CAPECITABINE

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Trade Names	CAPECITABINE XELODA
Synonyms	Capecitabine Capecitabine accord Capecitabine medac Capecitabine sun Capecitabine teva Capecitibine Capecytabine Capiibine Captabin Ecansya NSC-759853 RO 09-1978/000 RO-09-1978000 RO-091978000 Xeloda
Status
Molecule Category	UNKNOWN
ATC	L01BC06
UNII	6804DJ8Z9U
EPA CompTox	DTXSID3046451


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	GAGWJHPBXLXJQN-UORFTKCHSA-N
Smiles	CCCCCOC(=O)Nc1nc(=O)n([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)cc1F
InChI	InChI=1S/C15H22FN3O6/c1-3-4-5-6-24-15(23)18-12-9(16)7-19(14(22)17-12)13-11(21)10(20)8(2)25-13/h7-8,10-11,13,20-21H,3-6H2,1-2H3,(H,17,18,22,23)/t8-,10-,11-,13-/m1/s1

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C15H22FN3O6
Molecular Weight	359.35
AlogP	0.76
Hydrogen Bond Acceptor	8.0
Hydrogen Bond Donor	3.0
Number of Rotational Bond	6.0
Polar Surface Area	122.91
Molecular species	NEUTRAL
Aromatic Rings	1.0
Heavy Atoms	25.0

Bioactivity

Mechanism of Action	Action	Reference
DNA inhibitor	INHIBITOR	PubMed DailyMed


Protein: Thymidylate synthase Description: Thymidylate synthase Organism : Homo sapiens P04818 ENSG00000176890

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Hydrolase	-	-	-	-	20

Assay Description	Organism	Bioactivity	Reference
Cytotoxicity against human RKOp27 cells by MTT assay	Homo sapiens	4.33 nM
Inhibition of human FAAH at 1 uM	Homo sapiens	19.86 %
Cytotoxicity against human NCI-H69 cells after 3 days MTT assay	Homo sapiens	300.0 ug.mL-1
Cytotoxicity against human PZ-HPV-7 cells after 3 days MTT assay	Homo sapiens	160.0 ug.mL-1
Cytotoxicity against human MCF7 cells after 3 days MTT assay	Homo sapiens	710.0 ug.mL-1
Cytotoxicity against human HeLa cells after 3 days MTT assay	Homo sapiens	50.0 ug.mL-1
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of Caco-2 cells at 10 uM after 48 hours by high content imaging	Homo sapiens	11.73 %
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	-6.93 %		SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate	Severe acute respiratory syndrome coronavirus 2	5.473 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.06 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.02 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.02 %		Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging	Chlorocebus sabaeus	-0.06 %

Related Entries

Cross References

Resources	Reference
ChEBI	31348
ChEMBL	CHEMBL1773
DrugBank	DB01101
DrugCentral	480
FDA SRS	6804DJ8Z9U
Human Metabolome Database	HMDB0015233
Guide to Pharmacology	6799
KEGG	C12650
PharmGKB	PA448771
PubChem	60953
SureChEMBL	SCHEMBL8153
ZINC	ZINC000003806413

CONTENTS

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).