ContaminantDB: Flucytosine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:28:21 UTC

Update Date

2026-05-14 16:57:49 UTC

Accession Number

CHEM002344

Identification

Common Name

Flucytosine

Class

Small Molecule

Description

Flucytosine is only found in individuals that have used or taken this drug. It is a fluorinated cytosine analog that is used as an antifungal agent. [PubChem]Although the exact mode of action is unknown, it has been proposed that flucytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase.

Contaminant Sources

HMDB Contaminants - Urine
STOFF IDENT Compounds
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Amine
Antifungal Agent
Antimetabolite
Drug
Metabolite
Organic Compound
Organofluoride
Synthetic Compound

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
5-FC	ChEBI
5-Fluorocystosine	ChEBI
5-Fluorocytosine	ChEBI
Ancobon	ChEBI
Ancotil	ChEBI
Flucytosina	ChEBI
Flucytosinum	ChEBI
5-Fluorocytosin	HMDB
5-Flurocytosine	HMDB
Flucytosin	HMDB
Fluocytosine	HMDB
Fluorcytosine	HMDB
Dermatech brand OF flucytosine	HMDB
Roche brand OF flucytosine	HMDB
Alcobon	HMDB
CSP Brand OF flucytosine	HMDB
ICN pharmaceuticals brand OF flucytosine	HMDB
Allphar brand OF flucytosine	HMDB

Chemical Formula

C₄H₄FN₃O

Average Molecular Mass

129.093 g/mol

Monoisotopic Mass

129.034 g/mol

CAS Registry Number

2022-85-7

IUPAC Name

4-amino-5-fluoro-1,2-dihydropyrimidin-2-one

Traditional Name

flucytosine

SMILES

NC1=C(F)C=NC(=O)N1

InChI Identifier

InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)

InChI Key

XRECTZIEBJDKEO-UHFFFAOYSA-N

Chemical Taxonomy

Description

belongs to the class of organic compounds known as halopyrimidines. These are aromatic compounds containing a halogen atom linked to a pyrimidine ring. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrimidines and pyrimidine derivatives

Direct Parent

Halopyrimidines

Alternative Parents

Substituents

Aminopyrimidine
Halopyrimidine
Pyrimidone
Aryl fluoride
Aryl halide
Hydropyrimidine
Heteroaromatic compound
Azacycle
Amine
Primary amine
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Organic nitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:5100 )
aminopyrimidine (CHEBI:5100 )
pyrimidone (CHEBI:5100 )
nucleoside analogue (CHEBI:5100 )
pyrimidine antifungal drug (CHEBI:5100 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antifungal agent

Biological Roles

antifungal agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	296°C
Boiling Point	Not Available
Solubility	1.5E+004 mg/L (at 25°C)

Predicted Properties

Property	Value	Source
Water Solubility	1.92 g/L	ALOGPS
logP	-0.24	ALOGPS
logP	-0.95	ChemAxon
logS	-1.8	ALOGPS
pKa (Strongest Acidic)	8.16	ChemAxon
pKa (Strongest Basic)	1.06	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	67.48 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	38.22 m³·mol⁻¹	ChemAxon
Polarizability	9.97 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004i-5900000000-62cd06162d248f459f77	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002r-9400000000-acd1b588a4052f6fc2dd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-002r-9400000000-a4e7dd3c4c886861c0ea	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-9200000000-b3fb9cad9c2b375b08c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-9100000000-11fb61e55faa71878d87	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-9000000000-13935b6ab4a3d8adaa08	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-000i-9000000000-cd981efe159dd44555f4	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-a228aa7f5ecaf516455f	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-001i-0900000000-ec5b7f7d9f3c75649dc2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF , positive	splash10-03e9-0900000000-15df2a7b685c4dd4ca17	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-7110f8accb80c700a2a5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-89290e0501d587938afb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-7248b6df062077397b61	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-1900000000-df83e87e1bcbc8311be6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-01q9-3900000000-42649a5ceee8a4619fc3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-08gr-9800000000-8cb7a586d34dd7913561	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0900000000-973610269bb11b2539b9	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-f98fd5ea350e99bcbb13	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 0V, Positive	splash10-001i-0900000000-f0b5eaeae6c5f2a922c3	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 30V, Positive	splash10-0bti-9300000000-c7808ed54724dbe0b4db	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-001i-0900000000-3daf46ab201d0847e716	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-4900000000-08676c044da012e58509	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0007-9000000000-fc78e7fb18ada3e97d98	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-2900000000-d0b2503a7f5865ac1efd	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00nu-9100000000-ee11917ba44963a8210b	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-e5c5889e9b5cd0c8cae9	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum

Toxicity Profile

Route of Exposure

Rapidly and virtually completely absorbed following oral administration. Bioavailability 78% to 89%.

Mechanism of Toxicity

Although the exact mode of action is unknown, it has been proposed that flucytosine acts directly on fungal organisms by competitive inhibition of purine and pyrimidine uptake and indirectly by intracellular metabolism to 5-fluorouracil. Flucytosine enters the fungal cell via cytosine permease; thus, flucytosine is metabolized to 5-fluorouracil within fungal organisms. The 5-fluorouracil is extensively incorporated into fungal RNA and inhibits synthesis of both DNA and RNA. The result is unbalanced growth and death of the fungal organism. It also appears to be an inhibitor of fungal thymidylate synthase.

Metabolism

Flucytosine is deaminated, possibly by gut bacteria or by the fungal targets, to 5-fluorouracil, the active metabolite. Route of Elimination: Flucytosine is excreted via the kidneys by means of glomerular filtration without significant tubular reabsorption. A small portion of the dose is excreted in the feces. Half Life: 2.4 to 4.8 hours.

Toxicity Values

LD50: 15 gm/kg (Oral, Rat) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

For the treatment (in combination with amphotericin B) of serious infections caused by susceptible strains of Candida (septicemia, endocarditis and urinary system infections) and/or Cryptococcus (meningitis and pulmonary infections).

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

In the management of overdosage, prompt gastric lavage or the use of an emetic is recommended. Adequate fluid intake should be maintained, by the intravenous route if necessary, since Ancobon is excreted unchanged via the renal tract. The hematologic parameters should be monitored frequently; liver and kidney function should be carefully monitored. Should any abnormalities appear in any of these parameters, appropriate therapeutic measures should be instituted. Since hemodialysis has been shown to rapidly reduce serum concentrations in anuric patients, this method may be considered in the management of overdosage. (5)

Concentrations

Not Available

External Links

DrugBank ID

DB01099

HMDB ID

HMDB0015231

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID