Marvin  11161211412D          

 26 28  0  0  0  0            999 V2000
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    8.5173  -11.3942    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2219  -12.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5345   -9.7556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8068  -10.9817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5173  -12.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2219  -13.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9381  -13.8692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9381  -12.2192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5001  -13.8692    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.2391  -10.1739    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5345   -8.9306    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6427  -13.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7954  -12.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6427  -12.6317    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9610   -9.7728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7954  -13.4567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657  -10.1910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3532  -13.8692    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    7.1079   -9.7442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6657  -11.0160    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0907  -11.3942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1037  -10.2025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.3876   -9.7785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3860  -10.1509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3802  -10.9759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  5  1  0  0  0  0
  3  6  2  0  0  0  0
  4  1  1  0  0  0  0
  5  1  2  0  0  0  0
  6  2  1  0  0  0  0
  7  3  1  0  0  0  0
  8  7  1  0  0  0  0
  9  3  1  0  0  0  0
 10 17  1  0  0  0  0
 11  4  1  0  0  0  0
 12  4  2  0  0  0  0
 13 15  1  0  0  0  0
 14  6  1  0  0  0  0
 15  9  2  0  0  0  0
 16 11  1  0  0  0  0
 17 14  2  0  0  0  0
 18 16  1  0  0  0  0
 19 13  1  0  0  0  0
 20  1  1  0  0  0  0
 21 18  1  0  0  0  0
 22  5  1  0  0  0  0
 23 24  1  0  0  0  0
 24 18  1  0  0  0  0
 25 20  2  0  0  0  0
 26 25  1  0  0  0  0
 26 22  2  0  0  0  0
 10  7  2  0  0  0  0
 13  8  2  0  0  0  0
M  END
> <ID>
CHEBI:31653

> <NAME>
glafenine

> <DEFINITION>
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.

> <STAR>
3

> <SECONDARY_ID>
CHEBI:344737

> <SYNONYM>
Glycerylaminophenaquine; Glifanan; Glifan; Glicafan; Glaphenine; Glaphenin; Glafenin; 4-(2'-beta,gamma-Dihydroxypropoxycarbonylphenylamino)-7-chloroquinoline; 4-((2-Carboxyphenyl)amino)-7-chloroquinoline alpha-monoglyceride; 2,3-Dihydroxypropyl N-(7-chloro-4-quinolyl) anthranilate

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

> <INN>
glafeninum; glafenine; glafenine; glafenina

> <FORMULA>
C19H17ClN2O4

> <MASS>
372.80200

> <MONOISOTOPIC_MASS>
372.08768

> <CHARGE>
0

> <SMILES>
OCC(O)COC(=O)c1ccccc1Nc1ccnc2cc(Cl)ccc12

> <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)

> <INCHIKEY>
GWOFUCIGLDBNKM-UHFFFAOYSA-N

> <BEILSTEIN_REGISTRY_NUMBER>
497124

> <CAS_REGISTRY_NUMBER>
3820-67-5

> <REAXYS_REGISTRY_NUMBER>
497124

> <CHEMIDPLUS>
3820-67-5

> <KEGG_DRUG_ACCESSION>
D01351

> <LINCS_ACCESSION>
LSM-4419

> <NIST_CHEMISTRY_WEBBOOK>
3820-67-5

> <WIKIPEDIA_ACCESSION>
Glafenine

> <PUBMED_CITATION>
19567678; 2210868

$$$$