Search type

Query format

Minimum Tanimoto similarity

Fingerprint

Tox | Related Drugs | BioActivity |

Stem definition	Drug id	CAS RN
	1188	2022-85-7

Description:

Molecule	Description
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

Molecule

Description

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:

Dose	Unit	Route
10	g	O
10	g	P

ADMET properties:

Property	Value	Reference
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):

Property	Description	Value	Unit	Confidence	Similarity
pfas-class	PFAS structural alert (1 = True, 0 = False)	0

Approvals:

Date	Agency	Company	Orphan
Nov. 26, 1971	FDA	VALEANT

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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)-ethanol amorolfine bromochlorosalicylanilide butenafine chlorphenesin carbamate ciclopirox dimazole ethyl hydroxybenzoate haloprogin liranaftate methylrosaniline naftifine show all 23 →

J02AX Other antimycotics for systemic use 5 drugs

anidulafungin caspofungin ibrexafungerp micafungin rezafungin

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

Disease	Relation	SNOMED_ID	DOID
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 level	Dissociation constant	Type (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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
5-hydroxytryptamine receptor 2A	GPCR	P28223	5HT2A_HUMAN		IC50	5.10	WOMBAT-PK
Thymidylate synthase	Enzyme		TYSY_CRYNB	INHIBITOR			CHEMBL	CHEMBL
Thymidylate synthase	Enzyme		TYSY_CANAL	INHIBITOR			DRUGBANK	CHEMBL
ATP-dependent molecular chaperone HSP82	Cytosolic other		HSP82_YEAST		EC50	6.15	WOMBAT-PK

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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