Gemcitabine hydrochloride (CHEM019651)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:22:04 UTC
Update Date2016-11-09 01:16:02 UTC
Accession NumberCHEM019651
Identification
Common NameGemcitabine hydrochloride
ClassSmall Molecule
DescriptionA 2'-deoxycytidine hydrochloriode having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine hydrochloride is used in the treatment of various carcinomas, including non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.
Contaminant Sources
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2',2'-Difluorodeoxycytidine monohydrochlorideChEBI
2'-Deoxy-2',2'-difluorocytidine monohydrochlorideChEBI
Gemcitabine HCLChEBI
GemzarKegg
DFdCydMeSH
GemcitabineMeSH
Gemcitabine, (D-threo-pentafuranosyl)-isomerMeSH
2',2'-DifluorodeoxycytidineMeSH
2',2'-DFDCMeSH
Gemcitabine, (alpha-D-threo-pentofuranosyl)-isomerMeSH
2'-Deoxy-2',2''-difluorocytidine-5'-O-monophosphateMeSH
Gemcitabine, (beta-D-threo-pentafuranosyl)-isomerMeSH
2'-Deoxy-2'-difluorocytidineMeSH
2',2'-Difluoro-2'-deoxycytidineMeSH
Chemical FormulaC9H12ClF2N3O4
Average Molecular Mass299.659 g/mol
Monoisotopic Mass299.048 g/mol
CAS Registry Number122111-03-9
IUPAC Name1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-imino-1,4-dihydropyrimidin-2-ol hydrochloride
Traditional Namegemcitabine hydrochloride
SMILESCl.[H][C@]1(CO)O[C@@]([H])(N2C=CC(=N)N=C2O)C(F)(F)[C@]1([H])O
InChI IdentifierInChI=1S/C9H11F2N3O4.ClH/c10-9(11)6(16)4(3-15)18-7(9)14-2-1-5(12)13-8(14)17;/h1-2,4,6-7,15-16H,3H2,(H2,12,13,17);1H/t4-,6-,7-;/m1./s1
InChI KeyOKKDEIYWILRZIA-OSZBKLCCSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.
KingdomOrganic compounds
Super ClassNucleosides, nucleotides, and analogues
ClassPyrimidine nucleosides
Sub ClassPyrimidine 2'-deoxyribonucleosides
Direct ParentPyrimidine 2'-deoxyribonucleosides
Alternative Parents
Substituents
  • Pyrimidine 2'-deoxyribonucleoside
  • Aminopyrimidine
  • Pyrimidone
  • Hydropyrimidine
  • Pyrimidine
  • Imidolactam
  • Heteroaromatic compound
  • Tetrahydrofuran
  • Fluorohydrin
  • Halohydrin
  • Secondary alcohol
  • Oxacycle
  • Organoheterocyclic compound
  • Azacycle
  • Hydrochloride
  • Organic oxide
  • Organopnictogen compound
  • Primary amine
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Organofluoride
  • Organohalogen compound
  • Organic oxygen compound
  • Alkyl fluoride
  • Alcohol
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Alkyl halide
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP0.28ALOGPS
logP-0.49ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)1.89ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area109.37 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity64.66 m³·mol⁻¹ChemAxon
Polarizability21.77 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-8d9731714472b2257b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-8d9731714472b2257b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0udi-0009000000-8d9731714472b2257b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-0090000000-43c300530ecb5470b45eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0002-0090000000-43c300530ecb5470b45eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-0090000000-43c300530ecb5470b45eSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDBSALT000092
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkGemcitabine
Chemspider IDNot Available
ChEBI ID31647
PubChem Compound ID60749
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General ReferencesNot Available