CAMSIRUBICIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H32N2O9
Molecular Weight	528.551
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C2C(=N)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=GNCWGPLZJLZZPI-KUIJCEFOSA-N

InChI=1S/C27H32N2O9/c1-11-23(31)14(28)8-17(37-11)38-16-10-27(35,6-7-30)9-13-19(16)26(34)20-21(25(13)33)24(32)12-4-3-5-15(36-2)18(12)22(20)29/h3-5,11,14,16-17,23,29-31,33-35H,6-10,28H2,1-2H3/t11-,14-,16-,17-,23+,27-/m0/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/31016866 | https://www.ncbi.nlm.nih.gov/pubmed/25698442 | https://clinicaltrials.gov/ct2/show/study/NCT02267083 | https://www.cancer.gov/publications/dictionaries/cancer-drug/def/anthracycline-analogue-gpx-150

GPX-150 is an anthracycline compound that is being tested for treatment in patients with soft-tissue sarcomas. This doxorubicin (DOX) analog does not show the cumulative dose-dependent cardiotoxicity of DOX. It works by reducing the formation of reactive oxygen species and the cardiotoxic metabolite, doxorubiciniol, the two pathways that are linked to the irreversible cardiotoxicity seen with DOX. Phase 1 clinical trials showed no irreversible, cumulative dose-dependent cardiotoxicity. A phase 2 study investigating the safety and efficacy of GPX-150 in patients with soft tissue sarcoma has been completed. No patients developed any evidence of irreversible, cumulative dose-dependent chronic cardiotoxicity. Toxicities reported include grade 3 anemia, neutropenia, and grade 4 leukopenia.

Approval Year

Name

Type

Language

CAMSIRUBICIN

Official Name

English

GPX150

Preferred Name

English

5-IMINO-13-DEOXYDOXORUBICIN

Common Name

English

Camsirubicin [WHO-DD]

Common Name

English

GPX-150

Common Name

English

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

Systematic Name

English

camsirubicin [INN]

Common Name

English

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

Systematic Name

English

(8R,10S)-10-((3-AMINO-2,3,6-TRIDEOXY-.ALPHA.-L-LYXOHEXOPYRANOSYL) OXY)-6,8,11-TRIHYDROXY-8-(2-HYDROXYETHYL)- 12-IMINO-1-METHOXY-7,9,10,12-TETRAHYDROTETRACEN-5(8H)- ONE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1594