Fludarabine phosphate

Modify Date: 2024-01-02 14:30:01

Fludarabine phosphate Structure
Fludarabine phosphate structure
 Common Name Fludarabine phosphate
CAS Number 75607-67-9 Molecular Weight 365.212
Density 2.4±0.1 g/cm3 Boiling Point 864.2±75.0 °C at 760 mmHg
Molecular Formula C10H13FN5O7P Melting Point 203 °C(dec.)
MSDS N/A Flash Point 476.4±37.1 °C

 Use of Fludarabine phosphate


Fludarabine (phosphate) is an analogue of adenosine and deoxyadenosine, which is able to compete with dATP for incorporation into DNA and inhibit DNA synthesis.

 Names

Name fludarabine phosphate
Synonym More Synonyms

 Fludarabine phosphate Biological Activity

Description Fludarabine (phosphate) is an analogue of adenosine and deoxyadenosine, which is able to compete with dATP for incorporation into DNA and inhibit DNA synthesis.
Related Catalog
In Vitro Fludarabine phosphate significantly reduces the cell viability in a dose-dependent manner. Fludarabine phosphate exhibits no effect in all tested concentrations when combined with either PBS or control vector, ACE-GFP. Fludarabine phosphate causes a significant decrease in cell viability for 24 h after exposure to ACE-PNP when compared to PBS and ACE-GFP at concentrations of 2.5, 5 and 10 μg/mL[2].
In Vivo F-araAMP (100 mg/kg given 15 times, 167 mg/kg given 9 times, or 250 mg/kg given 3 times, i.p.) leads to complete regressions of all tumors and cures of all mice. Parental D54 tumors (i.e. without E. coli PNP) are not sensitive to treatment with F-araAMP. Intratumoral injection of Ad/PNP followed by IT F-araAMP can elicit a substantial regressive effect on otherwise refractory solid tumors in a fashion substantially superior to viral PNP transduction followed by systemic prodrug administration[1]. The comparison of ACE-GFP/fludarabine phosphate with ACE-GFP/PBS demonstrats that fludarabine phosphate alone has no growth inhibitory activity on KU-19-19 tumors[2].
Cell Assay Briefly, 2×103 KU-19-19 cells are seeded in each well of 96-well plates and allowed to grow overnight. Cells are then exposed to PBS, ACE-GFP or ACE-PNP for 3 h. Twenty-four hours post-infection, the cells are treated with various concentrations of fludarabine phosphate. After the 24-h incubation, cytotoxicity is determined by using WST-1; 4-[3-(4-iodophenyl)-2-(4-nitrophenyl)-2H-5-tetrazolio]-1,3-benzene disulfonate. The absorbance value is determined at 450 nm by a microplate reader.
Animal Admin Mice: Parental and E. coli PNP expressing D54MG (human glioma) tumor cells (2×107 cells) are injected subcutaneously into the flanks of nude mice (nu/nu). D54 tumor cells stably transduced with E. coli PNP are prepared as described previously. Tumors are measured with calipers and an estimate of the weight calculated using the equation, (length × width2)/2=mm3, and converted to mg assuming unit density. Unless stated otherwise, therapeutic drugs and the adenoviral vector expressing E. coli PNP (Ad/PNP), or vehicle controls are injected into D54 tumors in 150 μL volumes by 8 separate injections of approximately 20 μL each in an effort to evenly distribute the administered agent. At least 6 mice are studied in each treatment group. Mice are monitored daily and body weights and tumor dimensions collected twice weekly. T-C (tumor growth delay) is determined as the difference in median days to 2 doublings (median days to 600 mg for the D54 and DU145 (human prostate cancer) analysis) between drug-treated and vehicle-treated groups. For the NIH-H322M (human non-small cell lung cancer) study, because of tumor proliferation characteristics, total growth inhibition (TGI) is used as the evaluation point. TGI is equal to the control group mean delta minus the treated group mean delta divided by the control group mean delta, where delta is the change in tumor weight for each animal between day 36 and day 59. The time to the evaluation point for each animal is used as the end point for the student's t-test, Mann-Whitney rank sum test, or a life table analysis in order to statistically compare growth data between treatment groups. All key results are repeated under similar conditions and findings confirmed. Treatments are initiated when tumors are 250 to 300 mg (appr 1-1.5% of total animal weight).
References

[1]. Sorscher EJ, et al. In vivo antitumor activity of intratumoral fludarabine phosphate in refractory tumors expressing E. coli purine nucleoside phosphorylase. Cancer Chemother Pharmacol. 2012 Aug;70(2):321-9.

[2]. Kikuchi E, et al. Delivery of replication-competent retrovirus expressing Escherichia coli purine nucleoside phosphorylase increases the metabolism of the prodrug, fludarabine phosphate and suppresses the growth of bladder tumor xenografts. Cancer Gene Th

 Chemical & Physical Properties

Density 2.4±0.1 g/cm3
Boiling Point 864.2±75.0 °C at 760 mmHg
Melting Point 203 °C(dec.)
Molecular Formula C10H13FN5O7P
Molecular Weight 365.212
Flash Point 476.4±37.1 °C
Exact Mass 365.053650
PSA 195.88000
LogP 0.41
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.879

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
UO7440900
CHEMICAL NAME :
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-
CAS REGISTRY NUMBER :
75607-67-9
LAST UPDATED :
198910
DATA ITEMS CITED :
6
MOLECULAR FORMULA :
C10-H13-F-N5-O7-P
MOLECULAR WEIGHT :
365.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
18750 mg/kg/5D-I
TOXIC EFFECTS :
Brain and Coverings - encephalitis Sense Organs and Special Senses (Eye) - visual field changes
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 70,1225,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
17760 mg/kg/5D-I
TOXIC EFFECTS :
Brain and Coverings - demyelination Behavioral - hallucinations, distorted perceptions Behavioral - coma
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 70,1225,1986
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
14245 mg/kg/5D
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - effect, not otherwise specified Behavioral - excitement Skin and Appendages - sweating
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 70,1449,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
23125 mg/kg/5D-I
TOXIC EFFECTS :
Brain and Coverings - encephalitis Sense Organs and Special Senses (Eye) - visual field changes Behavioral - somnolence (general depressed activity)
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 70,1225,1986
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Human - man
DOSE/DURATION :
11655 mg/kg/5D-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - visual field changes Sense Organs and Special Senses (Eye) - ptosis Behavioral - somnolence (general depressed activity)
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 70,1449,1986
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1236 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: PB83-195685

 Safety Information

Hazard Codes T
Risk Phrases R25:Toxic if swallowed.
Safety Phrases S45
RIDADR UN 2811 6.1/PG 3
HS Code 2934999090

 Synthetic Route

2-Fluoroadenosine structure

2-Fluoroadenosine

CAS#:146-78-1

~41%

Fludarabine phosphate Structure

Fludarabine pho...

CAS#:75607-67-9

Literature: ADORKEM TECHNOLOGY SPA Patent: WO2005/40183 A2, 2005 ; Location in patent: Page/Page column 4-5 ;
Trimethyl phosphate structure

Trimethyl phosphate

CAS#:512-56-1

2-Fluoroadenosine structure

2-Fluoroadenosine

CAS#:146-78-1

~%

Fludarabine phosphate Structure

Fludarabine pho...

CAS#:75607-67-9

Literature: US5296589 A1, ;

 Customs

HS Code 2934999090
Summary 2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Articles12

More Articles
Population pharmacokinetic/dynamic model of lymphosuppression after fludarabine administration.

Cancer Chemother. Pharmacol. 75(1) , 67-75, (2015)

Quantitative relationships between 9-β-D-arabinofuranosyl-2-fluoroadenine (F-ara-A) concentrations and lymphosuppression have not been reported, but would be useful for regimen design. A population ph...

Fludarabine phosphate in lymphoma: an important new therapeutic agent.

Cancer Treat. Res. 85 , 3-14, (1996)

Fludarabine phosphate in the treatment of chronic lymphocytic leukemia: biology, clinical impact, and future directions.

Cancer Treat. Res. 64 , 105-19, (1993)

 Synonyms

2-Fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine
2-fluoro-araamp
Fludara
Fludarabin Phosphate
Fludarabine (phosphate)
2-fluoro-ara-C-5'-O-phosphate
2-Fluoroadenine arabinoside 5'-monophosphate
fludarabinemonophosphate
Fludarabine 5'-Phosphate
fludarabine hcl
fludarabine monophosphate
Fludura
Fludarabine Phosphate (Fludara)
Fludarabine 5'-monophosphate
Fludarabine phosphate
fludarabine
9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-
FLUDARUBINE PHOSPHATE
[(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate
F-ara-AMP
FAMP
MFCD00866418
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