Marvin  11060915002D          

 18 19  0  0  1  0            999 V2000
    0.0000   -0.8250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    0.4125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6674   -2.1349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6674   -2.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.9195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4125   -2.9195    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2370   -1.4285    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8974   -3.5870    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.6500    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8974   -3.5870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5619   -4.3407    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4643   -2.3484    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  1  1  0  0  0
  1  2  1  0  0  0  0
  2 13  2  0  0  0  0
  1  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5 15  1  0  0  0  0
  3  6  2  0  0  0  0
  6  5  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 10 16  1  1  0  0  0
 10 11  1  0  0  0  0
 11 14  1  6  0  0  0
 16 17  1  0  0  0  0
  9 18  1  0  0  0  0
M  END
> <ID>
CHEBI:175901

> <NAME>
gemcitabine

> <DEFINITION>
A 2'-deoxycytidine having geminal fluoro substituents in the 2'-position. An inhibitor of ribonucleotide reductase, gemcitabine is used in the treatment of various carcinomas, particularly non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:42752; CHEBI:5295

> <SYNONYM>
4-amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one; 2'-Deoxy-2',2'-difluorocytidine; 2',2'-Difluorodeoxycytidine

> <IUPAC_NAME>
2'-deoxy-2',2'-difluorocytidine

> <INN>
gemcitabinum; gemcitabine; gemcitabina

> <FORMULA>
C9H11F2N3O4

> <MASS>
263.19810

> <MONOISOTOPIC_MASS>
263.07176

> <CHARGE>
0

> <SMILES>
Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1

> <INCHI>
InChI=1S/C9H11F2N3O4/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)/t4-,6-,7-/m1/s1

> <INCHIKEY>
SDUQYLNIPVEERB-QPPQHZFASA-N

> <BEILSTEIN_REGISTRY_NUMBER>
5382060

> <CAS_REGISTRY_NUMBER>
95058-81-4

> <REAXYS_REGISTRY_NUMBER>
5382060

> <CHEMIDPLUS>
95058-81-4

> <DRUGBANK_ACCESSION>
DB00441

> <KEGG_COMPOUND_ACCESSION>
C07650

> <KEGG_DRUG_ACCESSION>
D02368

> <LINCS_ACCESSION>
LSM-5333

> <PDBECHEM_ACCESSION>
GEO

> <WIKIPEDIA_ACCESSION>
Gemcitabine

> <PUBMED_CITATION>
11034044; 11061612; 11088063; 11122828; 11132538; 11142482; 11221019; 11356111; 11374818; 11489002; 11504793; 11510027; 11585734; 11595724; 11807603; 11859947; 11901308; 12057041; 12057046; 12057157; 12115355; 12142097; 12520460; 12571808; 12722678; 12722691; 12743987; 12761494; 12798170; 12917815; 12954073; 14606642; 14653877; 14720338; 15131028; 15160243; 15221904; 15282439; 15297392; 15542781; 15637766; 15744590; 16001951; 16041610; 16080557; 16143373; 16149285; 16317298; 16500746; 16555971; 16584929; 16807461; 16807463; 16894289; 16905983; 17101674; 17296311; 17296587; 17347561; 17429628; 17460420; 17602464; 17639396; 17887663; 17939651; 17941128; 17987263; 18035967; 18050344; 18086345; 18166944; 18186604; 18257544; 18348652; 18773046; 18789834; 18819792; 18981552; 19034448; 19177022; 19399788; 19839926; 19879060; 22763439; 28594276; 28608357; 28912244

$$$$