Epirubicin Hydrochloride
Basic information
- CAS
56390-09-1- Standard SMILES
COc1cccc2c1C(=O)c1c(O)c3c(c(O)c1C2=O)C[C@@](O)(C(=O)CO)C[C@@H]3O[C@H]1C[C@H](N)[C@@H](O)[C@H](C)O1.Cl- InChIKey
MWWSFMDVAYGXBV-FGBSZODSSA-N- Molecular formula
- C27H30ClNO11
- Average molar mass
- 580 g/mol
- Monoisotopic mass
- 579.15073846
Overview
Epirubicin hydrochloride is an anthracycline. It has a role as an antineoplastic agent.
Names & identifiers
- Preferred name
- Epirubicin Hydrochloride
- IUPAC
- (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
- English name
- Epirubicin hydrochloride
- Molecular formula
- C27H30ClNO11
- Molecular weight
- 579.98
Names & synonyms
Epirubicin hydrochloride56390-09-1Epirubicin HClFarmorubicinaIMI-28NSC-759195WP-69722966TX7J5DTXSID508602975,12-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-, hydrochloride, (8S-cis)-Pharmorubicin PfsRefChem:55118
Show more names
EbeweAdrialCS-1396Epirubin HCIEpirubicin EbeweFarmorubicin-RTU(8s-cis)-rochloridEpirubicinHc,LEp5,Epirubicin HCl API
Hydrochloride, EpirubicinIMI28DTXCID001475450(2S,4S)-4-(3-Amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranosyloxy)-2,5,12-trihydroxy-2-hydroxyacetyl-7-methoxy-1,2,3,4-tetrahydrotetracene-6,11-dione monohydrochloride(8S-cis)-10-((3-Amino-2,3,6-trideoxy-beta-L-arabino-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-5,12-naphthacenedione Hydrochloride3-Glycoloyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-10-methoxy-6,11-dioxo-1-naphthacenyl-3-amino-2,3,6-trideoxy-alpha-L-arabino-hexopyranoside HydrochlorideEllenceMFCD00941448
Properties
Computed structural properties
- Topological polar surface area
- 206 Ų
- Hydrogen bond donors
- 7
- Hydrogen bond acceptors
- 12
- Rotatable bonds
- 5
- Heavy atoms
- 40
- Formal charge
- 0
- Complexity
- 977
Experimental & physicochemical properties
Human Drugs
Breast Feeding; Lactation; Milk, Human; Antineoplastic Agents; Anthracyclines; Antibiotics, Antineoplastic; Topoisomerase II Inhibitors
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Collision Cross Section225.2 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 185 °C · 185°C dec.
- alpha
- 20 · D20 +274° (c = 0.01 in methanol)
- RTECS
- 9295750 · QI9295750
- Flash point
- 443.8 ℃ · 443.8℃
- storage temp.
- -20 °C · Inert atmosphere,Store in freezer, under -20°C
- solubility
- 100 mM, · Soluble in DMSO to 100mM, or in ethanol to 10mM
- form
- powder
- pka
- 11.33 · 11.33 (pKa₃)(Temp: 25 °C; Solvent: Sodium chloride 0.9)
- color
- red to deep red
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H302 (99.2%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 130 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory Information
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-, hydrochloride, (8S,10S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 4 (99.2%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Epirubicin hydrochloride
Ambiguous-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Gloves
- wgk
- 3
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
EPIRUBICIN HYDROCHLORIDE
Anthracycline Topoisomerase Inhibitor [EPC]; Topoisomerase Inhibitors [MoA]; Anthracyclines [CS]
MeSH Pharmacological Classification
Chemical substances, produced by microorganisms, inhibiting or preventing the proliferation of neoplasms.
Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II.
Applications
DescriptionEpirubicin hydrochloride is an antitumor antibiotic which is epimeric with doxorubicin a t the 4’-position of the amino sugar moiety. It has shown utility in the treatment of mammary, gastric, colorectal, pulmonary and ovarian carcinomas, as well as malignant lymphoma and melanoma and soft tissue sarcoma. It is reported to be less sardiotoxic than doxorubicin.
DescriptionEpirubicin is a stereoisomer of the antitumor anthracycline doxorubicin that undergoes β-glucuronidation, which partially detoxifies the dose-limiting side effects that are present with doxorubicin. Compared to doxorubicin, epirubicin is equally cytotoxic to HeLa cells (ID50s = 9 μM). When used either alone or in combination therapies, epirubicin has been shown to demonstrate high rates of complete or partial remission in various cancers including advanced ovary, lymphomas, breast, pancreas, gastric, hepatocellular carcinoma, head and neck tumors, and colorectal.
UsesUsed as an antineoplastic
UsesCell-permeable anthracycline anti-tumor antibiotic
Related reactions
2 records
Compound notes
Loading…