CAS 207128-22-1 2',3'-Dideoxy-3'-fluorouridine (HCID 162450)

Substructure search Find similar structures

Basic information

CAS: 207128-22-1
Standard SMILES: O=c1ccn([C@H]2C[C@H](F)[C@@H](CO)O2)c(=O)[nH]1
InChIKey: BKIUEHLYJFLWPK-SHYZEUOFSA-N
Molecular formula: C9H11FN2O4
Average molar mass: 230.19 g/mol
Monoisotopic mass: 230.070285

Names & identifiers

Preferred name: 2',3'-Dideoxy-3'-fluorouridine
IUPAC: 1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
English name: 2',3'-DIDEOXY-3'-FLUOROURIDINE
Molecular formula: C9H11FN2O4
Molecular weight: 230.19

Names & synonyms

2',3'-Dideoxy-3'-fluorouridine41107-56-6Fddurd3'-Fluoro-2',3'-dideoxyuridineDTXSID9010340595-(2,4-Dioxo-1,2,3,4-tetrahydropyrimidine)-3-fluoro-2-hydroxymethyltetrahydrofuranRefChem:529152DTXCID201371305415-360-8637-011-03'-FddU207128-22-1

Show more names

FddU2’,3’-Dideoxy-3’-fluorouridine, FddU2',3'-DIDEOXY-3'-FLUOROURIDINE USP/EP/BP2’,3’-Dideoxy-3’-fluorouridine, FddU, anti-HIV1-(2,3-DIDEOXY-3-FLUORO-BETA-D-RIBOFURANOSYL)URACIL

1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dioneMFCD001920151-((2R,4S,5R)-4-Fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneUridine, 2',3'-dideoxy-3'-fluoro-2,4(1H,3H)-Pyrimidinedione, 1-(2,3-dideoxy-3-fluoro-b-D-erythro-pentofuranosyl)-1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dione2 inverted exclamation mark ,3 inverted exclamation mark -Dideoxy-3 inverted exclamation mark -fluorouridine1-[(2R,4S,5R)-4-fluoro-5-(hydroxymethyl)oxolan-2-yl]-1,2,3,4-tetrahydropyrimidine-2,4-dione

Database identifiers

CAS: 207128-22-1、41107-56-6

Properties

Computed structural properties

XLogP: -0.5
Topological polar surface area: 78.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 5
Rotatable bonds: 2
Heavy atoms: 16
Formal charge: 0
Complexity: 346

Physicochemical properties

Melting point: 184 · 184-188 °C(lit.)
Density: 1.5 · 1.50±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C Freezer
solubility: Aqueous Base (Slightly, Sonicated), DMSO (Slightly), Methanol (Slightly), Water
pka: 9.39 · 9.39±0.10(Predicted)
form: Solid
color: White to Off-White
optical activity: 20 · [α]20/D +10.5°, c = 0.5 in 1 M NaOH
BRN: 6064366 · 6064366
InChI: 1S/C9H11FN2O4/c10-5-3-8(16-6(5)4-13)12-2-1-7(14)11-9(12)15/h1-2,5-6,8,13H,3-4H2,(H,11,14,15)/t5-,6+,8+/m0/s1
InChIKey: BKIUEHLYJFLWPK-SHYZEUOFSA-N
SMILES: OC[C@H]1O[C@H](C[C@@H]1F)N2C=CC(=O)NC2=O
EWG's Food Scores: 1 · 1
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H341: Suspected of causing genetic defects [Warning Germ cell mutagenicity]

P203, P280, P318, P405, and P501 (click each P-code to see the statement)

Warning

Hazard information

Regulatory InformationStatus: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/9343

Hazard Classes and Categories · 4 items

Muta. 2 (100%)

Germ cell mutagenicity - category 2

Muta. 2

Regulatory information

Regulatory InformationStatus: Active Update: 10-11-2008 https://echa.europa.eu/registration-dossier/-/registered-dossier/9343

Safety data

PPE: dust mask type N95 (US), Eyeshields, Gloves
wgk: 1
hs_code: 29349990
risk_code: 68
Signal word: Warning
Symbol(GHS): GHS08
hazard_code: Xn
safety_code: 22-36/37
Storage Class: 13 - Non Combustible Solids
Hazard statements: H341
REACH Registrations: Inactive

Chemistry & industry

Applications · 3 items

Uses2'',3''-Dideoxy-3''-fluorouridine is a reactant used in the synthesis of 5''-trityl nucleosides as inhibitors of Plasmodium falciparum dUTPase.

Uses2′,3′-Dideoxy-3′-fluorouridine can be used as a starting material in the synthesis of: 3′-fluoro 2′,3′-dideoxynucleoside analogs for in vitro antiviral activity studies. 3′-fluoro deoxyuridine monophosphate analogs as potential anti parasites.

General Description2′,3′-Dideoxy-3′-fluorouridine (3′-fluoro-2′,3′-dideoxyuridine, FddUrd) is a fluorinated pyrimidine nucleoside analog of uridine. It has been studied extensively for its potential use as an antiviral agent against HIV.