Fludarabine phosphate

Iupac Name：[(2R,3S,4S,5R)-5-(6-amino-2-fluoropurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methyl dihydrogen phosphate

Molecular Weight：365.214

Modify Date.: 2022-10-26 21:55

Introduction: Fludarabine phosphate is an antimetabolite indicated for the treatment of B celllymphocytic leukemia. It is reportedly effective in patients refractory to othertherapies. Fludarabine phosphate acts by inhibiting primer RNA synthesis. Its sideeffects include bone marrow suppression, anemia, thrombocytopenia and neutropenia. View more+

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1. Names and Identifiers

1.1 Name: Fludarabine phosphate
1.2 Synonyms: [(2R,3R,4S,5R)-5-(6-amino-2-fluoro-purin-9-yl)-3,4-dihydroxy-oxolan-2-yl]methoxyphosphonic acid [(2R,3S,4S,5R)-5-(6-amino-2-fluoro-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl]methyl dihydrogen phosphate 2-F-ara-AMP 2-Fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)-9H-purin-6-amine 2-Fluoroadenine arabinoside 5′-monophosphate 2-Fluoroadenine arabinoside 5'-monophosphate 2-Fluoroadenine arabinoside 5-monophosphate 2-Fluoro-ARA AMP 2-fluoro-araamp 2-fluoro-ara-C-5'-O-phosphate 9-beta-Arabinofuranosyl-2-fluoroadenine-5-phosphate 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5-(dihydrogen phosphate) 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-.beta.-D-arabinofuranosyl)- 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-β-D-arabinofuranosyl)- FAMP F-ara-AMP Fludara Fludarabin Phosphate fludarabine Fludarabine (phosphate) Fludarabine 5′-dihydrogen phosphate Fludarabine 5′-monophosphate Fludarabine 5'-monophosphate Fludarabine 5-monophosphate Fludarabine 5'-Phosphate fludarabine hcl Fludarabine monophosphate Fludarabine Phosphate (Fludara) Fludarabine phosphate (JAN/USP) Fludarabine phosphate [USAN:BAN] fludarabinemonophosphate FLUDARUBINE PHOSPHATE Fludura MFCD00866418 NSC 312887 NSC 328002 Trimeric Sodium Phosphate

1.3 CAS No.: 75607-67-9

1.4 CID: 30751

1.5 EINECS(EC#): 616-242-0

1.6 Molecular Formula: C10H13FN5O7P (isomer)

1.7 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

1.8 InChkey: GIUYCYHIANZCFB-FJFJXFQQSA-N

1.9 Canonical Smiles: C1=NC2=C(N=C(N=C2N1C3C(C(C(O3)COP(=O)(O)O)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)COP(=O)(O)O)O)O)F)N

2. Properties

2.1 Density: 2.39

2.1 Melting point: 203°C(dec.)(lit.)

2.1 Boiling point: 864.2 oC at 760 mmHg

2.1 Refractive index: 1.878

2.1 Flash Point: 476.4 oC

2.1 Precise Quality: 365.05400

2.1 PSA: 195.88000

2.1 logP: -1.14270

2.1 Solubility: DMSO: soluble1mg/mL

2.2 Appearance: White to Almost white powder to crystal

2.3 Storage: Keep Cold.

2.4 Chemical Properties: White or almost white, crystalline powder, hygroscopic.

2.5 Color/Form: White to Yellow Solid

2.6 Physical: Solid

2.7 pKa: 1.86±0.10(Predicted)

2.8 Water Solubility: DMSO: soluble1mg/mL

3. Use and Manufacturing

3.1 Definition: ChEBI: A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Onc incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used 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 atleast one standard alkylating-agent containing regimenas.

3.2 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 56 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

H341 (98.21%): Suspected of causing genetic defects [Warning Germ cell mutagenicity]
H350 (28.57%): May cause cancer [Danger Carcinogenicity]
H360 (32.14%): May damage fertility or the unborn child [Danger Reproductive toxicity]
H361 (67.86%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]
H372 (28.57%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]

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
P201, P202, P260, P264, P270, P281, P308+P313, P314, P405, and P501

3.3 Usage: anticonvulsant

4. Safety and Handling

4.1 Hazard Codes: T

4.1 WGK Germany: 3

4.1 RTECS: UO7440900

4.1 Specification: ? Fludarabine phosphate (CAS NO.75607-67-9), its Synonyms are Fludarabine monophosphate ; 2-Fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)-9H-purin-6-amine ; 2-Fluoro-ARA AMP ; 2-Fluoroadenine arabinoside 5'-monophosphate ; 9-beta-Arabinofuranosyl-2-fluoroadenine-5'-phosphate ; 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-(dihydrogen phosphate) ; 9-beta-D-Arabinofuranosyl-2-fluoroadenine 5'-monophosphate ; Fludara ; 9H-Purin-6-amine, 2-fluoro-9-(5-O-phosphono-beta-D-arabinofuranosyl)- .

4.2 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
child	TDLo	intravenous	18750mg/kg/5D (18750mg/kg)	BRAIN AND COVERINGS: ENCEPHALITIS SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE	Cancer Treatment Reports. Vol. 70, Pg. 1225, 1986.
man	TDLo	intravenous	11655mg/kg/5D (11655mg/kg)	SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: PTOSIS: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Cancer Treatment Reports. Vol. 70, Pg. 1449, 1986.
man	TDLo	intravenous	17760mg/kg/5D (17760mg/kg)	BRAIN AND COVERINGS: DEMYELINATION BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" BEHAVIORAL: COMA	Cancer Treatment Reports. Vol. 70, Pg. 1225, 1986.
mouse	LD50	intravenous	1236mg/kg (1236mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	National Technical Information Service. Vol. PB83-195685,
women	LDLo	intravenous	14245mg/kg/5D (14245mg/kg)	SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE BEHAVIORAL: EXCITEMENT SKIN AND APPENDAGES (SKIN): SWEATING: OTHER	Cancer Treatment Reports. Vol. 70, Pg. 1449, 1986.
women	TDLo	intravenous	23125mg/kg/5D (23125mg/kg)	BRAIN AND COVERINGS: ENCEPHALITIS SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)	Cancer Treatment Reports. Vol. 70, Pg. 1225, 1986

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Germ cell mutagenicity, Category 2

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H341 Suspected of causing genetic defects H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention	P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

75607-67-9Total: 2 Synthesis Route

146-78-1 79 Suppliers

75607-67-9 373 Suppliers

Literatures:
ADORKEM TECHNOLOGY SPA Patent: WO2005/40183 A2, 2005 ; Location in patent: Page/Page column 4-5 ;
Yield: ~41%

512-56-1 158 Suppliers

146-78-1 79 Suppliers

75607-67-9 373 Suppliers

Literatures:
US5296589 A1, ;
Yield: null

7. Precursor and Product

precursor:

146-78-1

512-56-1

product :

146-78-1

8. Other Information

8.0 Merck: 14,4126

8.1 Chemical Properties: White or almost white, crystalline powder, hygroscopic.

8.2 Uses: anticonvulsant

8.3 Definition: ChEBI: A purine arabinonucleoside monophosphate having 2-fluoroadenine as the nucleobase. A prodrug, it is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. Onc incorporated into DNA, 2-fluoro-ara-ATP functions as a DNA chain terminator. It is used 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 regimenas.

8.4 Brand name: Fludara (Berlex).

8.5 Usage: A chemotherapy drug used in the treatment of hematological malignancies. Fludarabine phosphate is rapidly dephosphorylated to 2-fluoro-ara-A and then phosphorylated intracellularly by deoxycytidine kinase to the active triphosphate, 2-fluoro-ara-ATP. This metabolite may inhibit DNA polymerase-?, ribonucleotide reductase and DNA primase, thereby interrupting DNA synthesis and inhibiting tumor cell growth.

9. Computational chemical data

Molecular Weight: 365.214g/mol
Molecular Formula: C₁₀H₁₃FN₅O₇P
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 365.05366293
Monoisotopic Mass: 365.05366293
Complexity: 514
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 5
Hydrogen Bond Acceptor Count: 12
Topological Polar Surface Area: 186
Heavy Atom Count: 24
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: AAADccBzuQIAAAAAAAAAAAAAAAAAAWJAAAAsAAAAAAAAAFgB+AAAHwAQCCAACBzhlwYF8L9MFxCgQQZhZICAgC0REKABUCAoVBCDWAJAyEAeRAgPAALTACDwMAIAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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