Identification

Name
Fluconazole
Accession Number
DB00196  (APRD00327)
Type
Small Molecule
Groups
Approved, Investigational
Description

Triazole antifungal agent that is used to treat oropharyngeal candidiasis and cryptococcal meningitis in AIDS.

Structure
Thumb
Synonyms
  • Diflucan
  • Difluconazole
  • Fluconazol
  • Fluconazolum
  • Triflucan
External IDs
UK-49,858 / UK-49858
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Act FluconazoleTablet50 mgOralActavis Pharma Company2007-12-03Not applicableCanada
Act FluconazoleTablet100 mgOralActavis Pharma Company2007-12-03Not applicableCanada
DiflucanTablet200 mg/1OralPhysicians Total Care, Inc.1990-01-292012-06-30Us
DiflucanSolution2 mg/1mLIntravenousRoerig2006-06-082006-06-08Us
DiflucanPowder, for suspension350 mg/35mLOralRoerig1993-12-23Not applicableUs
DiflucanTablet100 mg/1OralRoerig1990-01-29Not applicableUs
DiflucanTablet100 mg/1OralRemedy Repack2012-09-122017-02-27Us
DiflucanSolution2 mg/1mLIntravenousRoerig2006-06-082006-06-08Us
DiflucanTablet150 mg/1OralPhysicians Total Care, Inc.1990-01-292010-06-30Us
DiflucanSolution2 mg/1mLIntravenousRoerig2006-06-082006-06-08Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-fluconazoleTablet50 mgOralApotex Corporation1998-10-13Not applicableCanada
Apo-fluconazoleTablet200 mgOralApotex CorporationNot applicableNot applicableCanada
Apo-fluconazoleTablet100 mgOralApotex Corporation1998-10-13Not applicableCanada
Direct RxTablet200 mg/1OralDirect Rx2015-01-012015-08-03Us
Dom-fluconazoleTablet50 mgOralDominion Pharmacal2002-07-09Not applicableCanada
Dom-fluconazoleTablet100 mgOralDominion Pharmacal2002-07-09Not applicableCanada
FluconazoleTablet50 mg/1OralTaro Pharmaceuticals U.S.A., Inc.2004-07-29Not applicableUs
FluconazoleTablet50 mg/1OralZydus Pharmaceuticals Usa, Inc.2017-04-06Not applicableUs
FluconazoleInjection, solution2 mg/1mLIntravenousSagent Pharmaceuticals2009-09-012022-05-31Us
FluconazoleTablet150 mg/1OralMed Vantx, Inc.2011-12-21Not applicableUs
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-fluconazole-150Capsule150 mgOralApotex Corporation2000-03-20Not applicableCanada
Bio-fluconazoleCapsule150 mgOralBiomed PharmaNot applicableNot applicableCanada
CanesoralCapsule150 mgOralBayer2010-03-10Not applicableCanada
Co Fluconazole-150Capsule150 mgOralCobalt Laboratories2009-07-21Not applicableCanada
Diflucan OneCapsule150 mgOralPfizer Laboratories Div Pfizer Inc.1995-12-31Not applicableCanada
Dom-fluconazoleCapsule150 mgOralDominion PharmacalNot applicableNot applicableCanada
FluconazoleCapsule150 mgOralSorres Pharma Inc2009-06-172014-06-20Canada
FluconazoleCapsule150 mgOralPendopharm Division Of De Pharmascience IncNot applicableNot applicableCanada
FluconazoleCapsule150 mgOralPharmel IncNot applicableNot applicableCanada
Fluconazole 150Capsule150 mgOralTaro Pharmaceuticals, Inc.Not applicableNot applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Canesoral Combi-pakFluconazole (150 mg) + Clotrimazole (1 %)Capsule; CreamOral; Topical; VaginalBayer2010-03-10Not applicableCanada
Clotrimaderm-fluconazole Combi-packFluconazole (150 mg) + Clotrimazole (1 %)Capsule; Cream; KitOral; TopicalTaro Pharmaceuticals, Inc.2017-02-14Not applicableCanada
Clotrimazole-fluconazole Combi-packFluconazole (150 mg) + Clotrimazole (1 %)Capsule; Cream; KitOral; TopicalTaro Pharmaceuticals, Inc.2017-02-03Not applicableCanada
Monicure ComboFluconazole (150 mg) + Miconazole nitrate (2 %)Capsule; Cream; KitOral; TopicalInsight Pharmaceuticals2012-10-25Not applicableCanada
International/Other Brands
Elazor / Flucazol / Flucostat / Flunizol / Pritenzol / Trican / Triflucan
Categories
UNII
8VZV102JFY
CAS number
86386-73-4
Weight
Average: 306.2708
Monoisotopic: 306.104065446
Chemical Formula
C13H12F2N6O
InChI Key
RFHAOTPXVQNOHP-UHFFFAOYSA-N
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
IUPAC Name
2-(2,4-difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol
SMILES
OC(CN1C=NC=N1)(CN1C=NC=N1)C1=C(F)C=C(F)C=C1

Pharmacology

Indication

For the treatment of fungal infections.

Associated Conditions
Pharmacodynamics

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.

Mechanism of action

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.

TargetActionsOrganism
ALanosterol 14-alpha demethylase
inhibitor
Yeast
Absorption

90%

Volume of distribution
Not Available
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]
Toxicity

Symptoms of overdose include hallucinations and paranoid behavior.

Affected organisms
  • Fungi
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Fluconazole.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Fluconazole.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Fluconazole.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Fluconazole.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Fluconazole.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Fluconazole.
AbacavirFluconazole may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbemaciclibThe serum concentration of Abemaciclib can be increased when it is combined with Fluconazole.
AbexinostatThe risk or severity of QTc prolongation can be increased when Fluconazole is combined with Abexinostat.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Fluconazole.
Food Interactions
  • Take without regard to meals.

References

Synthesis Reference
US4404216
General References
Not Available
External Links
Human Metabolome Database
HMDB0014342
KEGG Drug
D00322
PubChem Compound
3365
PubChem Substance
46505735
ChemSpider
3248
BindingDB
25817
ChEBI
46081
ChEMBL
CHEMBL106
Therapeutic Targets Database
DAP000628
PharmGKB
PA449653
HET
TPF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Fluconazole
ATC Codes
J02AC01 — FluconazoleD01AC15 — FluconazoleJ01RA07 — Azithromycin, fluconazole and secnidazole
AHFS Codes
  • 08:14.08 — Azoles
PDB Entries
1ea1 / 2ij7 / 2wuz / 2wv2 / 2wx2 / 3khm / 3l4d / 4wmz / 4zdz / 4ze3
show 5 more
FDA label
Download (16.9 KB)
MSDS
Download (73.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableHealthy Volunteers2
1CompletedNot AvailableMetabolic Detoxication, Phase I1
1CompletedBasic ScienceAlzheimer's Disease (AD)1
1CompletedBasic ScienceDrug Drug Interaction (DDI)1
1CompletedBasic ScienceHealthy Volunteers2
1CompletedBasic ScienceTumors, Solid1
1CompletedOtherHealthy Volunteers1
1CompletedTreatmentAdvanced Solid Tumors1
1CompletedTreatmentBacterial Infections / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
1CompletedTreatmentCardio Respiratory Arrest / Infections, Fungal1
1CompletedTreatmentEndometriosis / Prostate Cancer1
1CompletedTreatmentGraft Versus Host Disease (GVHD) / Transplantation, Stem Cell1
1CompletedTreatmentHealthy Participants1
1CompletedTreatmentHealthy Volunteers3
1CompletedTreatmentHealthy Volunteers / Pulmonary Disease, Chronic Obstructive1
1CompletedTreatmentCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections1
1CompletedTreatmentInvasive Aspergillosis1
1CompletedTreatmentCandidiasis infection1
1RecruitingBasic ScienceNASH - Nonalcoholic Steatohepatitis1
1RecruitingTreatmentAdvanced Solid Tumors / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Mantle Cell Lymphoma (MCL) / Marginal Zone Lymphoma / Primary Mediastinal Lymphoma1
1RecruitingTreatmentNeoplasms1
1WithdrawnBasic ScienceHealthy Volunteers1
1WithdrawnTreatmentMalignant Lymphomas1
1, 2CompletedDiagnosticHealthy Volunteers1
1, 2CompletedTreatmentHIV Associated Neurocognitive Disorders (HAND)1
1, 2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
2CompletedBasic ScienceVery Low Birth Weight Infant1
2CompletedPreventionIntra-abdominal Perforation1
2CompletedTreatmentBlastomycosis / Histoplasmosis / Sporotrichosis1
2CompletedTreatmentCandida Vulvovaginitis1
2CompletedTreatmentCandidemia / Candidiasis, Invasive / Mycoses1
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal2
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
2CompletedTreatmentMeningitis, Cryptococcal1
2CompletedTreatmentMoniliasis, Vulvovaginal / Mycoses / Vaginitis, Monilial / Vulvovaginal Candidiasis / Yeast Infections1
2CompletedTreatmentSporotrichosis1
2CompletedTreatmentVulvovaginal Candidiasis2
2CompletedTreatmentVulvovaginal Candidiasis / Vulvovaginitis / Yeast Infection Vaginal / Yeast Infections1
2RecruitingTreatmentCandidemia / Candidiasis, Invasive / Fungaemia / Infections, Fungal / Mycoses1
2RecruitingTreatmentCrohn's Disease (CD)2
2RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Meningitis / Meningitis streptococcal / Meningoencephalitis1
2TerminatedDiagnosticHyperlipidemias1
2TerminatedTreatmentCrohn's Disease Aggravated1
2TerminatedTreatmentCryptococcal Infection Disseminated1
2, 3Active Not RecruitingTreatmentHuman Immunodeficiency Virus (HIV) / Meningitis, Cryptococcal1
2, 3CompletedTreatmentHead and Neck Carcinoma / Infection NOS / Oral Complications1
2, 3CompletedTreatmentMinor burns1
2, 3Not Yet RecruitingTreatmentCandidiasis infection1
2, 3RecruitingTreatmentMinor burns1
3Active Not RecruitingSupportive CareHematopoietic/Lymphoid Cancer / Infections, Fungal1
3CompletedPreventionAppendicitis Acute / Perforated Gastroduodenal Ulcer / Small intestinal obstruction1
3CompletedPreventionBacterial Diseases / Other Mycoses / Sexually Transmitted Infections (STIs)1
3CompletedPreventionCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
3CompletedPreventionLeukopenia1
3CompletedPreventionMycoses / Transplantation, Liver1
3CompletedPreventionCandidiasis infection1
3CompletedSupportive CareAdult Acute Megakaryoblastic Leukemia / Adult Acute Megakaryoblastic Leukemia (M7) / Adult Acute Minimally Differentiated Myeloid Leukemia (M0) / Adult Acute Monoblastic Leukemia / Adult Acute Monoblastic Leukemia (M5a) / Adult Acute Monocytic Leukemia / Adult Acute Monocytic Leukemia (M5b) / Adult Acute Myeloblastic Leukemia With Maturation (M2) / Adult Acute Myeloblastic Leukemia Without Maturation (M1) / Adult Acute Myeloid Leukemia in Remission / Adult Acute Myeloid Leukemia With 11q23 (MLL) Abnormalities / Adult Acute Myeloid Leukemia With Del(5q) / Adult Acute Myeloid Leukemia With Inv(16)(p13.1q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With Inv(16)(p13;q22) / Adult Acute Myeloid Leukemia With Maturation / Adult Acute Myeloid Leukemia With Minimal Differentiation / Adult Acute Myeloid Leukemia With t(16;16)(p13.1;q22); CBFB-MYH11 / Adult Acute Myeloid Leukemia With T(16;16)(p13;q22) / Adult Acute Myeloid Leukemia With T(8;21)(q22;q22) / Adult Acute Myeloid Leukemia With t(8;21); (q22; q22.1); RUNX1-RUNX1T1 / Adult Acute Myeloid Leukemia With t(9;11)(p22.3;q23.3); MLLT3-KMT2A / Adult Acute Myeloid Leukemia Without Maturation / Adult Acute Myelomonocytic Leukemia / Adult Acute Myelomonocytic Leukemia (M4) / Adult Erythroleukemia / Adult Erythroleukemia (M6a) / Adult Pure Erythroid Leukemia / Adult Pure Erythroid Leukemia (M6b) / Alkylating Agent-Related Acute Myeloid Leukemia / Childhood Acute Erythroid Leukemia / Childhood Acute Erythroleukemia (M6) / Childhood Acute Megakaryoblastic Leukemia / Childhood Acute Megakaryocytic Leukemia (M7) / Childhood Acute Minimally Differentiated Myeloid Leukemia (M0) / Childhood Acute Monoblastic Leukemia / Childhood Acute Monoblastic Leukemia (M5a) / Childhood Acute Monocytic Leukemia / Childhood Acute Monocytic Leukemia (M5b) / Childhood Acute Myeloblastic Leukemia With Maturation (M2) / Childhood Acute Myeloblastic Leukemia Without Maturation (M1) / Childhood Acute Myeloid Leukemia in Remission / Childhood Acute Myeloid Leukemia With Maturation / Childhood Acute Myeloid Leukemia With Minimal Differentiation / Childhood Acute Myeloid Leukemia Without Maturation / Childhood Acute Myelomonocytic Leukemia / Childhood Acute Myelomonocytic Leukemia (M4) / Infections, Fungal / Leukemia Acute Myeloid Leukemia (AML) / Myeloid Neoplasm / Neutropenias / Recurrent Adult Acute Myeloid Leukemia / Recurrent Childhood Acute Myeloid Leukemia / Secondary Acute Myeloid Leukemia (Secondary AML, sAML) / Untreated Adult Acute Myeloid Leukemia / Untreated Childhood Acute Myeloid Leukemia and Other Myeloid Malignancies / Untreated Childhood Myeloid Neoplasm1
3CompletedSupportive CareMalignancies1
3CompletedTreatmentAspergillosis / Candidiasis infection / Fungaemia / Mycoses1
3CompletedTreatmentCandidemia1
3CompletedTreatmentCandidemia / Candidiasis, Invasive1
3CompletedTreatmentCandidiasis, Invasive1
3CompletedTreatmentCoccidioidomycosis1
3CompletedTreatmentDiabetes Mellitus (DM) / Vulvovaginal Candidiasis1
3CompletedTreatmentEsophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV)1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Infection, Mycobacterium Avium-Intracellulare / Mycoses1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Mycoses1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
3CompletedTreatmentInfection NOS / Leukemias / Malignant Lymphomas1
3CompletedTreatmentOral Candidiasis1
3CompletedTreatmentTinea Capitis1
3CompletedTreatmentVaginal Discharge1
3CompletedTreatmentVulvovaginal Candidiasis1
3CompletedTreatmentCandidiasis infection2
3Not Yet RecruitingTreatmentAntifungal Drugs in Onychomycosis1
3RecruitingTreatmentCandidemia / Infections, Fungal / Invasive Candidiases / Mycoses1
3TerminatedNot AvailableCandidemia1
3TerminatedTreatmentAIDS-Related Opportunistic Infections / Cryptococcal infections / Cryptococcus Neoformans1
3TerminatedTreatmentLeishmaniasis, Cutaneous1
3Unknown StatusPreventionLiver Transplanted Patients1
4CompletedPreventionCentral Nervous System Fungal Infections / Fungaemia / Lung Diseases, Fungal / Mycoses1
4CompletedPreventionCryptococcus Neoformans / Meningitis, Cryptococcal1
4CompletedPreventionCandidiasis infection1
4CompletedTreatmentAcquired Immune Deficiency Syndrome (AIDS) / Candidiasis infection / Oral Candidiasis1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1
4CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis1
4CompletedTreatmentOropharyngeal Candidiasis1
4CompletedTreatmentVulvovaginal Candidiasis2
4CompletedTreatmentCandidiasis infection1
4SuspendedTreatmentCoccidioidomycosis1
4Unknown StatusDiagnosticPulmonary Candidiasis1
4WithdrawnTreatmentCandidiasis infection / Sepsis1
Not AvailableActive Not RecruitingNot AvailableCentral Nervous System Fungal Infections / Central Nervous System Infections / Meningitis, Cryptococcal / Meningitis, Fungal1
Not AvailableActive Not RecruitingNot AvailableSystemic Fungal Infections1
Not AvailableActive Not RecruitingScreeningMeningitis, Cryptococcal1
Not AvailableCompletedNot AvailableDeep Mycosis1
Not AvailableCompletedNot AvailableFungal Infection by Site1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableCandidiasis infection1
Not AvailableCompletedBasic ScienceDrug Drug Interaction (DDI) / Healthy Volunteers / Warfarin1
Not AvailableCompletedBasic ScienceHeart Diseases / Vascular Diseases1
Not AvailableCompletedPreventionBlood Diseases / Graft Versus Host Disease (GVHD) / Hematopoietic Stem Cell Transplantation (HSCT) / Leukemias / Multiple Myeloma (MM) / Myelodysplastic Syndromes / Transplantation, Bone Marrow1
Not AvailableCompletedTreatmentCoccidioidomycosis / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
Not AvailableCompletedTreatmentEsophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentCandidiasis infection / Esophageal Candidiasis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHistoplasmosis / Human Immunodeficiency Virus (HIV) Infections1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Meningitis, Cryptococcal13
Not AvailableCompletedTreatmentCandidiasis infection / Human Immunodeficiency Virus (HIV) Infections / Mycoses1
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Oral Candidiasis2
Not AvailableUnknown StatusTreatmentAutism Spectrum Conditions/Disorders1

Pharmacoeconomics

Manufacturers
  • Pfizer chemicals div pfizer inc
  • Aurobindo pharma usa inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Taro pharmaceutical industries ltd
  • Pfizer inc
  • Acs dobfar info sa
  • Apotex inc richmond hill
  • Hospira inc
  • App pharmaceuticals llc
  • Bedford laboratories div ben venue laboratories inc
  • Claris lifesciences ltd
  • Hikma farmaceutica portugal lda
  • Teva parenteral medicines inc
  • Baxter healthcare corp
  • Bedford laboratories
  • Pfizer central research
  • Apotex inc
  • Aurobindo pharma ltd
  • Dr reddys laboratories inc
  • Gedeon richter usa inc
  • Genpharm inc
  • Glenmark generics ltd
  • Mylan pharmaceuticals inc
  • Pliva inc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Unique pharmaceutical laboratories
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Apotex Inc.
  • Apotheca Inc.
  • APP Pharmaceuticals
  • AQ Pharmaceuticals Inc.
  • A-S Medication Solutions LLC
  • Atlantic Biologicals Corporation
  • Aurobindo Pharma Ltd.
  • Baxter International Inc.
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Cipla Ltd.
  • Claris Lifesciences Inc.
  • Comprehensive Consultant Services Inc.
  • Direct Pharmaceuticals Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Doctor Reddys Laboratories Ltd.
  • Glenmark Generics Ltd.
  • Greenstone LLC
  • H.J. Harkins Co. Inc.
  • Haemonetics Corp.
  • Hikma Pharmaceuticals
  • Hospira Inc.
  • Ivax Pharmaceuticals
  • J.B. Chemicals & Pharmaceuticals
  • Lake Erie Medical and Surgical Supply
  • Medisca Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Novopharm Ltd.
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • Par Pharmaceuticals
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Pfizer Inc.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Ranbaxy Laboratories
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Roxane Labs
  • Sagent Pharmaceuticals
  • Sandhills Packaging Inc.
  • Shanghai Ziyuan Pharmaceutical Co. Ltd.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Taro Pharmaceuticals USA
  • Teva Pharmaceutical Industries Ltd.
  • UDL Laboratories
  • West-Ward Pharmaceuticals
Dosage forms
FormRouteStrength
TabletOral200 mg
Capsule; creamOral; Topical; Vaginal
CapsuleOral150 mg
Powder, for solutionOral50 mg
InjectionIntravenous2 mg/1mL
Injection, solutionIntravenous2 mg/1mL
Injection, solutionIntravenous200 mg/100mL
Injection, solutionIntravenous400 mg/200mL
Powder, for suspensionOral10 mg/1mL
Powder, for suspensionOral1400 mg/35mL
Powder, for suspensionOral350 mg/35mL
Powder, for suspensionOral40 mg/1mL
SolutionIntravenous2 mg/1mL
SolutionOral10 mg/1mL
SolutionOral40 mg/1mL
TabletOral100 mg/1
TabletOral150 mg/1
TabletOral200 mg/1
TabletOral50 mg/1
SolutionIntravenous2 mg
Capsule; cream; kitOral; Topical
TabletOral100 mg
TabletOral50 mg
TabletOral150 mg
Prices
Unit descriptionCostUnit
Diflucan 40 mg/ml Suspension 35ml Bottle203.65USD bottle
Fluconazole 40 mg/ml Suspension 35ml Bottle135.99USD bottle
Diflucan 10 mg/ml Suspension 35ml Bottle56.06USD bottle
Fluconazole 10 mg/ml Suspension 35ml Bottle35.94USD bottle
Diflucan 150 mg tablet24.71USD tablet
Diflucan 200 mg tablet20.82USD tablet
Diflucan 150 mg Capsule16.44USD capsule
Fluconazole 200 mg tablet14.26USD tablet
Fluconazole powder14.08USD g
Fluconazole 150 mg tablet13.93USD tablet
Diflucan 100 mg tablet12.61USD tablet
Apo-Fluconazole-150 150 mg Capsule9.18USD capsule
Co Fluconazole 150 mg Capsule9.18USD capsule
Mylan-Fluconazole 150 mg Capsule9.18USD capsule
Pms-Fluconazole 150 mg Capsule9.18USD capsule
Fluconazole 100 mg tablet8.95USD tablet
Diflucan 50 mg tablet8.05USD tablet
Apo-Fluconazole 100 mg Tablet5.81USD tablet
Mylan-Fluconazole 100 mg Tablet5.81USD tablet
Fluconazole 50 mg tablet5.7USD tablet
Co Fluconazole 100 mg Tablet5.42USD tablet
Novo-Fluconazole 100 mg Tablet5.42USD tablet
Pms-Fluconazole 100 mg Tablet5.42USD tablet
Apo-Fluconazole 50 mg Tablet3.28USD tablet
Mylan-Fluconazole 50 mg Tablet3.28USD tablet
Co Fluconazole 50 mg Tablet3.06USD tablet
Novo-Fluconazole 50 mg Tablet3.06USD tablet
Pms-Fluconazole 50 mg Tablet3.06USD tablet
Diflucan-dextr 200 mg/100 ml1.28USD ml
Diflucan-saline 200 mg/100 ml1.28USD ml
Diflucan 2 mg/ml0.6USD ml
Fluconazole 2 mg/ml0.33USD ml
Fluconazole Omega 2 mg/ml0.33USD ml
Fluconazole-dext 200 mg/100 ml0.32USD ml
Fluconazole-ns 200 mg/100 ml0.19USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)138-140 °CNot Available
water solubility1 mg/LNot Available
logP0.4Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.39 mg/mLALOGPS
logP0.58ALOGPS
logP0.56ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)12.71ChemAxon
pKa (Strongest Basic)2.56ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area81.65 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity97.2 m3·mol-1ChemAxon
Polarizability26.52 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9894
Blood Brain Barrier+0.9382
Caco-2 permeable+0.8867
P-glycoprotein substrateNon-substrate0.6008
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.9004
Renal organic cation transporterNon-inhibitor0.6461
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.565
CYP450 1A2 substrateNon-inhibitor0.6312
CYP450 2C9 inhibitorNon-inhibitor0.5497
CYP450 2D6 inhibitorNon-inhibitor0.809
CYP450 2C19 inhibitorInhibitor0.532
CYP450 3A4 inhibitorNon-inhibitor0.8196
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.524
Ames testNon AMES toxic0.548
CarcinogenicityNon-carcinogens0.7298
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4136 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8229
hERG inhibition (predictor II)Non-inhibitor0.6614
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-339ec0708a6a6299e4d1
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ea278fc262275613a1fe
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-bbdadb624a7360b26fa3
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00kf-6900000000-0316b801589bae74a3f9
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9100000000-d7b76913f55978a00d10
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-45cd8f87d45358745d5b
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-2f3230e2968762340fb0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-ea0bdd0dd4905f7ca2a7
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-643df112c60eecdd6f26
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-00kf-6900000000-636d53fe2393f25b4cc4
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9100000000-2d05579f16a7ce194afb
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-bb834fc848ba7398b278
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-014i-9000000000-e3f46745a82b72dc28b0
LC-MS/MS Spectrum - LC-ESI-ITFT , negativeLC-MS/MSsplash10-0006-0900000000-565636d9f9e684b11429
LC-MS/MS Spectrum - LC-ESI-QFT , negativeLC-MS/MSsplash10-0006-0900000000-224c620bb2943c3558aa
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-d00a2d66aa1d04145279
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0019000000-9ddd55ba2decdc6d3007
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0079-0091000000-5501d6ab39e3fb2e3676
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1690000000-fb006053901bf08be9c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1920000000-a0f9f745307937304b45
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00g0-1900000000-f3d3042120b194b579d4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00bi-1900000000-8d82f395b99e530cb46e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0a4i-0019000000-cf2933c2544adb816b0b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0079-0091000000-066891bc3d77fcb69c5d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1590000000-5d278aae398bb4d6c6b6
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00y0-1920000000-3dcfbc3d71451cc9331c
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-00g0-1900000000-c4af46372e623cdeb3dd
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0fi9-1900000000-c15061f8dd5425cdede4
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0090000000-af8c5257ccffbdd94e82
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0696000000-6b076061ba56c532c132
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0abi-2795000000-c36fbab24191f149ce46
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0g70-2920000000-a8a6188f5a32495c6efa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05g0-1795000000-7cf5f5c74fd37b2b188f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00dr-0390000000-5ae132600e3f7f3b30a1

Taxonomy

Description
This compound belongs to the class of organic compounds known as fluorobenzenes. These are compounds containing one or more fluorine atoms attached to a benzene ring.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Fluorobenzenes
Alternative Parents
Aryl fluorides / Triazoles / Tertiary alcohols / Heteroaromatic compounds / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds / Organofluorides / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Fluorobenzene / Aryl fluoride / Aryl halide / Azole / Tertiary alcohol / 1,2,4-triazole / Heteroaromatic compound / Organoheterocyclic compound / Azacycle / Aromatic alcohol
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
tertiary alcohol, triazole antifungal drug, conazole antifungal drug, difluorobenzene (CHEBI:46081)

Targets

Kind
Protein
Organism
Yeast
Pharmacological action
Yes
Actions
Inhibitor
General Function
Sterol 14-demethylase activity
Specific Function
Catalyzes C14-demethylation of lanosterol which is critical for ergosterol biosynthesis. It transforms lanosterol into 4,4'-dimethyl cholesta-8,14,24-triene-3-beta-ol.
Gene Name
ERG11
Uniprot ID
P10613
Uniprot Name
Lanosterol 14-alpha demethylase
Molecular Weight
60674.965 Da
References
  1. Bellamine A, Lepesheva GI, Waterman MR: Fluconazole binding and sterol demethylation in three CYP51 isoforms indicate differences in active site topology. J Lipid Res. 2004 Nov;45(11):2000-7. Epub 2004 Aug 16. [PubMed:15314102]
  2. Guinea J, Sanchez-Somolinos M, Cuevas O, Pelaez T, Bouza E: Fluconazole resistance mechanisms in Candida krusei: the contribution of efflux-pumps. Med Mycol. 2006 Sep;44(6):575-8. [PubMed:16966178]
  3. Chau AS, Chen G, McNicholas PM, Mann PA: Molecular basis for enhanced activity of posaconazole against Absidia corymbifera and Rhizopus oryzae. Antimicrob Agents Chemother. 2006 Nov;50(11):3917-9. Epub 2006 Sep 11. [PubMed:16966400]

Enzymes

Details
1. Cytochrome P450 3A4
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567]
  2. Kunze KL, Wienkers LC, Thummel KE, Trager WF: Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos. 1996 Apr;24(4):414-21. [PubMed:8801056]
  3. Sakaeda T, Iwaki K, Kakumoto M, Nishikawa M, Niwa T, Jin JS, Nakamura T, Nishiguchi K, Okamura N, Okumura K: Effect of micafungin on cytochrome P450 3A4 and multidrug resistance protein 1 activities, and its comparison with azole antifungal drugs. J Pharm Pharmacol. 2005 Jun;57(6):759-64. [PubMed:15969931]
  4. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  5. Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L55). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  6. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  7. Drug Interactions & Labeling - FDA [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567]
  2. Kunze KL, Wienkers LC, Thummel KE, Trager WF: Warfarin-fluconazole. I. Inhibition of the human cytochrome P450-dependent metabolism of warfarin by fluconazole: in vitro studies. Drug Metab Dispos. 1996 Apr;24(4):414-21. [PubMed:8801056]
  3. Kantola T, Backman JT, Niemi M, Kivisto KT, Neuvonen PJ: Effect of fluconazole on plasma fluvastatin and pravastatin concentrations. Eur J Clin Pharmacol. 2000 Jun;56(3):225-9. [PubMed:10952477]
  4. Debruyne D, Coquerel A: Pharmacokinetics of antifungal agents in onychomycoses. Clin Pharmacokinet. 2001;40(6):441-72. [PubMed:11475469]
  5. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [PubMed:10709776]
  6. `Clin-Info. (2006). In Compendium of Pharmaceuticals and Specialties: The Canadian Drug Reference for Health Professionals (pp. L55). Canadian Pharmacists Association. [ISBN:1-894402-22-7]
  7. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
  8. Fluconazole FDA label [File]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Niwa T, Shiraga T, Takagi A: Effect of antifungal drugs on cytochrome P450 (CYP) 2C9, CYP2C19, and CYP3A4 activities in human liver microsomes. Biol Pharm Bull. 2005 Sep;28(9):1805-8. [PubMed:16141567]
  2. Venkatakrishnan K, von Moltke LL, Greenblatt DJ: Effects of the antifungal agents on oxidative drug metabolism: clinical relevance. Clin Pharmacokinet. 2000 Feb;38(2):111-80. doi: 10.2165/00003088-200038020-00002. [PubMed:10709776]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Drug Interactions: Cytochrome P450 Drug Interaction Table [Link]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
Gene Name
CYP11B1
Uniprot ID
P15538
Uniprot Name
Cytochrome P450 11B1, mitochondrial
Molecular Weight
57572.44 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Wang EJ, Lew K, Casciano CN, Clement RP, Johnson WW: Interaction of common azole antifungals with P glycoprotein. Antimicrob Agents Chemother. 2002 Jan;46(1):160-5. [PubMed:11751127]
  2. Ekins S, Kim RB, Leake BF, Dantzig AH, Schuetz EG, Lan LB, Yasuda K, Shepard RL, Winter MA, Schuetz JD, Wikel JH, Wrighton SA: Three-dimensional quantitative structure-activity relationships of inhibitors of P-glycoprotein. Mol Pharmacol. 2002 May;61(5):964-73. [PubMed:11961113]
  3. Yasuda K, Lan LB, Sanglard D, Furuya K, Schuetz JD, Schuetz EG: Interaction of cytochrome P450 3A inhibitors with P-glycoprotein. J Pharmacol Exp Ther. 2002 Oct;303(1):323-32. [PubMed:12235267]

Drug created on June 13, 2005 07:24 / Updated on November 20, 2018 13:19