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Fludarabine

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Name

Fludarabine

EINECS 244-525-5
CAS No. 21679-14-1 Density 2.17 g/cm3
PSA 139.54000 LogP -1.25970
Solubility DMF: 20 mg/mL, clear, faintly yellow Melting Point 265-268 °C
Formula C10H12FN5O4 Boiling Point 747.3 °C at 760 mmHg
Molecular Weight 285.235 Flash Point 405.8 °C
Transport Information N/A Appearance white solid
Safety 26-36/37-45 Risk Codes 23/24/25-36/37/38-39/23/24/25-39
Molecular Structure Molecular Structure of 21679-14-1 (Fludarabine) Hazard Symbols R23/24/25:; R36/37/38:; R39:;
Synonyms

Adenine,9-b-D-arabinofuranosyl-2-fluoro- (8CI);2-Fluoro Ara-A;2-Fluoro-9-b-D-arabinofuranosyladenine;2-Fluoroadenine arabinoside;9-b-D-Arabinofuranosyl-2-fluoroadenine;9-b-D-Arabinosyl-2-fluoroadenine;F-ara-A;NSC 118218;NSC 118218H;Fludarabine Base;

Article Data 25

Fludarabine Specification

The CAS register number of Fludarabine is 21679-14-1. It also can be called as 2-Fluoroadenine-9-bata-D-arabinofuranoside and the IUPAC name about this chemical is (2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol. The molecular formula about this chemical is C10H12FN5O4 and the molecular weight is 285.23. It belongs to the following product categories, such as Intermediates & Fine Chemicals; Pharmaceuticals and so on.

Physical properties about Fludarabine are: (1)# of Rule of 5 Violations: 1; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 14.4; (5)ACD/KOC (pH 7.4): 14.41; (6)#H bond acceptors: 9; (7)#H bond donors: 5; (8)#Freely Rotating Bonds: 5; (9)Polar Surface Area: 83.76Å2; (10)Index of Refraction: 1.876; (11)Molar Refractivity: 59.82 cm3; (12)Molar Volume: 131 cm3; (13)Polarizability: 23.71x10-24cm3; (14)Surface Tension: 98.5 dyne/cm; (15)Enthalpy of Vaporization: 114.32 kJ/mol; (16)Boiling Point: 747.3 °C at 760 mmHg; (17)Vapour Pressure: 1.86E-23 mmHg at 25°C.

The Fludarabine is a purine analog, and it can be given both orally and intravenously. It inhibits DNA synthesis by interfering with ribonucleotide reductase and DNA polymerase. It works against both dividing and resting cells. This chemical can be used in the treatment of chronic lymphocytic leukemia, producing higher response rates than alkylating agents such as chlorambucil alone. And it is also used in various combinations with cyclophosphamide, mitoxantrone, dexamethasone and rituximab in the treatment of indolent non-hodgkins lymphomas. Because of its immunosuppressive effects, this chemical is also used in some conditioning regimens prior to non myeloablative allogeneic stem cell transplant. As part of the Flag regimen, it is used together with cytarabine and granulocyte colony-stimulating factor in the treatment of acute myeloid leukaemia.

When you are using this chemical, please be cautious about it as the following:
This chemical is toxic by inhalation, in contact with skin and if swallowed and it is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing and gloves. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice and in case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). This chemical is associated with profound lymphopenia, so, increases the risk of opportunistic infections significantly. There are always difficulties when harvesting peripheral blood stem cells from patients previously treated with fludarabine.

You can still convert the following datas into molecular structure:
(1)SMILES: Fc1nc(c2ncn(c2n1)[C@@H]3O[C@@H]([C@@H](O)[C@@H]3O)CO)N
(2)InChI: InChI=1/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1
(3)InChIKey: HBUBKKRHXORPQB-FJFJXFQQBJ
(4)Std. InChI: InChI=1S/C10H12FN5O4/c11-10-14-7(12)4-8(15-10)16(2-13-4)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,14,15)/t3-,5-,6+,9-/m1/s1
(5)Std. InChIKey: HBUBKKRHXORPQB-FJFJXFQQSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 375mg/kg (375mg/kg)   Cancer Research. Vol. 42, Pg. 2587, 1982.
 

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