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Compound Detail

CHEMBL1773

CAPECITABINE
💊 Approved Drug
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💊 Approved Drug
CCCCCOC(=O)Nc1nc(=O)n([C@@H]2O[C@H](C)[C@@H](O)[C@H]2O)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1773
Name CAPECITABINE
Phase Approved
Structure Type MOL
InChI Key GAGWJHPBXLXJQN-UORFTKCHSA-N
Therapeutic ✓ Yes
Active Moiety CHEMBL185

Known Names

Capecitabina Capecitabine Capecitabine accord Capecitabine component of xeliri capecitibine Capecitabine component of xelox Capecitabine medac Capecitabine sun Capecitabine teva Capecitibine Capecytabine Capiibine Captabin +8 more
3
Targets
4
Activities
1
Assay Types
0
PK Parameters
20
Publications
20
Known Names
20
Indications
3
Mechanisms

Molecular Properties

359.4
MW (Da)
0.76
ALogP
8
HBA
3
HBD
122.9
PSA (Ų)
0.64
QED
0
Ro5 Violations
6
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1998
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Oral

Flags

Black Box Warning Prodrug
USAN Stem -citabine
USAN Year 1995

Extended Properties

Molecular Formula C15H22FN3O6
MW 359.35
Aromatic Rings 1
Heavy Atoms 25
NP-Likeness 0.38

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thymidylate synthase inhibitor INHIBITOR Thymidylate synthase ✓ ✓
DNA inhibitor INHIBITOR DNA ✓ ✓
RNA inhibitor INHIBITOR RNA ✓ ✓

Indications

Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Colonic Neoplasms Colonic Neoplasms Colonic Neoplasms Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Neoplasms Neoplasms Stomach Neoplasms Stomach Neoplasms Stomach Neoplasms Stomach Neoplasms Adenocarcinoma Adenocarcinoma Biliary Tract Neoplasms

ATC Classification

L01BC06
capecitabine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 4 meas. best 8.36

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.36 6.86 4.3 2
KG-1
CHEMBL612264
 IC50 5.05 5.05 8900.0 1
HCT-116
CHEMBL394
 IC50 4.47 4.47 34200.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 4.33 nM 8.36 Cytotoxicity against human RKOp27 cells by MTT assay 19345581
NON-PROTEIN TARGET IC50 = 4330.0 nM 5.36 Cytotoxicity against human RKOp27 cells after 3 days by MTT assay 20356655
KG-1 IC50 = 8900.0 nM 5.05 Antiproliferative activity against human KG-1 cells assessed as reduction in cel... 35300092
HCT-116 IC50 = 34200.0 nM 4.47 Antiproliferative activity against human HCT-116 cells assessed as reduction in ... 35300092

Literature References

PubMed DOI Target Context # Activities
- 10.5281/zenodo.13943903 ADMET 89
22796042 10.1016/j.ejmech.2012.06.023 Salmonella typhimurium 20
11814824 10.1016/s0960-894x(01)00782-x Mus musculus 16
34628244 10.1016/j.ejmech.2021.113888 ADMET 14
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
37468498 10.1038/s41467-023-40064-9 Nuclear receptor subfamily 1 group I member 2 3
22796042 10.1016/j.ejmech.2012.06.023 L1210 3
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
19932971 10.1016/j.bmc.2009.10.052 Liver carboxylesterase 1 2
37468498 10.1038/s41467-023-40064-9 Peroxisome proliferator-activated receptor gamma 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
31610375 10.1016/j.ejmech.2019.111728 HCT-116 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 2
12617910 10.1016/s0960-894x(02)01082-x Mus musculus 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine