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1679-14-1 molecular structure
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{[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid

ChemBase ID: 944
Molecular Formular: C10H13FN5O7P
Molecular Mass: 365.2116842
Monoisotopic Mass: 365.05366263
SMILES and InChIs

SMILES:
P(=O)(OC[C@H]1O[C@@H](n2c3nc(F)nc(N)c3nc2)[C@@H](O)[C@@H]1O)(O)O
Canonical SMILES:
O[C@H]1[C@H](O)[C@H](O[C@H]1n1cnc2c1nc(F)nc2N)COP(=O)(O)O
InChI:
InChI=1S/C10H13FN5O7P/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(18)5(17)3(23-9)1-22-24(19,20)21/h2-3,5-6,9,17-18H,1H2,(H2,12,14,15)(H2,19,20,21)/t3-,5-,6+,9-/m1/s1
InChIKey:
GIUYCYHIANZCFB-FJFJXFQQSA-N

Cite this record

CBID:944 http://www.chembase.cn/molecule-944.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
{[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy}phosphonic acid
IUPAC Traditional name
fludarabine
Brand Name
Fludara
Fludura
Synonyms
FAMP
Fludarabine 5'-monophosphate
Fludarabine monophosphate
Fludarabine phosphate
Fludarabine
Fludara
Fludarabine Phosphate(Fludara)
CAS Number
1679-14-1
75607-67-9
PubChem SID
46507525
160964407
PubChem CID
30751

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 1.3406203  H Acceptors 10 
H Donor LogD (pH = 5.5) -4.035218 
LogD (pH = 7.4) -5.1241035  Log P -1.9500656 
Molar Refractivity 74.9321 cm3 Polarizability 28.966225 Å3
Polar Surface Area 186.07 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -2.51  LOG S -2.09 
Solubility (Water) 2.97e+00 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
3.53 mg/ml expand Show data source
DMSO expand Show data source
Hydrophobicity(logP)
-2.8 expand Show data source
Storage Condition
-20°C expand Show data source
Target
Antimetabolites expand Show data source
Purity
97% expand Show data source
Salt Data
Phosphate expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank - DB01073 external link
Item Information
Drug Groups approved
Description Fludarabine (marketed as fludarabine phosphate under the trade name Fludara) is a chemotherapy drug used in the treatment of hematological malignancies. [Wikipedia]
Indication For the treatment of adult patients with B-cell chronic lymphocytic leukemia (CLL) who have not responded to or whose disease has progressed during treatment with at least one standard alkylating-agent containing regimen
Pharmacology Fludarabine is a chemotherapy drug used in the treatment of chronic lymphocytic leukemia. It acts at DNA polymerase alpha, ribonucleotide reductase and DNA primase, results in the inhibition of DNA synthesis, and destroys the cancer cells.
Affected Organisms
Humans and other mammals
Absorption Bioavailability is 55% following oral administration.
Half Life 20 hours
Protein Binding 19-29%
Clearance * 117-145 mL/min [patients with B-cell CLL receiving IV administration of a single dose of 40 mg/m2]
References
Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. [Pubmed]
Gonzalez H, Leblond V, Azar N, Sutton L, Gabarre J, Binet JL, Vernant JP, Dighiero G: Severe autoimmune hemolytic anemia in eight patients treated with fludarabine. Hematol Cell Ther. 1998 Jun;40(3):113-8. [Pubmed]
Tournilhac O, Cazin B, Lepretre S, Divine M, Maloum K, Delmer A, Grosbois B, Feugier P, Maloisel F, Villard F, Villemagne B, Bastit D, Belhadj K, Azar N, Michallet M, Manhes G, Travade P: Impact of frontline fludarabine and cyclophosphamide combined treatment on peripheral blood stem cell mobilization in B-cell chronic lymphocytic leukemia. Blood. 2004 Jan 1;103(1):363-5. Epub 2003 Sep 11. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1229 external link
Research Area: Cancer
Biological Activity:
Fludarabine Phosphate (Fludara) is a nucleoside analogue and formulated as the monophosphate form of F-ara-AMP(fludarabine, IC50 < 3 μM). To enhance solubility, Fludara is formulated as the monophosphate (F-ara-AMP, fudarabine), which is instantaneously and quantitatively dephosphorylated to the parent nucleoside upon intravenous infusion. Inside the cells rephosphorylation occurs which leads to fuoroadenine arabinoside triphosphate (F-ara-ATP),the major cytotoxic metabolite of F-ara-A. This metabolite inhibits several key processes necessary for the DNA replication, i.e. enzymes required in the DNA synthesis, such as ribonucleotide reductase, DNA primase, DNA polymerase, 3’-5’ exonuclease activity of DNA polymerase d and e and DNA ligase I. [1] Fludarabine can also induce pro-inflammatory stimulation of monocytic cells, as evaluated by increased expression of ICAM-1 and IL-8 release. [2] Fludarabine did not affect the growth of ovarian cancer cell lines, whereas it induced a marked and dose-dependent inhibition of proliferation in melanoma cell lines. [3]

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Rai KR, Peterson BL, Appelbaum FR, Kolitz J, Elias L, Shepherd L, Hines J, Threatte GA, Larson RA, Cheson BD, Schiffer CA: Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7. Pubmed
  • • Gonzalez H, Leblond V, Azar N, Sutton L, Gabarre J, Binet JL, Vernant JP, Dighiero G: Severe autoimmune hemolytic anemia in eight patients treated with fludarabine. Hematol Cell Ther. 1998 Jun;40(3):113-8. Pubmed
  • • Tournilhac O, Cazin B, Lepretre S, Divine M, Maloum K, Delmer A, Grosbois B, Feugier P, Maloisel F, Villard F, Villemagne B, Bastit D, Belhadj K, Azar N, Michallet M, Manhes G, Travade P: Impact of frontline fludarabine and cyclophosphamide combined treatment on peripheral blood stem cell mobilization in B-cell chronic lymphocytic leukemia. Blood. 2004 Jan 1;103(1):363-5. Epub 2003 Sep 11. Pubmed
  • • Zaffaroni N et al. Eur J Cancer. 1996;32A(10)
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PATENTS

PATENTS

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INTERNET

INTERNET

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