Basic information
- Standard SMILES
Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1- InChIKey
OKKDEIYWILRZIA-OSZBKLCCSA-N- Molecular formula
- C9H12ClF2N3O4
- Average molar mass
- 299.66 g/mol
- Monoisotopic mass
- 299.04843998
Overview
Gemcitabine Hydrochloride is the hydrochloride salt of an analogue of the antimetabolite nucleoside deoxycytidine with antineoplastic activity. Gemcitabine is converted intracellularly to the active metabolites difluorodeoxycytidine di- and triphosphate (dFdCDP, dFdCTP). dFdCDP inhibits ribonucleotide reductase, thereby decreasing the deoxynucleotide pool available for DNA synthesis; dFdCTP is incorporated into DNA, resulting in DNA strand termination and apoptosis.
Names & identifiers
- Preferred name
- Gemcitabine Hydrochloride
- IUPAC
- 4-amino-1-[(2R,4R,5R)-3,3-difluoro-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one;hydrochloride
Names & synonyms
GEMCITABINE HYDROCHLORIDE122111-03-9Gemcitabine HClLY188011 hydrochloride2'-Deoxy-2',2'-difluorocytidine monohydrochloride2'-deoxy-2',2'-difluorocytidine hydrochlorideINFUGEMGemcitabine (as hydrochloride)Cytidine, 2'-deoxy-2',2'-difluoro-, monohydrochlorideDTXSID3047849Gemcitabine HCIU347PV74IL
Show more names
LY-188011 HYDROCHLORIDE2',2'-Difluorodeoxycytidine monohydrochlorideDTXCID3027827NSC613327CHEBI:31647RefChem:57768FF10832FF 10832
Database identifiers
- CAS
122111-03-9- PubChem CID
- 60749
- DTXSID
DTXSID3047849- ChEMBL
CHEMBL1637- UNII
- U347PV74IL
- EC Number
- 601-823-3
Properties
Computed structural properties
- Topological polar surface area
- 108 Ų
- Hydrogen bond donors
- 4
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 426
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Safety & regulation
GHS classification
GHS Classification
Danger
H302 (11.3%): Harmful if swallowed [Warning Acute toxicity, oral]
P203, P264, P264+P265, P270, P280, P301+P317, P302+P352, P305+P351+P338, P317, P318, P321, P330, P332+P317, P337+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 62 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (11.3%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Gemcitabine hydrochloride
vMost-DILI-concern
8
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
GEMCITABINE HYDROCHLORIDE
Nucleic Acid Synthesis Inhibitors [MoA]; Nucleoside Metabolic Inhibitor [EPC]
MeSH Pharmacological ClassificationAntimetabolites that are useful in cancer chemotherapy.
Related reactions
18 records
Linked notes
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