53910-25-1
Product Name:
PENTOSTATIN
Formula:
C11H16N4O4
Synonyms:
(8R)-3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3,4,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol;2ʹ-Deoxycoformycin, (8R)-3-(2-deoxy-β-D-erythro- pentofuranosyl)-3,6,7,8-tetrahydroimidazo[4,5-d][1,3]diazepin-8-ol, Pentostatin, S. antibioticus;2′-dCF;DCF;Deoxycoformycin
Inquiry
CHEMICAL AND PHYSICAL PROPERTIES
| Physical Description | Solid |
|---|---|
| Color/Form | White crystals from methanol/water |
| Melting Point | 220 °C |
| Solubility | 30 mg/mL |
| LogP | -1.1 |
| Stability/Shelf Life | Commercially available pentostatin powder for injection should be stored at 2-8 °C. ... When stored at 2-8 °C, the manufacturer states that currently available pentostatin powder for injection is stable for 18 mo after the date of manufacture when stored as directed. ... Pentostatin is compatible with 5% dextrose injection, 0.9% sodium chloride injection, and lactated Ringer's. When reconstituted with 0.9% sodium chloride injection to a final concentration of 2 mg/ml, pentostatin solutions are physically and chemically stable for at least 72 hr at room temperature (22-25 °C). When diluted to a final concentration of 20 ug/ml, the drug is chemically compatible at room temperature with 0.9% sodium chloride or lactated Ringer's injection for at least 48 hr and with 5% dextrose injection for at least 24 hr. Up to an 8-10% loss in potency has been reported to occur within 48 hr in such solutions diluted in 5% dextrose, However, because such reconstituted and/or diluted pentostatin solutions contain no preservatives, the manufacturer recommends that they be used within 8 hr when stored at room temperature in ambient light, and that unused portions be discarded. |
| Optical Rotation | Specific optical rotation: + 76.4 deg at 25 °C/D (concentration by volume = 1 g 100 ml water); specific optical rotation: + 73.0 deg at 23 °C/D (concentration by volume = 1 g in 100 ml water pH 7 buffer) |
| Dissociation Constants | 5.2 |
| Other Experimental Properties | Pentostatin differs from the physiologic nucleosides, adenosine and deoxyadenosine, by the interposition of a methylene group between N-1 and C-6 of the purine ring, resulting in a 7-membered (imidazobenzopin) rather than a 6-membered ring, and by the deletion of an amino group from, and the addition of a hydroxyl group to, the ring; the sugar moiety, deoxyribose, is common to both pentostatin and deoxyadenosine, while adenosine contains ribose. The resultant stereochemical and tautomeric differences in the compounds provide an increased binding affinity of pentostatin for the catalytic center of adenosine deaminase compared with the affinities of these physiologic substrates for the enzyme. Pentostatin is thought to resemble closely the transition-state intermediates of the adenosine deaminase reaction involving these nucleosides (ie, the intermediaries formed during the deamination of adenosine and deoxyadenosine to inosine and deoxyinosine, respectively), The drug is a purine antagonist antimetabolite that acts as an adenosine deaminase inhibitor. |
SAFETY INFORMATION
| Signal word | Danger |
|---|---|
| Pictogram(s) |
 Skull and Crossbones Acute Toxicity GHS06 |
| GHS Hazard Statements |
H301:Acute toxicity,oral |
| Precautionary Statement Codes |
P301+P310:IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
COMPUTED DESCRIPTORS
| Molecular Weight | 268.27 g/mol |
|---|---|
| XLogP3 | -2.1 |
| Hydrogen Bond Donor Count | 4 |
| Hydrogen Bond Acceptor Count | 6 |
| Rotatable Bond Count | 2 |
| Exact Mass | 268.11715500 g/mol |
| Monoisotopic Mass | 268.11715500 g/mol |
| Topological Polar Surface Area | 112 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 356 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 4 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
PRODUCT INTRODUCTION
description
A potent inhibitor of adenosine deaminase. The drug is effective in the treatment of many lymphoproliferative malignancies, particularly hairy-cell leukemia. It is also synergistic with some other antineoplastic agents and has immunosuppressive activity.