Details of the Drug

General Information of Drug (ID: DM13VTW)

Drug Name
Flucytosine
Synonyms
Alcobon; Ancobon; Ancotil; Ancotyl; Flucitosina; Flucystine; Flucytosin; Flucytosinum; Flucytosone; Fluocytosine; Fluorcytosine; Fluorocytosine; Flucitosina [DCIT]; F0321; LT00771985; Ancobon (TN); Flucytosinum [INN-Latin]; GL663142 & 5FC; Ro 2-9915; Ro 29915 E/265601; Ro-2-9915; Flucytosine (JP15/USP/INN); Flucytosine [USAN:INN:BAN:JAN]; Cytosine, 5-fluoro-(6CI,7CI,8CI); GL663142 & 4-Amino-5-fluoropyrimidin-2(1H)-one; 2(1H)-Pyrimidinone, 4-amino-5-fluoro-); 2-Hydroxy-4-amino-5-fluoropyrimidine; 4-Amino-5-fluoro-2(1H)-pyrimidinone; 4-Amino-5-fluoro-2-hydroxypyrimidine; 4-Amino-5-fluoro-2-hyroxypyrimidine; 4-Amino-5-fluoropyrimidin-2(1H)-one; 5-FC; 5-Flucytosine; 5-Fluorocystosine; 5-Fluorocytosin; 5-Fluorocytosine; 5-Fluorocytosine-6-3H; 5-Flurocytosine; 5-fluoro cytosine; 5987P; 6-Amino-2-oxo-5-fluoropyrimidine; 6-amino-5-fluoro-1H-pyrimidin-2-one; 9074P
Indication
Disease Entry ICD 11 Status REF
Cryptococcal meningitis N.A. Approved [1]
Endocarditis BB40-BA42 Approved [2]
Therapeutic Class
Antifungal Agents
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 129.09
Logarithm of the Partition Coefficient (xlogp) -0.9
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 3: high solubility and low permeability [3]
Bioavailability
84% of drug becomes completely available to its intended biological destination(s) [4]
Clearance
The drug present in the plasma can be removed from the body at the rate of 2 mL/min/kg [5]
Elimination
99% of drug is excreted from urine in the unchanged form [3]
Half-life
The concentration or amount of drug in body reduced by one-half in 2.4 - 4.8 hours [5]
Metabolism
The drug is metabolized via the gut bacteria or by the fungal targets to 5-fluorouracil (the active metabolite) []
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 1161.94055 micromolar/kg/day [6]
Unbound Fraction
The unbound fraction of drug in plasma is 1% [5]
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 0.68 L/kg [5]
Water Solubility
The ability of drug to dissolve in water is measured as 15 mg/mL [3]
Adverse Drug Reaction (ADR)
ADR Term Variation Related DOT DOT ID REF
Bone marrow failure Not Available DPYD OTWRF2NR [7]
Chemical Identifiers
Formula
C4H4FN3O
IUPAC Name
6-amino-5-fluoro-1H-pyrimidin-2-one
Canonical SMILES
C1=NC(=O)NC(=C1F)N
InChI
InChI=1S/C4H4FN3O/c5-2-1-7-4(9)8-3(2)6/h1H,(H3,6,7,8,9)
InChIKey
XRECTZIEBJDKEO-UHFFFAOYSA-N
Cross-matching ID
PubChem CID
3366
ChEBI ID
CHEBI:5100
CAS Number
2022-85-7
DrugBank ID
DB01099
TTD ID
D0S5WG
INTEDE ID
DR2287
ACDINA ID
D00281
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Candida Thymidylate synthase (Candi TMP1) TTU6BFZ TYSY_CANAL Inhibitor [2]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Apoptosis regulator Bcl-2 (BCL2) OT9DVHC0 BCL2_HUMAN Gene/Protein Processing [8]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [8]
Dihydropyrimidine dehydrogenase (DPYD) OTWRF2NR DPYD_HUMAN Drug Response [7]
E3 ubiquitin-protein ligase Mdm2 (MDM2) OTOVXARF MDM2_HUMAN Gene/Protein Processing [8]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Flucytosine (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Ocrelizumab DMEZ2KH Moderate Additive immunosuppressive effects by the combination of Flucytosine and Ocrelizumab. Multiple sclerosis [8A40] [9]
Omacetaxine mepesuccinate DMPU2WX Moderate Additive myelosuppressive effects by the combination of Flucytosine and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [10]
Valganciclovir DMS2IUH Moderate Increased risk of nephrotoxicity by the combination of Flucytosine and Valganciclovir. Virus infection [1A24-1D9Z] [11]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Allura red AC dye E00338 33258 Colorant
Butylparaben E00142 7184 Antimicrobial preservative
FD&C blue no. 1 E00263 19700 Colorant
methylparaben E00149 7456 Antimicrobial preservative
Propyl 4-hydroxybenzoate E00141 7175 Antimicrobial preservative
Quinoline yellow WS E00309 24671 Colorant
Sodium lauryl sulfate E00464 3423265 Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Sunset yellow FCF E00255 17730 Colorant
Beta-D-lactose E00099 6134 Diluent; Dry powder inhaler carrier; Lyophilization aid
Ferric hydroxide oxide yellow E00539 23320441 Colorant
Ferrosoferric oxide E00231 14789 Colorant
Lactose monohydrate E00393 104938 Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate E00208 11177 lubricant
Potassium hydroxide E00233 14797 Alkalizing agent
Povidone E00667 Not Available Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Silicon dioxide E00670 Not Available Anticaking agent; Opacifying agent; Viscosity-controlling agent
Sodium hydroxide E00234 14798 Alkalizing agent
Sodium propionate E00445 2723816 Antimicrobial preservative
Talc E00520 16211421 Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide E00322 26042 Coating agent; Colorant; Opacifying agent
Water E00035 962 Solvent
⏷ Show the Full List of 21 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Flucytosine 250 mg capsule 250 mg Oral Capsule Oral
Flucytosine 500 mg capsule 500 mg Oral Capsule Oral
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 Flucytosine FDA Label
2 Antifungal agents: mode of action in yeast cells. Rev Esp Quimioter. 2006 Jun;19(2):130-9.
3 BDDCS applied to over 900 drugs
4 Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
5 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
6 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
7 ADReCS-Target: target profiles for aiding drug safety research and application. Nucleic Acids Res. 2018 Jan 4;46(D1):D911-D917. doi: 10.1093/nar/gkx899.
8 Mechanisms of thymidine kinase/ganciclovir and cytosine deaminase/ 5-fluorocytosine suicide gene therapy-induced cell death in glioma cells. Oncogene. 2005 Feb 10;24(7):1231-43. doi: 10.1038/sj.onc.1208290.
9 Product Information. Ocrevus (ocrelizumab). Genentech, South San Francisco, CA.
10 Product Information. Synribo (omacetaxine). Teva Pharmaceuticals USA, North Wales, PA.
11 Cerner Multum, Inc. "Australian Product Information.".