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Gemcitabine base

CAT: 0926-ND04237-02Size: 25 gDry Ice: NoHazardous: No
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CAT#:0926-ND04237-02Size:25 g
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CAS Number
95058-81-4
Synonyms
2-Deoxy-2',2'-difluorocytidine;4-Amino-1-[3,3-difluoro-4-hydroxy-5- (hydroxymethyl) oxolan-2-yl]pyrimidin-2-one;2'-Deoxy-2',2'-difluor o-D-cytidine;2',2'-Difluoro-2'-deoxycytidine
MDL Number
MFCD00869720
Smiles
C1=CN (C (=O) N=C1N) [C@H]2C ([C@@H] ([C@H] (O2) CO) O) (F) F
Molecular Formula
C9H11F2N3O4
Molecular Weight
263.2 g/mol
Controlled
No

Chemical Information

Gemcitabine

Gemcitabine is 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. It has a role as a radiosensitizing agent, an antimetabolite, an antineoplastic agent, a xenobiotic, an immunosuppressive agent, an antiviral drug, a photosensitizing agent, a prodrug, a DNA synthesis inhibitor, an EC 1.17.4.1 (ribonucleoside-diphosphate reductase) inhibitor and an environmental contaminant. It is a pyrimidine 2'-deoxyribonucleoside and an organofluorine compound.

CAS Number95058-81-4
PubChem CID60750
IUPAC Name4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Molecular FormulaC9H11F2N3O4
Molecular Weight263.20
XLogP-1.5
Topological Polar Surface Area108
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Heavy Atom Count18
Formal Charge0
Complexity426
SMILES
C1=CN(C(=O)N=C1N)[C@H]2C([C@@H]([C@H](O2)CO)O)(F)F
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
Chemical Structure
2D Structure
2D structure of Gemcitabine
CAS: 95058-81-4
CID: 60750
Formula: C9H11F2N3O4
MW: 263.20
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight263.20
XLogP3-1.5
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count6
Rotatable Bond Count2
Exact Mass263.07176216
Monoisotopic Mass263.07176216
Topological Polar Surface Area108 Ų
Heavy Atom Count18
Formal Charge0
Complexity426
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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