Fludarabine

Modify Date: 2024-01-01 18:07:43

Fludarabine Structure
Fludarabine structure
 Common Name Fludarabine
CAS Number 21679-14-1 Molecular Weight 285.232
Density 2.2±0.1 g/cm3 Boiling Point 747.3±70.0 °C at 760 mmHg
Molecular Formula C10H12FN5O4 Melting Point 265-268ºC
MSDS Chinese USA Flash Point 405.8±35.7 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Fludarabine


Fludarabine(NSC 118218), a DNA synthesis inhibitor, is a chemotherapy drug used in the treatment of hematological malignancies.Target:Fludarabine or fludarabine ph osphate (Fludara) is a chemotherapy drug used in the treatment of hematological malignancies (cancers of blood cells such as leukemias and lymphomas). It is a purine analog, which interferes with DNA synthesis. Fludarabine is highly effective in the treatment of chronic lymphocytic leukemia, producing higher response rates than alkylating agents such as chlorambucil alone.Fludarabine is a purine analog, and can be given both orally and intravenously. Fludarabine inhibits DNA synthesis by interfering with ribonucleotide reductase and DNA polymerase. It is active against both dividing and resting cells. Being phosphorylated, fludarabine is ionized at physiologic pH and is effectually trapped in blood. This provides some level of specificity for blood cells, both cancerous and healthy. Fludarabine is associated with the development of severe autoimmune hemolytic anemia in a proportion of patients. Difficulties are often encountered when harvesting peripheral blood stem cells from patients previously treated with fludarabine.

 Names

Name (2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
Synonym More Synonyms

 Fludarabine Biological Activity

Description Fludarabine(NSC 118218), a DNA synthesis inhibitor, is a chemotherapy drug used in the treatment of hematological malignancies.Target:Fludarabine or fludarabine ph osphate (Fludara) is a chemotherapy drug used in the treatment of hematological malignancies (cancers of blood cells such as leukemias and lymphomas). It is a purine analog, which interferes with DNA synthesis. Fludarabine is highly effective in the treatment of chronic lymphocytic leukemia, producing higher response rates than alkylating agents such as chlorambucil alone.Fludarabine is a purine analog, and can be given both orally and intravenously. Fludarabine inhibits DNA synthesis by interfering with ribonucleotide reductase and DNA polymerase. It is active against both dividing and resting cells. Being phosphorylated, fludarabine is ionized at physiologic pH and is effectually trapped in blood. This provides some level of specificity for blood cells, both cancerous and healthy. Fludarabine is associated with the development of severe autoimmune hemolytic anemia in a proportion of patients. Difficulties are often encountered when harvesting peripheral blood stem cells from patients previously treated with fludarabine.
Related Catalog
References

[1]. Rai KR, et al. Fludarabine compared with chlorambucil as primary therapy for chronic lymphocytic leukemia. N Engl J Med. 2000 Dec 14;343(24):1750-7.

[2]. Tournilhac O, et al. 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.

 Chemical & Physical Properties

Density 2.2±0.1 g/cm3
Boiling Point 747.3±70.0 °C at 760 mmHg
Melting Point 265-268ºC
Molecular Formula C10H12FN5O4
Molecular Weight 285.232
Flash Point 405.8±35.7 °C
Exact Mass 285.087341
PSA 139.54000
LogP -0.40
Vapour Pressure 0.0±2.6 mmHg at 25°C
Index of Refraction 1.876
Storage condition 2-8°C
Water Solubility DMF: 20 mg/mL, clear, faintly yellow

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
AU6207000
CHEMICAL NAME :
Adenine, 9-beta-D-arabinofuranosyl-2-fluoro-
CAS REGISTRY NUMBER :
21679-14-1
LAST UPDATED :
198909
DATA ITEMS CITED :
4
MOLECULAR FORMULA :
C10-H12-F-N5-O4
MOLECULAR WEIGHT :
285.27
WISWESSER LINE NOTATION :
T56 BN DN FN HNJ GF IZ D- BT5OTJ CQ DQ E1Q

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
375 mg/kg
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain
TYPE OF TEST :
DNA inhibition

MUTATION DATA

TYPE OF TEST :
Mutation in mammalian somatic cells
TEST SYSTEM :
Rodent - hamster Ovary
DOSE/DURATION :
100 umol/L
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 210,291,1989

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn
Risk Phrases R23/24/25;R36/37/38;R39
Safety Phrases S26-S36/37-S45
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS AU6207000

 Articles87

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Quantitative structure-activity relationship and complex network approach to monoamine oxidase A and B inhibitors.

J. Med. Chem. 51 , 6740-51, (2008)

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Trend analysis of a database of intravenous pharmacokinetic parameters in humans for 670 drug compounds.

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 Synonyms

UNII-P2K93U8740
9-b-D-Arabinofuranosyl-2-fluoro-9H-purin-6-amine
9-β-D-Arabinofuranosyl-2-fluoroadenine
MFCD00132942
9H-Purin-6-amine, 9-β-D-arabinofuranosyl-2-fluoro-
Fludarabine des-phosphate
9-(β-D-Arabinofuranosyl)-2-fluoro-9H-purin-6-amine
9-b-D-Arabinofuranosyl-2-fluoroadenine
(2R,3S,4S,5R)-2-(6-Amino-2-fluoro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Fludarabine
EINECS 244-525-5
2-Fluoro-9-b-D-arabinofuranosyladenine
F-Ara-A
2-Fluoroadenine-9-β-D-arabinofuranoside
2-F-araA
Adenine, 9-β-D-arabinofuranosyl-2-fluoro-
2-Fluorovidarabine
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Related Compounds: More...
fludarabine
75607-67-9
Fludarabine-Cl
2734853-80-4
Fludarabine Base
19768-92-4
[3H]-Fludarabine
21679-15-2
Fludarabine triphosphate
74832-57-8
Fludarabine Phosphate iMpurity B
149297-79-0
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