Basic information
- CAS
53910-25-1- Standard SMILES
OCC1OC(n2cnc3c2NC=NC[C@H]3O)CC1O- InChIKey
FPVKHBSQESCIEP-LDIRUYLGSA-N- Molecular formula
- C11H16N4O4
- Average molar mass
- 268.27 g/mol
- Monoisotopic mass
- 268.117155
Overview
See also: Pentostatin (annotation moved to); 2'-Deoxycoformycin (annotation moved to).
Names & identifiers
- Preferred name
- (8R)-3-(4-Hydroxy-5-(Hydroxymethyl)Oxolan-2-Yl)-7,8-Dihydro-4H-Imidazo(4,5-D)(1,3)Diazepin-8-Ol
- IUPAC
- (8R)-3-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-8-ol
- English name
- PENTOSTATIN
- Molecular formula
- C11H16N4O4
- Molecular weight
- 268.27
Names & synonyms
(8R)-3-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-7,8-dihydro-4H-imidazo[4,5-d][1,3]diazepin-8-ol(8R)-3-(4-Hydroxy-5-(Hydroxymethyl)Oxolan-2-Yl)-7,8-Dihydro-4H-Imidazo(4,5-D)(1,3)Diazepin-8-OlRefChem:1050743Co-VPD-ADIDeaminase inhibitor (PD)Vira A deaminase inhibitorCovidarabineDeaminase inhibitorNiapent(8R)-3-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-oldCF
Show more names
Nipentdeoxycoformycin2’dcfci-825yk-176Cl 825Coforin
SCHEMBL172758CHEMBL360191FPVKHBSQESCIEP-LDIRUYLGSA-NEBC-07874NSC247520NSC-247520NCI60_001818AB01273933-01
Database identifiers
- CAS
53910-25-1
Properties
Computed structural properties
- XLogP
- -2.1
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 356
Physicochemical properties
- Melting point
- 154 · 154-157C
- alpha
- 25 · D25 +76.4° (c = 1 in water); D23 +73.0° (c = 1, pH 7 buffer)
- Boiling point
- 411.43 °C · 411.43°C (rough estimate)
- Density
- 1.2576 · 1.2576 (rough estimate)
- refractive index
- 1.6081 · 1.6081 (estimate)
- storage temp.
- -20 °C · -20°C
- solubility
- 2 O: · H2O: soluble10mg/mL, clear
- form
- White solid
- pka
- 5.2 · 5.2(at 25℃)
- color
- white to beige
- optical activity
- 70 to · [α]/D +70 to +80°, c = 1 in H2O
- ex/em
- 504 nm; · λex 504 nm; λem 525 nm; pH 9
- 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
- InChIKey
- FPVKHBSQESCIEP-JQCXWYLXSA-N
- SMILES
- [C@H]1(O)C[C@H](N2C=NC3=C2N=CNC[C@H]3O)O[C@@H]1CO
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- ridadr
- UN 2811 6.1 / PGIII
- hs_code
- 2933998090
- Toxicity
- LD50 oral in mouse: 227mg/kg
- risk_code
- 22
- Signal word
- Danger
- Symbol(GHS)
- GHS06
- hazard_code
- Xn
- Hazard statements
- H301
- Precautionary statements
- P301+P310
- Hazardous Substances Data
- 53910-25-1(Hazardous Substances Data)
Chemistry & industry
Applications
DescriptionPentostatin, an adenosine deaminase inhibitor, is an orphan drug introduced for the treatment of hairy cell leukemia. The agent is considered a significant advance over alpha-interferon, the only other drug available for this indication. The majority of patients treated with pentostatin have been reported to remain in remission for at least four years. It is also under investigation for the treatment of other kinds of leukemia and in transplant rejection.
DescriptionBecause of their antitumor activity via inhibition of DNA synthesis, purine nucleoside derivatives resistant to deamination have been developed for the treatment of various leukemias. Pentostatin is a purine nucleoside analog that irreversibly inhibits adenosine deaminase (Ki = 0.9 pM) and thus interrupts DNA synthesis in dividing cells. Pentostatin has been reported to display strong efficacy in the clinical treatment of hairy cell leukemia as well as relapsed chronic lymphocytic leukemia.
UsesPentostatin is a potent antitumour antibiotic isolated from a Streptomyces species. Pentostatin is a potent inhibitor of adenine deaminase and has been used therapeutically as an antitumour agent.
UsesPentostatin is a potent antitumor antibiotic isolated from a Streptomyces species. Pentostatin is a potent inhibitor of adenine deaminase and has been used therapeutically as an antitumor agent.
UsesAn adenosine deaminase inhibitor used as an anti-cancer therapeutic drug. Shown to be effective in the treatment of hairy cell leukemia as well as having use in the treatment of other types of cancer such as chronic lymphocytic leukemia.
General DescriptionThe drug is available in 10-mg vials for IV use. The drug isused to treat leukemias such as hairy cell leukemia, chroniclymphocytic leukemia, and lymphoblastic leukemia. Themechanism of action involves inhibition of the enzymeadenosine deaminase yielding increased cellular levels ofdeoxyadenosine and deoxyadenosine triphosphate (dATP).The increased levels of dATP are cytotoxic to lymphocytes.Pentostatin is a fermentation product of Streptomyces antibioticus.Resistance appears to involve decreased cellulartransport or increased expression of catabolic enzymes.Acid instability prevents oral administration, and the drug isonly administered by IV. The drug is distributed in totalbody water but does not enter the CNS. The majority of thedosage is excreted unchanged in the urine. Fatal pulmonary toxicity has occurred when pentostatin and fludarabine areused in combination. Toxicities include myelosuppression,immunosuppression, nausea, vomiting, headache, lethargy,and fatigue.
Related reactions
1 records
Compound notes
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