Amino quinuride

Structural formula
General
Surname	Amino quinuride
other names	Aminoquinuride Aminoquinuridum Aminochine carbamide N , N -Bis (4-amino-2-methyl-6-quinonyl) urea surfing
Molecular formula	C 21 H 20 N 6 O
Brief description	white to yellowish powder, very faint odor (dihydrochloride heptahemihydrate)
External identifiers / databases
CAS number 3811-56-1 5424-37-3 (diydrochloride heptahemihydrate) PubChem 71166 ChemSpider 64306 DrugBank DB04452 Wikidata Q471662
properties
Molar mass	372.42 g mol −1
Physical state	firmly
Melting point	255 ° C (decomposition)
solubility	Slightly soluble in water (20 ° C), very poorly soluble in ethanol (dihydrochloride heptahemihydrate)
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: 413 P: no P-phrases
Toxicological data	178 mg kg −1 ( LD 50 ,  mouse ,  ip )
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Aminochinurid or often surfing [ sʊʀfeːn ] (as surfing insulin ) is a disinfectant with a urea backbone and is a pharmaceutical excipient for the production of insulin . It was discovered in the Hoechst laboratories in 1937 .

properties

Aminoquinuride is a white powder which is only slightly soluble in water under normal conditions and very slightly soluble in ethanol. On the other hand, it dissolves well in boiling water.

use

Aminoquinuride and its dihydrochloride are used as disinfectants for various indications, for example as a component of powders; but also in solution for wound irrigation.

In insulin production

Amino quinuride has also been used in the production of delay insulins since 1938 . It took advantage of the property that it forms insoluble, salt-like complexes with insulin. The complex with pig or bovine insulin obtained in this way can be injected subcutaneously in suspension and, due to its very low solubility, represents a depot from which insulin is gradually released. The release is similar to that of NPH insulin . The disadvantage of this form of application, however, was that the suspension had to be carefully slurried before the injection, and allergic reactions to aminoquinuride also frequently occurred. In 2005 the last preparations with surfing insulin from the manufacturer Berlin-Chemie were withdrawn from the market.

literature

• F. Umber, FK Störring and W. Föllmer: Successes with a new type of depot insulin without added protamine (surfing insulin) (3rd communication) , in: Klinische Wochenschrift , Volume 17, No. 13 of March 26, 1938, p. 443 -446; doi: 10.1007 / BF01775866 .

Individual evidence

1. ↑ ^{a b c} Hager's Handbook of Pharmaceutical Practice, Volume 7 (substances AD), 5th edition, Ed .: F. von Bruchhausen et al., Springer-Verlag, Berlin 1993, ISBN 3-540-52632-3 , p. 196.
2. ↑ ^{a b c d} Hunnius Pharmaceutical Dictionary, 9th edition, Ed .: HPT Ammon, de Gruyter Verlag, Berlin 2004, ISBN 3-11-017487-1 , p. 69,783.
3. ↑ ^{a b} Datasheet Surfen hydrate from Sigma-Aldrich , accessed on May 17, 2011 ( PDF ).
4. ↑ Peter Hürter, Thomas Danne: Diabetes in Children and Adolescents: Clinic, Therapy, Rehabilitation. 6th edition, Springer Verlag, Berlin 2004, ISBN 3-540-21186-1 , p. 185.
5. ↑ Background information "The History of Insulin" ( Memento from July 29, 2016 in the Internet Archive ) at sanofi-aventis.de
6. ^ Thomas R. Weihrauch, Hanns Peter Wolff: Internal Therapy 2006/2007. 16th edition, publisher: TR Weihrauch, Urban & Fischer Verlag / Elsevier GmbH, Munich 2006, ISBN 3-437-21803-4 , p. 951.