Doxorubicin hydrochlorideProduct ingredient for Doxorubicin

Name
Doxorubicin hydrochloride
Drug Entry
Doxorubicin

Doxorubicin is a cytotoxic anthracycline antibiotic isolated from cultures of Streptomyces peucetius var. caesius along side with daunorubicin, another cytotoxic agent, in 1970.3,39,31 Although they both have aglyconic and sugar moieties, doxorubicin's side chain terminates with a primary alcohol group compared to the methyl group of daunorubicin.39 Although its detailed molecular mechanisms have yet to be understood, doxorubicin is generally thought to exert its effect through DNA intercalation, which eventually leads to DNA damage and the generation of reactive oxygen species.31 Thanks to its efficacy and broad effect, doxorubicin was approved by the FDA in 1974 to treat a variety of cancer, including but not limited to breast, lung, gastric, ovarian, thyroid, non-Hodgkin’s and Hodgkin’s lymphoma, multiple myeloma, sarcoma, and pediatric cancers.1,31,42 However, one of the major side effects of doxorubicin is cardiotoxicity, which excludes patients with poor heart function and requires treatment termination once the maximally tolerated cumulative dose is reached.40

Accession Number
DBSALT000060
Structure
Synonyms
Doxorubicin HCl
UNII
82F2G7BL4E
CAS Number
25316-40-9
Weight
Average: 579.98
Monoisotopic: 579.1507385
Chemical Formula
C27H30ClNO11
InChI Key
MWWSFMDVAYGXBV-RUELKSSGSA-N
InChI
InChI=1S/C27H29NO11.ClH/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;1H/t10-,13-,15-,17-,22+,27-;/m0./s1
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 hydrochloride
SMILES
Cl.[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(O)=C12)C(=O)C1=C(OC)C=CC=C1C3=O)C(=O)CO)O[C@H]1C[C@H](N)[C@H](O)[C@H](C)O1
PubChem Compound
45356759
ChemSpider
391993
ChEBI
31522
ChEMBL
CHEMBL359744
Wikipedia
Doxorubicin
Predicted Properties
PropertyValueSource
Water Solubility1.18 mg/mLALOGPS
logP1.41ALOGPS
logP0.53Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)8Chemaxon
pKa (Strongest Basic)9.93Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count12Chemaxon
Hydrogen Donor Count6Chemaxon
Polar Surface Area206.07 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity134.59 m3·mol-1Chemaxon
Polarizability53.41 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon