flucytosine 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AXL,BRAF,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EIF2AK3,ERBB2,FLT3,GRK2,ITK,JAK1,MAP3K21,MAP4K1,MAPK7,NTRK1,NTRK2,PDK1,PDK2,PRKCD,PRKDC,SIK2,SIK3,STK33,TEK,ULK1 29
kinase-selectivity-class ACVR2A,ACVR2B,AXL,CDK9,GRK2,GSK3A,MAP2K3,MAP3K14,MAP3K21,MAPK7,SIK2,STK33,TEK 13
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 146.76 55.39 29 861 6990 90620567
Drug ineffective 145.76 55.39 113 777 1384185 89243372
Cryptococcosis 82.40 55.39 14 876 1457 90626100
Meningitis cryptococcal 59.65 55.39 11 879 1822 90625735

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
Drug ineffective 285.51 43.76 237 1871 629960 41989267
Immune reconstitution inflammatory syndrome 272.38 43.76 69 2039 10074 42609153
Meningitis cryptococcal 101.23 43.76 25 2083 3258 42615969
Cryptococcosis 81.84 43.76 21 2087 3190 42616037
Disseminated cryptococcosis 81.81 43.76 19 2089 1906 42617321
Ischaemic stroke 57.49 43.76 26 2082 22207 42597020
Intracranial pressure increased 56.36 43.76 17 2091 4657 42614570
Cerebral cyst 55.01 43.76 10 2098 295 42618932
Cerebral ventricle collapse 48.79 43.76 8 2100 126 42619101

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
Drug ineffective 428.92 39.15 343 2769 1520197 109065990
Immune reconstitution inflammatory syndrome 424.76 39.15 97 3015 16129 110570058
Cryptococcosis 161.09 39.15 35 3077 4596 110581591
Meningitis cryptococcal 149.02 39.15 33 3079 4729 110581458
Disseminated cryptococcosis 114.68 39.15 24 3088 2633 110583554
Drug ineffective for unapproved indication 68.17 39.15 40 3072 102798 110483389
Ischaemic stroke 65.61 39.15 29 3083 41234 110544953
Acute kidney injury 64.55 39.15 84 3028 635346 109950841
Renal impairment 61.13 39.15 47 3065 188398 110397789
Intracranial pressure increased 60.40 39.15 19 3093 10516 110575671
Renal failure 57.60 39.15 49 3063 226525 110359662
Cerebral cyst 55.81 39.15 10 3102 484 110585703
Osteomyelitis fungal 50.64 39.15 9 3103 416 110585771
Cerebral ventricle collapse 50.63 39.15 8 3104 179 110586008
Muscle abscess 44.94 39.15 10 3102 1459 110584728
Liver transplant failure 44.46 39.15 7 3105 153 110586034
Central nervous system lesion 42.06 39.15 16 3096 15537 110570650
Cerebral infarction 41.97 39.15 23 3089 51815 110534372
Brain oedema 40.41 39.15 19 3093 31079 110555108
Drug resistance 40.16 39.15 23 3089 56351 110529836
Pneumonia cryptococcal 39.49 39.15 10 3102 2532 110583655

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
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000935 Antifungal Agents
MeSH PA D000963 Antimetabolites
CHEBI has role CHEBI:33281 antimicrobial agent
CHEBI has role CHEBI:35441 antiinfective agent
CHEBI has role CHEBI:35610 antineoplastic agent
CHEBI has role CHEBI:35674 antihypertensive agent
CHEBI has role CHEBI:50266 prodrug

Related Drugs by ATC class:

D01AE Other antifungals for topical use 23 drugs
2-(4-chlorphenoxy)-ethanolamorolfinebromochlorosalicylanilidebutenafinechlorphenesin carbamateciclopiroxdimazoleethyl hydroxybenzoatehaloproginliranaftatemethylrosanilinenaftifine show all 23 →
J02AX Other antimycotics for systemic use 5 drugs
anidulafungincaspofunginibrexafungerpmicafunginrezafungin

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6834 CAPSULE 250 mg ORAL ANDA 19 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 0904-6835 CAPSULE 500 mg ORAL ANDA 19 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 23155-860 CAPSULE 250 mg ORAL ANDA 13 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 23155-860 CAPSULE 250 mg ORAL ANDA 13 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 23155-861 CAPSULE 500 mg ORAL ANDA 13 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 23155-861 CAPSULE 500 mg ORAL ANDA 13 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 42385-983 CAPSULE 250 mg ORAL ANDA 12 sections
Flucytosine Human Prescription Drug Label 1 42385-984 CAPSULE 500 mg ORAL ANDA 12 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 59651-332 CAPSULE 500 mg ORAL ANDA 21 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 64380-897 CAPSULE 250 mg ORAL ANDA 13 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 64380-898 CAPSULE 500 mg ORAL ANDA 13 sections
Flucytosine HUMAN PRESCRIPTION DRUG LABEL 1 68151-0084 CAPSULE 250 mg ORAL ANDA 14 sections