Chemistry:Pentostatin

Short description: Chemical compound

Pentostatin

Clinical data
Trade names	Nipent
AHFS/Drugs.com	Monograph
MedlinePlus	a692004
Pregnancy category	US: D (Evidence of risk)
Routes of administration	Intravenous
ATC code	L01XX08 (WHO)
Legal status
Legal status	CA: ℞-only UK: POM (Prescription only) US: ℞-only
Pharmacokinetic data
Bioavailability	n/a
Protein binding	4%
Metabolism	Hepatic, minor
Elimination half-life	2.6 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	53910-25-1 Y
PubChem CID	439693
IUPHAR/BPS	4805
DrugBank	DB00552 Y
ChemSpider	388759 Y
UNII	395575MZO7
KEGG	D00155 Y
ChEBI	CHEBI:27834
ChEMBL	ChEMBL1580 Y
Chemical and physical data
Formula	C11H16N4O4
Molar mass	268.273 g·mol−1
3D model (JSmol)	Interactive image
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
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Pentostatin (or deoxycoformycin, trade name Nipent, manufactured by SuperGen) is an anticancer chemotherapeutic drug.

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.

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. 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.

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