4-Amino-5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Basic information
- CAS
10356-76-0- Standard SMILES
Nc1nc(=O)n(C2CC(O)C(CO)O2)cc1F- InChIKey
IDYKCXHJJGMAEV-UHFFFAOYSA-N- Molecular formula
- C9H12FN3O4
- Average molar mass
- 245.21 g/mol
- Monoisotopic mass
- 245.08118403
Names & identifiers
- Preferred name
- 4-Amino-5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- IUPAC
- 4-amino-5-fluoro-1-[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
MLS0027028544-amino-5-fluoro-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one5-Flurodeoxycytidine5-fluor-deoxycytidine4-amino-5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one2'-deoxy-5-fluoro-CytidineCytidine, 2'-deoxy-5-fluoro-;Cytidine, 2'-deoxy-5-fluoro-CHEMBL110020SCHEMBL162122824-Amino-5-fluoro-1-[(4S,5R)-4-hydroxy-5-(hydroxymethyl)-2-tetrahydrofuryl]pyrimidin-2(1H)-ones2477AKOS040759236
Show more names
FCDRFdCyd5--F-dCNSC 48006Ro 5-10905-F-2'-dC5-Fluoro-25-F-2'-deoxycytidine5-fluorodeoxycytidine5-fluor-desoxycytidin
SB17172SMR001566676SY348216WLN: T6N CNJ DZ EF F- BT5OTJ EO14-amino-5-fluoro-1-[4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidin-2-one
Database identifiers
- CAS
10356-76-0- PubChem CID
- 240980
- ChEMBL
CHEMBL110020
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
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.
- InChI
- 1S/C9H12FN3O4/c10-4-2-13(9(16)12-8(4)11)7-1-5(15)6(3-14)17-7/h2,5-7,14-15H,1,3H2,(H2,11,12,16)/t5-,6+,7+/m0/s1
- InChIKey
- IDYKCXHJJGMAEV-RRKCRQDMSA-N
- SMILES
- NC1=NC(=O)N(C=C1F)[C@H]2C[C@H](O)[C@@H](CO)O2
- CAS DataBase Reference
- 10356 · 10356-76-0(CAS DataBase Reference)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 3
- rtecs
- HA3850000
- hs_code
- 2940.00.6000
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H332-H335
- Precautionary statements
- P261-P280-P305+P351+P338
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
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Compound notes
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