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

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Property	Value	Reference
EoM (Fraction excreted unchanged in urine)	99 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	84 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
t_half (Half-life)	4.20 hours	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	3	Benet LZ, Broccatelli F, Oprea TI
CL (Clearance)	2 mL/min/kg	Lombardo F, Berellini G, Obach RS
S (Water solubility)	15 mg/mL	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
fu (Fraction unbound in plasma)	1 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.68 L/kg	Lombardo F, Berellini G, Obach RS

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Approvals:

Date	Agency	Company	Orphan
Nov. 26, 1971	FDA	VALEANT

FDA Adverse Event Reporting System (Female)

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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	120.09	51.45	24	608	6060	63482330
Drug ineffective	65.07	51.45	64	568	1044701	62443689

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FDA Adverse Event Reporting System (Male)

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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	166.75	44.31	43	1295	8716	34946877
Drug ineffective	157.45	44.31	132	1206	456619	34498974
Meningitis cryptococcal	77.18	44.31	18	1320	2386	34953207
Disseminated cryptococcosis	64.18	44.31	14	1324	1372	34954221
Cerebral cyst	57.10	44.31	10	1328	310	34955283
Cryptococcosis	56.43	44.31	14	1324	2405	34953188
Intracranial pressure increased	54.17	44.31	15	1323	3940	34951653
Muscle abscess	50.50	44.31	10	1328	610	34954983
Liver transplant failure	45.67	44.31	7	1331	92	34955501

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FDA Adverse Event Reporting System (Geriatric)

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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	279.43	41.43	66	2006	13775	79728541
Drug ineffective	219.98	41.43	196	1876	1080717	78661599
Cryptococcosis	104.52	41.43	23	2049	3470	79738846
Meningitis cryptococcal	88.02	41.43	20	2052	3486	79738830
Disseminated cryptococcosis	71.38	41.43	15	2057	1819	79740497
Cerebral cyst	58.03	41.43	10	2062	419	79741897
Intracranial pressure increased	57.48	41.43	17	2055	8305	79734011
Muscle abscess	48.74	41.43	10	2062	1078	79741238
Liver transplant failure	46.63	41.43	7	2065	120	79742196

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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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
CHEBI has role	CHEBI:50266	Prodrugs
FDA EPC	N0000175467	Nucleoside Analog Antifungal
FDA EXT	N0000175459	Nucleoside Analog
MeSH PA	D000890	Anti-Infective Agents
MeSH PA	D000935	Antifungal Agents
MeSH PA	D000963	Antimetabolites
MeSH PA	D009676	Noxae

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

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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

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🐶 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:

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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

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External reference:

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ID	Source
1LD	PDB_CHEM_ID
002898	NDDF
186215	MMSL
227633	RXNORM
2729	INN_ID
28506006	SNOMEDCT_US
3366	PUBCHEM_CID
387155003	SNOMEDCT_US
4017792	VUID
4017792	VANDF

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Pharmaceutical products:

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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	0187-3554	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	0054-0427	CAPSULE	250 mg	ORAL	ANDA	22 sections
flucytosine	HUMAN PRESCRIPTION DRUG LABEL	1	0054-0428	CAPSULE	500 mg	ORAL	ANDA	22 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

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