Doxorubicin hydrochloride
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MedKoo CAT#: 100280

CAS#: 25316-40-9 (HCl)

Description: Doxorubicin is an anthracycline antibiotic with antineoplastic activity. Doxorubicin, isolated from the bacterium Streptomyces peucetius var. caesius, is the hydroxylated congener of daunorubicin. Doxorubicin intercalates between base pairs in the DNA helix, thereby preventing DNA replication and ultimately inhibiting protein synthesis. Additionally, doxorubicin inhibits topoisomerase II which results in an increased and stabilized cleavable enzyme-DNA linked complex during DNA replication and subsequently prevents the ligation of the nucleotide strand after double-strand breakage. Doxorubicin also forms oxygen free radicals resulting in cytotoxicity secondary to lipid peroxidation of cell membrane lipids; the formation of oxygen free radicals also contributes to the toxicity of the anthracycline antibiotics, namely the cardiac and cutaneous vascular effects.


Chemical Structure

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Doxorubicin hydrochloride
CAS# 25316-40-9 (HCl)

Theoretical Analysis

MedKoo Cat#: 100280
Name: Doxorubicin hydrochloride
CAS#: 25316-40-9 (HCl)
Chemical Formula: C27H30ClNO11
Exact Mass: 0.00
Molecular Weight: 579.980
Elemental Analysis: C, 55.91; H, 5.21; Cl, 6.11; N, 2.42; O, 30.34

Price and Availability

Size Price Availability Quantity
100mg USD 90 Ready to ship
200mg USD 150 Ready to ship
500mg USD 250 Ready to ship
1g USD 450 Ready to ship
2g USD 750 Ready to ship
5g USD 1650 Ready to ship
10g USD 2950 Ready to Ship
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Related CAS #: 23214-92-8 (free base)   25316-40-9 (HCl)  

Synonym: FI106; FI-106; FI 106; ADR; Doxo; Dox HCl; Adriamycin; Adriacin; Adriblastina; Adriblastine; Adrimedac; DOXOCELL; Doxolem; Doxorubin; Farmiblastina; Rubex.

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

InChi Key: MWWSFMDVAYGXBV-RUELKSSGSA-N

InChi Code: 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

SMILES Code: O=C1C2=C(O)C(C[C@](C(CO)=O)(O)C[C@@H]3O[C@H]4C[C@H](N)[C@H](O)[C@H](C)O4)=C3C(O)=C2C(C5=C1C=CC=C5OC)=O.[H]Cl

Appearance: 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, DMSO:PBS, and water

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: Doxorubicin hydrochloride is a potent human DNA topoisomerase I and topoisomerase II inhibitor with IC50s of 0.8 μM and 2.67 μM, respectively.
In vitro activity: To study the anti-cancer activity of doxorubicin on OSCC cells, the H357 cells were incubated with various concentration of doxorubicin for 48hr’s and cell viability was determined by MTT assay. As shown in (Figure 5a) doxorubicin was able to decline the cell growth from 1 μM and it continues until 100 μM concentrations. The half maximal inhibitory concentration (IC50) of doxorubicin in H357 cells is 50 μM. Further, immunoblot study suggests that doxorubicin significantly reduced DDX3 protein expression levels as compared to DMSO treated cells (Figure 5b). Later, the molecular interaction of the doxorubicin with DDX3 was confirmed by molecular docking analysis. Results showed that, doxorubicin form a strong hydrogen bond interactions with Thr 198, Thr 201 (Figure 5c) and π-π stacking with Tyr 200 amino acid residues (Figure 5d). Overall, it suggests that doxorubicin directly interacts with DDX3 by forming intra and inter molecular interaction with active site amino acid residues. Reference: Bioinformation. 2016; 12(7): 347–353. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5311078/
In vivo activity: Male C57BL/6 J mice were treated for 2 weeks with 2 mg/kg (low dose) or 4 mg/kg (high dose) of DOX (doxorubicin) weekly. Arterial stiffness was assessed in vivo with ultrasound imaging (abdominal aorta pulse wave velocity (aaPWV)) and applanation tonometry (carotid-femoral PWV) combined with ex vivo vascular stiffness and reactivity evaluation. The high dose increased aaPWV, while cfPWV did not reach statistical significance. Phenylephrine (PE)-contracted aortic segments showed a higher Peterson's modulus (Ep) in the high dose group, while Ep did not differ when vascular smooth muscle cells (VSMCs) were relaxed by a NO donor (DEANO). In addition, aortic rings of DOX-treated mice showed increased PE contraction, decreased basal nitric oxide (NO) index and impaired acetylcholine-induced endothelium-dependent relaxation. DOX treatment contributed to endothelial cell loss and reduced endothelial nitric oxide synthase (eNOS) expression in the aorta. Reference: Toxicol Lett. 2021 Apr 22:S0378-4274(21)00108-9. https://www.sciencedirect.com/science/article/abs/pii/S0378427421001089?via%3Dihub

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 43.7 75.31
DMSO:PBS (pH 7.2) (1:1) 0.5 0.86
Ethanol 1.0 1.72
Water 49.7 85.64

Preparing Stock Solutions

The following data is based on the product molecular weight 579.98 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: 1. Botlagunta M, Kollapalli B, Kakarla L, Gajarla SP, Gade SP, Dadi CL, Penumadu A, Javeed S. In vitro anti-cancer activity of doxorubicin against human RNA helicase, DDX3. Bioinformation. 2016 Oct 18;12(7):347-353. doi: 10.6026/97320630012347. PMID: 28246464; PMCID: PMC5311078. 2. Jiang D, Lynch C, Medeiros BC, Liedtke M, Bam R, Tam AB, Yang Z, Alagappan M, Abidi P, Le QT, Giaccia AJ, Denko NC, Niwa M, Koong AC. Identification of Doxorubicin as an Inhibitor of the IRE1α-XBP1 Axis of the Unfolded Protein Response. Sci Rep. 2016 Sep 16;6:33353. doi: 10.1038/srep33353. PMID: 27634301; PMCID: PMC5025885. 3. Bosman M, Favere K, Neutel CHG, Jacobs G, De Meyer GRY, Martinet W, Van Craenenbroeck EM, Guns PDF. Doxorubicin induces arterial stiffness: a comprehensive in vivo and ex vivo evaluation of vascular toxicity in mice. Toxicol Lett. 2021 Apr 22:S0378-4274(21)00108-9. doi: 10.1016/j.toxlet.2021.04.015. Epub ahead of print. PMID: 33895255. 4. Andersen CL, Liu M, Wang Z, Ye X, Xiao S. Chemotherapeutic agent doxorubicin alters uterine gene expression in response to estrogen in ovariectomized CD-1 adult mice†. Biol Reprod. 2019 Apr 1;100(4):869-871. doi: 10.1093/biolre/ioy259. PMID: 30561525; PMCID: PMC6483053.
In vitro protocol: 1. Botlagunta M, Kollapalli B, Kakarla L, Gajarla SP, Gade SP, Dadi CL, Penumadu A, Javeed S. In vitro anti-cancer activity of doxorubicin against human RNA helicase, DDX3. Bioinformation. 2016 Oct 18;12(7):347-353. doi: 10.6026/97320630012347. PMID: 28246464; PMCID: PMC5311078. 2. Jiang D, Lynch C, Medeiros BC, Liedtke M, Bam R, Tam AB, Yang Z, Alagappan M, Abidi P, Le QT, Giaccia AJ, Denko NC, Niwa M, Koong AC. Identification of Doxorubicin as an Inhibitor of the IRE1α-XBP1 Axis of the Unfolded Protein Response. Sci Rep. 2016 Sep 16;6:33353. doi: 10.1038/srep33353. PMID: 27634301; PMCID: PMC5025885.
In vivo protocol: 1. Bosman M, Favere K, Neutel CHG, Jacobs G, De Meyer GRY, Martinet W, Van Craenenbroeck EM, Guns PDF. Doxorubicin induces arterial stiffness: a comprehensive in vivo and ex vivo evaluation of vascular toxicity in mice. Toxicol Lett. 2021 Apr 22:S0378-4274(21)00108-9. doi: 10.1016/j.toxlet.2021.04.015. Epub ahead of print. PMID: 33895255. 2. Andersen CL, Liu M, Wang Z, Ye X, Xiao S. Chemotherapeutic agent doxorubicin alters uterine gene expression in response to estrogen in ovariectomized CD-1 adult mice†. Biol Reprod. 2019 Apr 1;100(4):869-871. doi: 10.1093/biolre/ioy259. PMID: 30561525; PMCID: PMC6483053.

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