Fluconazole

Summary

Fluconazole (CHEMBL106) is an approved small-molecule P450 inhibitor (ATC J02AC01); indicated across 38 conditions including vulvovaginal candidiasis and cryptococcal meningitis.

At a glance

• Status: Approved (max clinical phase 4)
• Modality: Small molecule
• ATC class: J02AC01 (+1 more)
• Indications: 38 conditions
• Clinical trials: 186
• Chemistry: 306.27 Da · C13H12F2N6O

Identifiers

Drug identity and classification

Field	Value
ChEMBL ID	CHEMBL106
Name	Fluconazole
Type	Small molecule
Max phase	4
FDA approved	yes
PubChem CID	3365
ChEBI	CHEBI:46081
ATC	J02AC01, D01AC15
Molecular formula	C13H12F2N6O
Molecular weight	306.27
InChIKey	RFHAOTPXVQNOHP-UHFFFAOYSA-N

SMILES: C1=CC(=C(C=C1F)F)C(CN2C=NC=N2)(CN3C=NC=N3)O

IUPAC name: 2-(2,4-difluorophenyl)-1,3-bis(1,2,4-triazol-1-yl)propan-2-ol

ChEBI definition: A member of the class of triazoles that is propan-2-ol substituted at position 1 and 3 by 1H-1,2,4-triazol-1-yl groups and at position 2 by a 2,4-difluorophenyl group. It is an antifungal drug used for the treatment of mucosal candidiasis and for systemic infections including systemic candidiasis, coccidioidomycosis, and cryptococcosis.

Pharmacological roles (ChEBI): P450 inhibitor.

Other ChEBI roles (chemical / environmental): environmental contaminant, xenobiotic.

Also known as: Alkanazole, BAYT-006267, BAYT006267, Canesten oral, Diflucan, Diflucan one, Difluconazole, Fluconazol, Fluconazole, Fluconazoli, NSC-758661, Triflucan

Parent form; salt/anhydrous children: CHEMBL1163001

Patent coverage: 17,227 distinct patent families (58,942 SureChEMBL compound mentions), from 2 matched compound structure(s). One matched structure accounts for 57,897 (98%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.

Targets

Targets

Broader ChEMBL bioactivity targets: 16 (assay-derived). Sample: Sterol 14-alpha demethylase, Prelamin-A/C, Mycocyclosin synthase, Sterol 14-alpha demethylase cyp51A, Lanosterol 14-alpha demethylase, Cytochrome P450 11B1, mitochondrial, Aromatase, Alpha-1A adrenergic receptor, Cytochrome P450 11B2, mitochondrial, Androgen receptor.

Bioactivity

ChEMBL activities: 28 potent at pChembl ≥ 5 of 50 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):

Target	pChembl	Type	Value	Unit	Activity ID
P10613	7.35	Kd	45	nM	CHEMBL_ACT_5229901
P10613	7.01	IC50	98	nM	CHEMBL_ACT_25911468
P10613	6.96	IC50	110	nM	CHEMBL_ACT_24969908
P10613	6.94	IC50	116	nM	CHEMBL_ACT_22911803
P10613	6.87	IC50	134	nM	CHEMBL_ACT_24389515
P10613	6.85	IC50	140	nM	CHEMBL_ACT_24748094
P10613	6.83	IC50	148	nM	CHEMBL_ACT_24835657
P10613	6.8	IC50	159	nM	CHEMBL_ACT_25640956
P9WPP9	6.7	Kd	200	nM	CHEMBL_ACT_5230881
Q7Z1V1	6.64	Kd	230	nM	CHEMBL_ACT_15105822
Q7Z1V1	6.64	Kd	230	nM	CHEMBL_ACT_15202547
LMNA	6.3	Potency	501.2	nM	CHEMBL_ACT_3647906
Q7Z1V1	6.06	IC50	880	nM	CHEMBL_ACT_18544861
HSP90AA1	5.33	AC50	4687	nM	CHEMBL_ACT_7461034
ADRA1A	5.32	AC50	4794	nM	CHEMBL_ACT_25137741
P9WPP7	5.22	Kd	6000	nM	CHEMBL_ACT_5230885
CYP3A4	5.21	IC50	6200	nM	CHEMBL_ACT_26153937
CYP3A4	5.1	IC50	8000	nM	CHEMBL_ACT_16348402
CYP3A4	5.1	IC50	8000	nM	CHEMBL_ACT_17729653
CYP3A4	5.1	IC50	8000	nM	CHEMBL_ACT_27407810
CYP3A4	5.1	IC50	8000	nM	CHEMBL_ACT_28612559
CYP2C19	5.09	IC50	8200	nM	CHEMBL_ACT_16271128
CYP2C19	5.09	IC50	8200	nM	CHEMBL_ACT_17729647
CYP2C19	5.09	IC50	8200	nM	CHEMBL_ACT_27407807
CYP2C19	5.09	IC50	8200	nM	CHEMBL_ACT_28612556
CYP2C9	5.04	IC50	9210	nM	CHEMBL_ACT_16637029
CYP3A4	5	IC50	10000	nM	CHEMBL_ACT_17706612
CYP3A4	5	IC50	10000	nM	CHEMBL_ACT_17707408

Target pathways

No target-pathway data for this drug (no mapped target genes).

Indications & clinical

Indications

38 indications (4 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).

Indication	Trial phase	MONDO	EFO
vulvovaginal candidiasis	4	MONDO:0006014	EFO:0007543
Cryptococcal meningitis	4	MONDO:0005723	EFO:0007228
candidiasis	4	MONDO:0002026	MONDO:0002026
urinary tract infection	4	MONDO:0100338	EFO:0003103
candidemia	3	MONDO:0044070	EFO:1001282
aspergillosis	3	MONDO:0005657	EFO:0007157
neoplasm	3	MONDO:0005070	EFO:0000616
cutaneous leishmaniasis	3	MONDO:0005446	EFO:0005046
Crohn disease	3	MONDO:0005011	EFO:0000384
HIV infectious disease	3	MONDO:0005109	EFO:0000764
leukopenia	3	MONDO:0003785	EFO:0004233
coccidioidomycosis	3	MONDO:0005706	EFO:0007211
oral candidiasis	3	MONDO:0005886	EFO:0007406
tinea pedis	3	MONDO:0005984	EFO:0007512
candidiasis, invasive	3	MONDO:0044067	EFO:1001283
vaginal discharge	3	MONDO:0002770	EFO:0009365
fungal infectious disease	3	MONDO:0002041	MONDO:0002041
vaginitis	3	MONDO:0002234	MONDO:0002234
bacterial infectious disease	3	MONDO:0005113	EFO:0000771
bacterial vaginosis	3	MONDO:0005316	EFO:0003932
inflammatory bowel disease	3	MONDO:0005265	EFO:0003767
blastomycosis	2	MONDO:0005672	EFO:0007174
histoplasmosis	2	MONDO:0018312	EFO:0007310
sporotrichosis	2	MONDO:0005968	EFO:0007494
intracranial hypertension	2	MONDO:0006810	EFO:1000992
vulvovaginitis	2	MONDO:0007019	EFO:1001240
acute myeloid leukemia	1	MONDO:0018874	EFO:0000222
chronic obstructive pulmonary disease	1	MONDO:0005002	EFO:0000341
lymphoma	1	MONDO:0005062	EFO:0000574
overactive bladder	1	MONDO:0006624	EFO:1000781
metabolic dysfunction-associated steatohepatitis	1	MONDO:0007027	EFO:1001249
graft versus host disease	1	MONDO:0013730	MONDO:0013730
respiratory syncytial virus infectious disease	1	MONDO:0001577	EFO:1001413
Alzheimer disease	1	MONDO:0004975	MONDO:0004975
pityriasis versicolor	1	MONDO:0005915	EFO:0007439

3 further indication records had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.

Clinical trials

Total trials: 186.

Phase distribution

Phase	Trials
PHASE1	48
PHASE3	42
Not specified	42
PHASE2	24
PHASE4	20
PHASE2/PHASE3	5
PHASE1/PHASE2	3
EARLY_PHASE1	2

Top trials by phase / activity

NCT	Phase	Status	Title
NCT05176379	PHASE4	RECRUITING	Endothelial Derived Hyperpolarization Factor and Vascular Control
NCT06709196	PHASE4	RECRUITING	Clinical Trial Testing Whether Targeted Antibiotic Prophylaxis Can Reduce Infections After Cystectomy Compared to Empiric Prophylaxis
NCT06770530	PHASE4	RECRUITING	Introduction of Mycotic Prophylaxis At Cystectomy Trial.
NCT06922344	PHASE4	RECRUITING	Comparison of Efficacy of Oral Fluconazole Versus Oral Itraconazole in the Treatment of Pityriasis Versicolor
NCT07342153	PHASE4	RECRUITING	Comparing the Efficacy of Oral Fluconazole Versus Oral Itraconazole in Treating Resistant Tinea Corporis
NCT00000951	PHASE4	COMPLETED	A Study to Compare the Use of Fluconazole as Continuous Therapy Versus Periodic Therapy in HIV-Positive Patients With Recurrent Thrush
NCT00001107	PHASE4	COMPLETED	Comparison of Two Treatments to Prevent Invasive Fungal Infections in Patients Who Have Received Liver Transplants
NCT00001542	PHASE4	COMPLETED	Fluconazole Prophylaxis of Thrush in AIDS
NCT00304772	PHASE4	WITHDRAWN	Fluconazole Versus Micafungin for Candida Bloodstream Infection in Non-Neutropenic Patients
NCT00496197	PHASE4	COMPLETED	Study Will Evaluate The Safety And Efficacy Of Anidulafungin In Patients With Candidemia Or Invasive Candidiasis
NCT00537888	PHASE4	UNKNOWN	Clinical Significance of Smear or Culture Positive for Candida Spp. From Sputum Three Times a Week
NCT00553137	PHASE4	COMPLETED	Single Dose Versus Two Weeks Course of Fluconazole in the Treatment of Oropharyngeal Candidiasis in HIV Infected Individuals in Tanzania
NCT00841971	PHASE4	COMPLETED	Anidulafungin Versus Fluconazole for the Prevention of Fungal Infections in Liver Transplant Recipients
NCT01535469	PHASE4	COMPLETED	Operational Research for Cryptococcal Antigen Screening
NCT02180100	PHASE4	COMPLETED	Terconazole Vaginal Suppository vs Fluconazole for the Treatment of Severe Vulvovaginal Candidiasis
NCT02180828	PHASE4	COMPLETED	Clotrimazole Vaginal Tablet vs Fluconazole for Severe Vulvovaginal Candidiasis
NCT02181946	PHASE4	COMPLETED	Effects of Nevirapine on the Steady State Pharmacokinetics of Fluconazole in HIV Positive Patients
NCT02663674	PHASE4	TERMINATED	Efficacy Study of Fluconazole to Treat Coccidioidomycosis Pneumonia (Valley Fever)
NCT04122560	PHASE4	COMPLETED	Fluconazole Pharmacokinetics, Including Bioavailability, in Obese Subjects After an Intravenous and Oral Administration
NCT04626258	PHASE4	UNKNOWN	Fluconazol Versus Medical Honey in the Treatment of Recurrent Vulvovaginal Candidiasis
NCT03945448	PHASE2/PHASE3	RECRUITING	Single Dose Liposomal Amphotericin for Asymptomatic Cryptococcal Antigenemia
NCT05367089	PHASE3	RECRUITING	The Effect of Medical Grade Honey Formulation (L-Mesitran) Administration on Recurrent Vulvovaginal Candidiasis Symptoms
NCT05421858	PHASE3	RECRUITING	A Phase 3 Efficacy and Safety Study of Fosmanogepix for the Treatment of Adult Participants With Candidemia and/or Invasive Candidiasis.
NCT06274554	PHASE3	RECRUITING	Testing the Role of Anti-fungal Therapy in Improving the Response to Therapies for Crohn’s Disease
NCT07311759	PHASE3	ACTIVE_NOT_RECRUITING	Safety and Efficacy of Intralesional 0.5% Triamcinolone Acetonide in 0.2% Fluconazole Solution vs 0.1% Topical Mometasone Furoate With 2% Miconazole Nitrate Cream in the Treatment of Chronic Paronychia: An Intraindividual Randomized Controlled Trial.
NCT00000676	PHASE3	COMPLETED	Randomized Comparative Study of Fluconazole Versus Clotrimazole Troches in the Prevention of Serious Fungal Infection in Patients With AIDS or Advanced AIDS-Related Complex. (A Nested Study of ACTG 081)
NCT00001017	PHASE3	COMPLETED	Comparison of Fluconazole and Amphotericin B in the Treatment of Brain Infections in Patients With AIDS
NCT00001937	PHASE3	COMPLETED	Comparing the Effectiveness of Fluconazole and a New Medicine (FK463) in Preventing Fungal Infections in Bone Marrow Transplant Patients
NCT00002122	PHASE3	COMPLETED	A Randomized Study of Daily and Intermittent Prophylactic Regimens for the Prevention of Disseminated Mycobacterium Avium Complex (MAC) and Fungal Infections in HIV-Infected Patients
NCT00002277	PHASE3	COMPLETED	A Comparison of Fluconazole and Amphotericin B in the Treatment of Fungal Infections
NCT00002339	PHASE3	COMPLETED	A Study of Fluconazole in the Treatment of Fungal Infections of the Throat in Patients With Weakened Immune Systems
NCT00002446	PHASE3	COMPLETED	Safety and Effectiveness of Fluconazole Versus SCH 56592 to Treat Thrush in HIV-Positive Patients
NCT00002533	PHASE2/PHASE3	COMPLETED	Fluconazole in Preventing Mucositis in Patients Undergoing Radiation Therapy for Head and Neck Cancer
NCT00003883	PHASE3	COMPLETED	Itraconazole Compared With Fluconazole to Prevent Infections in Patients Undergoing Peripheral Stem Cell or Bone Marrow Transplantation
NCT00056368	PHASE3	COMPLETED	The Safety and Efficacy of Anidulafungin Versus Comparator in Patients With Candidemia and Invasive Candidiasis
NCT00075803	PHASE3	COMPLETED	Comparison of Fluconazole vs Voriconazole to Treat Fungal Infections for Blood and Marrow Transplants (BMT CTN 0101)
NCT00170430	PHASE3	COMPLETED	Reducing Vaginal Infections in Women
NCT00189709	PHASE3	COMPLETED	Micafungin Versus Fluconazole in the Treatment of Invasive Candidiasis and Candidemia
NCT00353561	PHASE3	COMPLETED	Diabetes Mellitus and Vulvovaginal Candidiasis
NCT00423267	PHASE3	COMPLETED	POS vs FLU for First Line Treatment of Coccidioidomycosis (Study P04558Am1)(COMPLETED)

Clinical evidence (CIViC)

No CIViC predictive evidence (expected for non-precision-medicine drugs).

Pharmacology

Pharmacogenomics

No CPIC/DPWG dosing guideline, but PharmGKB curates 0 clinical and 18 variant annotation(s) for this drug (gene-keyed; see PharmGKB).

Related molecules

Related molecules

No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).