1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE
- Product Name
- 1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE
- CAS No.
- 3820-67-5
- Chemical Name
- 1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE
- Synonyms
- r1707;glifan;adalgur;Alcidon;glafenin;dolomate;alicidon;glicafan;glifanan;Gilfanar
- CBNumber
- CB5107351
- Molecular Formula
- C19H17ClN2O4
- Formula Weight
- 372.8
- MOL File
- 3820-67-5.mol
1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE Property
- Melting point:
- 170℃
- Boiling point:
- 618℃
- Density
- 1.428
- refractive index
- 1.6800 (estimate)
- Flash point:
- 328℃
- storage temp.
- 2-8°C(protect from light)
- solubility
- 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
- 38.46g/L(temperature not stated)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- G406500
- Product name
- Glafenine
- Packaging
- 100mg
- Price
- $290
- Updated
- 2021/12/16
- Product number
- A124438
- Product name
- 2,3-Dihydroxypropyl2-(((7-chloroquinolin-4-yl)amino)benzoate
- Purity
- 98+%
- Packaging
- 100mg
- Price
- $16
- Updated
- 2021/12/16
- Product number
- A124438
- Product name
- 2,3-Dihydroxypropyl2-(((7-chloroquinolin-4-yl)amino)benzoate
- Purity
- 98+%
- Packaging
- 250mg
- Price
- $23
- Updated
- 2021/12/16
- Product number
- AS440902
- Product name
- Glafenine
- Purity
- ≥98%
- Packaging
- 250mg
- Price
- $29
- Updated
- 2021/12/16
- Product number
- A124438
- Product name
- 2,3-Dihydroxypropyl2-(((7-chloroquinolin-4-yl)amino)benzoate
- Purity
- 98+%
- Packaging
- 1g
- Price
- $63
- Updated
- 2021/12/16
1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE Chemical Properties,Usage,Production
Originator
Glifanan,Roussel,France,1965
Uses
Glafenine is a non-narcotic analgesic agent. Glafenine shows significant antiinflammatory activity. Glafenine is widely used for the treatment of pains of various origins.
Definition
ChEBI: 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.
Manufacturing Process
Step A: Preparation of (2,3-isopropylidenedioxy)-propyl o-nitrobenzoate - 59.6
g of 2,2-dimethyl-4hydroxymethyl-1,3-dioxolane were dissolved under
agitation in 60 cc of anhydrous pyridine. The solution was cooled to +5°c and
86.5 g of o-nitrobenzoyl chloride (prepared by Leckermann et al., Ber. vol.80,
p.488, 1947) were slowly introduced into it. The reaction mixture was agitated
for a period of two hours at room temperature and then was poured into 500
cc of ether. The mixture was filtered and the filtrate was washed successively
with 0.5 N sulfuric acid solution, with aqueous sodium bicarbonate solution
and finally with water until the wash waters were neutral. The washed solution
was dried over sodium sulfate and filtered again. The filtrate was distilled to
dryness under vacuum to obtain 116.5 g (being a yield of 92%) of (2,3-
isopropylidenedioxy)-propyl o-nitrobenzoate in the form of a yellow oil which
distilled at 178°C to 180°C at a pressure of 1 mm.
Step B: Preparation of (2,3-isopropylidenedioxy)-propyl anthranilate - 80 g of
(2,3-isopropyl-idenedioxy)propyl o-nitrobenzoate, obtained as described in
Step A, were subjected to hydrogenation for a period of one hour in 800 cc of
absolute alcohol in the presence of 2 g of palladized carbon black as catalyst.
The reaction mixture was filtered and the filtrate was evaporated under
vacuum to obtain 70.5 g (being a yield of 98.5%) of (2,3-
isopropylidenedioxy)-propyl anthranilate in the form of a yellow oil which
distilled at 159°C to 160°C under 0.5 mm of pressure.
Step C: Preparation of the (α-monoglyceride of 4-(2'-carboxyphenylamino)-7-
chloro-quinoline - A mixture of 48 g of (2,3-isopropylidenedioxy)-propyl
anthranilate, 36 g of 4.7-dichloro-quinoline, 36 cc of concentrated hydrochloric
acid and 300 cc of water was agitated while heating to reflux for a period of
two hours. The reaction mixture was filtered and the filtrate was allowed to
stand at a temperature of 0°C for a period of three hours. The hydrochloride
salt was then vacuum filtered and the salt was taken up in 600 cc 50%
methanol at reflux. The solution was made alkaline by the addition of 120 cc
of ammonia solution and iced for a period of one hour. The crystalline
precipitate obtained was vacuum filtered, washed with water and dried to
obtain 38.5 g (being a yield of 56%) of the α-monoglyceride of 4-(2'-
carboxyphenylamino-7-chloro-quinoline having a melting point of 165°C.
The product occurred in the form of pale yellow prisms and was insoluble in
water, ether, benzene, diluted alcohols, olive oil and chloroform, slightly
soluble in absolute alcohol, dioxane, tetrahydrofuran and acetone, and soluble
in dilute aqueous acids and alkalis.
brand name
Disipan;Espasmo-giliganan;Exidol;Glafezon;Glifadex;Glifanan;Glifarelax;Osodent.
Therapeutic Function
Analgesic
World Health Organization (WHO)
Glafenine, a quinolylanthranilate derivative, was introduced in 1965 for use as an analgesic. By the late 1970s its use had been associated with severe allergic responses, including anaphylactoid reactions, which led to its withdrawal in one country whereas in others a warning to this effect is required in the product information. In 1992, on the advice of the Committee for Proprietary Medicinal Products of the European Communities, glafenine was eventually withdrawn worldwide by the major manufacturer.
Hazard
Moderately toxic by ingestion. Human systemic effects.
1-GLYCERYL N-[7-CHLORO-4-QUINOLYL]ANTHRANILATE HYDROCHLORIDE Preparation Products And Raw materials
Raw materials
Preparation Products
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