BERUBICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C34H35NO11
Molecular Weight	633.6418
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@@](O)(CC2=C(O)C3=C(C(=O)C4=C(C=CC=C4OC)C3=O)C(O)=C12)C(=O)CO)O[C@H]5C[C@H](N)[C@H](OCC6=CC=CC=C6)[C@H](C)O5

InChI

InChIKey=FIGNGSHKNAHTSH-JJMFXPFOSA-N

InChI=1S/C34H35NO11/c1-16-33(44-15-17-7-4-3-5-8-17)20(35)11-24(45-16)46-22-13-34(42,23(37)14-36)12-19-26(22)32(41)28-27(30(19)39)29(38)18-9-6-10-21(43-2)25(18)31(28)40/h3-10,16,20,22,24,33,36,39,41-42H,11-15,35H2,1-2H3/t16-,20-,22-,24-,33+,34-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C34H35NO11
Molecular Weight	633.6418
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://gmpnews.net/2018/04/cns-pharmaceuticals-commenced-a-crowdfunding-campaign-for-its-gmb-drug/ | https://www.docguide.com/berubicin-shows-efficacy-recurrent-glioblastoma-multiforme | https://adisinsight.springer.com/drugs/800019645

Berubicin, an anthracycline derivative, is a DNA binding agent and potent topoisomerase II poison. Reata Pharmaceuticals were developing it as a treatment for brain cancer as it can breach the blood-brain barrier. It had also been in early clinical trials for the treatment of lung cancer and malignant gliomas. However, studies have been terminated. In October 2006, it was granted orphan drug designation from the FDA for the treatment of malignant gliomas. According to a CNS Pharmaceuticals media release in April 2018, berubicin will be studied for glioblastoma patients, these investigations will be funded in part by an equity crowdfunding campaign.

Originator

Approval Year

Sample Use Guides

In Vivo Use Guide

administered berubicin as a 2-hour intravenous infusion on each of the first 3 days of a 21-day cycle in 35 patients (arm A; 1.2-9.6 mg/m2) or once weekly for 4 weeks every 5 weeks in 19 patients (arm B; 7.5-13.3 mg/m2).

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:06:13 UTC 2023` Edited by `admin` on `Fri Dec 15 16:06:13 UTC 2023`
Record UNII	6QPN83HK2M
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BERUBICIN

Official Name

English

Berubicin [WHO-DD]

Common Name

English

5,12-NAPHTHACENEDIONE, 10-((3-AMINO-2,3,6-TRIDEOXY-4-O-(PHENYLMETHYL)-.ALPHA.-L-LYXO-HEXOPYRANOSYL)OXY)-7,8,9,10-TETRAHYDRO-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-, (8S,10S)-

Common Name

English

berubicin [INN]

Common Name

English

(8S,10S)-10-((3-AMINO-4-O-BENZYL-2,3,6-TRIDEOXY-A-L-LYXO-HEXOPYRANOSYL)OXY)-6,8,11-TRIHYDROXY-8-(HYDROXYACETYL)-1-METHOXY-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

748420