53910-25-1 Usage
Description
Pentostatin, also known as Nipent, is a potent antitumor antibiotic derived from a Streptomyces species. It functions as an adenosine deaminase inhibitor, which plays a crucial role in its anti-cancer properties. Pentostatin is a white solid and is classified as an orphan drug, primarily used for the treatment of hairy cell leukemia.
Used in Anticancer Applications:
Pentostatin is used as an anti-cancer therapeutic drug for its efficacy in treating hairy cell leukemia, chronic lymphocytic leukemia, and lymphoblastic leukemia. It works by inhibiting the enzyme adenosine deaminase, leading to increased cellular levels of deoxyadenosine and deoxyadenosine triphosphate (dATP). The elevated levels of dATP are cytotoxic to lymphocytes, making Pentostatin a valuable agent in cancer treatment.
Used in Pharmaceutical Industry:
Pentostatin is used as an active pharmaceutical ingredient in the development of anti-cancer drugs. Its potent inhibition of adenine deaminase and effectiveness against various leukemias make it a significant compound in the pharmaceutical sector.
Used in Clinical Trials:
Pentostatin is also used in clinical trials for the investigation of its potential in treating other types of leukemia and in transplant rejection, showcasing its versatility and importance in medical research.
Originator
Warner-Lambert (Parke-Davis) (U.S.A.)
Indications
Pentostatin (Nipent, deoxycoformycin) is a purine isolated
from fermentation cultures of the microbe
Streptomyces antibioticus. Its mechanism of action involves
inhibition of the enzyme adenosine deaminase,
which plays an important role in purine salvage pathways
and DNA synthesis.The resulting accumulation of
deoxyadenosine triphosphate (dATP) is highly toxic to
lymphocytes.
Pentostatin is effective in the therapy of hairy cell
leukemia, producing remissions in 80 to 90% of patients
and complete remissions in more than 50%. The major
toxic effects of the drug include myelosuppression, nausea,
and skin rashes.
Biological Activity
Irreversible inhibitor of adenosine deaminase (K i = 2.5 pM). Anticancer agent.
Biochem/physiol Actions
Pentostatin/2′-deoxycoformycin is used to treat patients with Waldenstr?m′s macroglobulinemia.
Clinical Use
Pentostatin is a ring-expanded purine ribonucleoside that inhibits adenosine deaminase and is
used in the treatment of hairy cell leukemia. The elevated levels of deoxyadenosine triphosphate that result
from inhibition of this degradative enzyme inhibit the action of ribonucleotide reductase (the enzyme that
converts ribose diphosphate to deoxyribose diphosphate), thus halting DNA synthesis within the tumor cell.
Safety Profile
Poison by intravenous route. An experimental teratogen. Human mutation data reported. When heated to decomposition it emits toxic fumes of NOx.
Drug interactions
Potentially hazardous interactions with other drugs
Antipsychotics: avoid with clozapine (increased risk
of agranulocytosis).
Cytotoxics: increased risk of toxicity with high-dose
cyclophosphamide - avoid; increased pulmonary
toxicity with fludarabine (unacceptably high
incidence of fatalities).
Metabolism
Only a small amount is metabolised via the liver.
It is primarily excreted unchanged by the kidneys
(30-90% excreted by kidneys within 24 hours).
Check Digit Verification of cas no
The CAS Registry Mumber 53910-25-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,3,9,1 and 0 respectively; the second part has 2 digits, 2 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 53910-25:
(7*5)+(6*3)+(5*9)+(4*1)+(3*0)+(2*2)+(1*5)=111
111 % 10 = 1
So 53910-25-1 is a valid CAS Registry Number.
InChI:InChI=1/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
53910-25-1Relevant articles and documents
METHOD FOR THE SYNTHESIS OF PENTOSTATIN
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Page/Page column 7; 8, (2018/03/28)
The present invention relates to a method for the stereo-selective production of pentostatin comprising an enzymatic transglycosylation reaction between 6,7-dihydroimidazo-[4,5-d]-[1,3]diazepin-8(3H)-one and a 2'-deoxyribonucleoside, followed by an ruthenium-catalyzed asymmetric transfer hydrogenation.
THERAPEUTIC FOR HEPATIC CANCER
-
, (2011/02/18)
A novel pharmaceutical composition for treating or preventing hepatocellular carcinoma and a method of treatment are provided. A pharmaceutical composition for treating or preventing liver cancer is obtained by combining a chemotherapeutic agent with an anti-glypican 3 antibody. Also disclosed is a pharmaceutical composition for treating or preventing liver cancer which comprises as an active ingredient an anti-glypican 3 antibody for use in combination with a chemotherapeutic agent, or which comprises as an active ingredient a chemotherapeutic agent for use in combination with an anti-glypican 3 antibody. Using the chemotherapeutic agent and the anti-glypican 3 antibody in combination yields better therapeutic effects than using the chemotherapeutic agent alone, and mitigates side effects that arise from liver cancer treatment with the chemotherapeutic agent.
SYNTHESIS AND MANUFACTURE OF PENTOSTATIN AND ITS PRECURSORS, ANALOGS AND DERIVATIVES
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, (2008/06/13)
Methods and compositions are provided for efficiently preparing and manufacturing pentostatin. Also provided are novel precursors of pentostatin, pentostatin analogs and derivatives. In one aspect of the invention, a method is provided for total chemical synthesis of pentostatin via a route of heterocyclic ring expansion. For example, a heterocyclic pharmaceutical intermediate for drugs such as pentostatin, e.g., the diazepinone precursor, can be obtained efficiently through a ring expansion of an O-C-N functionality in a hypoxanthine or 2'-deoxyinosine derivative. The methods and compositions can also be used to synthesize and manufacture heterocyclic compounds other than pentostatin, especially pharmaceutically important heterocyclic compounds.
