| Stereochemistry | ABSOLUTE |
| Molecular Formula | C10H12ClN5O4 |
| Molecular Weight | 301.686 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NC1=NC=NC2=C1N=C(Cl)N2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O
InChI
InChIKey=MHDPPLULTMGBSI-UUOKFMHZSA-N
InChI=1S/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
| Molecular Formula | C10H12ClN5O4 |
| Molecular Weight | 301.686 |
| Charge | 0 |
| Count |
MOL RATIO
1 MOL RATIO (average) |
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
8-chloroadenosine (8-Cl-Ado) is a ribonucleoside analog. The mechanism of its action remains poorly understood, however, it is known that the drug inhibits RNA synthesis. It has significant cytotoxic activity against lymphoid and myeloid malignant cells. The nucleoside analog 8-Cl-Ado is phosphorylated into its cytotoxic triphosphate 8-Cl-ATP. The accumulation of the cytotoxic metabolite results in a parallel decrease of the ATP cellular pools. 8-Cl-Ado gets incorporated into RNA during transcription, hindering this process. In addition, this triphosphate inhibits ATP-dependent poly(A) tail synthesis, and, as a consequence, mRNA processing is inhibited, resulting in vitro cytotoxicity in several solid and hematological malignancies. This agent is currently in clinical trials for the treatment of chronic lymphocytic leukemia and acute myeloid leukemia.
Approval Year
Sourcing
PubMed
Patents
Sample Use Guides
A Phase I Study of 8-Chloro-Adenosine in Previously Treated Patients With Chronic Lymphocytic Leukemia /Small Lymphocytic Lymphoma: Starting dose 45 mg/m2 intravenous over 1 hr daily for 5 days every 4 weeks
Route of Administration:
Intravenous