ContaminantDB: Glafenine

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References XML

Record Information

Version

1.0

Creation Date

2016-06-03 11:26:09 UTC

Update Date

2016-11-09 01:23:01 UTC

Accession Number

CHEM043915

Identification

Common Name

Glafenine

Class

Small Molecule

Description

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.

Contaminant Sources

STOFF IDENT Compounds

Contaminant Type

Not Available

Chemical Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,3-Dihydroxypropyl N-(7-chloro-4-quinolyl) anthranilate	ChEBI
4-((2-Carboxyphenyl)amino)-7-chloroquinoline alpha-monoglyceride	ChEBI
4-(2'-beta,gamma-Dihydroxypropoxycarbonylphenylamino)-7-chloroquinoline	ChEBI
Glafenin	ChEBI
Glafenina	ChEBI
Glafeninum	ChEBI
Glaphenin	ChEBI
Glaphenine	ChEBI
Glicafan	ChEBI
Glifan	ChEBI
Glifanan	ChEBI
Glycerylaminophenaquine	ChEBI
2,3-Dihydroxypropyl N-(7-chloro-4-quinolyl) anthranilic acid	Generator
4-((2-Carboxyphenyl)amino)-7-chloroquinoline a-monoglyceride	Generator
4-((2-Carboxyphenyl)amino)-7-chloroquinoline α-monoglyceride	Generator
4-(2'-b,g-Dihydroxypropoxycarbonylphenylamino)-7-chloroquinoline	Generator
4-(2'-Β,γ-dihydroxypropoxycarbonylphenylamino)-7-chloroquinoline	Generator
Exidol	MeSH
2,3-Dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoic acid	Generator

Chemical Formula

C₁₉H₁₇ClN₂O₄

Average Molecular Mass

372.802 g/mol

Monoisotopic Mass

372.088 g/mol

CAS Registry Number

3820-67-5

IUPAC Name

2,3-dihydroxypropyl 2-[(7-chloroquinolin-4-yl)amino]benzoate

Traditional Name

glafenine

SMILES

OCC(O)COC(=O)C1=CC=CC=C1NC1=C2C=CC(Cl)=CC2=NC=C1

InChI Identifier

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)

InChI Key

GWOFUCIGLDBNKM-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Substituents

4-aminoquinoline
Haloquinoline
Chloroquinoline
Aminobenzoic acid or derivatives
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Aniline or substituted anilines
Aminopyridine
Glycerolipid
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Pyridine
Benzenoid
Vinylogous amide
Heteroaromatic compound
Secondary alcohol
Amino acid or derivatives
1,2-diol
Carboxylic acid ester
Azacycle
Secondary amine
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Alcohol
Organohalogen compound
Organic oxygen compound
Organochloride
Organonitrogen compound
Organic nitrogen compound
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

carboxylic ester (CHEBI:31653 )
organochlorine compound (CHEBI:31653 )
secondary amino compound (CHEBI:31653 )
glycol (CHEBI:31653 )
aminoquinoline (CHEBI:31653 )

Biological Properties

Status

Detected and Not Quantified

Origin

Not Available

Cellular Locations

Not Available

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Not Available

Appearance

Not Available

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
logP	4.16	ChemAxon
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	6.41	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	91.68 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	97.55 m³·mol⁻¹	ChemAxon
Polarizability	38.11 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-9071000000-dff2f89f2b0cab69da00	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_2_3) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00fr-5049000000-8901c68d0c0af3d68589	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-057i-9264000000-68c1c2c87ae686e9aeac	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgi-6090000000-57546fba388e8e8e3585	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0fka-2097000000-ea2b748ceb67e9365973	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-3091000000-973d7efb5cefa17cf58a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-3190000000-bcf1cb465f07b97cdb45	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0069000000-714a23e2c4e106e5b089	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-0090000000-3c31059821086ca363e2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-001i-0090000000-55fb72df4c42c194793e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0092000000-98f784f71c8134e9a0e1	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udj-0090000000-e8cd0c8677a7b3eed40e	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0090000000-10d10decaad5bf043060	Spectrum

Toxicity Profile

Route of Exposure

Not Available

Mechanism of Toxicity

Not Available

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

Not Available

Uses/Sources

Not Available

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Not Available

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB08963

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Glafenine

Chemspider ID

Not Available

ChEBI ID

31653

PubChem Compound ID

3474

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

1. https://www.ncbi.nlm.nih.gov/pubmed/?term=19567678

2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2210868

Glafenine (CHEM043915)

Structure for CHEM043915: Glafenine