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MedKoo Cat#: 317878 | Name: Fluconazole
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Fluconazole is an antifungal medication that is administered orally or intravenously. It is used to treat a variety of fungal infections, especially Candida infections of the vagina, mouth, throat, and bloodstream. It is also used to prevent infections in people with weak immune systems, including those with neutropenia due to cancer chemotherapy, transplant patients, and premature babies. Its mechanism of action involves interfering with synthesis of the fungal cell membrane.

Chemical Structure

Fluconazole
Fluconazole
CAS#86386-73-4

Theoretical Analysis

MedKoo Cat#: 317878

Name: Fluconazole

CAS#: 86386-73-4

Chemical Formula: C13H12F2N6O

Exact Mass: 306.1041

Molecular Weight: 306.27

Elemental Analysis: C, 50.98; H, 3.95; F, 12.41; N, 27.44; O, 5.22

Price and Availability

Size Price Availability Quantity
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 350.00 Ready to ship
5g USD 550.00 Ready to ship
10g USD 850.00 Ready to ship
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Related CAS #
No Data
Synonym
Fluconazole, Diflucan, Triflucan, Elazor, Biozolene
IUPAC/Chemical Name
2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol
InChi Key
RFHAOTPXVQNOHP-UHFFFAOYSA-N
InChi Code
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
SMILES Code
OC(CN1N=CN=C1)(C2=CC=C(F)C=C2F)CN3N=CN=C3
Appearance
White to off-white crystalline powder.
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Certificate of Analysis
View CoA: current batch, Lot#C21B09B08
Safety Data Sheet (SDS)
View Safety Data Sheet (SDS)
Instruction
View handling instruction
Biological target:
14-α Demethylase
In vitro activity:
Candida parapsilosis (C. parapsilosis) is a common non-albicans Candida species ranked as the second common cause of bloodstream infections. Azole resistance and elevated echinocandin MICs have been reported for these fungi. This study was conducted to determine the interactions between azoles and echinocandins against C. parapsilosis species complex. Fifteen fluconazole-resistant clinical isolates of C. parapsilosis complex were included: C. parapsilosis sensu stricto (n = 7), C. orthopsilosis (n = 5) and C. metapsilosis (n = 3). The activity of azoles (fluconazole, itraconazole) and echinocandins (anidulafungin, micafungin) alone and in combination was determined using checkerboard broth microdilution. The results were determined based on the fractional inhibitory concentration index (FICI). In vitro combination of fluconazole with anidulafungin was found to be synergistic (FICI 0.07-0.37) and decreased the MIC range from 4-64 μg/mL to 0.5-16 μg/mL for fluconazole and from 2-8 μg/mL to 0.125-1 μg/mL for anidulafungin. Similarly, interactions of fluconazole with micafungin (FICI 0.25-0.5), itraconazole with anidulafungin (FICI 0.15-0.37) and itraconazole with micafungin (FICI 0.09-0.37) were synergistic. The combination of fluconazole and itraconazole with either anidulafungin or micafungin demonstrated synergistic interactions against C. parapsilosis species complex, especially against isolates with elevated MIC values. However, the use of these combinations in clinical practice and the clinical relevance of in vitro combination results remain unclear. Referencees: Ahmadi A, Mahmoudi S, Rezaie S, Hashemi SJ, Dannaoui E, Badali H, Ghaffari M, Aala F, Izadi A, Maleki A, Meis JF, Khodavaisy S. In vitro synergy of echinocandins with triazoles against fluconazole-resistant Candida parapsilosis complex isolates. J Glob Antimicrob Resist. 2020 Jun;21:331-334. doi: 10.1016/j.jgar.2019.11.003. Epub 2019 Nov 9. PMID: 31715297.
In vivo activity:
Treatment of azole-resistant Candida albicans infections continues to pose significant challenges. With limited options of licensed agents, drug combinations may be a practical treatment alternative. In our previous studies, the combinations minocycline/fluconazole (MINO/FLC) and doxycycline/fluconazole (DOXY/FLC) shown synergistic effects in vitro. It is necessary to explore their appropriate dosage, potential toxicity and in vivo efficacy. The Galleria mellonella infection model was employed to study the in vivo efficacy of MINO/FLC and DOXY/FLC by survival analysis, quantification of C. albicans fungal burden and histological studies. The survival rates of G. mellonella larvae infected with lethal doses of resistant C. albicans CA10 increased significantly when treated with the drug combinations compared with FLC treatment alone, and the fungal burden was reduced by almost four-fold. The histopathological study showed that fewer infected areas in larvae were observed and the destructive degree was less when larvae were exposed to the drug combinations. These findings suggest that combination of a tetracycline antibiotic (MINO or DOXY) with FLC has antifungal activity against azole-resistant C. albicans in vivo. This is in agreement with several previous in vitro studies and provides preliminary in vivo evidence that such a combination might be useful therapeutically. References: Gu W, Yu Q, Yu C, Sun S. In vivo activity of fluconazole/tetracycline combinations in Galleria mellonella with resistant Candida albicans infection. J Glob Antimicrob Resist. 2018 Jun;13:74-80. doi: 10.1016/j.jgar.2017.11.011. Epub 2017 Nov 27. PMID: 29191612.
Solvent mg/mL mM
Solubility
DMSO 61.0 199.17
Water 0.0 3.27
Ethamol 61.0 199.17
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 306.27 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
Ahmadi A, Mahmoudi S, Rezaie S, Hashemi SJ, Dannaoui E, Badali H, Ghaffari M, Aala F, Izadi A, Maleki A, Meis JF, Khodavaisy S. In vitro synergy of echinocandins with triazoles against fluconazole-resistant Candida parapsilosis complex isolates. J Glob Antimicrob Resist. 2020 Jun;21:331-334. doi: 10.1016/j.jgar.2019.11.003. Epub 2019 Nov 9. PMID: 31715297.
In vitro protocol:
Ahmadi A, Mahmoudi S, Rezaie S, Hashemi SJ, Dannaoui E, Badali H, Ghaffari M, Aala F, Izadi A, Maleki A, Meis JF, Khodavaisy S. In vitro synergy of echinocandins with triazoles against fluconazole-resistant Candida parapsilosis complex isolates. J Glob Antimicrob Resist. 2020 Jun;21:331-334. doi: 10.1016/j.jgar.2019.11.003. Epub 2019 Nov 9. PMID: 31715297.
In vivo protocol:
Gu W, Yu Q, Yu C, Sun S. In vivo activity of fluconazole/tetracycline combinations in Galleria mellonella with resistant Candida albicans infection. J Glob Antimicrob Resist. 2018 Jun;13:74-80. doi: 10.1016/j.jgar.2017.11.011. Epub 2017 Nov 27. PMID: 29191612.
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PubMed PMID: 24550039. 5: De Rosa FG, Motta I, Corcione S, Cattel F, Di Perri G, D'Avolio A. Anidulafungin versus fluconazole: clinical focus on IDSA and ESCMID guidelines. Infez Med. 2014 Jun;22(2):107-11. Review. PubMed PMID: 24955796. 6: Liu S, Hou Y, Chen X, Gao Y, Li H, Sun S. Combination of fluconazole with non-antifungal agents: a promising approach to cope with resistant Candida albicans infections and insight into new antifungal agent discovery. Int J Antimicrob Agents. 2014 May;43(5):395-402. doi: 10.1016/j.ijantimicag.2013.12.009. Epub 2014 Jan 22. Review. PubMed PMID: 24503221. 7: Ericson JE, Benjamin DK Jr. Fluconazole prophylaxis for prevention of invasive candidiasis in infants. Curr Opin Pediatr. 2014 Apr;26(2):151-6. doi: 10.1097/MOP.0000000000000060. Review. PubMed PMID: 24626156; PubMed Central PMCID: PMC4042246. 8: Jørgensen KJ, Gøtzsche PC, Dalbøge CS, Johansen HK. Voriconazole versus amphotericin B or fluconazole in cancer patients with neutropenia. Cochrane Database Syst Rev. 2014 Feb 24;2:CD004707. doi: 10.1002/14651858.CD004707.pub3. Review. PubMed PMID: 24563222. 9: Zhang C, Cheng J, Jiang Y, Liu J. Application of caspofungin in China compared with amphotericin B and fluconazole. Ther Clin Risk Manag. 2014 Sep 10;10:737-41. doi: 10.2147/TCRM.S47146. eCollection 2014. Review. PubMed PMID: 25228811; PubMed Central PMCID: PMC4164385. 10: Egunsola O, Adefurin A, Fakis A, Jacqz-Aigrain E, Choonara I, Sammons H. Safety of fluconazole in paediatrics: a systematic review. Eur J Clin Pharmacol. 2013 Jun;69(6):1211-21. doi: 10.1007/s00228-012-1468-2. Epub 2013 Jan 17. Review. PubMed PMID: 23325436; PubMed Central PMCID: PMC3651820. 11: Cheong JW, McCormack J. Fluconazole resistance in cryptococcal disease: emerging or intrinsic? Med Mycol. 2013 Apr;51(3):261-9. doi: 10.3109/13693786.2012.715763. Epub 2012 Sep 19. Review. PubMed PMID: 22989195. 12: Rosa MI, Silva BR, Pires PS, Silva FR, Silva NC, Silva FR, Souza SL, Madeira K, Panatto AP, Medeiros LR. Weekly fluconazole therapy for recurrent vulvovaginal candidiasis: a systematic review and meta-analysis. Eur J Obstet Gynecol Reprod Biol. 2013 Apr;167(2):132-6. doi: 10.1016/j.ejogrb.2012.12.001. Epub 2012 Dec 29. Review. PubMed PMID: 23280281. 13: Nakai N, Katoh N. Fixed drug eruption caused by fluconazole: a case report and mini-review of the literature. Allergol Int. 2013 Mar;62(1):139-41. doi: 10.2332/allergolint.12-LE-0464. Epub 2012 Nov 25. Review. PubMed PMID: 23172357. 14: Watt K, Manzoni P, Cohen-Wolkowiez M, Rizzollo S, Boano E, Jacqz-Aigrain E, Benjamin DK. Triazole use in the nursery: fluconazole, voriconazole, posaconazole, and ravuconazole. Curr Drug Metab. 2013 Feb;14(2):193-202. Review. PubMed PMID: 22935068; PubMed Central PMCID: PMC3541435. 15: Gupta AK, Drummond-Main C, Paquet M. Evidence-based optimal fluconazole dosing regimen for onychomycosis treatment. J Dermatolog Treat. 2013 Feb;24(1):75-80. doi: 10.3109/09546634.2012.703308. Epub 2012 Jul 25. Review. PubMed PMID: 22694221. 16: Blyth CC, Barzi F, Hale K, Isaacs D. Chemoprophylaxis of neonatal fungal infections in very low birthweight infants: efficacy and safety of fluconazole and nystatin. J Paediatr Child Health. 2012 Sep;48(9):846-51. doi: 10.1111/j.1440-1754.2012.02543.x. Review. PubMed PMID: 22970680. 17: Pai VV, Bhandari P, Kikkeri NN, Athanikar SB, Sori T. Fixed drug eruption to fluconazole: a case report and review of literature. Indian J Pharmacol. 2012 Sep-Oct;44(5):643-5. doi: 10.4103/0253-7613.100403. Review. PubMed PMID: 23112430; PubMed Central PMCID: PMC3480801. 18: Castagnola E, Jacqz-Aigrain E, Kaguelidou F, Maragliano R, Stronati M, Rizzollo S, Farina D, Manzoni P. Fluconazole use and safety in the nursery. Early Hum Dev. 2012 May;88 Suppl 2:S11-5. doi: 10.1016/S0378-3782(12)70005-1. Review. PubMed PMID: 22633503. 19: Ethier MC, Science M, Beyene J, Briel M, Lehrnbecher T, Sung L. Mould-active compared with fluconazole prophylaxis to prevent invasive fungal diseases in cancer patients receiving chemotherapy or haematopoietic stem-cell transplantation: a systematic review and meta-analysis of randomised controlled trials. Br J Cancer. 2012 May 8;106(10):1626-37. doi: 10.1038/bjc.2012.147. Review. PubMed PMID: 22568999; PubMed Central PMCID: PMC3349180. 20: Turner K, Manzoni P, Benjamin DK, Cohen-Wolkowiez M, Smith PB, Laughon MM. Fluconazole pharmacokinetics and safety in premature infants. Curr Med Chem. 2012;19(27):4617-20. Review. PubMed PMID: 22876898; PubMed Central PMCID: PMC3522083.