Tìm theo
Fluconazole
Các tên gọi khác (8 ) :
  • 2-(2,4-DIFLUOROPHENYL)-1,3-di(1H-1,2,4-triazol-1-yl)propan-2-ol
  • 2,4-Difluoro-alpha,alpha-bis(1H-1,2,4-triazol-1-ylmethyl)benzyl alcohol
  • Biozole
  • Diflucan
  • Elazor
  • Fluconazol
  • Fluconazolum
  • Triflucan
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 86386-73-4
ATC: D01AC15, J02AC01
ĐG : Advanced Pharmaceutical Services Inc.
CTHH: C13H12F2N6O
PTK: 306.2708
Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. [PubChem]
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C13H12F2N6O
Phân tử khối
306.2708
Monoisotopic mass
306.104065446
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
InChI Key
InChIKey=RFHAOTPXVQNOHP-UHFFFAOYSA-N
IUPAC Name
2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
Traditional IUPAC Name
fluconazole
SMILES
OC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1
Độ tan chảy
138-140 °C
Độ hòa tan
1 mg/L
logP
0.4
logS
-2.3
pKa (strongest acidic)
12.71
pKa (Strongest Basic)
2.56
PSA
81.65 Å2
Refractivity
97.2 m3·mol-1
Polarizability
26.52 Å3
Rotatable Bond Count
5
H Bond Acceptor Count
5
H Bond Donor Count
1
Physiological Charge
0
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS. [PubChem] Fluconazole interacts with 14-α demethylase, a cytochrome P-450 enzyme necessary to convert lanosterol to ergosterol. As ergosterol is an essential component of the fungal cell membrane, inhibition of its synthesis results in increased cellular permeability causing leakage of cellular contents. Fluconazole may also inhibit endogenous respiration, interact with membrane phospholipids, inhibit the transformation of yeasts to mycelial forms, inhibit purine uptake, and impair triglyceride and/or phospholipid biosynthesis.
Dược Động Học :
▧ Absorption :
90%
▧ Protein binding :
11 to 12%
▧ Metabolism :
Hepatic
▧ Route of 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.
▧ Half Life :
30 hours (range 20-50 hours)
▧ 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]
Độc Tính : Symptoms of overdose include hallucinations and paranoid behavior.
Chỉ Định : For the treatment of fungal infections.
Tương Tác Thuốc :
  • Acenocoumarol Fluconazole may increase the serum concentration of acenocoumarol by decreasing its metabolism.
  • Alfentanil Increases the effect and toxicity of alfentanil
  • Alprazolam Fluconazole may increase the effect of the benzodiazepine, alprazolam.
  • Amitriptyline Fluconazole may increase the effect and toxicity of the tricyclic antidepressant, amitriptyline, by decreasing its metabolism. Additive QTc-prolonging effects may also occur. Monitor for changes in the therapeutic and adverse effects of amitriptyline if fluconazole is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Anisindione Fluconazole may increase the serum concentration of anisindione by decreasing its metabolism.
  • Artemether Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Atorvastatin Increased risk of myopathy/rhabdomyolysis
  • Bromazepam Fluconazole may increase the serum concentration of bromazepam by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of bromazepam if fluconazole is initiated, discontinued or dose changed.
  • Carbamazepine Fluconazole may increase the therapeutic and adverse effects of carbamazepine.
  • Carisoprodol Strong CYP2C19 inhibitors such as fluconazole may decrease the metabolism of CYP2C19 substrates such as carisoprodol. Consider an alternative for one of the interacting drugs in order to avoid toxicity of the substrate. Some combinations are specifically contraindicated by manufacturers. Suggested dosage adjustments are also offered by some manufacturers. Please review applicable package inserts. Monitor for increased effects of the CYP substrate if a CYP inhibitor is initiated/dose increased, and decreased effects if a CYP inhibitor is discontinued/dose decreased.
  • Celecoxib Fluconazole may increase the effect of celecoxib.
  • Chlordiazepoxide Fluconazole may increase the effect of the benzodiazepine, chlordiazepoxide.
  • Cilostazol Fluconazole may decrease the effect of cilostazol.
  • Cisapride Increased risk of cardiotoxicity and arrhythmias
  • Clonazepam Fluconazole may increase the effect of the benzodiazepine, clonazepam.
  • Clorazepate Fluconazole may increase the effect of the benzodiazepine, clorazepate.
  • Conivaptan Antifungal Agents (Azole Derivatives, Systemic) may decrease the metabolism of Conivaptan. Concomitant use of conivaptan with strong CYP3A4 inhibitors (e.g., azole antifungals) is contraindicated.
  • Cyclophosphamide Fluconazole reduces metabolism and clearance of cyclophosphamide.
  • Cyclosporine Fluconazole may increase the therapeutic and adverse effects of the cyclosporine.
  • Diazepam Fluconazole may increase the effect of the benzodiazepine, diazepam.
  • Dicoumarol Fluconazole may increase the serum concentration of dicumarol by decreasing its metabolism.
  • Dihydroergotamine Possible ergotism and severe ischemia with this combination
  • Eplerenone This CYP3A4 inhibitor increases the effect and toxicity of eplerenone
  • Ergotamine Possible ergotism and severe ischemia with this combination
  • Estazolam Fluconazole may increase the effect of the benzodiazepine, estazolam.
  • Ethotoin Increases the effect of hydantoin
  • Everolimus Fluconazole may increase everolimus levels/toxicity.
  • Fentanyl Fluconazole may increase levels/toxicity of fentanyl.
  • Fesoterodine Fluconazole is a moderate CYP3A4 inhibitor thus reducing clearance. Monitor for adverse effects when using concomitant therapy with fesoterodine.
  • Flurazepam Fluconazole may increase the effect of the benzodiazepine, flurazepam.
  • Fluvastatin Fluconazole may increase the serum concentration of fluvastatin by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of fluvastatin if fluconazole is initiated, discontinued or dose changed.
  • Fosphenytoin Fluconazole may increase the effect of hydantoin.
  • Halazepam Fluconazole may increase the effect of the benzodiazepine, halazepam.
  • Haloperidol Fluconazole may increase the effect and toxicity of haloperidol.
  • Imipramine Fluconazole may increase the effect and toxicity of the tricyclic antidepressant, imipramine, by decreasing its metabolism. Additive QTc-prolonging effects may also occur. Monitor for changes in the therapeutic and adverse effects of imipramine if fluconazole is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Ivacaftor Moderate CYP3A4 inhibitors may increase levels of ivacaftor. Consider dose reduction.
  • Lovastatin Increased risk of myopathy/rhabdomyolysis
  • Lumefantrine Additive QTc-prolongation may occur. Concomitant therapy should be avoided.
  • Mephenytoin Increases the effect of hydantoin
  • Midazolam Fluconazole may increase the effect of the benzodiazepine, midazolam.
  • Nortriptyline Fluconazole may increase the effect and toxicity of the tricyclic antidepressant, nortriptyline, by decreasing its metabolism. Additive QTc-prolonging effects may also occur. Monitor for changes in the therapeutic and adverse effects of nortriptyline if fluconazole is initiated, discontinued or dose changed. Monitor for the development of torsades de pointes during concomitant therapy.
  • Ospemifene Fluconazole, a moderate CYP3A / strong CYP2C9 / moderate CYP2C19 inhibitor, should not be used with ospemifene. Fluconazole increases the systemic exposure of ospemifene by 2.7-fold. Administration of fluconazole with ospemifene may increase the risk of adverse events.
  • Phenytoin Fluconazole may increase the therapeutic and adverse effects of phenytoin.
  • Pimozide Increased risk of cardiotoxicity and arrhythmias
  • Quazepam Fluconazole may increase the effect of the benzodiazepine, quazepam.
  • Ramelteon Fluconazole may increase the serum levels and toxcity of ramelteon.
  • Ranolazine Increased levels of ranolazine - risk of toxicity
  • Rifabutin Fluconazole may increase levels/toxicity of rifabutin.
  • Rifampicin Rifampin may decrease the effect of fluconazole.
  • Silodosin Strong UGT2B7 inhibitors may increase levels of silodosin. Monitor concomitant therapy closely.
  • Simvastatin Increased risk of myopathy/rhabdomyolysis
  • Tacrolimus Additive QTc-prolongation may occur increasing the risk of serious ventricular arrhythmias. Concomitant therapy should be used with caution. The antifungal, fluconazole, may also increase serum concentrations of tacrolimus.
  • Tamoxifen Fluconzole may reduce clearance rate of Tamoxifen. Monitor for changes in therapeutic/adverse effects of Tamoxifen if Fluconazole is initiated, discontinued or dose changed.
  • Tamsulosin Fluconzole, a CYP3A4 inhibitor, may decrease the metabolism and clearance of Tamsulosin, a CYP3A4 substrate. Monitor for changes in therapeutic/adverse effects of Tamsulosin if Fluconazole is initiated, discontinued, or dose changed.
  • Terfenadine Increased risk of cardiotoxicity and arrhythmias
  • Thiothixene May cause additive QTc-prolonging effects. Increased risk of ventricular arrhythmias. Consider alternate therapy. Thorough risk:benefit assessment is required prior to co-administration.
  • Tipranavir Fluconazole may increase the serum concentration of Tipranavir. Dose adjustments are not required.
  • Tofacitinib Fluconazole (and other strong CYP2C19 inhibitors and moderate CYP3A4 inhibitors), when used in combination with tofacitinib, may increase tofacitinib concentration. It is recommended to modify therapy by reducing the adult dose of tofacitinib from 5mg twice a day to 5mg daily.
  • Tolbutamide Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Tolbutamide, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in Fluconazole therapeutic and adverse effects if Delavirdine is initiated, discontinued or dose changed.
  • Tolterodine Fluconazole may decrease the metabolism and clearance of tolterodine. Adjust tolterodine dose and monitor for efficacy and toxicity.
  • Tolvaptan Fluconazole is a moderate inhibitor of CYP3A4 and will considerably increase tolvaptan serum concentrations
  • Torasemide Fluconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of Torasemide, a CYP2C9 substrate, by decreasing Torasemide metabolism and clearance. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Torasemide if Fluconazole is initiated, discontinued or dose changed.
  • Toremifene Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Consider alternate therapy. A thorough risk:benefit assessment is required prior to co-administration.
  • Tramadol Fluconazole may increase Tramadol toxicity by decreasing Tramadol metabolism and clearance.
  • Trazodone The CYP3A4 inhibitor, Fluconazole, may increase Trazodone efficacy/toxicity by decreasing Trazodone metabolism and clearance. Monitor for changes in Trazodone efficacy/toxicity if Fluconazole is initiated, discontinued or dose changed.
  • Triazolam Fluconazole may increase the effect of the benzodiazepine, triazolam.
  • Trimethoprim The strong CYP2C9 inhibitor, Fluconazole, may decrease the metabolism and clearance of Trimethoprim, a CYP2C9 substrate. Consider alternate therapy or monitor for changes in therapeutic and adverse effects of Trimethoprim if Fluconazole is initiated, discontinued or dose changed.
  • Trimipramine Additive QTc-prolongation may occur, increasing the risk of serious ventricular arrhythmias. Fluconazole, a strong CYP2C19 inhibitor, may also decrease the metabolism and clearance of Trimipramine, a CYP2C19 substrate. Concomitant therapy should be used with caution.
  • Valdecoxib Fluconazole may increase the effect and toxicity of valdecoxib.
  • Verapamil Fluconazole may increase the serum concentration of Verapamil by decreasing Verapamil metabolism. This likely occurs via Fluconazole-mediated CYP3A4 inhibition. Monitor for changes in the therapeutic/adverse effects of Verapamil if Fluconazole is initiated, discontinued, or dose changed.
  • Vinblastine Increases the effect and toxicity of anticancer agent
  • Vincristine Increases the effect and toxicity of anticancer agent
  • Voriconazole Fluconazole, a strong CYP2C9 inhibitor, may increase the serum concentration of voriconazole by decreasing its metabolism. Additive QTc prolongation may also occur. Consider alternate therapy or monitor for QTc prolongation and changes in the therapeutic and adverse effects of voriconazole if fluconazole is initiated, discontinued or dose changed.
  • Vorinostat Additive QTc prolongation may occur. Consider alternate therapy or monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
  • Warfarin Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism of warfarin. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of warfarin if fluconazole is initiated, discontinued or dose changed.
  • Zafirlukast Fluconazole, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of zafirlukast. Consider alternate therapy or monitor for changes in zafirlukast therapeutic and adverse effects if fluconazole is initiated, discontinued or dose changed.
  • Ziprasidone Additive QTc-prolonging effects may increase the risk of severe arrhythmias. Concomitant therapy is contraindicated.
  • Zolpidem Fluconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of zolpidem by decreasing its metabolism. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of zolpidem if fluconazole is initiated, discontinued or dose changed.
  • Zuclopenthixol Additive QTc prolongation may occur. Consider alternate therapy or use caution and monitor for QTc prolongation as this can lead to Torsade de Pointes (TdP).
Liều Lượng & Cách Dùng : Capsule - Oral
Liquid - Intravenous
Powder, for solution - Oral
Solution - Intravenous
Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Diflucan
  • Công ty :
    Sản phẩm biệt dược : Elazor
  • Công ty :
    Sản phẩm biệt dược : Flucazol
  • Công ty :
    Sản phẩm biệt dược : Flucostat
  • Công ty :
    Sản phẩm biệt dược : Flunizol
  • Công ty :
    Sản phẩm biệt dược : Monicure
  • Công ty :
    Sản phẩm biệt dược : Pritenzol
  • Công ty :
    Sản phẩm biệt dược : Trican
  • Công ty :
    Sản phẩm biệt dược : Triflucan
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00196
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=3365
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505735
KEGG Drug
http://www.genome.jp/dbget-bin/www_bget?drug:D00322
ChemSpider
http://www.chemspider.com/Chemical-Structure.3248.html
BindingDB
http://www.bindingdb.org/bind/chemsearch/marvin/MolStructure.jsp?monomerid=25817
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0054-0002-85
PharmGKB
http://www.pharmgkb.org/drug/PA449653
Wikipedia
http://en.wikipedia.org/wiki/Fluconazole
RxList
http://www.rxlist.com/cgi/generic/flucon.htm
Drugs.com
http://www.drugs.com/cdi/fluconazole.html
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