day following that.<ref name="AMH2006"/>
  
 
===Contraindications===
 
===Contraindications===
−
Fluconazole is contraindicated in patients that:<ref name="AMH2006">Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
+
Fluconazole is contraindicated in patients that:<ref name="AMH2006"/>
 
* Have known hypersensitivity to other azole medicine <!-- Pfizer Diflucan data sheet in the package said so in section 4.3 -->
 
* Have known hypersensitivity to other azole medicine <!-- Pfizer Diflucan data sheet in the package said so in section 4.3 -->
−
* Are taking Terfenadine, if 400 mg per day multidose of Fluconazole is administered <!-- Pfizer Diflucan data sheet in the package said so in section 4.3 -->
+
* Are taking Terfenadine, if 400&nbsp;mg per day multidose of Fluconazole is administered <!-- Pfizer Diflucan data sheet in the package said so in section 4.3 -->
 
* Are in concomitant use of [[cisapride]], due to risk of serious [[cardiac arrhythmia]]s (relative contraindication)
 
* Are in concomitant use of [[cisapride]], due to risk of serious [[cardiac arrhythmia]]s (relative contraindication)
 
* Are pregnant.
 
* Are pregnant.
  
 
===Precautions===
 
===Precautions===
−
Fluconazole therapy has been associated with [[QT interval]] prolongation, which may lead to serious [[cardiac arrhythmia]]s. Thus, it is used with caution in patients with risk factors for prolonged QT interval such as electrolyte imbalance or use of other drugs that may prolong the QT interval (particularly [[cisapride]]).{{fact}}
 
  
−
Fluconazole has also rarely been associated with severe or lethal [[hepatotoxicity]] and [[liver function test]]s are usually performed regularly during prolonged fluconazole therapy. In aAddition, it is used with caution in patients with pre-existing liver disease.<ref name="DiflucanPI">Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.</ref>
+
Fluconazole is secreted in human milk at concentrations similar to plasma. Therefore, the use of
 +
fluconazole in nursing mothers is not recommended.<ref>[http://media.pfizer.com/files/products/uspi_diflucan.pdf Product information from Pfizer Inc]</ref>
  
−
High concentrations of fluconazole have been detected in human [[breast milk]] from patients receiving fluconazole therapy, thus its use is not recommended in breastfeeding mothers.<ref name="DiflucanPI">Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.</ref>
+
Fluconazole therapy has been associated with [[QT interval]] prolongation, which may lead to serious [[cardiac arrhythmia]]s. Thus, it is used with caution in patients with risk factors for prolonged QT interval such as electrolyte imbalance or use of other drugs that may prolong the QT interval (particularly [[cisapride]]).{{Citation needed|date=July 2010}}
  
−
Some people are allergic to azole(s). People allergic to other azole drugs might be allergic to Fluconazole.<ref>http://aac.asm.org/cgi/reprint/AAC.01500-08v1.pdf</ref> That is, some azole drugs have adverse side-effects.<br />
+
Fluconazole has also rarely been associated with severe or lethal [[hepatotoxicity]] and [[liver function test]]s are usually performed regularly during prolonged fluconazole therapy. In addition, it is used with caution in patients with pre-existing liver disease.<ref name="DiflucanPI"/>
−
"Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome." <ref>http://informahealthcare.com/doi/abs/10.1081/ERC-120015045?cookieSet=1&journalCode=erc</ref><br />
+
  
−
<blockquote>
+
High concentrations of fluconazole have been detected in human [[breast milk]] from patients receiving fluconazole therapy, thus its use is not recommended in breastfeeding mothers.<ref name="DiflucanPI"/>
−
Fluconazole/Diflucan is in the FDA pregnancy category C. <br />This means that it is not known whether it will be harmful to an unborn baby. Do not take Fluconazole/Diflucan without first talking to your doctor if you are pregnant or could become pregnant during treatment. <br /><br />
+
  
−
Do not take Fluconazole/Diflucan if you are taking cisapride (Propulsid). <br />Combined with cisapride (Propulsid), Diflucan could cause serious, even fatal, heart problems. <br /><br />
+
Some people are allergic to azole(s). People allergic to other azole drugs might be allergic to fluconazole.<ref>http://aac.asm.org/cgi/reprint/AAC.01500-08v1.pdf</ref> That is, some azole drugs have adverse side-effects.  Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome.<ref>{{cite journal | last1=Kragie | first1=Laura | last2=Turner | first2=Stephanie D. | last3=Patten | first3=Christopher J. | last4=Crespi | first4=Charles L. | last5=Stresser | first5=David M. | title=Assessing Pregnancy Risks of Azole Antifungals Using a High Throughput Aromatase Inhibition Assay | journal=Endocrine Research | volume=28 | issue=3 | pages=129 | year=2002 | pmid=12489563 | doi=10.1081/ERC-120015045}}</ref>
  
 +
<blockquote>
 +
Fluconazole/Diflucan is in the FDA pregnancy category C. <br />This means that it is not known whether it will be harmful to an unborn baby. Do not take Fluconazole/Diflucan without first talking to your doctor if you are pregnant or could become pregnant during treatment. <br />
 +
Do not take Fluconazole/Diflucan if you are taking [[cisapride]] (Propulsid). <br />Combined with cisapride (Propulsid), Diflucan could cause serious, even fatal, heart problems. <br />
 
In rare cases, Fluconazole/Diflucan has caused severe liver damage, sometimes resulting in death. <br />
 
In rare cases, Fluconazole/Diflucan has caused severe liver damage, sometimes resulting in death. <br />
−
Notify your doctor immediately if you develop nausea, vomiting, abdominal pain, unusual fatigue, loss of appetite, yellow skin or eyes, itching, dark urine, or clay-colored stools. <br />These symptoms may be early signs of liver damage.{{fact}} <br /><br />
+
Notify your doctor immediately if you develop nausea, vomiting, abdominal pain, unusual fatigue, loss of appetite, yellow skin or eyes, itching, dark urine, or clay-colored stools. <br />These symptoms may be early signs of liver damage.{{Citation needed|date=July 2010}} <br />
−
 
+
 
Severe allergic reaction like [[anaphylaxis]] has been reported (as listed in the data sheet of pfizer Diflucan).
 
Severe allergic reaction like [[anaphylaxis]] has been reported (as listed in the data sheet of pfizer Diflucan).
−
In rare cases, Fluconazole/Diflucan has also caused [[anaphylaxis]], sometimes resulting in death.  
+
In rare cases, Fluconazole/Diflucan has also caused [[anaphylaxis]], sometimes resulting in death.
−
Notify your doctor immediately if you develop a rash while taking Fluconazole/Diflucan.<ref>http://www.med-store.info/fluconazole.html</ref>
+
Notify your doctor immediately if you develop a rash while taking Fluconazole/Diflucan.<ref>http://www.med-store.info/fluconazole.html</ref>{{Verify credibility|date=August 2010}}
 
</blockquote>
 
</blockquote>
  
 
===Adverse effects===
 
===Adverse effects===
−
[[Adverse drug reaction]]s associated with fluconazole therapy include:<ref name="AMH2006">Rossi S, editor. [[Australian Medicines Handbook]] 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3</ref>
+
[[Adverse drug reaction]]s associated with fluconazole therapy include:<ref name="AMH2006"/>
 
*Common (≥1% of patients): rash, headache, dizziness, nausea, vomiting, abdominal pain, diarrhea, and/or elevated liver enzymes
 
*Common (≥1% of patients): rash, headache, dizziness, nausea, vomiting, abdominal pain, diarrhea, and/or elevated liver enzymes
 
*Infrequent (0.1–1% of patients): [[Anorexia (symptom)|anorexia]], fatigue, constipation
 
*Infrequent (0.1–1% of patients): [[Anorexia (symptom)|anorexia]], fatigue, constipation
Line 100: Line 100:
  
 
===Drug interactions===
 
===Drug interactions===
−
Fluconazole is an inhibitor of the human [[cytochrome P450]] system, particularly the isozymes [[CYP2C9]] and [[CYP3A4]]. In theory, therefore, fluconazole decreases the metabolism and increases the concentration of any drug metabolised by these enzymes. In addition, its potential effect on [[QT interval]] increases the risk of [[cardiac arrhythmia]] if used concurrently with other drugs that prolong the QT interval. [[Berberine]] has been shown to exert synergistic effects with fluconazole even in drug-resistant Candida albicans infections.<ref>Xu Y, Wang Y, Yan L, et al.  (September 14, 2009) Proteomic Analysis Reveals a Synergistic Mechanism of Fluconazole and Berberine against Fluconazole-Resistant Candida albicans: Endogenous ROS Augmentation. ''Journal of Proteome Research''. Publication Date (Web)[http://pubs.acs.org/doi/pdf/10.1021/pr9005074 Free Full Text]</ref>
+
Fluconazole is an inhibitor of the human [[cytochrome P450]] system, particularly the isozymes [[CYP2C9]] and [[CYP3A4]]. In theory, therefore, fluconazole decreases the metabolism and increases the concentration of any drug metabolised by these enzymes. In addition, its potential effect on [[QT interval]] increases the risk of [[cardiac arrhythmia]] if used concurrently with other drugs that prolong the QT interval. [[Berberine]] has been shown to exert synergistic effects with fluconazole even in drug-resistant ''Candida albicans'' infections.<ref>Xu Y, Wang Y, Yan L, et al.  (September 14, 2009) Proteomic Analysis Reveals a Synergistic Mechanism of Fluconazole and Berberine against Fluconazole-Resistant Candida albicans: Endogenous ROS Augmentation. ''Journal of Proteome Research''. Publication Date (Web)[http://pubs.acs.org/doi/pdf/10.1021/pr9005074 Free Full Text]</ref>
  
 
==Synthesis==
 
==Synthesis==
Line 111: Line 111:
  
 
==References==
 
==References==
−
{{reflist}}
+
{{Reflist}}
  
 
{{Antifungals}}
 
{{Antifungals}}

Latest revision as of 15:44, 27 September 2010

Fluconazole
160px
160px
Systematic (IUPAC) name
2-(2,4-difluorophenyl)-
1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
Clinical data
Pregnancy
category
Routes of
administration		 Oral, IV, topical
Legal status
Legal status
  • S3/S4 (Au), POM (UK), ℞-only (U.S.)
Pharmacokinetic data
Bioavailability >90%
Protein binding 11–12%
Metabolism Hepatic 11%
Biological half-life 30 hours (range 20-50 hours)
Excretion Renal 61–88%
Identifiers
CAS Number 86386-73-4
ATC code D01AC15 (WHO) J02AC01
PubChem CID 3365
DrugBank APRD00327
ChemSpider 3248
Chemical data
Formula C13H12F2N6O
Molar mass 306.271 g/mol[[Script error: No such module "String".]]
  (verify)
Script error: No such module "TemplatePar".Expression error: Unexpected < operator.

Fluconazole (pronounced /fluːˈkɒnəzoʊl/) is a triazole antifungal drug used in the treatment and prevention of superficial and systemic fungal infections. In a bulk powder form, it appears as a white crystalline powder, and it is very slightly soluble in water and soluble in alcohol.[1] It is commonly marketed under the trade name Diflucan or Trican (Pfizer). In Mexico it is sold over the counter as Alfumet. It is marketed under the brand name "candivast" in the Persian Gulf area.

Pharmacology

Mode of action

Like other imidazole- and triazole-class antifungals, fluconazole inhibits the fungal cytochrome P450 enzyme 14α-demethylase. Mammalian demethylase activity is much less sensitive to fluconazole than fungal demethylase. This inhibition prevents the conversion of lanosterol to ergosterol, an essential component of the fungal cytoplasmic membrane, and subsequent accumulation of 14α-methyl sterols.[2] Fluconazole is primarily fungistatic, however may be fungicidal against certain organisms in a dose-dependent manner.[citation needed] It is interesting to note that, when fluconazole was in development at Pfizer, it was decided early in the process to avoid producing any chiral centers in the drug so that subsequent synthesis and purification would not encounter difficulties with enantiomer separation and associated variations in biological effect.[citation needed] A number of related compounds were found to be extremely potent teratogens, and were subsequently discarded.[citation needed]

Microbiology

Fluconazole is active against the following microorganisms:[3]

Pharmacokinetics

Following oral dosing, fluconazole is almost completely absorbed within two hours.[citation needed] Bioavailability is not significantly affected by the absence of stomach acid. Concentrations measured in the urine, tears, and skin are approximately 10 times the plasma concentration, whereas saliva, sputum, and vaginal fluid concentrations are approximately equal to the plasma concentration, following a standard dose range of between 100 mg and 400 mg per day.[citation needed] The elimination half-life of fluconazole follows zero order kinetics, and only 10% of elimination is due to metabolism, the remainder is excreted in urine and sweat. Patients with impaired renal function will be at risk of overdose as well as patients taking drugs such as warfarin.[citation needed]

Clinical use

Indications

Fluconazole is a prescription drug indicated for the treatment and prophylaxis of fungal infections where other antifungals have failed or are not tolerated (e.g., due to adverse effects), including:[4]

Fluconazole can be used first-line for the following indications:[4]

Dosage

Dosage varies with indication and between patient groups, ranging from: a two-week course of 150 mg/day for vulvovaginal candidiasis, to 150–300 mg once weekly for resistant skin infections or some prophylactic indications. A dosage of 500–600 mg/day may be used for systemic or severe infections, and, in urgent infections such as meningitis caused by yeast, 800 mg/day have been used. Pediatric doses are measured at 6–12 mg/kg/d. A loading dose will be indicated when entering a daily dosage schedule; for example, a loading dose of 200 mg on the first day is commonly used with 150 mg/day following that.[4]

Contraindications

Fluconazole is contraindicated in patients that:[4]

  • Have known hypersensitivity to other azole medicine
  • Are taking Terfenadine, if 400 mg per day multidose of Fluconazole is administered
  • Are in concomitant use of cisapride, due to risk of serious cardiac arrhythmias (relative contraindication)
  • Are pregnant.

Precautions

Fluconazole is secreted in human milk at concentrations similar to plasma. Therefore, the use of fluconazole in nursing mothers is not recommended.[5]

Fluconazole therapy has been associated with QT interval prolongation, which may lead to serious cardiac arrhythmias. Thus, it is used with caution in patients with risk factors for prolonged QT interval such as electrolyte imbalance or use of other drugs that may prolong the QT interval (particularly cisapride).[citation needed]

Fluconazole has also rarely been associated with severe or lethal hepatotoxicity and liver function tests are usually performed regularly during prolonged fluconazole therapy. In addition, it is used with caution in patients with pre-existing liver disease.[2]

High concentrations of fluconazole have been detected in human breast milk from patients receiving fluconazole therapy, thus its use is not recommended in breastfeeding mothers.[2]

Some people are allergic to azole(s). People allergic to other azole drugs might be allergic to fluconazole.[6] That is, some azole drugs have adverse side-effects. Some azole drugs may disrupt estrogen production in pregnancy, affecting pregnancy outcome.[7]

Fluconazole/Diflucan is in the FDA pregnancy category C.
This means that it is not known whether it will be harmful to an unborn baby. Do not take Fluconazole/Diflucan without first talking to your doctor if you are pregnant or could become pregnant during treatment.
Do not take Fluconazole/Diflucan if you are taking cisapride (Propulsid).
Combined with cisapride (Propulsid), Diflucan could cause serious, even fatal, heart problems.
In rare cases, Fluconazole/Diflucan has caused severe liver damage, sometimes resulting in death.
Notify your doctor immediately if you develop nausea, vomiting, abdominal pain, unusual fatigue, loss of appetite, yellow skin or eyes, itching, dark urine, or clay-colored stools.
These symptoms may be early signs of liver damage.[citation needed]
Severe allergic reaction like anaphylaxis has been reported (as listed in the data sheet of pfizer Diflucan). In rare cases, Fluconazole/Diflucan has also caused anaphylaxis, sometimes resulting in death. Notify your doctor immediately if you develop a rash while taking Fluconazole/Diflucan.[8][unreliable source?]

Adverse effects

Adverse drug reactions associated with fluconazole therapy include:[4]

Drug interactions

Fluconazole is an inhibitor of the human cytochrome P450 system, particularly the isozymes CYP2C9 and CYP3A4. In theory, therefore, fluconazole decreases the metabolism and increases the concentration of any drug metabolised by these enzymes. In addition, its potential effect on QT interval increases the risk of cardiac arrhythmia if used concurrently with other drugs that prolong the QT interval. Berberine has been shown to exert synergistic effects with fluconazole even in drug-resistant Candida albicans infections.[9]

Synthesis

800px Richardson, R. K.; 1983, U.S. Patent 4,404,216.

See also

References

Cite error: Invalid <references> tag; parameter "group" is allowed only.

Use <references />, or <references group="..." />
Wall/
membrane
Ergosterol
inhibitors
topical: (Fluconazole#, Fosfluconazole)
systemic: (Fluconazole, Hexaconazole, Itraconazole, Posaconazole, Voriconazole)
topical: Thiabendazole
topical: (Natamycin, Nystatin#)
systemic: (Amphotericin B#)
Intracellular
Others

M: MYC

drug (fung)

de:Fluconazol

es:Fluconazol fr:Fluconazole it:Fluconazolo hu:Flukonazol nl:Fluconazol ja:フルコナゾール pl:Flukonazol pt:Fluconazol ru:Флуконазол fi:Flukonatsoli

zh:氟康唑
  1. ↑ MP Biomedicals
  2. ↑ 2.0 2.1 2.2 Pfizer Australia Pty Ltd. Diflucan (Australian Approved Product Information). West Ryde (NSW): Pfizer Australia; 2004.
  3. ↑ Sweetman S, editor. Martindale: The complete drug reference. 34th ed. London: Pharmaceutical Press; 2004. ISBN 0-85369-550-4
  4. ↑ 4.0 4.1 4.2 4.3 4.4 Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
  5. ↑ Product information from Pfizer Inc
  6. ↑ http://aac.asm.org/cgi/reprint/AAC.01500-08v1.pdf
  7. ↑ Kragie, Laura; Turner, Stephanie D.; Patten, Christopher J.; Crespi, Charles L.; Stresser, David M. (2002). "Assessing Pregnancy Risks of Azole Antifungals Using a High Throughput Aromatase Inhibition Assay". Endocrine Research. 28 (3): 129. doi:10.1081/ERC-120015045. PMID 12489563. 
  8. ↑ http://www.med-store.info/fluconazole.html
  9. ↑ Xu Y, Wang Y, Yan L, et al. (September 14, 2009) Proteomic Analysis Reveals a Synergistic Mechanism of Fluconazole and Berberine against Fluconazole-Resistant Candida albicans: Endogenous ROS Augmentation. Journal of Proteome Research. Publication Date (Web)Free Full Text
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