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Compound Detail

CHEMBL106

FLUCONAZOLE
💊 Approved Drug
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💊 Approved Drug
OC(Cn1cncn1)(Cn1cncn1)c1ccc(F)cc1F

Basic Information

ChEMBL ID CHEMBL106
Name FLUCONAZOLE
Phase Approved
Structure Type MOL
InChI Key RFHAOTPXVQNOHP-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Alkanazole BAYT-006267 BAYT006267 Canesten oral Diflucan Diflucan one Difluconazole Fluconazol Fluconazole Fluconazoli NSC-758661 Triflucan +3 more
30
Targets
113
Activities
4
Assay Types
30
PK Parameters
20
Publications
15
Known Names
20
Indications
1
Mechanisms

Molecular Properties

306.3
MW (Da)
0.74
ALogP
7
HBA
1
HBD
81.7
PSA (Ų)
0.75
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1990
Availability Prescription
Chirality Achiral

Routes of Administration

Oral Parenteral
USAN Stem -conazole
USAN Year 1988

Extended Properties

Molecular Formula C13H12F2N6O
MW 306.28
Aromatic Rings 3
Heavy Atoms 22
NP-Likeness -0.86

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Cytochrome P450 51 inhibitor INHIBITOR Lanosterol 14-alpha demethylase

Indications

Candidiasis Candidiasis, Vulvovaginal Meningitis, Cryptococcal Urinary Tract Infections Aspergillosis Bacterial Infections Candidemia Candidiasis, Invasive Candidiasis, Oral Coccidioidomycosis Crohn Disease HIV Infections Infections Inflammatory Bowel Diseases Leishmaniasis, Cutaneous Leukopenia Mycoses Neoplasms Neoplasms Tinea Pedis

ATC Classification

D01AC15
fluconazole
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
J02AC01
fluconazole
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOTICS FOR SYSTEMIC USE

Activity Summary

IC50 91 meas. best 9.0
Kd 20 meas. best 7.35
EC50 1 meas. best 4.86
Ki 1 meas. best 4.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Candida albicans
CHEMBL366
IC50 9.0 6.1533 1.0 18
Cryptococcus neoformans
CHEMBL365
IC50 8.3 5.9757 5.0 7
Lanosterol 14-alpha demethylase
CHEMBL1780
Kd 7.35 7.35 45.0 1
Lanosterol 14-alpha demethylase
CHEMBL1780
IC50 7.01 6.8943 98.0 7
Unchecked
CHEMBL612545
Kd 6.85 5.4388 141.0 8
Sterol 14alpha-demethylase
CHEMBL5090
Kd 6.7 5.1267 200.0 3
Sterol 14-alpha demethylase
CHEMBL1075110
Kd 6.64 6.64 230.0 2
Sterol 14-alpha demethylase
CHEMBL1075110
IC50 6.06 6.06 880.0 1
Trichophyton rubrum
CHEMBL612649
IC50 5.75 5.66 1800.0 2
Trichophyton mentagrophytes
CHEMBL613162
IC50 5.71 4.9367 1950.0 6
Toxoplasma gondii
CHEMBL612888
IC50 5.52 5.52 3000.0 1
Candida parapsilosis
CHEMBL612868
IC50 5.47 5.47 3400.0 1
Saccharomyces cerevisiae
CHEMBL361
IC50 5.46 4.9133 3500.0 3
14-alpha sterol demethylase
CHEMBL1681624
Kd 5.39 5.39 4030.0 1
Candida tropicalis
CHEMBL612870
IC50 5.37 5.37 4300.0 1
Mycocyclosin synthase
CHEMBL1681615
Kd 5.22 5.22 6000.0 1
Cytochrome P450 3A4
CHEMBL340
IC50 5.21 4.9027 6200.0 11
Unchecked
CHEMBL612545
IC50 5.15 5.15 7140.0 1
Aspergillus fumigatus
CHEMBL363
IC50 5.13 5.13 7350.0 3
Cytochrome P450 2C19
CHEMBL3622
IC50 5.09 5.09 8200.0 4
Cytochrome P450 2C9
CHEMBL3397
IC50 5.04 4.6375 9210.0 8
Trypanosoma cruzi
CHEMBL368
IC50 5.0 5.0 9960.0 2
Leishmania amazonensis
CHEMBL612877
IC50 5.0 5.0 10100.0 1
HL-60
CHEMBL383
IC50 4.94 4.94 11600.0 1
Sterol 14-alpha demethylase cyp51A
CHEMBL1681623
Kd 4.92 4.92 11930.0 1
Cytochrome P450 11B2, mitochondrial
CHEMBL2722
IC50 4.89 4.89 13000.0 1
Naegleria fowleri
CHEMBL3301413
EC50 4.86 4.86 13900.0 1
PC-3
CHEMBL390
IC50 4.78 4.78 16490.0 1
MDA-MB-231
CHEMBL400
IC50 4.72 4.72 19210.0 1
Aromatase
CHEMBL1978
IC50 4.66 4.66 22000.0 1
Nakaseomyces glabratus
CHEMBL612647
IC50 4.53 4.53 29500.0 1
Unchecked
CHEMBL612545
Ki 4.52 4.52 30000.0 1
Cytochrome P450 11B1, mitochondrial
CHEMBL1908
IC50 4.52 4.52 30000.0 1
Lanosterol 14-alpha demethylase
CHEMBL3849
Kd 4.4 4.28 40000.0 2

Pharmacokinetic Data

Parameter Value Units Species
AUC 19.6 ng.hr.mL-1 Rattus norvegicus
AUC 19600.0 ng.hr.mL-1 Rattus norvegicus
AUC 100000.0 ng.hr.mL-1 Homo sapiens
CL 0.31 mL.min-1.kg-1 Homo sapiens
CL 0.1 mL.min-1.kg-1 Homo sapiens
CL 0.31 mL.min-1.kg-1 Homo sapiens
CL 0.31 mL.min-1.kg-1 Homo sapiens
CL 0.9 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.kg-1 Homo sapiens
CL 1.0 mL.min-1.g-1 Mus musculus
F 80.0 % Homo sapiens
F 90.0 % Homo sapiens
Fu 0.89 - -
Fu 0.814 - -
Fu 0.89 - Homo sapiens
Fu 0.89 - Homo sapiens
Fu 0.89 - Homo sapiens
Fu 0.89 - Homo sapiens
Fu 0.9 - Homo sapiens
Ka 6.47 10'-4L/mol Homo sapiens
Ka 6.22 10'-4L/mol Homo sapiens
Ka 5.65 10'-4L/mol Homo sapiens
Ka 7.0 10'-4L/mol Homo sapiens
Ka 6.19 10'-4L/mol Homo sapiens
Ka 7.18 10'-4L/mol Homo sapiens
Ka 5.62 10'-4L/mol Homo sapiens
Ka 6.22 10'-4L/mol Homo sapiens
Ka 6.12 10'-4L/mol Homo sapiens
Ka 5.55 10'-4L/mol Homo sapiens
Ka 4.8 10'-4L/mol Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Candida albicans IC50 = 1.0 nM 9.0 Antimicrobial activity against Candida albicans ATCC 90028 assessed as inhibitio... 31287681
Cryptococcus neoformans IC50 = 5.0 nM 8.3 Antimicrobial activity against Cryptococcus neoformans ATCC 90113 assessed as in... 31287681
Lanosterol 14-alpha demethylase Kd = 45.0 nM 7.35 Binding affinity to Candida albicans CYP51 20660663
Lanosterol 14-alpha demethylase IC50 = 98.0 nM 7.01 Inhibition of candida albicans CYP51 14alpha demethylase activity incubated for ... 38888292
Lanosterol 14-alpha demethylase IC50 = 110.0 nM 6.96 Inhibition of CYP51 in Candida albicans ATCC SC5314 assessed as reduction in sub... 36282007
Lanosterol 14-alpha demethylase IC50 = 116.0 nM 6.94 Inhibition of Candida albicans ATCC SC5314 CYP51 incubated for 30 mins by spectr... 33183866
Cryptococcus neoformans IC50 = 130.0 nM 6.89 Antifungal activity against wild-type fluconazole-sensitive Cryptococcus neoform... 29580849
Lanosterol 14-alpha demethylase IC50 = 134.0 nM 6.87 Inhibition of CYP51 in Candida albicans ATCC SC5314 measured after 30 mins by HP... 34772530
Lanosterol 14-alpha demethylase IC50 = 140.0 nM 6.85 Inhibition of CYP51 in Candida albicans SC5314 using Eburicol as substrate prein... 36074863
Unchecked Kd = 141.0 nM 6.85 Binding affinity to recombinant Naegleria fowleri CYP51 assessed as dissociation... 38085955
Lanosterol 14-alpha demethylase IC50 = 148.0 nM 6.83 Inhibition of CYP51 in Candida albicans ATCC SC5314 incubated for 30 mins using ... 34731761
Lanosterol 14-alpha demethylase IC50 = 159.0 nM 6.8 Inhibition of Candida albicans ATCC SC5314 CYP51 using lanosterol as substrate i... 37705322
Sterol 14alpha-demethylase Kd = 200.0 nM 6.7 Binding affinity to Mycobacterium tuberculosis CYP51 19075057
Sterol 14-alpha demethylase Kd = 230.0 nM 6.64 Binding affinity to recombinant full-length Trypanosoma cruzi CYP51 by UV-spectr... 25580906
Sterol 14-alpha demethylase Kd = 230.0 nM 6.64 Binding affinity to Trypanosoma cruzi CYP51 25240098
Unchecked Kd = 230.0 nM 6.64 Binding affinity to Candida albicans CYP56 by spectrophotometry 18663031
Candida albicans IC50 = 300.0 nM 6.52 Antifungal activity against Candida albicans CAAL93 assessed as reduction in fun... 34116159
Candida albicans IC50 = 400.0 nM 6.4 Antifungal activity against Candida albicans ATCC 60193 after 48 hrs by CLSI met... 18458131
Candida albicans IC50 = 400.0 nM 6.4 Antifungal activity against Candida albicans ATCC 200955 after 48 hrs by CLSI me... 18458131
Candida albicans IC50 = 500.0 nM 6.3 Antifungal activity against Candida albicans ATCC 14053 after 48 hrs by CLSI met... 18458131

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 581
20385871 10.1128/aac.00153-10 Cryptococcus bacillisporus 217
18056277 10.1128/aac.01070-07 Candida albicans 117
19786600 10.1128/aac.01031-09 Nakaseomyces glabratus 100
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 89
17438048 10.1128/aac.01176-06 Sporothrix schenckii 63
35922963 10.1021/acs.jmedchem.2c00794 Cryptococcus neoformans 47
37584282 10.1021/acs.jmedchem.3c00488 Nakaseomyces glabratus 46
37705322 10.1021/acs.jmedchem.3c00942 Candida albicans 46
17502416 10.1128/aac.01237-06 Candida albicans 42
20733039 10.1128/aac.00348-10 Candida albicans 42
37672929 10.1016/j.ejmech.2023.115782 Candida albicans 41
37975824 10.1021/acs.jmedchem.3c01771 Candida albicans 39
19786600 10.1128/aac.01031-09 Candida albicans 37
26276437 10.1016/j.ejmech.2015.07.032 Cryptococcus bacillisporus 37
20086148 10.1128/aac.01645-09 Candida albicans 35
26276437 10.1016/j.ejmech.2015.07.032 Cryptococcus neoformans 35
29648811 10.1021/acs.jmedchem.7b01729 Candida albicans 34
37037787 10.1021/acs.jmedchem.3c00165 Candida albicans 32

Data from ChEMBL 36 via Core Engine