doxorubicin   Click here for help

GtoPdb Ligand ID: 7069

Synonyms: Adriamycin® | Caelyx® (liposomal doxorubicin) | Doxil® | doxorubicin hydrochloride
Approved drug PDB Ligand
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
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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
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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
Classification Click here for help
Compound class Natural product or derivative
Approved drug? Yes (FDA (1974), EMA (1996))
WHO Essential Medicine WHO Essential Medicines List (EML) (23rd List, 2023). Access PDF version.
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IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
3005 doxorubicin
Synonyms Click here for help
Adriamycin® | Caelyx® (liposomal doxorubicin) | Doxil® | doxorubicin hydrochloride
Database Links Click here for help
CAS Registry No. 23214-92-8
ChEMBL Ligand CHEMBL53463
DrugBank Ligand DB00997
DrugCentral Ligand 960
GtoPdb PubChem SID 178103648
Immunopaedia Search doxorubicin
PubChem CID 31703
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UniChem Compound Search for chemical match using the InChIKey AOJJSUZBOXZQNB-TZSSRYMLSA-N
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Wikipedia Doxorubicin