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Compound Detail

CHEMBL1463

FLUCYTOSINE
💊 Approved Drug
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💊 Approved Drug
Nc1nc(=O)[nH]cc1F

Basic Information

ChEMBL ID CHEMBL1463
Name FLUCYTOSINE
Phase Approved
Structure Type MOL
InChI Key XRECTZIEBJDKEO-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Alcobon Ancoban Ancobon Ancotil Flourocytosine Flucitosina Flucytosine Flucytosinum Fluorocytosine NSC-103805 RO 2-9915 RO-2-9915 +1 more
3
Targets
7
Activities
2
Assay Types
16
PK Parameters
20
Publications
13
Known Names
15
Indications
2
Mechanisms

Molecular Properties

129.1
MW (Da)
-0.51
ALogP
3
HBA
2
HBD
71.8
PSA (Ų)
0.50
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1971
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

Black Box Warning
USAN Year 1969

Extended Properties

Molecular Formula C4H4FN3O
MW 129.09
Aromatic Rings 1
Heavy Atoms 9
NP-Likeness -0.72

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thymidylate synthase inhibitor INHIBITOR Thymidylate synthase
Thymidylate synthase inhibitor INHIBITOR Thymidylate synthase

Indications

Candidiasis Infections Meningitis Intracranial Hypertension Meningitis, Cryptococcal Astrocytoma Brain Neoplasms Carcinoma, Hepatocellular Colorectal Neoplasms Digestive System Neoplasms Glioblastoma Gliosarcoma Neoplasms Neoplasms Oligodendroglioma

ATC Classification

D01AE21
flucytosine
Level 1: DERMATOLOGICALS
Level 2: ANTIFUNGALS FOR DERMATOLOGICAL USE
J02AX01
flucytosine
Level 1: ANTIINFECTIVES FOR SYSTEMIC USE
Level 2: ANTIMYCOTICS FOR SYSTEMIC USE

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 5 meas. best 6.39
EC50 2 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
EC50 6.6 6.6 252.0 1
Candida albicans
CHEMBL366
IC50 6.39 6.275 410.0 2
ATP-dependent molecular chaperone HSP82
CHEMBL1293251
EC50 6.15 6.15 711.0 1
Unchecked
CHEMBL612545
IC50 4.97 4.5133 10590.0 3

Pharmacokinetic Data

Parameter Value Units Species
AUC 576000.0 ng.hr.mL-1 Homo sapiens
AUC 1289000.0 ng.hr.mL-1 Homo sapiens
CL 6.7 L/hr Homo sapiens
CL 3.8 L/hr Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 0.02 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
F 80.0 % Homo sapiens
F 83.5 % Homo sapiens
Fu 1.0 - Homo sapiens
Fu 1.0 - Homo sapiens
MRT 5.7 hr Homo sapiens
T1/2 0.5 hr Mus musculus
T1/2 2.5 hr Homo sapiens
T1/2 4.2 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
17438048 10.1128/aac.01176-06 Sporothrix schenckii 62
19704126 10.1128/aac.00607-09 Candida dubliniensis 62
17043122 10.1128/aac.00446-06 Cryptococcus neoformans 39
17194824 10.1128/aac.01188-06 Homo sapiens 32
18625775 10.1128/aac.00541-08 Candida albicans 28
19414575 10.1128/aac.00880-08 Clavispora lusitaniae 21
20823283 10.1128/aac.00605-10 Nakaseomyces glabratus 20
16472241 10.2174/1570163043334794 Hepatotoxicity 18
19223630 10.1128/aac.01543-08 NON-PROTEIN TARGET 16
18212095 10.1128/aac.01384-07 NON-PROTEIN TARGET 15
19786601 10.1128/aac.01026-09 Molecular identity unknown 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
18955539 10.1128/aac.01216-08 Cryptococcus neoformans 12
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
17049255 10.1016/j.bmc.2006.09.038 Cryptococcus neoformans 10
17452487 10.1128/aac.00173-07 Magnusiomyces capitatus 10
18794382 10.1128/aac.00491-08 Aspergillus fumigatus 10
19015325 10.1128/aac.00844-08 Saccharomyces cerevisiae 10
17981473 10.1016/j.bmc.2007.10.034 Cryptococcus neoformans 9
18955539 10.1128/aac.01216-08 Cryptococcus bacillisporus 9

Data from ChEMBL 36 via Core Engine