ESORUBICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H29NO10
Molecular Weight	527.5199
Optical Activity	UNSPECIFIED
Defined Stereocenters	5 / 5
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@H](N)C[C@H](C)O1)O[C@H]2C[C@@](O)(CC3=C(O)C4=C(C(=O)C5=C(OC)C=CC=C5C4=O)C(O)=C23)C(=O)CO

InChI

InChIKey=ITSGNOIFAJAQHJ-BMFNZSJVSA-N

InChI=1S/C27H29NO10/c1-11-6-12(28)7-18(37-11)38-16-9-27(35,17(30)10-29)8-14-20(16)26(34)22-21(24(14)32)23(31)13-4-3-5-15(36-2)19(13)25(22)33/h3-5,11-12,16,18,29,32,34-35H,6-10,28H2,1-2H3/t11-,12+,16-,18-,27-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H29NO10
Molecular Weight	527.5199
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://adisinsight.springer.com/drugs/800000832 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/esorubicin | https://www.ncbi.nlm.nih.gov/pubmed/2045860 | https://www.ncbi.nlm.nih.gov/pubmed/2702800 | https://www.ncbi.nlm.nih.gov/pubmed/2346128

Esorubicin (4'-deoxydoxorubicin, NSC 267469) is a synthetic derivative of the anthracycline antineoplastic antibiotic doxorubicin with potential antineoplastic activity. Esorubicin intercalates into DNA and inhibits topoisomerase II, thereby inhibiting DNA replication and ultimately, interfering with RNA and protein synthesis. This agent exhibits less cardiotoxicity than the parent antibiotic doxorubicin, but may cause more severe myelosupression compared to other compounds within the anthracycline class. Esorubicin was being clinically tested for the treatment of solid tumors as well as lymphomas an leukemias. Esorubicin development has been discontinued.

Originator

Approval Year

PubMed

Title	Date	PubMed
Phase I trial of esorubicin (4'deoxydoxorubicin).	1984 Sep	6470753
Phase II trial of esorubicin in advanced pancreatic adenocarcinoma.	1986 May	3708621
High incidence of local venous reactions to esorubicin.	1987	3597000
Fatal esorubicin-induced cardiomyopathy: report of a case and review of the literature.	1988	3286024
Clinical evaluation of the cardiac toxicity of 4'-deoxy-doxorubicin.	1988 Apr	3403095
The rat model in the comparative evaluation of anthracyclines cardiotoxicity.	1989 Dec 31	2617699
Effect of amrinone on anthracycline-induced lethal and cardiac toxicity in mice and rats.	1990	2283890
Esorubicin (4'-deoxydoxorubicin, NSC 267469) in advanced breast cancer. A phase II study of the CALGB.	1990 Jun	2346128
Clinical cardiotoxicity of esorubicin (4'-deoxydoxorubicin,DxDx): prospective studies with serial gated heart scans and reports of selected cases. A Cancer and Leukemia Group B report.	1990 May	2166722

Sample Use Guides

In Vivo Use Guide

Phase II trial was utilizing esorubicin (4'-deoxydoxorubicin) given in a dosage of 30 mg/m2 intravenously every 3 weeks.

Route of Administration: Intravenous

In Vitro Use Guide

The effect of different Esorubicin concentrations (0.1 uM to 0.1 nM) has been tested on the in vitro growth of human normal hemopoietic progenitor cells and of three leukemic cell lines (K562, U 937, HL60). The highest drug concentration completely abolished both normal and leukemic proliferation. Lower doses of Esorubicin failed to induce any morphological or phenotypic differentiation of leukemic cell lines. A 24h pretreatment of the cells with 1 nM Esorubicin enhanced the in vitro proliferation of normal early myeloid progenitor cells, whereas it did not affect leukemic, myelomonocytic cell proliferation.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:06:45 GMT 2023` Edited by `admin` on `Fri Dec 15 16:06:45 GMT 2023`
Record UNII	RMC41L2WQ3
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ESORUBICIN

Official Name

English

(8S,10S)-10-(((2S,4R,6S)-4-AMINOTETRAHYDRO-6-METHYL-2H-PYRAN-2-YL)OXY)-8-GLYCOLOYL-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-1-METHOXY-5,12-NAPHTHACENEDIONE

Systematic Name

English

5,12-NAPHTHACENEDIONE, 10-((4-AMINOTETRAHYDRO-6-METHYL-2H-PYRAN-2-YL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (2S-(2.ALPHA,(8R*,10R*),4.BETA.,6.BETA))-

Common Name

English

esorubicin [INN]

Common Name

English

Esorubicin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1594