Fluconazole

Fluconazole
Clinical data
Trade names	Diflucan, others
AHFS/Drugs.com	Monograph
MedlinePlus	a690002
License data	US DailyMed: Fluconazole;
Pregnancy; category	AU: D; ;
Routes of; administration	By mouth, intravenous, topical
ATC code	D01AC15 (WHO) J02AC01 (WHO), J01RA07 (WHO);
Legal status
Legal status	AU: S3 (Pharmacist only) / S4; CA: ℞-only / OTC; UK: POM (Prescription only); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Bioavailability	>90% (oral)
Protein binding	11–12%
Metabolism	Liver 11%
Elimination half-life	30 hours (range 20–50 hours)
Excretion	Kidney 61–88%
Identifiers
	IUPAC name 2-(2,4-Difluorophenyl)-1,3-bis(1H-1,2,4-triazol-1-yl)propan-2-ol;
CAS Number	86386-73-4 ;
PubChem CID	3365;
DrugBank	DB00196 ;
ChemSpider	3248 ;
UNII	8VZV102JFY;
KEGG	D00322 ; C07002 ;
ChEBI	CHEBI:46081 ;
ChEMBL	ChEMBL106 ;
CompTox Dashboard (EPA)	DTXSID3020627 ;
ECHA InfoCard	100.156.133
Chemical and physical data
Formula	C13H12F2N6O
Molar mass	306.277 g·mol−1
3D model (JSmol)	Interactive image;
Melting point	139 °C (282 °F)
	SMILES OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F;
	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 ; Key:RFHAOTPXVQNOHP-UHFFFAOYSA-N ;
	(verify)

Fluconazole is an antifungal medication used for a number of fungal infections.^[5] This includes candidiasis, blastomycosis, coccidioidomycosis, cryptococcosis, histoplasmosis, dermatophytosis, and tinea versicolor.^[5] It is also used to prevent candidiasis in those who are at high risk such as following organ transplantation, low birth weight babies, and those with low blood neutrophil counts.^[5] It is given either by mouth or by injection into a vein.^[5]

Common side effects include vomiting, diarrhea, rash, and increased liver enzymes.^[5] Serious side effects may include liver problems, QT prolongation, and seizures.^[5] During pregnancy it may increase the risk of miscarriage while large doses may cause birth defects.^[6]^[5] Fluconazole is in the azole antifungal family of medication.^[5] It is believed to work by affecting the fungal cellular membrane.^[5]

Fluconazole was patented in 1981 and came into commercial use in 1988.^[7] It is on the World Health Organization's List of Essential Medicines.^[8] Fluconazole is available as a generic medication.^[5] In 2021, it was the 165th most commonly prescribed medication in the United States, with more than 3 million prescriptions.^[9]^[10]

^ "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.
^ "Diflucan- fluconazole tablet; Diflucan- fluconazole powder, for suspension". DailyMed. 21 September 2023. Archived from the original on 22 February 2024. Retrieved 22 February 2024.
^ "Active substance: Fluconazole" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 12 November 2020. Archived (PDF) from the original on 24 February 2024. Retrieved 22 December 2020.
^ Surov AO, Voronin AP, Vasilev NA, Churakov AV, Perlovich GL (20 December 2019). "Cocrystals of Fluconazole with Aromatic Carboxylic Acids: Competition between Anhydrous and Hydrated Solid Forms". Crystal Growth & Design. 20 (2): 1218–1228. doi:10.1021/acs.cgd.9b01490. S2CID 213008181.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Fluconazole". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ "Fluconazole (Diflucan): Drug Safety Communication - FDA Evaluating Study Examining Use of Oral Fluconazole (Diflucan) in Pregnancy". U.S. Food and Drug Administration (FDA). 26 April 2016. Archived from the original on 29 April 2016. Retrieved 29 April 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 978-3-527-60749-5. Archived from the original on 10 September 2017.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
^ "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
^ "Fluconazole - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 14 January 2024.

[1] "Product monograph brand safety updates". Health Canada. 7 July 2016. Retrieved 3 April 2024.

[Diflucan_FDA_label-2] "Diflucan- fluconazole tablet; Diflucan- fluconazole powder, for suspension". DailyMed. 21 September 2023. Archived from the original on 22 February 2024. Retrieved 22 February 2024.

[3] "Active substance: Fluconazole" (PDF). List of nationally authorised medicinal products. European Medicines Agency. 12 November 2020. Archived (PDF) from the original on 24 February 2024. Retrieved 22 December 2020.

[Sur2019-4] Surov AO, Voronin AP, Vasilev NA, Churakov AV, Perlovich GL (20 December 2019). "Cocrystals of Fluconazole with Aromatic Carboxylic Acids: Competition between Anhydrous and Hydrated Solid Forms". Crystal Growth & Design. 20 (2): 1218–1228. doi:10.1021/acs.cgd.9b01490. S2CID 213008181.

[AHFS2016-5] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Fluconazole". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.

[FDA2016Preg-6] "Fluconazole (Diflucan): Drug Safety Communication - FDA Evaluating Study Examining Use of Oral Fluconazole (Diflucan) in Pregnancy". U.S. Food and Drug Administration (FDA). 26 April 2016. Archived from the original on 29 April 2016. Retrieved 29 April 2016.

[Fis503-7] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 503. ISBN 978-3-527-60749-5. Archived from the original on 10 September 2017.

[WHO21st-8] World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.

[9] "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.

[10] "Fluconazole - Drug Usage Statistics". ClinCalc. Archived from the original on 8 July 2020. Retrieved 14 January 2024.

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