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25316-40-9 (Doxorubicin (hydrochloride))

1

Identification

Doxorubicin (hydrochloride) Doxorubicin (hydrochloride)
Name Doxorubicin (hydrochloride)
Formula C27H30ClNO11
MW 579.98
CAS No. 25316-40-9
EINECS 246-818-3
Smiles COC1=C2C(C(C(C(O)=C(C[[email protected]](C(CO)=O)(O)C[[email protected]@H]3O[[email protected]@]4([H])C[[email protected]](N)[[email protected]](O)[[email protected]](C)O4)C3=C5O)=C5C2=O)=O)=CC=C1.[H]Cl
Synonyms Adriamycin;Hydroxydaunorubicin hydrochloride; (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 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
2

Introduction

Doxorubicin Hcl(Adriamycin) is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis. IC50 Value: Target: Topo II; ADCs Toxin in vitro: Doxorubicin can block the synthesis of DNA by intercalating into the DNA strand, and inhibits DNA topoisomerase II (TOP2).

Background Information

An anthracycline antibiotic with antineoplastic activityReferences: 1. Liu YY, Gupta V, Patwardhan GA, Bhinge K, Zhao Y, Bao J, Mehendale H, Cabot MC, Li YT, Jazwinski SM. Glucosylceramide synthase upregulates MDR1 expression in the regulation of cancer drug resistance through cSrc and beta-catenin signaling. Mol Cancer. 2010 Jun 11;9(1):145. [Epub ahead of print] PubMed PMID: 20540746. 2. Zaremba T, Thomas H, Cole M, Plummer ER, Curtin NJ. Doxorubicin-induced suppression of poly(ADP-ribose) polymerase-1 (PARP-1) activity and expression and its implication for PARP inhibitors in clinical trials. Cancer Chemother Pharmacol. 2010 May 21. [Epub ahead of print] PubMed PMID: 20490796. 3. Angelini A, Di Ilio C, Castellani ML, Conti P, Cuccurullo F. Modulation of multidrug resistance p-glycoprotein activity by flavonoids and honokiol in human doxorubicin- resistant sarcoma cells (MES-SA/DX-5): implications for natural sedatives as chemosensitizing agents in cancer therapy. J Biol Regul Homeost Agents. 2010 Apr-Jun;24(2):197-205. PubMed PMID: 20487633. ......by AOBIOUS INC
Doxorubicin (Adriamycin) HCl is an antineoplastic agent used in the treatment of a wide range of cancers, including hematological malignancies, many types of carcinoma, and soft tissue sarcomas. Doxorubicin interacts with DNA by intercalation and inhibition of macromolecular biosynthesis. Doxorubicin stabilizes the topoisomerase II complex after it has broken the DNA chain for replication, preventing the DNA double helix from being resealed and thereby stopping the process of replication. In studies with isolated nuclei, adriamycin was also a more potent inhibitor of DNA synthesis than RNA synthesis. However, with intact cells, adriamycin inhibited both DNA and RNA synthesis to about the same extent. The inhibition produced by adriamycin on RNA synthesis in intact cells was greater than that observed in the cell-free systems. Adriamycin inhibited protein synthesis in a cell-free system consisting of polyribosomes, transfer RNA, and enzymes but did not inhibit protein synthesis in intact cells. Combination therapy experiments with sirolimus (rapamycin) and doxorubicin have shown promise in treating Akt-positive lymphomas in mice. ......by AbMole BioScience

Adriamycin is an anthracycline antibiotic, it works by intercalating DNA, while most serious adverse effect being life-threatening heart damage. It is commonly used in the treatment of a wide range of cancers, including hematological malignancies, many types of carcinoma, and soft tissue sarcomas.

......by AdooQ BioScience, LLC
Description ......by Apexbio Technology LLC
An antitumour agent that has been formulated as a salt to achieve higher water solubility; physicochemical properties and chromatographic behaviour will depend on whether the ph is buffered. In non-ph controlled systems the free base and salt may behave d ......by BOC Sciences
Doxorubicin hydrochloride is a Topoisomerase II (Top2) catalytic inhibitor, also is a broad spectrum antibiotic used in the treatment of cancers, with IC50 of 374 nM for Hela cells. ......by MedChemexpress Co., Ltd.
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. ......by MedKoo Biosciences, Inc.
Doxorubicin (Adriamycin) HCl is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis in tumor cells. ......by Selleck Chemicals LLC
Antineoplastic antibiotic obtained from Streptomyces peucetius. It is a hydroxy derivative of DAUNORUBICIN. ......by Target Molecule Corp.
Antitumor antibiotic agent that inhibits DNA topoisomerase II. DNA intercalator that inhibits nucleic acid synthesis and induces apoptosis. Reduces intracellular tau levels. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Cell lines H9c2 cells
Conditions 1 μg/ml, 2 hours
Method H9c2 cells were treated with increased concentrations of Doxorubicin (0.1, 0.3, 0.5, and 1.0 μg/ml, equal to 0.17, 0.52, 0.85, and 1.71 μM separately) for 2 h, or treated with 0.3 μg/ml (equal to 0.52 μM) of Doxorubicin for the different time points. Doxorubicin induces strong AMPKα (Thr 172) and its downstream Acetyl-CoA carboxylase (ACC, Ser 79) phosphorylation in both time- and dose-dependent manner. AMPKα phosphorylation became obvious after 1 h of Doxorubicin treatment which was further sustained for at least 6 h. LKB1, the possible upstream kinase for AMPK, was also activated by Doxorubicin in H9c2 cells.
Source Apexbio Technology LLC

Animal Experiment

Animal Models C57BL/10 mice
Dosage Form Intraperitoneal injection, 20 mg/kg
Applications Five days after doxorubicin injection, mice displayed significantly impaired systolic (LVP, -29%; dP/dtmax, -45%), diastolic (dP/dtmin, -44%; stiffness, +275%), and global (SV, -61%; HR, -18%; CO,-68%) left ventricular (LV) function when compared with the placebo group. Both cardiac lipid peroxidation activity (+37%) and cardiac nitrotyrosine protein expression (+204%) were increased when compared with placebo mice.
Source Apexbio Technology LLC
Animal Models Female athymic nude mice injected s.c. with MB231 cells
Dosage 3 mg/kg/day
Formulation Dissolved in DMSO, and diluted in saline
Administration Delivered intratumorly
Source Selleck Chemicals LLC
4

Physical and Chemical Properties

Appearance:red solid EBNumber:EB000022635

Storage condition

Store at -20°C by Apexbio Technology LLC
Store at or below -20 oC. by LC Laboratoies

Solubility

Soluble in DMSO > 10 mM by Apexbio Technology LLC
Soluble in DMSO at 100 mg/mL; very poorly soluble in ethanol; soluble in water at 10 mg/mL with slight warming; buffers, serum, or other additives may increase or decrease the aqueous solubility. by LC Laboratoies
Water > 50 mg/ml DMSO > 50 mg/ml by MedChemexpress Co., Ltd.
(25°C) * In vitro DMSO 100 mg/mL warming (172.41 mM); Water20 mg/mL (34.48 mM); Ethanol<1 mg/mL (<1 mM) by Selleck Chemicals LLC
5

Mechanism and Indication

6

Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Doxorubicin (hydrochloride) Hoffmann-La Roche Inc Chronic lymphocytic leukemia 2009/9/30 2011/6/30 Phase 4 Clinical
Doxorubicin (hydrochloride) Merck & Co Inc Breast tumor 2007/2/28 2009/10/31 Phase 4 Clinical
Doxorubicin (hydrochloride) Universita Cattolica del Sacro Cuore Breast tumor 2007/1/31 2009/12/31 Phase 4 Clinical
Doxorubicin (hydrochloride) Merck & Co Inc Metastatic breast cancer 2006/2/28 2006/8/31 Phase 4 Clinical
Doxorubicin (hydrochloride) Schering-Plough Corp Ovary tumor 2004/11/30 2008/1/31 Phase 4 Clinical
Doxorubicin (hydrochloride) - Launched
7

Safety Data of Doxorubicin (hydrochloride)

Hazard Symbols : T,T+,Xi
Risk Statements : 45-22-40-26/27/28-36/38
Safety Statements : 53-45-36/37/39-22-7/9
RTECS : QI9295900
WGKGermany : 3
8

Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC 1mg/USD11() USA
AbMole BioScience USA
Abcam 10mg/USD125() USA
AdooQ BioScience, LLC USA
Alfa Chemistry USA
American Custom Chemicals Corp. USA
Apexbio Technology LLC USA
Ark Pharm, Inc. 250mg/USD180(In stock) USA
BOC Sciences
Beijing Huafeng United Technology Co., Ltd. China
Beijing JingSource Pharmaceutical Technology Co., Ltd. China
BioVision, Inc., 5mg/USD80() USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 50mg/USD60();100mg/USD84() USA
Carbosynth Limited 100mg/USD70()
Cayman Chemical Company 5mg/USD25() USA
EMD Millipore 10mg/USD199() USA
Haikou Hengkangda Chemical Co., Ltd. China
J&K Scientific Ltd. 10mg/RMB299(ship in 3-4 weeks) China
LC Laboratoies 25mg/USD48(In stock);50mg/USD63(In stock);100mg/USD82(In stock);200mg/USD138(In stock);250mg/USD159(In stock);500mg/USD234(In stock);1g/USD427(In stock);2g/USD728(In stock);3g/USD927(In stock);5g/USD1480(In stock) USA
Lancrix Chemicals. 25mg/USD76() China
Maxchemco Co., Ltd. China
MedChemexpress Co., Ltd. 50mg/USD60();100mg/USD84() USA
MedKoo Biosciences, Inc. USA
Melone Pharmaceutical Co., Ltd. China
Pure Chemistry Scientific Inc. 1g/USD143(In stock) USA
Santa Cruz Biotechnology, Inc. 5mg/USD77() USA
Selleck Chemicals LLC 10mg/USD90(In stock);10mM/1mLIn DMSO/USD117(In stock);10mM(in 1mL DMSO)/USD117(in 1mL DMSO);25mg/USD210(In stock);100mg/USD670(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 50mg/USD60();100mg/USD84() China
Shanghai SPE Chemicals Co., Ltd. China
Shanghai Yingxuan Chempharm Co., Ltd. China
Spectrum Chemical Mfg. Corp. 25g/USD15982() USA
Target Molecule Corp. 10mg/USD67();50mg/USD112();100mg/USD198() USA
Tocris Bioscience Inc. 10mg/USD139() USA
Xingcheng Chempharm Co., Ltd. China
Yancheng Jiangzhong Chemicals Co., Ltd. China
Zhangjiagang Sunrise Fine Chemical Co., Ltd. China
10

Related Products

Other Forms of 25316-40-9

Name CAS No Formula MW
Doxorubicin 23214-92-8 C27H29NO11 543.52

Recommended Compounds in Topoisomerase ADC Cytotoxin Autophagy

Name CAS No Formula MW
Pirarubicin (Hydrochloride) 95343-20-7 C32H38ClNO12 664.1
Exatecan (Mesylate) 169869-90-3 C25H26FN3O7S 531.55
Flumequine 42835-25-6 C14H12FNO3 261.25
Nemorubicin 108852-90-0 C32H37NO13 643.64
Amsacrine (hydrochloride) 54301-15-4 C21H20ClN3O3S 429.92
Ellipticine 519-23-3 C17H14N2 246.31
DOXO-EMCH 151038-96-9 C37H42N4O13 750.75
Topotecan (Hydrochloride) 119413-54-6 C23H24ClN3O5 457.91
Topotecan 123948-87-8 C23H23N3O5 421.45
Tirapazamine 27314-97-2 C7H6N4O2 178.15
Teniposide 29767-20-2 C32H32O13S 656.65
TAS-103 174634-08-3 C20H19N3O2 333.38
TAS-103 (dihydrochloride) 174634-09-4 C20H21Cl2N3O2 406.31
Pixantrone (dimaleate) 144675-97-8 C21H23N5O6 441.44
Pixantrone 144510-96-3 C17H19N5O2 325.37
Pirarubicin 72496-41-4 C32H37NO12 627.64
SN-38 86639-52-3 C22H20N2O5 392.4
Irinotecan (hydrochloride) 100286-90-6 C33H39ClN4O6 623.14
Exatecan 171335-80-1 C24H22FN3O4 435.45
Etoposide 33419-42-0 C29H32O13 588.56

Recommended Compounds in Same Indication

Name CAS No Formula MW
Mocetinostat 726169-73-9 C23H20N6O 396.44
Volasertib 755038-65-4 C34H50N8O3 618.81
Olaparib 763113-22-0 C24H23FN4O3 434.46
CAL-101 870281-82-6 C22H18FN7O 415.42
Ostarine 841205-47-8 C19H14F3N3O3 389.33
Toremifene 89778-26-7 C26H28ClNO 405.96
Toremifene (Citrate) 89778-27-8 C32H36ClNO8 598.08
IDO5L 914471-09-3 C9H7ClFN5O2 271.6356
MK-0752 471905-41-6 C21H21ClF2O4S 442.9
Tivozanib 475108-18-0 C22H19ClN4O5 454.86
Cyclophosphamide 50-18-0 C7H15Cl2N2O2P 261.09
Fenretinide 65646-68-6 C26H33NO2 391.55
FK866 658084-64-1 C24H29N3O2 391.51
Retaspimycin 857402-23-4 C31H45N3O8 587.7
Retaspimycin (Hydrochloride) 857402-63-2 C31H46ClN3O8 624.17
Motesanib (Diphosphate) 857876-30-3 C22H29N5O9P2 569.44
LY2228820 862507-23-1 C26H37FN6O6S2 612.74
Litronesib 910634-41-2 C23H37N5O4S2 511.701
17-AAG (Hydrochloride) 911710-03-7 C31H44ClN3O8 622.15
Veliparib 912444-00-9 C13H16N4O 244.29
11

Route of Synthesis

12

References

[1]. Zykova MG, Medvedeva NV, Torkhovskaya TI, et al. Influence of doxorubicin inclusion into phospholipid nanoformulation on its antitumor activity in mice: increased efficiency for resistant tumor model. Exp Oncol. 2012 Dec;34(4):323-6.

[2]. Patel S, Sprung AU, Keller BA, et al. Identification of yeast DNA topoisomerase II mutants resistant to the antitumor drug doxorubicin: implications for the mechanisms of doxorubicin action and cytotoxicity. Mol Pharmacol. 1997 Oct;52(4):658-66.

[3]. Zeman SM, Phillips DR, Crothers DM. Characterization of covalent adriamycin-DNA adducts. Proc Natl Acad Sci U S A. 1998 Sep 29;95(20):11561-5.

[4]. Pourquier P, Montaudon D, Huet S, et al. Doxorubicin-induced alterations of c-myc and c-jun gene expression in rat glioblastoma cells: role of c-jun in drug resistance and cell death. Biochem Pharmacol. 1998 Jun 15;55(12):1963-71.

[5]. Gewirtz DA. A critical evaluation of the mechanisms of action proposed for the antitumor effects of the anthracycline antibiotics adriamycin and daunorubicin. Biochem Pharmacol. 1999 Apr 1;57(7):727-41.

Protocol Reference

[1] Chen M B, Wu X Y, Gu J H, et al. Activation of AMP-activated protein kinase contributes to doxorubicin-induced cell death and apoptosis in cultured myocardial H9c2 cells. Cell biochemistry and biophysics, 2011, 60(3): 311-322.

[2] Riad A, Bien S, Westermann D, et al. Pretreatment with statin attenuates the cardiotoxicity of Doxorubicin in mice. Cancer research, 2009, 69(2): 695-699.

......by Apexbio Technology LLC
13

More Information

Doxorubicin (hydrochloride)

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