Pentostatin

Pentostatin (or deoxycoformycin, trade name Nipent, manufactured by SuperGen) is an anticancer chemotherapeutic drug.[1]

Pentostatin
Clinical data
Trade namesNipent
AHFS/Drugs.comMonograph
MedlinePlusa692004
Routes of
administration
Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
Protein binding4%
MetabolismHepatic, minor
Elimination half-life2.6 to 16 hours, mean 5.7 hours
Identifiers
IUPAC name
  • (R)-3-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.164.991
Chemical and physical data
FormulaC11H16N4O4
Molar mass268.273 g·mol−1
3D model (JSmol)
SMILES
  • n1c3c(n(c1)[C@@H]2O[C@@H]([C@@H](O)C2)CO)N\C=N/C[C@H]3O
InChI
  • InChI=1S/C11H16N4O4/c16-3-8-6(17)1-9(19-8)15-5-14-10-7(18)2-12-4-13-11(10)15/h4-9,16-18H,1-3H2,(H,12,13)/t6-,7+,8+,9+/m0/s1 Y
  • Key:FPVKHBSQESCIEP-JQCXWYLXSA-N Y
  (verify)

Mechanism

It is classified as a purine analog, which is a type of antimetabolite.

It mimics the nucleoside adenosine and thus inhibits the enzyme adenosine deaminase, interfering with the cell's ability to process DNA.[2]

Cancer cells generally divide more often than healthy cells; DNA is highly involved in cell division (mitosis) and drugs which target DNA-related processes are therefore more toxic to cancer cells than healthy cells.

Uses

Pentostatin is used to treat hairy cell leukemia.[3] It is given by intravenous infusion once every two weeks for three to six months.

Additionally, pentostatin has been used to treat steroid-refractory acute and chronic graft-versus-host disease.[4]

Pentostatin is also used in chronic lymphocytic leukemia (CLL) patients who have relapsed.

References

  1. Kay NE, Geyer SM, Call TG, et al. (January 2007). "Combination chemoimmunotherapy with pentostatin, cyclophosphamide, and rituximab shows significant clinical activity with low accompanying toxicity in previously untreated B chronic lymphocytic leukemia". Blood. 109 (2): 405–11. doi:10.1182/blood-2006-07-033274. PMC 1785105. PMID 17008537.
  2. Sauter C, Lamanna N, Weiss MA (September 2008). "Pentostatin in chronic lymphocytic leukemia". Expert Opin Drug Metab Toxicol. 4 (9): 1217–22. doi:10.1517/17425255.4.9.1217. PMID 18721115.
  3. Cannon T, Mobarek D, Wegge J, Tabbara IA (October 2008). "Hairy cell leukemia: current concepts". Cancer Invest. 26 (8): 860–5. doi:10.1080/07357900801965034. PMID 18798068.
  4. Bolaños-Meade J, Jacobsohn DA, Margolis J, Ogden A, Wientjes MG, Byrd JC, Lucas DM, Anders V, Phelps M, Grever MR, Vogelsang GB (April 2005). "Pentostatin in steroid-refractory acute graft-versus-host disease". J Clin Oncol. 23 (12): 2661–8. doi:10.1200/JCO.2005.06.130. PMID 15837980.
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