Pentostatin

Pentostatin
Names
Trade namesNipent
Other names2'-deoxycoformycin (DCF)
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
Drug classPurine antagonist[1]
Main usesHairy cell leukemia, chronic lymphocytic leukemia (CLL), cutaneous T-cell lymphoma[1]
Side effectsNausea, fever, rash, cough, shortness of breath, itchiness, headache, low blood cells[1]
WHO AWaReUnlinkedWikibase error: ⧼unlinkedwikibase-error-statements-entity-not-set⧽
Pregnancy
category
  • US: D (Evidence of risk)
    Routes of
    use    		Intravenous
    Typical dose4 mg/m2[1]
    External links
    AHFS/Drugs.comMonograph
    MedlinePlusa692004
    Legal
    Legal status
    Pharmacokinetics
    Bioavailabilityn/a
    Protein binding4%
    MetabolismLiver, minor
    Elimination half-life2.6 to 16 hours, mean 5.7 hours
    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 checkY
    • Key:FPVKHBSQESCIEP-JQCXWYLXSA-N checkY

    Pentostatin, sold under the brand name Nipent, is a medication used to treat hairy cell leukemia, chronic lymphocytic leukemia (CLL), and cutaneous T-cell lymphoma.[1][2] It is given by injection into a vein.[1]

    Common side effects include nausea, fever, rash, cough, shortness of breath, itchiness, headache, and low blood cells.[1] Other side effects may include seizures, coma, kidney problems, lung toxicity, and infection.[1] Use in pregnancy may harm the baby.[1] It is a purine antagonist.[1]

    Pentostatin was approved for medical use in the United States in 1991.[1] In the United Kingdom 10 mg of medication costs the NHS about £730 as of 2021.[3] This amount in the United States is about 2,300 USD.[4]

    Medical uses

    Pentostatin is used to treat hairy cell leukemia.[5] 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.[6]

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

    Dosage

    It may be used at a dose of 4 mg/m2 every two weeks.[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.[7]

    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.

    References

    1. 1 2 3 4 5 6 7 8 9 10 11 12 "Pentostatin Monograph for Professionals". Drugs.com. Archived from the original on 16 August 2019. Retrieved 27 October 2021.
    2. ↑ "DailyMed - NIPENT- pentostatin injection, powder, lyophilized, for solution". dailymed.nlm.nih.gov. Archived from the original on 22 January 2021. Retrieved 27 October 2021.
    3. ↑ BNF 81: March-September 2021. BMJ Group and the Pharmaceutical Press. 2021. p. 964. ISBN 978-0857114105.
    4. ↑ "Nipent Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 24 January 2021. Retrieved 27 October 2021.
    5. ↑ 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.
    6. ↑ 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.
    7. ↑ 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.
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