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.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: doxorubicin

2D Structure
Click here for structure editor
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
Classification
Compound class Natural product or derivative
Approved drug? Yes (FDA (1974), EMA (1996))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name
(8S,10S)-10-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
International Nonproprietary Names
INN number INN
3005 doxorubicin
Synonyms
Adriamycin® | Caelyx® (liposomal doxorubicin) | Doxil® | doxorubicin hydrochloride
Database Links
CAS Registry No. 23214-92-8
ChEBI CHEBI:28748
ChEMBL Ligand CHEMBL53463
DrugBank Ligand DB00997
DrugCentral Ligand 960
GtoPdb PubChem SID 178103648
Immunopaedia Search doxorubicin
PubChem CID 31703
RCSB PDB Ligand DM2
Search Google for chemical match using the InChIKey AOJJSUZBOXZQNB-TZSSRYMLSA-N
Search Google for chemicals with the same backbone AOJJSUZBOXZQNB
Search PubMed clinical trials doxorubicin
Search PubMed titles doxorubicin
Search PubMed titles/abstracts doxorubicin
Search UniChem for chemical match using the InChIKey AOJJSUZBOXZQNB-TZSSRYMLSA-N
Search UniChem for chemicals with the same backbone AOJJSUZBOXZQNB
Wikipedia Doxorubicin