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53910-25-1 molecular structure
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(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol

ChemBase ID: 434
Molecular Formular: C11H16N4O4
Molecular Mass: 268.26914
Monoisotopic Mass: 268.11715501
SMILES and InChIs

SMILES:
[C@@H]1(C[C@@H]([C@H](O1)CO)O)n1c2N=CNC[C@H](c2nc1)O
Canonical SMILES:
OC[C@H]1O[C@H](C[C@@H]1O)n1cnc2c1N=CNC[C@H]2O
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

Cite this record

CBID:434 http://www.chembase.cn/molecule-434.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3H,6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
IUPAC Traditional name
(8R)-3-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-6H,7H,8H-imidazo[4,5-d][1,3]diazepin-8-ol
Brand Name
Co-V
Co-Vidarabine
Covidarabine
Nipent
PD-ADI
Vidarbine
Vira a Deaminase Inhibitor
Synonyms
2'-DCF
2'-Deoxycoformycin
2'-Dexoycoformycin
Deoxycoformycin
pentostatin
Pentostatin
CAS Number
53910-25-1
PubChem SID
46507116
160963897
PubChem CID
439693

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 13.062051  H Acceptors
H Donor LogD (pH = 5.5) -3.7633858 
LogD (pH = 7.4) -2.9345255  Log P -2.016391 
Molar Refractivity 64.9814 cm3 Polarizability 24.982864 Å3
Polar Surface Area 112.13 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.03  LOG S -1.4 
Solubility (Water) 1.07e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
30 mg/mL expand Show data source
Hydrophobicity(logP)
-1.1 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00552 external link
Item Information
Drug Groups approved; investigational
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. [PubChem]
Indication For the treatment of hairy cell leukaemia refractory to alpha interferon.
Pharmacology Pentostatin is an antineoplastic anti-metabolite used in the treatment of several forms of leukemia including acute nonlymphocytic leukemia and hairy cell leukemia. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (of the cell cycle), stopping normal development and division. It is a 6-thiopurine analogue of the naturally occurring purine bases hypoxanthine and guanine. Intracellular activation results in incorporation into DNA as a false purine base. An additional cytotoxic effect is related to its incorporation into RNA. Cytotoxicity is cell cycle phase-specific (S-phase).
Toxicity LD50=128 mg/kg (mouse), side effects include lethargy, rash, fatigue, nausea and myelosuppression.
Affected Organisms
Humans and other mammals
Biotransformation Primarily hepatic, but only small amounts are metabolized.
Absorption Not absorbed orally, crosses blood brain barrier.
Half Life 5.7 hours (with a range between 2.6 and 16 hrs)
Protein Binding 4%
Elimination In man, following a single dose of 4 mg/m2 of pentostatin infused over 5 minutes, approximately 90% of the dose was excreted in the urine as unchanged pentostatin and/or metabolites as measured by adenosine deaminase inhibitory activity.
Clearance * 68 mL/min/m2
References
[Link]
External Links
Wikipedia
Drugs.com

REFERENCES

REFERENCES

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PATENTS

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