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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H20N2O5
Molecular Weight 404.4153
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CZ-48

SMILES

CCC(=O)O[C@]1(CC)C(=O)OCC2=C1C=C3N(CC4=CC5=CC=CC=C5N=C34)C2=O

InChI

InChIKey=YCNIQYLWIPCLNY-QHCPKHFHSA-N
InChI=1S/C23H20N2O5/c1-3-19(26)30-23(4-2)16-10-18-20-14(9-13-7-5-6-8-17(13)24-20)11-25(18)21(27)15(16)12-29-22(23)28/h5-10H,3-4,11-12H2,1-2H3/t23-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H20N2O5
Molecular Weight 404.4153
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Camptothecin-20(S)-O-propionate (CZ48) is a prodrug of camptothecin, an alkaloid isolated from the Chinese tree Camptotheca acuminata, with potential antineoplastic activity. Upon entry into cells, camptothecin-20(S)-O-propionate is hydrolyzed by esterases into the active form camptothecin. Camptothecin selectively stabilizes topoisomerase I-DNA covalent complexes, thereby inhibiting religation of topoisomerase I-mediated single-strand DNA breaks and producing potentially lethal double-strand DNA breaks when encountered by the DNA replication machinery. CZ48 is being investigated in clinical trials for the treatment of advanced solid tumors and lymphomas.

Approval Year

Substance Class Chemical
Record UNII
4S145C552U
Record Status Validated (UNII)
Record Version