Pentostatin

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Pentostatin
Pentostatin structure.svg
Pentostatin ball-and-stick.png
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)
Legal status
Routes of
administration
Intravenous
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 YesY
ATC code L01XX08 (WHO)
PubChem CID: 439693
IUPHAR/BPS 4805
DrugBank DB00552 YesY
ChemSpider 388759 YesY
UNII 395575MZO7 YesY
KEGG D00155 YesY
ChEMBL CHEMBL1580 YesY
Chemical data
Formula C11H16N4O4
Molecular mass 268.269 g/mol
  • n1c3c(n(c1)[C@@H]2O[C@@H]([C@@H](O)C2)CO)N\C=N/C[C@H]3O
  • 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 YesY
  • Key:FPVKHBSQESCIEP-JQCXWYLXSA-N YesY
  (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

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