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
- External Links
- ChemSpider
- 29369350
- Predicted Properties
Property Value Source Water Solubility 1.18 mg/mL ALOGPS logP 1.41 ALOGPS logP 0.53 Chemaxon logS -2.7 ALOGPS pKa (Strongest Acidic) 8 Chemaxon pKa (Strongest Basic) 9.93 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 12 Chemaxon Hydrogen Donor Count 6 Chemaxon Polar Surface Area 206.07 Å2 Chemaxon Rotatable Bond Count 10 Chemaxon Refractivity 134.59 m3·mol-1 Chemaxon Polarizability 53.84 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon