NAV

Glafenine

Identification

Generic Name
Glafenine
DrugBank Accession Number
DB08963
Background

An anthranilic acid derivative with analgesic properties used for the relief of all types of pain. Glafenine is withdrawn from the American market.

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 372.802
Monoisotopic: 372.087684749
Chemical Formula
C19H17ClN2O4
Synonyms
  • Glafenina
  • Glafenine
  • Glafénine
  • Glafeninum
  • Glycerylaminophenaquine
External IDs
  • R 1707
  • R-1707
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

ATC Codes
N02BG03 — Glafenine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 4-aminoquinolines. These are organic compounds containing an amino group attached to the 4-position of a quinoline ring system.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Quinolines and derivatives
Sub Class
Aminoquinolines and derivatives
Direct Parent
4-aminoquinolines
Alternative Parents
Chloroquinolines / Aminobenzoic acids and derivatives / Benzoic acid esters / Aniline and substituted anilines / Benzoyl derivatives / Aminopyridines and derivatives / Glycerolipids / Aryl chlorides / Heteroaromatic compounds / Vinylogous amides
show 12 more
Substituents
1,2-diol / 4-aminoquinoline / Alcohol / Amine / Amino acid or derivatives / Aminobenzoic acid or derivatives / Aminopyridine / Aniline or substituted anilines / Aromatic heteropolycyclic compound / Aryl chloride
show 28 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
carboxylic ester, organochlorine compound, secondary amino compound, glycol, aminoquinoline (CHEBI:31653)
Affected organisms
Not Available

Chemical Identifiers

UNII
46HL4I09AH
CAS number
3820-67-5
InChI Key
GWOFUCIGLDBNKM-UHFFFAOYSA-N
InChI
InChI=1S/C19H17ClN2O4/c20-12-5-6-14-17(7-8-21-18(14)9-12)22-16-4-2-1-3-15(16)19(25)26-11-13(24)10-23/h1-9,13,23-24H,10-11H2,(H,21,22)
IUPAC Name
2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate
SMILES
OCC(O)COC(=O)C1=C(NC2=C3C=CC(Cl)=CC3=NC=C2)C=CC=C1

References

Synthesis Reference

U.S. Patent 3,232,944.

General References
  1. Kleinknecht D, Landais P, Goldfarb B: Analgesic and non-steroidal anti-inflammatory drug-associated acute renal failure: a prospective collaborative study. Clin Nephrol. 1986 Jun;25(6):275-81. [Article]
KEGG Drug
D01351
ChemSpider
3355
ChEBI
31653
ChEMBL
CHEMBL146095
Wikipedia
Glafenine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)165U.S. Patent 3,232,944.
Predicted Properties
PropertyValueSource
Water Solubility0.0338 mg/mLALOGPS
logP2.8ALOGPS
logP4.16Chemaxon
logS-4ALOGPS
pKa (Strongest Acidic)13.62Chemaxon
pKa (Strongest Basic)6.41Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area91.68 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity97.55 m3·mol-1Chemaxon
Polarizability38.11 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0092000000-22c71d5000c9ba732860
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0f7n-8090000000-1fc749107c12ad7831ea
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-a0daa7bdb1de19af39cf
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udj-1090000000-659164a83517bc093b41
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0190000000-a2fbd51ea08edd0da403
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0090000000-4825121f68c65b5328e6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-178.51091
predicted
DeepCCS 1.0 (2019)
[M+H]+180.96538
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.64388
predicted
DeepCCS 1.0 (2019)

Drug created at May 30, 2014 17:51 / Updated at May 10, 2021 12:36