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Gemcitabine

CAT: 1568-C08000-04Size: 1 gDry Ice: NoHazardous: No
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CAT#:1568-C08000-04Size:1 g
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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CAS Number
95058-81-4
Synonyms
LY-188011, NSC 613327
SKU
C08000-50mg
Target
Autophagy
Applications
Autophagy
Smiles
C1=CN (C (=O) N=C1N) C2C (C (C (O2) CO) O) (F) F
Molecular Formula
C9H11F2N3O4
Additionnal Information
Gemcitabine, a nucleic acid synthesis inhibitor, is a very potent and specific deoxycytidine analogue, used as chemotherapy. Gemcitabine induces a potent p53-dependent apoptosis.
Storage Conditions
Powder, 4°C,3 years (in the dark) ; in solvent, -80°C,1 year (in the dark)

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

Alternative Products

CatalogName
TRC-G305028-250MGGemcitabine
sc-2097423'-Epi Gemcitabine (Gemcitabine Impurity)
CS-O-61073Gemcitabine-d3
CS-EK-00286Gemcitabine Triphosphate
204970Gemcitabine elaidate

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