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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H31NO10
Molecular Weight 529.5357
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 13-DEOXYDOXORUBICIN

SMILES

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

InChI

InChIKey=RGVRUQHYQSORBY-JIGXQNLBSA-N
InChI=1S/C27H31NO10/c1-11-22(30)14(28)8-17(37-11)38-16-10-27(35,6-7-29)9-13-19(16)26(34)21-20(24(13)32)23(31)12-4-3-5-15(36-2)18(12)25(21)33/h3-5,11,14,16-17,22,29-30,32,34-35H,6-10,28H2,1-2H3/t11-,14-,16-,17-,22+,27-/m0/s1

HIDE SMILES / InChI

Description

13-deoxyadriamycin hydrochloride (13-Deoxydoxorubicin hydrochloride, GPX-100) is an anthracycline similar to doxorubicin. GPX-100 is unique among anthracyclines because it is not converted to doxorubicinol during metabolism in the body. This metabolite has been shown to be a major cause of damage to the heart (cardiotoxicity) in laboratory studies. GPX-100 belongs to the class of reactive oxygen species stimulants; RNA synthesis inhibitors and Type II DNA topoisomerase inhibitors. It was in phase II clinical trial for the treatment of cancer.

Originator

Approval Year

PubMed

Sample Use Guides

In Vivo Use Guide
Breast Cancer: Dosage Form - IV solution of sterilized lyophilized powder in Sodium Chloride (NaCl) for Injection, USP (0.9%). Doses - 140 mg/m2 GPX-100 with escalation to 170 mg/m2 and de-escalation to 105 mg/m2 depending upon clinical response and toxicity. Administration - One IV infusion every 3 weeks for up to 8 doses.
Route of Administration: Intravenous