doxorubicin   

GtoPdb Ligand ID: 7069

Synonyms: Adriamycin® | Caelyx® (liposomal doxorubicin) | Doxil® | doxorubicin hydrochloride
doxorubicin is an approved drug (FDA (1974), EMA (1996))
Comment: Doxorubicin is an anthracycline type anti-neoplastic drug.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 9
Hydrogen bond donors 6
Rotatable bonds 5
Topological polar surface area 206.07
Molecular weight 543.17
XLogP -0.04
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
Canonical SMILES OCC(=O)C1(O)CC(OC2CC(N)C(C(O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
Isomeric SMILES OCC(=O)[C@@]1(O)C[C@H](O[C@H]2C[C@H](N)[C@@H]([C@@H](O2)C)O)c2c(C1)c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2OC
InChI InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChI Key AOJJSUZBOXZQNB-TZSSRYMLSA-N
Bioactivity Comments
We have been unable to find publicly available affinity data for this drug at its proposed molecular target to substantiate its MMOA, and have therefore not tagged a primary drug target.
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DNA topoisomerase II alpha Hs Inhibitor Inhibition 6.0 pIC50 - 1
pIC50 6.0 (IC50 1x10-6 M) [1]
Description: In vitro inhibition of DNA relaxation and decatenation activities in a topoisomerase extract from human placenta.