SABARUBICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H37NO13
Molecular Weight	643.6351
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@H](N)[C@H](O)[C@H](C)O1)O[C@H]2[C@@H](O)C[C@]([H])(O[C@H]3C[C@@](O)(CC4=C(O)C5=C(C(=O)C6=CC=CC=C6C5=O)C(O)=C34)C(=O)CO)O[C@H]2C

InChI

InChIKey=VQHRZZISQVWPLK-UIRGBLDSSA-N

InChI=1S/C32H37NO13/c1-12-26(37)17(33)7-21(43-12)46-31-13(2)44-22(8-18(31)35)45-19-10-32(42,20(36)11-34)9-16-23(19)30(41)25-24(29(16)40)27(38)14-5-3-4-6-15(14)28(25)39/h3-6,12-13,17-19,21-22,26,31,34-35,37,40-42H,7-11,33H2,1-2H3/t12-,13-,17-,18-,19-,21-,22-,26+,31+,32-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C32H37NO13
Molecular Weight	643.6351
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	10 / 10
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://ascopubs.org/doi/abs/10.1200/jco.2008.26.15_suppl.19043 | https://www.ema.europa.eu/en/documents/orphan-designation/eu/3/04/255-public-summary-positive-opinion-orphan-designation-sabarubicin-treatment-small-cell-lung-cancer_en.pdf | https://www.ncbi.nlm.nih.gov/pubmed/23605632

Sabarubicin (previously known as MEN-10755), a disaccharide analog of doxorubicin that was developed by Menarini Pharmaceuticals for the treatment of solid tumors, including small cell lung cancer and prostate cancer. Sabarubicin exhibits a superior antitumor efficacy, presumably related to the activation of p53-independent apoptosis. The drug participated in phase II clinical trials to study its effectiveness in treating patients who have progressive prostate cancer that has not responded to hormone therapy and in chemotherapy-naive patients with extensive stage small cell lung cancer. On 21 December 2004, the European Commission granted the orphan designation to Menarini for sabarubicin for the treatment of small cell lung cancer.

Originator

Approval Year

PubMed

Title	Date	PubMed
Effect of MEN 10755, a new disaccharide analogue of doxorubicin, on sarcoplasmic reticulum Ca(2+) handling and contractile function in rat heart.	2000 Sep	10991929
Sabarubicin (MEN10755)-induced apoptosis is independent from mtDNA in A2780 human ovarian tumor cells.	2007 Nov-Dec	18225568
Sabarubicin.	2008	23605632
Interaction between double helix DNA fragments and the new antitumor agent sabarubicin, Men10755.	2010 Feb 15	20116264

Sample Use Guides

In Vivo Use Guide

Patients received 80 mg/m2 on day one of a 21 day cycle. Dose escalation to 90 mg/m2 was allowed if patients did not experience >Grade 1 toxicity on the first course.

Route of Administration: Intravenous

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:10:40 GMT 2023` Edited by `admin` on `Fri Dec 15 16:10:40 GMT 2023`
Record UNII	XS499WOZ93
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SABARUBICIN

Official Name

English

sabarubicin [INN]

Common Name

English

Sabarubicin [WHO-DD]

Common Name

English

SABARUBICIN [MART.]

Common Name

English

HEXOPYRANOSYL)-2,6-DIDEOXY-A-L-LYXO-HEXOPYRANOSYL)OXY)-6,9,11-TRIHYDROXY-9-(HYDROXYACETYL)-7,8,9,10-TETRAHYDROTETRACENE-5,12-DIONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1594