Fludarabine
- Iupac Name：(2R,3S,4S,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
- CAS No.: 21679-14-1
- Molecular Weight：285.235
- Modify Date.: 2023-02-13 21:20
- Introduction: 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 tha
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1. Names and Identifiers
- 1.1 Name
- Fludarabine
- 1.2 Synonyms
(2R,3R,5R)-2-(6-amino-2-fluoropurin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol (3ξ)-2-Fluoroadenosine 2F-Ara-A 2-Fluoro Ara-A 2-Fluoro-9-b-D-arabinofuranosyladenine 2-Fluoro-9-β-D-arabinofuranosyladenine 2-Fluoroadenine arabinoside 9-b-D-Arabinofuranosyl-2-fluoroadenine 9-b-D-Arabinosyl-2-fluoroadenine 9H-Purin-6-amine, 9-β-D-arabinofuranosyl-2-fluoro- 9-β-D-Arabinofuranosyl-2-fluoro-9H-purin-6-amine 9-β-D-Arabinofuranosyl-2-fluoroadenine 9-β-D-Arabinosyl-2-fluoroadenine Adenine, 9-β-D-arabinofuranosyl-2-fluoro- Adenine,9-b-D-arabinofuranosyl-2-fluoro- (8CI) Adenosine, 2-fluoro-, (3ξ)- F-ara-A Fludarabine Base NSC 118218 NSC 118218H
- 1.3 CAS No.
- 21679-14-1
- 1.4 CID
- 657237
- 1.5 EINECS(EC#)
- 244-525-5
- 1.6 Molecular Formula
- C10H12FN5O4 (isomer)
- 1.7 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
- 1.8 InChkey
- HBUBKKRHXORPQB-FJFJXFQQSA-N
- 1.9 Canonical Smiles
- C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)CO)O)O)F)N
- 1.10 Isomers Smiles
- C1=NC2=C(N=C(N=C2N1[C@H]3[C@H]([C@@H]([C@H](O3)CO)O)O)F)N
2. Properties
- 2.1 Density
- 2.17
- 2.1 Melting point
- 265-268°C
- 2.1 Boiling point
- 747.3°Cat760mmHg
- 2.1 Refractive index
- 1.876
- 2.1 Flash Point
- 405.8°C
- 2.1 Precise Quality
- 285.08700
- 2.1 PSA
- 139.54000
- 2.1 logP
- -1.25970
- 2.1 Solubility
- DMF: 20?mg/mL, clear, faintly yellow
- 2.2 Appearance
- white solid
- 2.3 Storage
- 2-8°C
- 2.4 Chemical Properties
- White Solid
- 2.5 Color/Form
- Powder
- 2.6 pKa
- 13.05±0.70(Predicted)
- 2.7 Water Solubility
- DMF: 20?mg/mL, clear, faintly yellow
- 2.8 Spectral Properties
- UV max: 262, 261, 262 nm (epsilon X10-3 13.2, 14.8, 15.0)
- 2.9 StorageTemp
- 2-8°C
3. Use and Manufacturing
- 3.1 GHS Classification
- Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 25 companies from 3 notifications to the ECHA C&L Inventory.
H302 (96%): Harmful if swallowed [Warning Acute toxicity, oral]
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Precautionary Statement Codes
P264, P270, P301+P312, P330, and P501
- 3.2 Usage
- Used as an antineoplastic
4. Safety and Handling
- 4.1 Risk Statements
- R23/24/25;R36/37/38;R39
- 4.1 Safety Statements
- S26;S36/37;S45
- 4.1 DisposalMethods
- SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
- 4.2 Formulations/Preparations
- FLUDARA (fludarabine phosphate) injection, powder, lyophilized, for solution.
- 4.3 WGK Germany
- 3
- 4.3 RTECS
- AU6207000
- 4.3 Toxicity
-
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
5. MSDS
2.Hazard identification
2.1 Classification of the substance or mixture
Acute toxicity - Oral, Category 4
2.2 GHS label elements, including precautionary statements
| Pictogram(s) |  |
| Signal word | Warning |
| Hazard statement(s) | H302 Harmful if swallowed |
| Precautionary statement(s) | |
| Prevention | P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. |
| Response | P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth. |
| Storage | none |
| Disposal | P501 Dispose of contents/container to ... |
2.3 Other hazards which do not result in classification
none
7. Computational chemical data
- Molecular Weight: 285.235g/mol
- Molecular Formula: C10H12FN5O4
- Compound Is Canonicalized: True
- XLogP3-AA: null
- Exact Mass: 285.08733204
- Monoisotopic Mass: 285.08733204
- Complexity: 367
- Rotatable Bond Count: 2
- Hydrogen Bond Donor Count: 4
- Hydrogen Bond Acceptor Count: 9
- Topological Polar Surface Area: 140
- Heavy Atom Count: 20
- Defined Atom Stereocenter Count: 4
- Undefined Atom Stereocenter Count: 0
- Defined Bond Stereocenter Count: 0
- Undefined Bond Stereocenter Count: 0
- Isotope Atom Count: 0
- Covalently-Bonded Unit Count: 1
- CACTVS Substructure Key Fingerprint: AAADccBzuQAAAAAAAAAAAAAAAAAAAWJAAAAsAAAAAAAAAFgB+AAAHwAQCAAACBzhlwYF8L9MFgCgAQZhZACAgC0REKABUCAoVBCDWAJAyEAeRAgPAALTACDwMAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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