Basic information
- CAS
3820-67-5- Standard SMILES
O=C(OCC(O)CO)c1ccccc1Nc1ccnc2cc(Cl)ccc12- InChIKey
GWOFUCIGLDBNKM-UHFFFAOYSA-N- Molecular formula
- C19H17ClN2O4
- Average molar mass
- 372.8 g/mol
- Monoisotopic mass
- 372.0876847
Overview
Glafenine is a carboxylic ester that is 2,3-dihydroxypropyl anthranilate in which the amino group is substituted by a 7-chloroquinolin-4-yl group. A non-steroidal anti-inflammatory drug, glafenine and its hydrochloride salt were used for the relief of all types of pain, but high incidence of anaphylactic reactions resulted in their withdrawal from the market. It has a role as an inhibitor, a non-steroidal anti-inflammatory drug and a non-narcotic analgesic. It is a glycol, a carboxylic ester, an organochlorine compound, an aminoquinoline and a secondary amino compound. It is functionally related to a glycerol and an anthranilic acid.
Names & identifiers
- Preferred name
- Glafenine
- IUPAC
- 2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate
- English name
- 1-Glyceryl N-[7-chloro-4-quinolyl]anthranilate hydrochloride
- Molecular formula
- C19H17ClN2O4
- Molecular weight
- 372.8
Names & synonyms
glafenine3820-67-5GlaphenineGlafeninGlapheninGlicafanGlifananGlycerylaminophenaquineGlifanGlafenina2,3-Dihydroxypropyl 2-((7-chloroquinolin-4-yl)amino)benzoateGlafeninum
Show more names
r1707adalgurAlcidondolomatealicidon
2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate2,3-Dihydroxypropyl N-(7-chloro-4-quinolyl) anthranilateR 1707CHEBI:31653R-1707NSC-75780846HL4I09AH4-((2-Carboxyphenyl)amino)-7-chloroquinoline alpha-monoglyceride
Database identifiers
- CAS
3820-67-5- PubChem CID
- 3474
- DTXSID
DTXSID1048546- ChEMBL
CHEMBL146095- ChEBI
CHEBI:31653- UNII
- 46HL4I09AH
- EC Number
- 223-315-7
- Nikkaji
- J3.409F
Properties
Computed structural properties
- XLogP
- 3.5
- Topological polar surface area
- 91.7 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 7
- Heavy atoms
- 26
- Formal charge
- 0
- Complexity
- 467
Experimental & physicochemical properties
LogP3.5
Collision Cross Section
187.3 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
179.29 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 170 ℃ · 170℃
- Boiling point
- 618 ℃ · 618℃
- Density
- 1.428 · 1.428
- refractive index
- 1.68 · 1.6800 (estimate)
- Flash point
- 328 ℃ · 328℃
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- 100 · DMSO:100.0(Max Conc. mg/mL);268.24(Max Conc. mM)
- form
- Solid
- pka
- pKa (20°C) 7.2
- color
- Light yellow to yellow
- Water Solubility
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Glafenine
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- rtecs
- CB2687000
- Toxicity
- LD50 orally in mice: >2 g/kg (Allais, Meier)
- risk_code
- 22
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xn
- safety_code
- 36
- Hazard statements
- H315-H319-H335
- Precautionary statements
- P261-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
N - Nervous system
QN - Nervous system
MeSH Pharmacological ClassificationA subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS.
Applications
UsesGlafenine is a non-narcotic analgesic agent. Glafenine shows significant antiinflammatory activity. Glafenine is widely used for the treatment of pains of various origins.
Upstream & downstream products
Upstream raw materials
Suppliers46 total
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
杭州摩库生物医药科技有限公司+86-057181025280; +8617767106207 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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