flucytosine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1188 2022-85-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • flucytosine
  • Ro-2-9915
  • Ro 2-9915
  • ancotil
  • ancobon
  • 5-fluorocytosine
A fluorinated cytosine analog that is used as an antifungal agent.
  • Molecular weight: 129.09
  • Formula: C4H4FN3O
  • CLOGP: -1.64
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 2
  • TPSA: 67.48
  • ALOGS: -1.78
  • ROTB: 0
  • Status: OFP
    • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
10 g O
10 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 15 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 99 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 1161.94 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 84 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.68 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 2 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 1 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 26, 1971 FDA VALEANT

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome 114.43 50.87 23 526 5493 50599082

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome 148.43 46.81 38 1055 7764 29565670
Drug ineffective 97.47 46.81 90 1003 363080 29210354
Disseminated cryptococcosis 66.96 46.81 14 1079 1164 29572270
Cerebral cyst 59.69 46.81 10 1083 246 29573188
Meningitis cryptococcal 58.90 46.81 14 1079 2086 29571348
Intracranial pressure increased 56.59 46.81 15 1078 3470 29569964
Cryptococcosis 54.67 46.81 13 1080 1939 29571495
Muscle abscess 53.41 46.81 10 1083 470 29572964

FDA Adverse Event Reporting System (Geriatric)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Immune reconstitution inflammatory syndrome 252.96 41.07 60 1664 12410 64484598
Drug ineffective 146.63 41.07 142 1582 840105 63656903
Cryptococcosis 81.15 41.07 18 1706 2737 64494271
Disseminated cryptococcosis 73.32 41.07 15 1709 1552 64495456
Meningitis cryptococcal 63.57 41.07 15 1709 2994 64494014
Cerebral cyst 60.07 41.07 10 1714 330 64496678
Intracranial pressure increased 59.95 41.07 17 1707 6972 64490036
Muscle abscess 50.36 41.07 10 1714 889 64496119
Liver transplant failure 46.44 41.07 7 1717 120 64496888

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC D01AE21 DERMATOLOGICALS
ANTIFUNGALS FOR DERMATOLOGICAL USE
ANTIFUNGALS FOR TOPICAL USE
Other antifungals for topical use
ATC J02AX01 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
ANTIMYCOTICS FOR SYSTEMIC USE
Other antimycotics for systemic use
FDA EXT N0000175459 Nucleoside Analog
FDA EPC N0000175467 Nucleoside Analog Antifungal
CHEBI has role CHEBI:50266 Prodrugs
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D000963 Antimetabolites
MeSH PA D009676 Noxae

Drug Use | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Systemic Cryptococcosis Treatment Adjunct indication
Synergy for Candida Infection indication
Systemic Candidiasis Treatment Adjunct indication
Candidal Urinary Tract Infection indication
Synergy for Cryptococcal Infection indication
Chromoblastomycosis off-label use 187079000
Hypokalemia contraindication 43339004
Leukopenia contraindication 84828003 DOID:615
Kidney disease contraindication 90708001 DOID:557
Radiation oncology AND/OR radiotherapy contraindication 108290001
Liver function tests abnormal contraindication 166603001
Disease of liver contraindication 235856003 DOID:409
Aplastic anemia due to drugs contraindication 267527002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Bone marrow depression contraindication 307762000
Breastfeeding (mother) contraindication 413712001
Granulocytopenic disorder contraindication 417672002




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 10.56 acidic
pKa2 2.7 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
5-hydroxytryptamine receptor 2A GPCR IC50 5.10 WOMBAT-PK
Thymidylate synthase Enzyme INHIBITOR CHEMBL CHEMBL
Thymidylate synthase Enzyme INHIBITOR DRUGBANK CHEMBL
ATP-dependent molecular chaperone HSP82 Cytosolic other EC50 6.15 WOMBAT-PK

External reference:

IDSource
4017792 VUID
N0000146153 NUI
D00323 KEGG_DRUG
4017792 VANDF
C0016278 UMLSCUI
CHEBI:5100 CHEBI
1LD PDB_CHEM_ID
CHEMBL1463 ChEMBL_ID
3366 PUBCHEM_CID
DB01099 DRUGBANK_ID
D005437 MESH_DESCRIPTOR_UI
2729 INN_ID
D83282DT06 UNII
227633 RXNORM
186215 MMSL
4733 MMSL
525 MMSL
d00038 MMSL
002898 NDDF
28506006 SNOMEDCT_US
387155003 SNOMEDCT_US
CHEMBL170073 ChEMBL_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0427 CAPSULE 250 mg ORAL ANDA 22 sections
flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0054-0428 CAPSULE 500 mg ORAL ANDA 22 sections
ANCOBON HUMAN PRESCRIPTION DRUG LABEL 1 0187-3554 CAPSULE 250 mg ORAL NDA 23 sections
ANCOBON HUMAN PRESCRIPTION DRUG LABEL 1 0187-3554 CAPSULE 250 mg ORAL NDA 23 sections
ANCOBON HUMAN PRESCRIPTION DRUG LABEL 1 0187-3555 CAPSULE 500 mg ORAL NDA 23 sections
ANCOBON HUMAN PRESCRIPTION DRUG LABEL 1 0187-3555 CAPSULE 500 mg ORAL NDA 23 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6834 CAPSULE 250 mg ORAL ANDA 20 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6834 CAPSULE 250 mg ORAL ANDA 20 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6835 CAPSULE 500 mg ORAL ANDA 20 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6835 CAPSULE 500 mg ORAL ANDA 20 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 40032-770 CAPSULE 500 mg ORAL ANDA 18 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 40032-771 CAPSULE 250 mg ORAL ANDA 18 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 42494-339 CAPSULE 250 mg ORAL NDA authorized generic 23 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 42494-340 CAPSULE 500 mg ORAL NDA authorized generic 23 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 42794-009 CAPSULE 250 mg ORAL ANDA 14 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 42794-010 CAPSULE 500 mg ORAL ANDA 14 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 43386-770 CAPSULE 500 mg ORAL ANDA 18 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 43386-771 CAPSULE 250 mg ORAL ANDA 18 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 50268-331 CAPSULE 250 mg ORAL ANDA 18 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 50268-332 CAPSULE 500 mg ORAL ANDA 18 sections
FLUCYTOSINE Human Prescription Drug Label 1 59651-331 CAPSULE 250 mg ORAL ANDA 21 sections
FLUCYTOSINE Human Prescription Drug Label 1 59651-331 CAPSULE 250 mg ORAL ANDA 21 sections
FLUCYTOSINE Human Prescription Drug Label 1 59651-332 CAPSULE 500 mg ORAL ANDA 21 sections
FLUCYTOSINE Human Prescription Drug Label 1 59651-332 CAPSULE 500 mg ORAL ANDA 21 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 60687-352 CAPSULE 250 mg ORAL ANDA 19 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 60687-363 CAPSULE 500 mg ORAL ANDA 19 sections
FLUCYTOSINE HUMAN PRESCRIPTION DRUG LABEL 1 60687-599 CAPSULE 250 mg ORAL ANDA 21 sections
FLUCYTOSINE HUMAN PRESCRIPTION DRUG LABEL 1 60687-610 CAPSULE 500 mg ORAL ANDA 21 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 63629-2147 CAPSULE 250 mg ORAL NDA authorized generic 23 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 63629-2147 CAPSULE 250 mg ORAL NDA authorized generic 23 sections