Daunorubicin free base
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MedKoo CAT#: 100961

CAS#: 20830-81-3 (free base)

Description: Daunorubicin exhibits cytotoxic activity through topoisomerase-mediated interaction with DNA, thereby inhibiting DNA replication and repair and RNA and protein synthesis.

Chemical Structure

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Daunorubicin free base
CAS# 20830-81-3 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 100961
Name: Daunorubicin free base
CAS#: 20830-81-3 (free base)
Chemical Formula: C27H29NO10
Exact Mass: 527.18
Molecular Weight: 527.526
Elemental Analysis: C, 61.48; H, 5.54; N, 2.66; O, 30.33

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Size Price Availability Quantity
5mg USD 150 Ready to Ship
10mg USD 250 Ready to ship
25mg USD 450 Ready to Ship
50mg USD 750 Ready to Ship
100mg USD 1250 Ready to Ship
200mg USD 2050 Ready to Ship
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Related CAS #: 371770-68-2 (citrate)   23541-50-6 (HCl)   20830-81-3 (free base)  

Synonym: Daunorubicin free base; FI6339; NSC 82151; NSC 83142; RP 13057; Rubidomycin; Rubomycin C; Daunamycin;

IUPAC/Chemical Name: (8S,10S)-8-acetyl-10-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,8,11-trihydroxy-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione

InChi Key: STQGQHZAVUOBTE-OGLJUIQQSA-N

InChi Code: InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16+,17-,22+,27+/m0/s1

SMILES Code: CC([C@](C[C@H]1O[C@@H]2O[C@H]([C@H]([C@H](C2)N)O)C)(CC(C(O)=C3C(C4=C5C(OC)=CC=C4)=O)=C1C(O)=C3C5=O)O)=O

Appearance: Dark Red Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 527.53 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Nikolskaya E, Sokol M, Faustova M, Zhunina O, Mollaev M, Yabbarov N, Tereshchenko O, Popov R, Severin E. The comparative study of influence of lactic and glycolic acids copolymers type on properties of daunorubicin loaded nanoparticles and drug release. Acta Bioeng Biomech. 2018;20(1):65-77. PubMed PMID: 29658530.

2: Uematsu N, Zhao Y, Kiyomi A, Yuan BO, Onda K, Tanaka S, Sugiyama K, Sugiura M, Takagi N, Hayakawa A, Hirano T. Chemo-sensitivity of Two-dimensional Monolayer and Three-dimensional Spheroid of Breast Cancer MCF-7 Cells to Daunorubicin, Docetaxel, and Arsenic Disulfide. Anticancer Res. 2018 Apr;38(4):2101-2108. PubMed PMID: 29599328.

3: Chakraborty M, Sellier C, Ney M, Villa P, Charlet-Berguerand N, Artero R, Llamusi B. Daunorubicin reduces MBNL1 titration by expanded CUG repeat RNA and rescues cardiac dysfunctions in a Drosophila model of myotonic dystrophy. Dis Model Mech. 2018 Mar 21. pii: dmm.032557. doi: 10.1242/dmm.032557. [Epub ahead of print] PubMed PMID: 29592894.

4: Seddon AN, Chaim J, Akin O, Drill E, Michael AG, Adel N, Tallman MS. Similar incidence of typhlitis in patients receiving various doses of daunorubicin or idarubicin as induction for acute myeloid leukemia. Leuk Res. 2018 May;68:48-50. doi: 10.1016/j.leukres.2018.03.004. Epub 2018 Mar 8. PubMed PMID: 29544131.

5: Kim M, Williams S. Daunorubicin and Cytarabine Liposome in Newly Diagnosed Therapy-Related Acute Myeloid Leukemia (AML) or AML With Myelodysplasia-Related Changes. Ann Pharmacother. 2018 Mar 1:1060028018764923. doi: 10.1177/1060028018764923. [Epub ahead of print] PubMed PMID: 29532662.

6: Cao J, Zheng H, Hu R, Liao J, Fei Z, Wei X, Xiong X, Zhang F, Zheng H, Li D. pH-Responsive Nanoparticles Based on Covalently Grafted Conjugates of Carboxymethyl Chitosan and Daunorubicin for the Delivery of Anti-Cancer Drugs. J Biomed Nanotechnol. 2017 Dec 1;13(12):1647-1659. doi: 10.1166/jbn.2017.2462. PubMed PMID: 29490753.

7: Ju RJ, Cheng L, Peng XM, Wang T, Li CQ, Song XL, Liu S, Chao JP, Li XT. Octreotide-modified liposomes containing daunorubicin and dihydroartemisinin for treatment of invasive breast cancer. Artif Cells Nanomed Biotechnol. 2018 Jan 30:1-13. doi: 10.1080/21691401.2018.1433187. [Epub ahead of print] PubMed PMID: 29381101.

8: Ju RJ, Cheng L, Qiu X, Liu S, Song XL, Peng XM, Wang T, Li CQ, Li XT. Hyaluronic acid modified daunorubicin plus honokiol cationic liposomes for the treatment of breast cancer along with the elimination vasculogenic mimicry channels. J Drug Target. 2018 Jan 24:1-13. doi: 10.1080/1061186X.2018.1428809. [Epub ahead of print] PubMed PMID: 29334266.

9: Kim SY, Park JH, Yoon SY, Cho YH, Lee MH. A pilot study of daunorubicin-augmented hyper-CVAD induction chemotherapy for adults with acute lymphoblastic leukemia. Cancer Chemother Pharmacol. 2018 Feb;81(2):393-398. doi: 10.1007/s00280-017-3514-3. Epub 2018 Jan 2. PubMed PMID: 29294168.

10: Maayah ZH, Abdelhamid G, Elshenawy OH, El-Sherbeni AA, Althurwi HN, McGinn E, Dawood D, Alammari AH, El-Kadi AOS. The Role of Soluble Epoxide Hydrolase Enzyme on Daunorubicin-Mediated Cardiotoxicity. Cardiovasc Toxicol. 2017 Dec 1. doi: 10.1007/s12012-017-9437-8. [Epub ahead of print] PubMed PMID: 29196978.

11: Nikanjam M, Capparelli EV, Lancet JE, Louie A, Schiller G. Persistent cytarabine and daunorubicin exposure after administration of novel liposomal formulation CPX-351: population pharmacokinetic assessment. Cancer Chemother Pharmacol. 2018 Jan;81(1):171-178. doi: 10.1007/s00280-017-3484-5. Epub 2017 Nov 22. PubMed PMID: 29167924; PubMed Central PMCID: PMC5756117.

12: Shi ZX, Li HY, Yang XD, Gao H, Li DG, Yang WH, Yao F, Yan LX. Yi-qi-yang-yin-tang increases the sensitivity of KG1a leukemia stem cells to daunorubicin by promoting cell cycle progression and regulating the expression of PTEN, TOPOII and mTOR. Oncol Lett. 2017 Dec;14(6):6441-6448. doi: 10.3892/ol.2017.7067. Epub 2017 Sep 26. PubMed PMID: 29163680; PubMed Central PMCID: PMC5686439.

13: Jackson DR, Shakya G, Patel AB, Mohammed LY, Vasilakis K, Wattana-Amorn P, Valentic TR, Milligan JC, Crump MP, Crosby J, Tsai SC. Structural and Functional Studies of the Daunorubicin Priming Ketosynthase DpsC. ACS Chem Biol. 2018 Jan 19;13(1):141-151. doi: 10.1021/acschembio.7b00551. Epub 2017 Dec 11. PubMed PMID: 29161022.

14: Sheng X, Parmentier JH, Tucci J, Pei H, Cortez-Toledo O, Dieli-Conwright CM, Oberley MJ, Neely M, Orgel E, Louie SG, Mittelman SD. Adipocytes Sequester and Metabolize the Chemotherapeutic Daunorubicin. Mol Cancer Res. 2017 Dec;15(12):1704-1713. doi: 10.1158/1541-7786.MCR-17-0338. Epub 2017 Nov 8. PubMed PMID: 29117945; PubMed Central PMCID: PMC5726435.

15: Hu C, Yu M, Ren Y, Li K, Maggio DM, Mei C, Ye L, Wei J, Jin J, Zhuang Z, Tong H. Publisher Correction: PP2A inhibition from LB100 therapy enhances daunorubicin cytotoxicity in secondary acute myeloid leukemia via miR-181b-1 upregulation. Sci Rep. 2017 Nov 7;7(1):15260. doi: 10.1038/s41598-017-14858-z. PubMed PMID: 29116110; PubMed Central PMCID: PMC5677121.

16: Jiang HN, Liu ZG, Hu R. [Embelin Reverses the Multi-drug Resistance of K562/D to Daunorubicin Independently of P-gp and MDR1 mRNA]. Zhongguo Shi Yan Xue Ye Xue Za Zhi. 2017 Oct;25(5):1342-1349. doi: 10.7534/j.issn.1009-2137.2017.05.011. Chinese. PubMed PMID: 29070105.

17: Li W, Lu M, Zhang Y, Xia D, Chen Z, Wang L, Yin N, Wang Z. Puerarin attenuates the daunorubicin-induced apoptosis of H9c2 cells by activating the PI3K/Akt signaling pathway via the inhibition of Ca2+ influx. Int J Mol Med. 2017 Dec;40(6):1889-1894. doi: 10.3892/ijmm.2017.3186. Epub 2017 Oct 12. PubMed PMID: 29039532.

18: Zhu K, Jiang B, Yang Y, Hu R, Liu Z. DACT1 overexpression inhibits proliferation, enhances apoptosis, and increases daunorubicin chemosensitivity in KG-1α cells. Tumour Biol. 2017 Oct;39(10):1010428317711089. doi: 10.1177/1010428317711089. PubMed PMID: 29037126.

19: Alves AC, Nunes C, Lima J, Reis S. Daunorubicin and doxorubicin molecular interplay with 2D membrane models. Colloids Surf B Biointerfaces. 2017 Dec 1;160:610-618. doi: 10.1016/j.colsurfb.2017.09.058. Epub 2017 Oct 3. PubMed PMID: 29028609.

20: Murphy T, Yee KWL. Cytarabine and daunorubicin for the treatment of acute myeloid leukemia. Expert Opin Pharmacother. 2017 Nov;18(16):1765-1780. doi: 10.1080/14656566.2017.1391216. Epub 2017 Oct 20. Review. PubMed PMID: 29017371.