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

Stem definition	Drug id	CAS RN
uracil type antineoplastics	26	51-21-8

Description:

Molecule	Description
Molfile Inchi Smiles Synonyms: 5-fluorouracil adrucil fluoroblastin fluorouracil 5-FU	A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid. Molecular weight: 130.08 Formula: C4H3FN2O2 CLOGP: -0.58 LIPINSKI: 0 HAC: 4 HDO: 2 TPSA: 58.20 ALOGS: -1.35 ROTB: 0 Status: OFP Legend: OFP - off patent OFM - off market ONP - on patent

Molecule

Description

Molfile Inchi Smiles

Synonyms:

5-fluorouracil
adrucil
fluoroblastin
fluorouracil
5-FU

A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.

Molecular weight: 130.08
Formula: C4H3FN2O2
CLOGP: -0.58
LIPINSKI: 0
HAC: 4
HDO: 2
TPSA: 58.20
ALOGS: -1.35
ROTB: 0

Status: OFP

Legend:
OFP - off patent
OFM - off market
ONP - on patent

Drug dosage:

None

ADMET properties:

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Property	Value	Reference
MRTD (Maximum Recommended Therapeutic Daily Dose)	92.25 µM/kg/day	Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
EoM (Fraction excreted unchanged in urine)	5 %	Benet LZ, Broccatelli F, Oprea TI
BA (Bioavailability)	28 %	Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
CL (Clearance)	26 mL/min/kg	Lombardo F, Berellini G, Obach RS
BDDCS (Biopharmaceutical Drug Disposition Classification System)	1	Benet LZ, Broccatelli F, Oprea TI
fu (Fraction unbound in plasma)	0.64 %	Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution)	0.23 L/kg	Lombardo F, Berellini G, Obach RS
t_half (Half-life)	0.12 hours	Lombardo F, Berellini G, Obach RS
S (Water solubility)	0.01 mg/mL	Bocci G, Oprea TI, Benet LZ

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Approvals:

Date	Agency	Company	Orphan
April 25, 1962	FDA	SPECTRUM PHARMS
Sept. 21, 2018	PMDA	Kyowa Hakko Kirin Co., Ltd.

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
Neutropenia	2100.75	13.66	1770	80901	173235	63233116
Febrile neutropenia	1119.22	13.66	1048	81623	117401	63288950
Mucosal inflammation	1072.96	13.66	701	81970	46227	63360124
Neuropathy peripheral	1043.75	13.66	990	81681	112677	63293674
Diarrhoea	778.91	13.66	2361	80310	713005	62693346
Disease progression	756.74	13.66	864	81807	121894	63284457
Thrombocytopenia	654.19	13.66	891	81780	150266	63256085
Palmar-plantar erythrodysaesthesia syndrome	595.65	13.66	372	82299	22643	63383708
Leukopenia	589.56	13.66	609	82062	76681	63329670
Neurotoxicity	581.81	13.66	329	82342	16661	63389690

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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
Neutropenia	1326.84	13.79	1858	92381	154920	34707772
Diarrhoea	1041.05	13.79	2830	91409	387082	34475610
Dermatitis acneiform	1007.62	13.79	437	93802	5752	34856940
Neuropathy peripheral	888.05	13.79	1107	93132	82156	34780536
Skin toxicity	772.85	13.79	336	93903	4448	34858244
Mucosal inflammation	745.63	13.79	703	93536	37919	34824773
Disease progression	632.29	13.79	1082	93157	106995	34755697
Stomatitis	623.98	13.79	667	93572	41847	34820845
Arteriospasm coronary	617.23	13.79	259	93980	3123	34859569
Paronychia	513.86	13.79	228	94011	3177	34859515

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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
Neutropenia	3120.86	12.60	3285	151372	284425	79305306
Neuropathy peripheral	2183.34	12.60	1962	152695	139343	79450388
Diarrhoea	1662.32	12.60	4569	150088	875920	78713811
Mucosal inflammation	1612.03	12.60	1265	153392	74315	79515416
Dermatitis acneiform	1504.17	12.60	607	154050	9386	79580345
Disease progression	1478.46	12.60	1803	152854	182559	79407172
Skin toxicity	1138.58	12.60	472	154185	7842	79581889
Thrombocytopenia	1125.52	12.60	1917	152740	263342	79326389
Febrile neutropenia	993.48	12.60	1680	152977	229319	79360412
Palmar-plantar erythrodysaesthesia syndrome	980.27	12.60	676	153981	32458	79557273

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FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

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Source	Code	Description
ATC	L01BC02	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
ATC	L01BC52	ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS ANTINEOPLASTIC AGENTS ANTIMETABOLITES Pyrimidine analogues
CHEBI has role	CHEBI:35221	antimetabolite
CHEBI has role	CHEBI:35610	antineoplastic agents
CHEBI has role	CHEBI:35703	Xenobiotic
CHEBI has role	CHEBI:35705	immunosuppressive agents
CHEBI has role	CHEBI:78298	environmental contaminants
CHEBI has role	CHEBI:132992	radiosensitizing agents
CHEBI has role	CHEBI:25435	mutagens
CHEBI has role	CHEBI:77746	Homo sapiens metabolite

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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
Actinic keratosis	indication	201101007	DOID:8866
Metastasis from malignant tumor of colon	indication	314998002
Malignant tumor of stomach	indication	363349007	DOID:10534
Malignant tumor of colon	indication	363406005	DOID:219
Small intestine cancer	indication	363509000	DOID:10154
Superficial basal cell carcinoma	indication	403914000
Adenocarcinoma of pancreas	indication	700423003	DOID:4074
Metastatic Breast Carcinoma	indication
Carcinoid syndrome	off-label use	35868009
Actinic cheilitis	off-label use	46795000

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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	8.02	acidic

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
Thymidylate synthase	Enzyme	P04818	TYSY_HUMAN	INHIBITOR			WOMBAT-PK	CHEMBL
Multidrug resistance-associated protein 5	Transporter	O15440	MRP5_HUMAN				WOMBAT-PK
ATP-binding cassette sub-family C member 11	Transporter	Q96J66	ABCCB_HUMAN				WOMBAT-PK
Aromatase	Enzyme	P11511	CP19A_HUMAN		IC50	6.20	CHEMBL
Thymidylate synthase	Enzyme		TYSY_MOUSE		IC50	7.70	CHEMBL
Uracil phosphoribosyltransferase	Enzyme		UPP_ECOLI		Ki	4.89	CHEMBL

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External reference:

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ID	Source
URF	PDB_CHEM_ID
002646	NDDF
1421	INN_ID
202632	RXNORM
3127006	SNOMEDCT_US
3385	PUBCHEM_CID
387172005	SNOMEDCT_US
4017806	VUID
4017806	VANDF
4694	MMSL

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Pharmaceutical products:

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Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Carac	HUMAN PRESCRIPTION DRUG LABEL	1	0187-5200	CREAM	5 mg	TOPICAL	NDA	24 sections
Efudex	HUMAN PRESCRIPTION DRUG LABEL	1	0187-3202	SOLUTION	0.50 g	TOPICAL	NDA	2 sections
Efudex	HUMAN PRESCRIPTION DRUG LABEL	1	0187-3202	SOLUTION	0.50 g	TOPICAL	NDA	2 sections
Efudex	HUMAN PRESCRIPTION DRUG LABEL	1	0187-3203	SOLUTION	1.25 g	TOPICAL	NDA	2 sections
Efudex	HUMAN PRESCRIPTION DRUG LABEL	1	0187-3203	SOLUTION	1.25 g	TOPICAL	NDA	2 sections
Efudex	HUMAN PRESCRIPTION DRUG LABEL	1	0187-3204	CREAM	2 g	TOPICAL	NDA	2 sections
Efudex	HUMAN PRESCRIPTION DRUG LABEL	1	0187-3204	CREAM	2 g	TOPICAL	NDA	2 sections
Fluoroplex	HUMAN PRESCRIPTION DRUG LABEL	1	16110-812	CREAM	10 mg	TOPICAL	NDA	23 sections
Fluoroplex	HUMAN PRESCRIPTION DRUG LABEL	1	16110-812	CREAM	10 mg	TOPICAL	NDA	23 sections
Fluorouracil	HUMAN PRESCRIPTION DRUG LABEL	1	0378-4791	CREAM	5 mg	TOPICAL	NDA authorized generic	19 sections

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