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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 of SABARUBICIN

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 10
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

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
Record UNII
XS499WOZ93
Record Status Validated (UNII)
Record Version