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Fluconazole(CAS No. 86386-73-4)

Fluconazole C13H12F2N6O (cas 86386-73-4) Molecular Structure

86386-73-4 Structure

Identification and Related Records

【Name】
Fluconazole
【CAS Registry number】
86386-73-4
【Synonyms】
Flucostat
Fluconazolum [Latin]
Biozolene
FLU
Zemyc
Forcan
FCZ
Diflucan
Flusol
Flukezol
Pritenzol
2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol
Biocanol
Fluzone
Cryptal
UK 49858
Syscan
Alflucoz
1H-1,2,4-Triazole-1-ethanol,R-(2,4-difluorophenyl)- R-(1H-1,2,4-triazol-1-ylmethyl)-
FLZ
Diflucan (TN)
Flucazol
FLC
Canzol
Oxifugol
Fluconazole (JAN/USAN)
Fungata
Mutum
FLCZ
Baten
alpha-(2,4-Difluorophenyl)-alpha-(1H-1,2,4-triazol-1-ylmethyl)-1H-1,2,4-triazole-1-ethanol
Fluconazol [Spanish]
Triflucan
Afungil
Zonal
Elazor
【Molecular Formula】
C13H12F2N6O (Products with the same molecular formula)
【Molecular Weight】
306.270786
【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
【Canonical SMILES】
C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O
【MOL File】
86386-73-4.mol

Chemical and Physical Properties

【Appearance】
white or off white crystalline powder
【Density】
1.49 g/cm3
【Melting Point】
138-140℃
【Boiling Point】
579.8 oC at 760 mmHg
【Flash Point】
304.4 oC
【Water】
DMSO: 5 mg/mL
【Solubilities】
DMSO: 5 mg/mL
【Color/Form】
White crystalline powder
Crystals from ethyl acetate/hexane
【Storage temp】
?20°C
【Computed Properties】
Molecular Weight:306.270786 [g/mol]
Molecular Formula:C13H12F2N6O
XLogP3:0.4
H-Bond Donor:1
H-Bond Acceptor:3
Rotatable Bond Count:5
Exact Mass:306.104065
MonoIsotopic Mass:306.104065
Topological Polar Surface Area:81.6
Heavy Atom Count:22
Formal Charge:0
Complexity:358
Isotope Atom Count:0
Defined Atom Stereocenter Count:0
Undefined Atom Stereocenter Count:0
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:1
Feature 3D Donor Count:1
Feature 3D Cation Count:4
Feature 3D Ring Count:3
Effective Rotor Count:5
Conformer Sampling RMSD:0.8
CID Conformer Count:80

Safety and Handling

【Hazard Codes】
Xn: Harmful;
【Risk Statements】
R36/37/38
【Safety Statements 】
26-36/37/39-24/25
【Safety】

Hazard Codes:?HarmfulXn,Xi
Risk Statements:?36/37/38-20/21/22
R36/37/38: Irritating to eyes, respiratory system and skin.?
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements:?26-36/37/39-24/25
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.?
S24/25: Avoid contact with skin and eyes.
RTECS:?XZ4810000
?Fluconazole (CAS NO.86386-73-4) is contraindicated in patients with:
Pregnancy
Known hypersensitivity to fluconazole or other azole antifungals
Concomitant use of cisapride, due to risk of serious cardiac arrhythmias (relative contraindication).

【Formulations/Preparations】
Trade names: Biozolene (Bioindustria), Diflucan (Mason, Pfizer, Roerig), Dimycon (Alkaloid), Elazor (Sigma-Tau), Flavizol (Gador), Fungata (Mack), Mutum (Raffo), Triflucan (Pfizer).
Fluconazole (DIFLUCAN) is marketed in the United States as tablets ... for oral administration, powder for oral suspension ... and iv solutions ... in saline and in dextrose solutions.
Oral: For suspension: 50 mg/5 mL Diflucan, (Pfizer), 200 mg/5 mL Diflucan, (Pfizer); Tablets: 50 mg* Diflucan (with povidone), (Pfizer), 100 mg Diflucan (with povidone), (Pfizer), 150 mg Diflucan (with povidone), (Pfizer), 200 mg Diflucan (with povidone), (Pfizer).
【Exposure Standards and Regulations】
The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl fluconazole, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
【Specification】

White to Off-White Solid
usageEng:Labelled Fluconazole (F421000). Used as an antifungal.
Safety Statements:26-36-36/37/39-24/25
26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice
36:Wear suitable protective clothing
36/37/39:Wear suitable protective clothing, gloves and eye/face protection
24/25:Avoid contact with skin and eyes
【Octanol/Water Partition Coefficient】
log Kow = 0.25 at 25 deg C (est)
【Report】

"The efficacy of?Fluconazole (CAS NO.86386-73-4) in the treatment of onchomycosis (fungal infection of the nails) has not been demonstrated." I was treated with Apo-Fluconazole for onychomycosis, and it would seem that it works fine. Although I don't have any medical experience, I was wondering if someone would comment on this statement for me. Schnarr 01:48, 20 April 2006 (UTC)
I had phimosis and my doctor prscribed?it as one of the medicines... I am wondering if dealing with a possible fungal infection can stop the preputial ring from forming... please give me some feedback if you have had this problem and how it was solved.. Brian (brianmatambo@gmail.com)

【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

K. Richardson, United Kingdom 2099818; US patent 4404216 (1982, 1983 both to Pfizer).
【Usage】

Used as an antifungal

Biomedical Effects and Toxicity

【Biological Activity】
Triazole antifungal agent. Effective against Candida strains in vitro and in vivo .
【Pharmacological Action】
- Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism.
- Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues.
【Therapeutic Uses】
Mesh Heading: Antifungal agents
MEDICATION: Antifungal; Orally active bistriazole antifungal agent
MEDICATION (VET): Used to treat systemic mycoses, particularly CNS-related conditions in dogs.
Fluconazole ... /is/ indicated for the prophylaxis of febrile neutropenia in patients with hematologic malignancies. /NOT included in US product labeling/
Fluconazole ... /is/ indicated in the treatment of extrameningeal crytococcosis caused by Cryptococcus neoformans. /NOT included in US product labeling/
Fluconazole ... /is/ indicated in the treatment of tinea manuum (ringworm of the hand). /NOT included in US product labeling/
Fluconazole ... /is/ indicated in the treatment of fungal septicemia. /NOT included in US product labeling/
Fluconazole ... /is/ indicated in the treatment of fungal pneumonia. /NOT included in US product labeling/
Fluconazole is indicated in the treatment of febrile neutropenia when fungal infections are suspected or proven. /NOT included in US product labeling/
Fluconazole ... /is/ indicated in nonimmunocompromised patients for the treatment of onychomycosis caused by tinea unguium, Trichophyton species and Candida species. /NOT included in US product labeling/
Fluconazole is indicated for the treatment and suppression of cryptococcal meningitis. /Included in US product labeling/
Fluconazole ... /is/ indicated in the treatment of pulmonary and disseminated coccidioidomycosis caused by Coccidioides immitis. /NOT included in US product labeling/
Fluconazole ... /is/ indicated in the treatment of vulvovaginal candidiasis caused by Candida species. /Included in US product labeling/
Fluconazole ... /is/ indicated for the treatment of serious infections, including peritonitis, pneumonia, and urinary tract infections, caused by susceptible Candida species. /Included in US product labeling/. Fluconazole is also indicated for the treatment of systemic infections caused by Candida species in neonates. /NOT included in US product labeling/
Fluconazole ... /is/ indicated for the treatment of esophageal and oropharyngeal candidiasis (thrush) caused by Candida species. /Included in US product labeling/
Fluconazole is indicated for the prophylaxis of candidiasis in patients undergoing bone marrow transplant who receive cytotoxic chemotherapy and/or radiation therapy. /Included in US product labeling/
【Biomedical Effects and Toxicity】
The pharmacokinetics of fluconazole are similar following IV or oral administration. The drug is rapidly and almost completely absorbed from the GI tract, and there is no evidence of first-pass metabolism. Oral bioavailability of fluconazole exceeds 90% in healthy, fasting adults; peak plasma concentrations of the drug generally are attained within 1-2 hours after oral administration. ... The rate and extent of GI absorption of fluconazole are not affected by food. The manufacturer states that the commercially available fluconazole suspensions are bioequivalent to the 100-mg fluconazole tablets.
Peak plasma fluconazole concentrations and AUCs increase in proportion to the dose over the oral dosage range of 50-400 mg. Steady-state plasma concentrations of fluconazole are attained within 5-10 days following oral doses of 50-400 mg given once daily. ... When fluconazole therapy is initiated with a single loading dose equal to twice the usual daily dosage and followed by the usual dosage given once daily thereafter, plasma concentrations of the drug reportedly approach steady state by the second day of therapy.
In healthy, fasting adults who received a single 1-mg/kg oral dose of fluconazole, peak plasma concentrations of the drug averaged 1.4 mcg/mL. Following oral administration of a single 400-mg dose of fluconazole in healthy, fasting adults, peak plasma concentrations average 6.72 mcg/mL (range: 4.12-8.1 mcg/mL).
In healthy adults receiving 50- or 100-mg doses of fluconazole given once daily by IV infusion over 30 minutes, serum concentrations of the drug 1 hour after dosing on the sixth or seventh day of therapy ranged from 2.14-2.81 or 3.86-4.96 mcg/mL, respectively.
In children 9 months to 13 years of age, oral administration of a single 2- or 8-mg/kg dose of fluconazole resulted in mean peak plasma concentrations of 2.9 or 9.8 mcg/mL, respectively. In a multiple-dose study in children 5-15 years of age, IV administration of 2-, 4-, or 8-mg/kg doses of fluconazole resulted in mean peak plasma concentrations of 5.5, 11.4, or 14.1 mcg/mL, respectively. In a limited study in premature neonates who received 6-mg/kg doses of fluconazole IV every 72 hours, peak serum concentrations of the drug ranged from 3.7-10.2 mcg/mL after the first dose and from 6-17.8 mcg/mL after the third dose (day 7).
Fluconazole is widely distributed into body tissues and fluids following oral or IV administration. Studies in mice using IV doses of radiolabeled fluconazole indicate that the drug is evenly distributed throughout body tissues. In adult humans with normal renal function, concentrations of the drug attained in urine and skin may be 10 times higher than concurrent plasma concentrations; concentrations attained in saliva, sputum, nails, blister fluid, blister skin, and vaginal tissue are approximately equal to concurrent plasma concentrations. Concentrations attained in vaginal secretions following administration of a single 150-mg oral dose reportedly are about 40-86% of concurrent plasma concentrations. Fluconazole concentrations in prostatic tissue reportedly average about 30% of concurrent plasma concentrations. In adults with bronchiectasis who received a single 150-mg oral dose of fluconazole, sputum concentrations of the drug in samples obtained at 4 and 24 hours after the dose averaged 3.7 and 2.23 mcg/mL, respectively, and were approximately equal to concurrent plasma concentrations. Studies in rabbits indicate that high concentrations of fluconazole are attained in the cornea, aqueous humor, and vitreous body following IV administration; these concentrations were higher in inflamed than uninflamed eyes.
Fluconazole, unlike some azole-derivative antifungal agents (eg, itraconazole, ketoconazole), distributes readily into CSF following oral or IV administration; CSF concentrations of fluconazole may be 50-94% of concurrent plasma concentrations regardless of the degree of meningeal inflammation.
The apparent volume of distribution of fluconazole approximates that of total body water and has been reported to be 0.7-1 L/kg. In a limited study, the estimated volume of distribution at steady state of fluconazole was slightly lower in HIV-infected adults than in healthy adults.
Unlike some azole-derivative antifungal agents (eg, itraconazole, ketoconazole, miconazole), which are highly protein bound, fluconazole is only 11-12% bound to plasma proteins.
It is not known whether fluconazole crosses the placenta in humans. The drug crosses the placenta in rats, and concentrations in amniotic fluid, placenta, fetus, and fetal liver are approximately equal to maternal plasma concentrations.
Fluconazole is distributed into human milk at concentrations similar to those achieved in plasma. Administration of a single 150-mg oral dose to several nursing women resulted in peak plasma fluconazole concentrations of 2.61 ug/mL (range: 1.57-3.65 ug/mL).
In patients with impaired renal function, plasma concentrations of fluconazole are higher and the half-life prolonged; elimination half-life of the drug is inversely proportional to the patient's creatinine clearance. In addition, there is limited evidence that elimination of the drug may be impaired in geriatric patients.
In healthy adults, fluconazole is eliminated principally by renal excretion. Renal clearance of the drug averages 0.27 mL/minute per kg in adults with normal renal function. In a limited, single-dose study, renal clearance of fluconazole averaged 0.79 L/hour in healthy adults, 0.58 L/hour in HIV-infected adults with CD4+ T-cell counts greater than 200 cu m, and 0.2 L/hour in those with CD4+ T-cell counts less than 200 cu m. Approximately 60-80% of a single oral or IV dose of fluconazole is excreted in urine unchanged, and about 11% is excreted in urine as metabolites. Small amounts of the drug are excreted in feces.
Fluconazole is removed by hemodialysis and peritoneal dialysis. The amount of the drug removed during hemodialysis depends on several factors (eg, type of coil used, dialysis flow rate). A 3-hour period of hemodialysis generally decreases plasma concentrations of the drug by 50%. In 2 adults with fungal peritonitis undergoing continuous ambulatory peritoneal dialysis (CAPD) and receiving an oral fluconazole dosage of 100 mg/kg daily, concentrations of the drug in peritoneal dialysis fluid ranged from 2.3-9 mcg/mL and concurrent plasma concentrations ranged from 3.2-9 mcg/mL.

Environmental Fate and Exposure Potential

【Environmental Fate/Exposure Summary】
TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 5.3X10+4(SRC), determined from a structure estimation method(2), indicates that fluconazole is expected to be immobile in soil(SRC). Volatilization of fluconazole from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.0X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Fluconazole is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 3.0X10-9 mm Hg(SRC), determined from a fragment constant method(4). Biodegradation data were not available(SRC, 2005).
AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 5.3X10+4(SRC), determined from a structure estimation method(2), indicates that fluconazole is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.0X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3.2(SRC), from an estimated log Kow of 0.25(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data were not available(SRC, 2005).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), fluconazole, which has an estimated vapor pressure of 3.0X10-9 mm Hg at 25 deg C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase fluconazole may be removed from the air by wet and dry deposition(SRC). Fluconazole does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

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