Epirubicin

Base Information

• Chemical Name: Epirubicin
• CAS No.: 56420-45-2
• Deprecated CAS: 57918-25-9
• Molecular Formula: C27H29NO11
• Molecular Weight: 579.988
• UNII: 3Z8479ZZ5X
• DSSTox Substance ID: DTXSID0022987
• Nikkaji Number: J81.933F
• Wikipedia: Epirubicin
• Wikidata: Q425122
• NCI Thesaurus Code: C62028
• RXCUI: 3995
• Metabolomics Workbench ID: 42800
• ChEMBL ID: CHEMBL417
• Mol file: 56420-45-2.mol

Synonyms:4' Epi Adriamycin;4' Epi Doxorubicin;4' Epi DXR;4' Epiadriamycin;4' Epidoxorubicin;4'-Epi-Adriamycin;4'-Epi-Doxorubicin;4'-Epi-DXR;4'-Epiadriamycin;4'-Epidoxorubicin;Ellence;EPI cell;EPI-cell;EPIcell;Epilem;Epirubicin;Epirubicin Hydrochloride;Farmorubicin;Farmorubicina;Farmorubicine;Hydrochloride, Epirubicin;IMI 28;IMI-28;IMI28;NSC 256942;NSC-256942;NSC256942;Pharmorubicin

Chemical Property of Epirubicin

Chemical Property:

• Refractive Index: 1.71
• Boiling Point: 810.3 °C at 760 mmHg
• PKA: 7.35±0.60(Predicted)
• Flash Point: 443.8 °C
• PSA: 206.07000
• Density: 1.61 g/cm³
• LogP: 0.70160
• XLogP3: 1.3
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 12
• Rotatable Bond Count: 5
• Exact Mass: 543.17406074
• Heavy Atom Count: 39
• Complexity: 977

Purity/Quality:

98%, ^*data from raw suppliers

Epirubicin ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• 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
• 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
• Recent ClinicalTrials: Study of Camrelizumab Plus Apatinib and Chemotherapy as Neoadjuvant Therapy in Participants With Triple Negative Breast Cancer (TNBC)
• Recent EU Clinical Trials: Epirubicin for the Treatment of Sepsis & Septic Shock
• Recent NIPH Clinical Trials: COMPARE
• Uses: Epirubicin is a cell permeable Topo II inhibitor. Antineoplastic.
• Therapeutic Function: Antineoplastic

Technology Process of Epirubicin

There total 3 articles about Epirubicin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

C57H58N2O22 → formaldehyd (50-00-0,30525-89-4,61233-19-0) + Epirubicin (56420-45-2)

Guidance literature:

With hydrogenchloride; In dimethylsulfoxide-d6; water-d2;

Reference yield:

epidoxoform → formaldehyd (50-00-0,30525-89-4,61233-19-0) + Epirubicin (56420-45-2)

Guidance literature:

With phosphate buffer; In dimethyl sulfoxide; at 37 ℃; Mechanism; Kinetics; var. temp.;

DOI:10.1021/jm970739s

Reference yield:

doxorubicin (23214-92-8) → (8S,10S)-10-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-6,8,11-trihydroxy-8-(2-hydroxy-acetyl)-1-methoxy-7,8,9,10-tetrahydro-naphthacene-5,12-dione (23214-92-8,56420-45-2,57819-79-1,62414-02-2,62960-37-6,76035-78-4,78684-29-4,79390-76-4,79549-07-8,98632-73-6,129784-92-5)

Guidance literature:

With adenosine 5'-diphosphate; In water; dimethyl sulfoxide; other reducing agent also investigated;

DOI:10.1246/cl.1987.933

upstream raw materials:

doxorubicin

Downstream raw materials:

3'-N-(N'',N''-dimethylformamidinyl)-4'-epidoxorubicin

N,N-dimethyl-4′-epi-doxorubicin

N3'-acetyl-4'-epidoxorubicin

Refernces

• 1、 Taatjes, Dylan J.,Fenick, David J.,Koch, Tad H.. "Epidoxoform: A hydrolytically more stable anthracycline-formaldehyde conjugate toxic to resistant tumor cells". . p. 1306 - 1314. Retrieved 2007/10/03.