13-DEOXYDOXORUBICIN HYDROCHLORIDE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H31NO10.ClH
Molecular Weight	565.997
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of 13-DEOXYDOXORUBICIN HYDROCHLORIDE

Structure Search

SMILES

Cl.COC1=C2C(=O)C3=C(O)C4=C(C[C@@](O)(CCO)C[C@@H]4O[C@H]5C[C@H](N)[C@H](O)[C@H](C)O5)C(O)=C3C(=O)C2=CC=C1

InChI

InChIKey=YZSQITAPLDJGKS-RYQLBYGJSA-N

InChI=1S/C27H31NO10.ClH/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;1H/t11-,14-,16-,17-,22+,27-;/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	C27H31NO10
Molecular Weight	529.5357
Charge	0
Count

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

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT00123877 | https://adisinsight.springer.com/drugs/800008795

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

Title	Date	PubMed
Reduction of 13-deoxydoxorubicin and daunorubicinol anthraquinones by human carbonyl reductase.	2005	16382174

Patents

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

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:06:07 GMT 2025` Edited by `admin` on `Mon Mar 31 18:06:07 GMT 2025`
Record UNII	L6ZON4CT5F
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GPX-100 HYDROCHLORIDE

Preferred Name

English

13-DEOXYDOXORUBICIN HYDROCHLORIDE

Common Name

English

(7S,9R)-7-((2R,4S,5S,6S)-4-AMINO-5-HYDROXY-6-METHYL-TETRAHYDROPYRAN-2-YL)OXY-6,9,11-TRIHYDROXY-9-(2-HYDROXYETHYL)-4-METHOXY-8,10-DIHYDRO-7H-TETRACENE-5,12-DIONE HYDROCHLORIDE

Systematic Name

English

13-DEOXYADRIAMYCIN HYDROCHLORIDE

Common Name

English

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

Systematic Name

English

NSC-273427

Code

English

GPX-100-

Code

English

Code System Code Type Description

EPA CompTox

DTXSID20639038