Doxorubicin citrateProduct ingredient for Doxorubicin

Name
Doxorubicin citrate
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
DBSALT002287
Structure
Synonyms
Not Available
UNII
AJQ2ZNG2WL
CAS Number
111266-55-8
Weight
Average: 735.648
Monoisotopic: 735.201063355
Chemical Formula
C33H37NO18
InChI Key
INEKNBHAPBIAFK-RUELKSSGSA-N
InChI
InChI=1S/C27H29NO11.C6H8O7/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;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/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; 2-hydroxypropane-1,2,3-tricarboxylic acid
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.COC1=C2C(=O)C3=C(O)C4=C(C[C@](O)(C[C@@H]4O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)C(=O)CO)C(O)=C3C(=O)C2=CC=C1
ChemSpider
29369350
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 Count10Chemaxon
Refractivity134.59 m3·mol-1Chemaxon
Polarizability53.84 Å3Chemaxon
Number of Rings5Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon