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95058-81-4 molecular structure
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4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

ChemBase ID: 324
Molecular Formular: C9H11F2N3O4
Molecular Mass: 263.1981464
Monoisotopic Mass: 263.07176229
SMILES and InChIs

SMILES:
FC1(F)[C@H](O)[C@H](O[C@H]1n1ccc(nc1=O)N)CO
Canonical SMILES:
OC[C@H]1O[C@H](C([C@@H]1O)(F)F)n1ccc(nc1=O)N
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

Cite this record

CBID:324 http://www.chembase.cn/molecule-324.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
IUPAC Traditional name
gemcitabine
Brand Name
DDFC
DFDC
GEO
Gemcin
Gemcitabina [INN-Spanish]
Gemcitabine HCl
Gemcitabine hydrochloride
Gemcitabinum [INN-Latin]
Gemtro
Gemzar
Synonyms
Gemcitabine
Gemzar
CAS Number
95058-81-4
MDL Number
MFCD00869720
PubChem SID
46506425
160963787
PubChem CID
60750

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.51707  H Acceptors
H Donor LogD (pH = 5.5) -1.4665402 
LogD (pH = 7.4) -1.4665728  Log P -1.4665396 
Molar Refractivity 53.2503 cm3 Polarizability 20.563793 Å3
Polar Surface Area 108.38 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 0.14  LOG S -1.07 
Solubility (Water) 2.23e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Soluble expand Show data source
Hydrophobicity(logP)
-1.4 expand Show data source
Storage Condition
-20°C expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
TSCA Listed
false expand Show data source
Purity
95+% expand Show data source
Salt Data
Free Base expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals
DrugBank - DB00441 external link
Item Information
Drug Groups approved
Description Gemcitabine is a nucleoside analog used as chemotherapy. It is marketed as Gemzar? by Eli Lilly and Company. As with fluorouracil and other analogues of pyrimidines, the drug replaces one of the building blocks of nucleic acids, in this case cytidine, during DNA replication. The process arrests tumor growth, as new nucleosides cannot be attached to the "faulty" nucleoside, resulting in apoptosis (cellular "suicide").
Gemcitabine is used in various carcinomas: non-small cell lung cancer, pancreatic cancer, bladder cancer and breast cancer. It is being investigated for use in oesophageal cancer, and is used experimentally in lymphomas and various other tumor types.
Indication For the first-line treatment of patients with metastatic breast cancer, locally advanced (Stage IIIA or IIIB), or metastatic (Stage IV) non-small cell lung cancer and as first-line treatment for patients with adenocarcinoma of the pancreas.
Pharmacology Gemcitabine is an antineoplastic anti-metabolite. Anti-metabolites masquerade as purine or pyrimidine - which become the building blocks of DNA. They prevent these substances becoming incorporated in to DNA during the "S" phase (or DNA synthesis phase of the cell cycle), stopping normal development and division. Gemcitabine blocks an enzyme which converts the cytosine nucleotide into the deoxy derivative. In addition, DNA synthesis is further inhibited because Gemcitabine blocks the incorporation of the thymidine nucleotide into the DNA strand.
Toxicity Myelosuppression, paresthesias, and severe rash were the principal toxicities, LD50=500 mg/kg (orally in mice and rats)
Affected Organisms
Humans and other mammals
Biotransformation Transformed via nucleoside kinases to two active metabolites, gemcitabine diphosphate and gemcitabine triphosphate. Can also undergo deamination via cytidine deaminase to an inactive uracil metabolite (dFdU).
Absorption 100%
Half Life Short infusions ranged from 32 to 94 minutes, and the value for long infusions vary from 245 to 638 minutes, depending on age and gender.
Protein Binding Plasma protein binding is negligible (<10%)
Distribution * 50 L/m^2 [infusions lasting <70 minutes]
* 370 L/m^2 [long infusions]
Clearance * 92.2 L/hr/m2 [Men 29 yrs]
* 75.7 L/hr/m2 [Men 45 yrs]
* 55.1 L/hr/m2 [Men 65 yrs]
* 40.7 L/hr/m2 [Men 79 yrs]
* 69.4 L/hr/m2 [Women 29 yrs]
* 57 L/hr/m2 [Women 45 yrs]
* 41.5 L/hr/m2 [Women 65 yrs]
* 30.7 L/hr/m2 [Women 79 yrs]
References
[Link]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1714 external link
Research Area: Cancer
Biological Activity:
Gemcitabine(Gemzar) belongs to the group of medicines called antimetabolites. It is used alone or in combination with other medicines to treat cancer of the breast, ovary, pancreas, and lung. Gemcitabine interferes with the growth of cancer cells, which are eventually destroyed. [1, 2]

REFERENCES

REFERENCES

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  • • http://www.mayoclinic.com/health/drug-information/DR601499
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PATENTS

PATENTS

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INTERNET

INTERNET

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