Pentostatin

Pentostatin: Pentostatin

Systematic (IUPAC) name

(8R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-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 cat. ?

Legal status ℞-only (US)

Routes Intravenous

Pharmacokinetic data

Bioavailability n/a

Protein binding 4%

Metabolism Hepatic, minor

Half-life 2.6 to 16 hours, mean 5.7 hours

Identifiers

CAS number 53910-25-1^Y

ATC code L01XX08

PubChem CID 439693

DrugBank APRD00202

ChemSpider 388759^Y

UNII 395575MZO7^Y

KEGG D00155^Y

ChEMBL CHEMBL1580^Y

Chemical data

Formula C₁₁H₁₆N₄O₄

Mol. mass 268.269 g/mol

SMILES eMolecules & PubChem

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 (Nipent, manufactured by SuperGen, San Ramon, CA, also deoxycoformycin) 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 CLL patients who have relapsed.

References

^ 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. http://www.bloodjournal.org/cgi/pmidlookup?view=long&pmid=17008537.

^ 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. http://www.informapharmascience.com/doi/abs/10.1517/17425255.4.9.1217.

^ 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. http://www.informaworld.com/openurl?genre=article&doi=10.1080/07357900801965034&magic=pubmed%7C%7C1B69BA326FFE69C3F0A8F227DF8201D0.

^ 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.

v · d · eIntracellular chemotherapeutic agents/antineoplastic agents (L01)

SPs/MIs
(M phase)

Block microtubule assembly

Vinca alkaloids (Vinblastine, Vincristine, Vinflunine, Vindesine, Vinorelbine)

Block microtubule disassembly

Taxanes (Cabazitaxel, Docetaxel, Larotaxel, Ortataxel, Paclitaxel, Tesetaxel) • Epothilones (Ixabepilone)

DNA replication
inhibitor

DNA precursors/
antimetabolites
(S phase)

Folic acid

dihydrofolate reductase inhibitor (Aminopterin, Methotrexate, Pemetrexed, Pralatrexate) • thymidylate synthase inhibitor (Raltitrexed, Pemetrexed)

Purine

adenosine deaminase inhibitor (Pentostatin)

halogenated/ribonucleotide reductase inhibitors (Cladribine, Clofarabine, Fludarabine)
thiopurine (Thioguanine, Mercaptopurine)

Pyrimidine

thymidylate synthase inhibitor (Fluorouracil, Capecitabine, Tegafur, Carmofur, Floxuridine)

DNA polymerase inhibitor (Cytarabine)

ribonucleotide reductase inhibitor (Gemcitabine)
hypomethylating agent (Azacitidine, Decitabine)

Deoxyribonucleotide

ribonucleotide reductase inhibitor (Hydroxycarbamide)

Topoisomerase inhibitors
(S phase)

I

Camptotheca (Camptothecin, Topotecan, Irinotecan, Rubitecan, Belotecan)

II

Podophyllum (Etoposide, Teniposide)

II+Intercalation

Anthracyclines (Aclarubicin, Daunorubicin, Doxorubicin, Epirubicin, Idarubicin, Amrubicin, Pirarubicin, Valrubicin, Zorubicin) • Anthracenediones (Mitoxantrone, Pixantrone)

Crosslinking of DNA
(CCNS)

Alkylating

Nitrogen mustards: Mechlorethamine • Cyclophosphamide (Ifosfamide, Trofosfamide) • Chlorambucil (Melphalan, Prednimustine) • Bendamustine • Uramustine • Estramustine

Nitrosoureas: Carmustine • Lomustine (Semustine) • Fotemustine • Nimustine • Ranimustine • Streptozocin

Alkyl sulfonates: Busulfan (Mannosulfan, Treosulfan)
Aziridines: Carboquone • ThioTEPA • Triaziquone • Triethylenemelamine

Alkylating-like

Platinum (Carboplatin, Cisplatin, Nedaplatin, Oxaliplatin, Triplatin tetranitrate, Satraplatin)

Nonclassical

Hydrazines (Procarbazine) • Triazenes (Dacarbazine, Temozolomide) • Altretamine • Mitobronitol

Intercalation

Streptomyces (Actinomycin, Bleomycin, Mitomycin, Plicamycin)

Photosensitizers/PDT
Aminolevulinic acid/Methyl aminolevulinate • Efaproxiral • Porphyrin derivatives (Porfimer sodium, Talaporfin, Temoporfin, Verteporfin)

Other

Enzyme inhibitors

FI (Tipifarnib) • CDK inhibitors (Alvocidib, Seliciclib) • PrI (Bortezomib) • PhI (Anagrelide) • IMPDI (Tiazofurine) • LI (Masoprocol) • PARP inhibitor (Olaparib) • HDAC (Vorinostat, Romidepsin)

Receptor antagonists

ERA (Atrasentan) • retinoid X receptor (Bexarotene) • sex steroid (Testolactone)

Other/ungrouped

Amsacrine • Trabectedin • retinoids (Alitretinoin, Tretinoin) • Arsenic trioxide • asparagine depleters (Asparaginase/Pegaspargase) • Celecoxib • Demecolcine • Elesclomol • Elsamitrucin • Etoglucid • Lonidamine • HAMLET (human alpha-lactalbumin made lethal to tumor cells) • Lucanthone • Mitoguazone • Mitotane • Oblimersen • Omacetaxine mepesuccinate • mTOR inhibitors (Everolimus, Temsirolimus)

M: NEO

tsoc, mrkr

tumr, epon, para

drug (L1i/1e/V03)

Categories:
Nucleosides
Antineoplastic antimetabolites

Pentostatin

Systematic (IUPAC) name
(8R)-3-(2-deoxy-β-D-erythro-pentofuranosyl)-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 cat.	?
Legal status	℞-only (US)
Routes	Intravenous
Pharmacokinetic data
Bioavailability	n/a
Protein binding	4%
Metabolism	Hepatic, minor
Half-life	2.6 to 16 hours, mean 5.7 hours
Identifiers
CAS number	53910-25-1^Y
ATC code	L01XX08
PubChem	CID 439693
DrugBank	APRD00202
ChemSpider	388759^Y
UNII	395575MZO7^Y
KEGG	D00155^Y
ChEMBL	CHEMBL1580^Y
Chemical data
Formula	C₁₁H₁₆N₄O₄
Mol. mass	268.269 g/mol
SMILES	eMolecules & PubChem
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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Look at other dictionaries:

Pentostatin — Strukturformel Allgemeines Name Pentostatin Andere Namen … Deutsch Wikipedia
pentostatin — An antineoplastic; a potent inhibitor of adenosine deaminase; interferes with the synthesis of nicotinamide adenine dinucleotide. SYN: 2 deoxycoformycin. * * * n. a cytotoxic drug that is used in treating hairy cell leukaemia; it … Medical dictionary
pentostatin — n. a cytotoxic drug that is used in treating hairy cell leukaemia; it works by interfering with the action of the enzyme adenosine deaminase. Pentostatin is administered by intravenous injection; side effects, which may be severe, include… … The new mediacal dictionary
pentostatin — noun A particular drug, isolated from Streptomyces antibioticus, used in chemotherapy … Wiktionary
pentostatin — An anticancer drug that belongs to the family of drugs called antimetabolites … English dictionary of cancer terms
Leukemia — For the journal, see Leukemia (journal). For animal diseases, see Leucosis. Leukemia Classification and external resources A Wright s stained bone marrow aspirate smear of patient with precursor B cell acute lymphoblastic leukemia … Wikipedia
Cyclophosphamide — Systematic (IUPAC) name … Wikipedia
Cladribine — Systematic (IUPAC) name 5 (6 amino 2 chloro purin 9 yl) 2 (hydroxymethyl)oxolan 3 ol Clinical data AHFS/Drugs.com … Wikipedia
Chemotherapy — A woman being treated with docetaxel chemotherapy for breast cancer. Cold mittens and wine coolers are placed on her hands and feet to reduce harm to her nails. Chemotherapy (sometimes cancer chemotherapy) is the treatment of cancer with an… … Wikipedia
Paclitaxel — Systematic (IUPAC) name (2α,4α,5β,7β,10β,13α) 4,10 bis(acetyloxy) … Wikipedia

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Pentostatin

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References

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