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Gemcitabine monophosphate

CAT: 0804-HY-108932-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-108932-01Size:1 mg
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24/48H Stock Items & 2 to 6 Weeks non Stock Items.
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Description
Gemcitabine monophosphate (Gemcitabine 5′-phosphate) is one of the active intermediates of Gemcitabine. Gemcitabine monophosphate has a synergistic anti-cancer effect and can be delivered by formulating it into nanoparticles[1][2].
CAS Number
116371-67-6
Product Name Alternative
Gemcitabine 5′-phosphate
UNSPSC
12352005
Hazard Statement
H315, H319, H335
Target
Apoptosis
Type
Reference compound
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/gemcitabine-monophosphate.html
Purity
99.98
Solubility
DMSO : 200 mg/mL (ultrasonic) |H2O : 100 mg/mL (ultrasonic)
Smiles
OP(OC[C@@H]1[C@@H](O)C(F)(F)[C@H](N2C=CC(N)=NC2=O)O1)(O)=O
Molecular Formula
C9H12F2N3O7P
Molecular Weight
343.18
Precautions
H315, H319, H335
References & Citations
[1]Zhang Y, et al. Codelivery of VEGF siRNA and gemcitabine monophosphate in a single nanoparticle formulation for effective treatment of NSCLC. Mol Ther. 2013 Aug;21 (8) :1559-69. |[2]Miao L, et al. Nanoparticles with Precise Ratiometric Co-Loading and Co-Delivery of Gemcitabine Monophosphate and Cisplatin for Treatment of Bladder Cancer. Adv Funct Mater. 2014 Nov 12;24 (42) :6601-6611.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, sealed storage, away from moisture)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Gemcitabine 5'-monophosphate
CAS Number116371-67-6
PubChem CID131634196
IUPAC Name[(2R,3R,5R)-5-(6-amino-2-oxo-1,6-dihydropyrimidin-3-yl)-4,4-difluoro-3-hydroxyoxolan-2-yl]methyl dihydrogen phosphate
Molecular FormulaC9H14F2N3O7P
Molecular Weight345.19
XLogP-5.4
Topological Polar Surface Area155
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Heavy Atom Count22
Formal Charge0
Complexity527
SMILES
C1=CN(C(=O)NC1N)[C@H]2C([C@@H]([C@H](O2)COP(=O)(O)O)O)(F)F
InChI
InChI=1S/C9H14F2N3O7P/c10-9(11)6(15)4(3-20-22(17,18)19)21-7(9)14-2-1-5(12)13-8(14)16/h1-2,4-7,15H,3,12H2,(H,13,16)(H2,17,18,19)/t4-,5?,6-,7-/m1/s1
InChIKey
WRQBYMGFHZCJEI-GFEXSSHISA-N
Chemical Structure
2D Structure
2D structure of Gemcitabine 5'-monophosphate
CAS: 116371-67-6
CID: 131634196
Formula: C9H14F2N3O7P
MW: 345.19
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight345.19
XLogP3-5.4
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count10
Rotatable Bond Count4
Exact Mass345.05374312
Monoisotopic Mass345.05374312
Topological Polar Surface Area155 Ų
Heavy Atom Count22
Formal Charge0
Complexity527
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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