5-Fluoro-2'-deoxycytidine
Basic information
- CAS
10356-76-0- Standard SMILES
Nc1nc(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1F- InChIKey
IDYKCXHJJGMAEV-RRKCRQDMSA-N- Molecular formula
- C9H12FN3O4
- Average molar mass
- 245.21 g/mol
- Monoisotopic mass
- 245.08118403
Overview
5-fluoro-2'-deoxycytidine is a fine white powder. (NTP, 1992)
Names & identifiers
- Preferred name
- 5-Fluoro-2'-deoxycytidine
- IUPAC
- 4-amino-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- English name
- 2'-Deoxy-5-fluorocytidine
- Molecular formula
- C9H12FN3O4
- Molecular weight
- 245.21
Names & synonyms
10356-76-05-FLUORO-2'-DEOXYCYTIDINE2'-Deoxy-5-fluorocytidine5-FluorodeoxycytidineFdCydFCdR5-Fluoro-2-deoxycytidineCytidine, 2'-deoxy-5-fluoro-NSC-48006Ro 5-1090KUA4693H5WDTXSID2030437
Show more names
5--F-dCNSC 480065-F-2'-dC5-Fluoro-25-F-2'-deoxycytidine5-fluor-desoxycytidin
RO-5-10904-amino-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-oneNSC480064-amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-oneRefChem:102613DTXCID0010437668-556-24-amino-5-fluoro-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one
Database identifiers
- CAS
10356-76-0- PubChem CID
- 515328
- DTXSID
DTXSID2030437- ChEMBL
CHEMBL1076257- ChEBI
CHEBI:230016- UNII
- KUA4693H5W
Properties
Computed structural properties
- XLogP
- -1.5
- Topological polar surface area
- 108 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 17
- Formal charge
- 0
- Complexity
- 398
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physical Description5-fluoro-2'-deoxycytidine is a fine white powder. (NTP, 1992)
Physicochemical properties
- Melting point
- 196 °C · 196 °C
- Boiling point
- 465 ℃ · 465℃
- Density
- 1.82 · 1.82
- refractive index
- 70 ° · 70 ° (C=1, H2O)
- Flash point
- 235 ℃ · 235℃
- storage temp.
- 2 · Keep in dark place,Inert atmosphere,2-8°C
- solubility
- 20 mg/mL · DMSO: >20mg/mL
- form
- powder
- pka
- 14.03 · 14.03±0.60(Predicted)
- color
- white to off-white
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO may be stored at -20° for up to 1 month.
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 38 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Fire HazardsFlash point data for this chemical are not available. It is probably combustible. (NTP, 1992)
Health HazardsACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits toxic fumes of fluoride ion and NOx. (NTP, 1992)
Reactive GroupAlcohols and Polyols
Air and Water ReactionsThis chemical is probably light and air sensitive.
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety & protection
Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
Chemistry & industry
Applications
Description5-Fluoro-2-Deoxycytidine is an antimetabolite consisting of a fluorinated pyrimidine analog with potential antineoplastic activity. As a prodrug, 5-fluoro-2-deoxycytidine is converted by intracellular deaminases to the cytotoxic agent 5-Fluorouracil (5-FU). 5-FU is subsequently metabolized to active metabolites including 5-fluoro-2-deoxyuridine monophosphate (FdUMP) and 5-fluorouridine triphosphate (FUTP). FdUMP binds to and inhibits thymidylate synthase, thereby reducing the production of thymidine monophosphate, which leads to depletion of thymidine triphosphate. This inhibits DNA synthesis and cell division. FUTP competes with uridine triphosphate for incorporation into the RNA strand thus leading to an inhibition of RNA and protein synthesis. Other fluorouracil metabolites also get incorporated into both DNA and RNA, thereby further hampering cellular growth.
Uses5-Fluoro-2''-deoxycytidine is a mechanism-based DNMT inhibitor.
Uses5-fluoro-2'-deoxycytidine has been used in trials studying the treatment of Neoplasms, Lung Neoplasms, Breast Neoplasms, Head and Neck Neoplasms, and Urinary Bladder Neoplasms, among others.
General DescriptionFine white powder.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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