Pentostatin

Pentostatin

Systematic (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
Clinical data
Trade names	Nipent
AHFS/Drugs.com	monograph
MedlinePlus	a692004
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intravenous
Legal status
Legal status	CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	n/a
Protein binding	4%
Metabolism	Hepatic, minor
Biological half-life	2.6 to 16 hours, mean 5.7 hours
Identifiers
CAS Number	53910-25-1
ATC code	L01XX08 (WHO)
PubChem	CID 439693
IUPHAR/BPS	4805
DrugBank	DB00552
ChemSpider	388759
UNII	395575MZO7
KEGG	D00155
ChEMBL	CHEMBL1580
Chemical data
Formula	C11H16N4O4
Molar mass	268.269 g/mol
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 Key:FPVKHBSQESCIEP-JQCXWYLXSA-N
(verify)

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

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 Onc 23 (12): 2661–8. doi:10.1200/JCO.2005.06.130. PMID 15837980.