ChemFOnt: Showing chemical card for Gemcitabine (CFc000008948)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:55:56 UTC

Chemfont ID

CFc000008948

Molecule Identification

Common Name

Gemcitabine

Definition

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').

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2',2'-Difluorodeoxycytidine	ChEBI
2'-Deoxy-2',2'-difluorocytidine	ChEBI
4-Amino-1-((2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)-tetrahydrofuran-2-yl)pyrimidin-2(1H)-one	ChEBI
Gemcitabina	ChEBI
Gemcitabinum	ChEBI
DFdCyd	HMDB
2',2'-Difluoro-2'-deoxycytidine	HMDB
2'-Deoxy-2'-difluorocytidine	HMDB
Gemcitabine, (D-threo-pentafuranosyl)-isomer	HMDB
Gemcitabine, (alpha-D-threo-pentofuranosyl)-isomer	HMDB
2'-Deoxy-2',2''-difluorocytidine-5'-O-monophosphate	HMDB
Gemcitabine hydrochloride	HMDB
2',2'-DFDC	HMDB
Gemzar	HMDB
Gemcitabine, (beta-D-threo-pentafuranosyl)-isomer	HMDB

Chemical Formula

C₉H₁₁F₂N₃O₄

Average Molecular Weight

263.1981

Monoisotopic Molecular Weight

263.071762265

IUPAC Name

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

Traditional Name

gemcitabine

CAS Registry Number

95058-81-4

SMILES

NC1=NC(=O)N(C=C1)[C@@H]1O[C@H](CO)[C@@H](O)C1(F)F

InChI Identifier

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

InChI Key

SDUQYLNIPVEERB-QPPQHZFASA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrimidine 2'-deoxyribonucleosides. Pyrimidine 2'-deoxyribonucleosides are compounds consisting of a pyrimidine linked to a ribose which lacks a hydroxyl group at position 2.

Kingdom

Organic compounds

Super Class

Nucleosides, nucleotides, and analogues

Class

Pyrimidine nucleosides

Sub Class

Pyrimidine 2'-deoxyribonucleosides

Direct Parent

Pyrimidine 2'-deoxyribonucleosides

Alternative Parents

Substituents

Pyrimidine 2'-deoxyribonucleoside
Aminopyrimidine
Pyrimidone
Hydropyrimidine
Pyrimidine
Imidolactam
Heteroaromatic compound
Tetrahydrofuran
Fluorohydrin
Halohydrin
Secondary alcohol
Organoheterocyclic compound
Azacycle
Oxacycle
Alkyl halide
Organopnictogen compound
Primary amine
Primary alcohol
Organooxygen compound
Organonitrogen compound
Organofluoride
Organohalogen compound
Organic oxygen compound
Alkyl fluoride
Alcohol
Organic nitrogen compound
Amine
Organic oxide
Hydrocarbon derivative
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

organofluorine compound (CHEBI:175901 )
pyrimidine 2'-deoxyribonucleoside (CHEBI:175901 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Cytoplasm (HMDB: HMDB0014584)
Membrane (HMDB: HMDB0014584)

Source

Exogenous

Exogenous (HMDB: HMDB0014584)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Gemcitabine Action Pathway (PathBank: SMP0000446)

Metabolic pathway

Gemcitabine Metabolism Pathway (PathBank: SMP0000603)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	22.3 g/L	ALOGPS
logP	0.14	ALOGPS
logP	-1.5	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	11.52	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	108.38 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	53.25 m³·mol⁻¹	ChemAxon
Polarizability	21.45 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon