Epirubicin hydrochloride - Moligand™, ≥98%(HPLC) , CAS No.56390-09-1

CAS: 56390-09-1 Cat. No.: E122334 Molecular Weight: 579.98 EC Number: 260-145-2

GRADE & PURITY Moligand™, ≥98%(HPLC)

Synonyms

CCG-100950 | EPIRUBICIN HYDROCHLORIDE (USP MONOGRAPH) | Epirubicin hydrochloride (USAN:USP:JAN) | 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hyd

Storage

Protected from light,Store at -20°C

Shipped In

Ice chest + Ice pads

Overview

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia

Epirubicin is a cell-permeable anthracycline antitumor antibiotic. It is a stereoisomer(4′-epi-isomer) of doxorubicin that exhibits reduced cardiotoxicity. It is used to inhibit topoisomerase II and DNA helicase activity. Epirubicin is used to study metastatic breast cancerand cardiac toxicity.

in solvent : -80°C, 6 months; -20°C, 1 month (protect from light)

Specifications

Synonyms

CCG-100950 | EPIRUBICIN HYDROCHLORIDE (USP MONOGRAPH) | Epirubicin hydrochloride (USAN:USP:JAN) | 5, 12-Naphthacenedione, 10-((3-amino-2, 3, 6-trideoxy-alpha-L-arabino-hexopyranosyl)oxy)-7, 8, 9, 10-tetrahydro-6, 8, 11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, hyd

Specifications & Purity

Moligand™, ≥98%(HPLC)

Biochemical and Physiological Mechanisms

Cell-permeable anthracycline antitumor antibiotic. Antineoplastic. A stereoisomer of doxorubicin that exhibits reduced cardiotoxicity. Its antitumor actions are mediated by targeting topoisomerase II. Epirubicin is antimitotic and cytotoxic. It inhibits n

Storage

Protected from light, Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Grade

Moligand™

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%(HPLC)

Names and Identifiers

• Pubchem Sid: 504753977
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504753977
• Canonical Smiles: CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl
• IUPAC Name: (7S,9S)-7-[(2R,4S,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione;hydrochloride
• InChIKey: MWWSFMDVAYGXBV-FGBSZODSSA-N
• 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
• Isomeric SMILES: C[C@H]1[C@@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O.Cl
• WGK Germany: 3
• RTECS: QI9295750
• Molecular Weight: 579.98
• Reaxy-Rn: 25324888
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=25324888&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Phenylpropanoids and polyketides
    • Class Anthracyclines

• Kingdom: Organic compounds
• Superclass: Phenylpropanoids and polyketides
• Class: Anthracyclines
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Anthracyclines
• Alternative Parents: Tetracenequinones Aminoglycosides Anthraquinones Hexoses O-glycosyl compounds Tetralins Anisoles Aryl ketones Alkyl aryl ethers Oxanes Alpha-hydroxy ketones Vinylogous acids Tertiary alcohols Secondary alcohols 1,2-aminoalcohols Polyols Oxacyclic compounds Acetals Hydrocarbon derivatives Hydrochlorides Monoalkylamines Organic oxides Organopnictogen compounds Primary alcohols
• Molecular Framework: Aromatic heteropolycyclic compounds
• Substituents: Anthracycline - Anthracyclinone-skeleton - Aminoglycoside core - Tetracenequinone - 9,10-anthraquinone - 1,4-anthraquinone - Anthracene - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Tetralin - Anisole - Aryl ketone - Alkyl aryl ether - Amino saccharide - Benzenoid - Monosaccharide - Oxane - Alpha-hydroxy ketone - Tertiary alcohol - Vinylogous acid - Secondary alcohol - Ketone - 1,2-aminoalcohol - Polyol - Oxacycle - Acetal - Organoheterocyclic compound - Ether - Alcohol - Carbonyl group - Primary aliphatic amine - Hydrochloride - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Organopnictogen compound - Organic oxygen compound - Amine - Organooxygen compound - Organic nitrogen compound - Primary alcohol - Primary amine - Aromatic heteropolycyclic compound
• Description: This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ALB Tchem Serum albumin (2651 Activities)

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PLK1 Tchem Serine/threonine-protein kinase PLK1 (28605 Activities)

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GLP1R Tclin Glucagon-like peptide 1 receptor (111429 Activities)

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PIN1 Tchem Peptidyl-prolyl cis-trans isomerase NIMA-interacting 1 (36611 Activities)

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BJ (6930 Activities)

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HEK293 (82097 Activities)

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Jurkat (10389 Activities)

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FEN1 Tchem Flap endonuclease 1 (12055 Activities)

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GNAS Tbio Guanine nucleotide-binding protein G(s), subunit alpha (103405 Activities)

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POLK Tbio DNA polymerase kappa (8653 Activities)

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POLI Tchem DNA polymerase iota (116820 Activities)

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POLH Tchem DNA polymerase eta (21678 Activities)

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ABCC2 Tchem Canalicular multispecific organic anion transporter 1 (1191 Activities)

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KDM4A Tchem Lysine-specific demethylase 4A (52245 Activities)

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ABCB11 Tchem Bile salt export pump (2311 Activities)

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ABCC3 Tbio Canalicular multispecific organic anion transporter 2 (718 Activities)

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SNCA Tchem Alpha-synuclein (10960 Activities)

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TSG101 Tbio Tumor susceptibility gene 101 protein (2874 Activities)

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TDP1 Tchem Tyrosyl-DNA phosphodiesterase 1 (345557 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

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GMNN Tbio Geminin (128009 Activities)

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CBX1 Tbio Chromobox protein homolog 1 (92434 Activities)

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ABCC4 Tchem Multidrug resistance-associated protein 4 (785 Activities)

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ATXN2 Tbio Ataxin-2 (54410 Activities)

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USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

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RGS4 Tchem Regulator of G-protein signaling 4 (13867 Activities)

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

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WRN Tbio Werner syndrome ATP-dependent helicase (8824 Activities)

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TARDBP Tchem TAR DNA-binding protein 43 (40113 Activities)

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Associated Targets(non-human)

Pseudomonas aeruginosa (123386 Activities)

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Klebsiella pneumoniae (43867 Activities)

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Staphylococcus aureus (210822 Activities)

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Acinetobacter baumannii (41033 Activities)

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Escherichia coli (133304 Activities)

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Cryptococcus neoformans (21258 Activities)

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Candida albicans (78123 Activities)

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rep Replicase polyprotein 1ab (378 Activities)

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Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

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Mechanisms of Action

Chemical and Physical Properties

• Solubility: Soluble in water (116 mg/mL) at 25 °C, DMSO (116 mg/mL) at 25 °C, ethanol (3 mg/mL) at 25 °C, acetone, and methanol.
• Sensitivity: Light sensitive；heat sensitive；Moisture sensitive
• Specific Rotation[α]: 310° (C=0.05,MeOH)
• Melt Point(°C): 185℃
• Molecular Weight: 580.000 g/mol
• Hydrogen Bond Donor Count: 7
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 579.151 Da
• Monoisotopic Mass: 579.151 Da
• Topological Polar Surface Area: 206.000 Ų
• Heavy Atom Count: 40
• Formal Charge: 0
• Complexity: 977.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 6
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Guangchun Liu, Shenglin Zhang, Ruoyan Lin, Xudong Cao, Lihong Yuan.  (2023)  Anti-tumor target screening of sea cucumber saponin Frondoside A: a bioinformatics and molecular docking analysis.  Frontiers in Oncology,      [PMID:38144520] [10.3389/fonc.2023.1307838]

2. Ruizhen Ru, Gengzhan Chen, Xiaoxia Liang, Xudong Cao, Lihong Yuan, Minjie Meng.  (2023)  Sea Cucumber Derived Triterpenoid Glycoside Frondoside A: A Potential Anti-Bladder Cancer Drug.  Nutrients,  15  (2): (378).  [PMID:36678249] [10.3390/nu15020378]

3. Ruizhen Ru, Yanzheng Guo, Juanxuan Mao, Zonghe Yu, Wen Huang, Xudong Cao, Huijian Hu, Minjie Meng, Lihong Yuan.  (2022)  Cancer Cell Inhibiting Sea Cucumber (Holothuria leucospilota) Protein as a Novel Anti-Cancer Drug.  Nutrients,  14  (4): (786).  [PMID:35215436] [10.3390/nu14040786]

4. He Cheng, Langlang Yi, Jianduo Wu, Guoqian Li, Gang Zhao, Zhixiang Xiao, Bo Hu, Lei Zhao, Jie Tian.  (2021)  Drug preconcentration and direct quantification in biofluids using 3D-Printed paper cartridge.  BIOSENSORS & BIOELECTRONICS,      [PMID:34052581] [10.1016/j.bios.2021.113266]

5. Chunyuan Song, Yanxia Dou, Lihui Yuwen, Youzhi Sun, Chen Dong, Fang Li, Yanjun Yang, Lianhui Wang.  (2018)  A gold nanoflower-based traceable drug delivery system for intracellular SERS imaging-guided targeted chemo-phototherapy.  Journal of Materials Chemistry B,  6  (19): (3030-3039).  [PMID:32254338] [10.1039/C8TB00587G]

6. Yunkun Li, Xiaoding Shen, Haitao Ding, Yuxin Zhang, Dayi Pan, Liping Su, Yahui Wu, Zaixiang Fang, Jie Zhou, Qiyong Gong, Kui Luo.  (2024)  Dendritic nanomedicine enhances chemo-immunotherapy by disturbing metabolism of cancer-associated fibroblasts for deep penetration and activating function of immune cells.  Acta Pharmaceutica Sinica B,      [PMID:39220877] [10.1016/j.apsb.2024.03.010]

7. Fuju Xu, Guangchun Liu, Chujie Zhao, Shenglin Zhang, Ruoyan Lin, Xudong Cao, Zonghe Yu, Peng Luo, Wen Huang, Lihong Yuan.  (2025)  Target Screening and Validation of the Antitumor Effect of Saponin Extract From Holothuria leucospilota.  CHEMISTRY & BIODIVERSITY,      [PMID:40522783] [10.1002/cbdv.202403399]