SABARUBICIN HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C32H37NO13.ClH
Molecular Weight	680.096
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[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=BSRQHWFOFMAZRL-BODGVHBXSA-N

InChI=1S/C32H37NO13.ClH/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;1H/t12-,13-,17-,18-,19-,21-,22-,26+,31+,32-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

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 18:06:58 GMT 2023` Edited by `admin` on `Fri Dec 15 18:06:58 GMT 2023`
Record UNII	2Y0GD160CC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SABARUBICIN HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

MEN-10755

Code

English

Code System Code Type Description

EPA CompTox

DTXSID80873335

Created by admin on Fri Dec 15 18:06:59 GMT 2023 , Edited by admin on Fri Dec 15 18:06:59 GMT 2023

PRIMARY

CAS

169317-77-5

Created by admin on Fri Dec 15 18:06:59 GMT 2023 , Edited by admin on Fri Dec 15 18:06:59 GMT 2023

PRIMARY

PUBCHEM

151896

Created by admin on Fri Dec 15 18:06:59 GMT 2023 , Edited by admin on Fri Dec 15 18:06:59 GMT 2023

PRIMARY

FDA UNII

2Y0GD160CC

Created by admin on Fri Dec 15 18:06:59 GMT 2023 , Edited by admin on Fri Dec 15 18:06:59 GMT 2023

PRIMARY

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