Carbromal

Structural formula
General
Non-proprietary name	Carbromal
other names	2-bromo- N -carbamoyl-2-ethylbutanamide ( IUPAC ); 2- Bromo- N -carbamoyl-2-ethylbutyric acid amide; 2-bromo-2-ethylbutyrylurea; Bromodiethylacetylurea; Bromadal; Dormitory; Planadalin; Uradal; Bromo diethylacetylcarbamide;
Molecular formula	C 7 H 13 BrN 2 O 2
Brief description	odorless and tasteless, white crystal powder or rhombic crystals
External identifiers / databases
EC number	201-046-6
ECHA InfoCard	100,000,952
PubChem	6488
Wikidata	Q382185
Drug information
ATC code	N05 CM04
Drug class	Hypnotic , sedative , ganglion blocker
properties
Molar mass	237.09 g · mol -1
Physical state	firmly
density	1.54 g cm −3 (25 ° C)
Melting point	116-119 ° C
solubility	very bad in water (333 mg l −1 ); moderately in ethanol (56 g l −1 ) and diethyl ether (71 g l −1 ); good in chloroform (333 g l −1 ); soluble in conc. Sulfuric acid , nitric acid and hydrochloric acid , acetone and benzene ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	316 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Carbromal is a drug with a sedative and sleep-inducing effect. The substance was patented by Bayer in 1909 and was launched on the market as a sedative and sleeping aid under the name Adalin . Nowadays the application is considered obsolete .

chemistry

Chemically, it is, this is a brominated urea - derivative (Bromacylureid) connected to the bromisoval is used. In addition, the bromoacylureides are structurally close to barbituric acid .

effect

Bromacylureides are less hypnotically effective than barbiturates . In the biotransformation of these agents are bromide - ion free, an elimination half-life have twelve days. This leads to an accumulation with prolonged use .

In one study, the hypnotic effect of 300 mg / kg carbromal could be completely reversed by a dose of 5 mg / kg caffeine . Another study looked at the carcinogenic effects of Carbromal; A correlation could be observed between the weeks of low dose administration and the occurrence of adrenal pheochromocytoma , especially in the group with the higher Carbromal dose.

Side effects

The side effects include a. Rashes; Skin reactions caused by active substances are known as dermatitis medicamentosa . Cases of carbromal addiction have also been reported in the literature.

Taking larger doses can lead to side effects typical of bromism .

literature

J. Bäumler, S. Rippstein: About the detection of Carbromal (Adalin ^® ) and its metabolites. In: Archiv der Pharmazie 296 (5) (1963). Pp. 301-306. doi : 10.1002 / ardp.19632960506

Web links

DrugBase

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on Carbromal in the Hazardous Substances Data Bank , accessed on November 18, 2014.
↑ Entry on Carbromal. In: Römpp Online . Georg Thieme Verlag, accessed on November 18, 2014.
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Entry on Carbromal in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ ^a ^b H. J. Roth, H. Fenner: Medicines. Thieme, Stuttgart a. New York, 1988. p. 272.
↑ Hermann Druckrey, Eva Müller, Margarete Stuhlmann: The Influence of the Sedative Effects by Antipyretics and Caffeine. In: Naunyn-Schmiedebergs Archive for Experimental Pathology and Pharmacology. 185, 1937, p. 221, doi : 10.1007 / BF01925281 .
↑ bioassay of Carbromal for possible carcinogenicity. In: National Cancer Institute carcinogenesis technical report series. Volume 173, 1979, pp. 1-135, PMID 12799690 .
↑ P. Borrie: A purpuric drug eruption caused by carbromal. In: British medical journal. Vol. 1, No. 4914, March 1955, pp. 645-646, PMID 13230580 , PMC 2061381 (free full text).
↑ HW Buck, JC Mitchell: Dermatitis Medicamentosa Caused by Diethyl Bromacetyl Carbamide (Carbromal). In: Canadian Medical Association journal. Vol. 89, No. 9, August 1963, p. 419, PMID 20327677 , PMC 1921693 (free full text).
^ M. Steel, JM Johnstone: Addiction to carbromal. In: British medical journal. Volume 2, number 5143, August 1959, p. 118, PMID 13671224 , PMC 1989911 (free full text).
↑ D. Lugassy, L. Nelson: Case files of the medical toxicology fellowship at the New York City poison control: bromism: forgotten, but not gone. In: Journal of medical toxicology: official journal of the American College of Medical Toxicology. Volume 5, Number 3, September 2009, pp. 151-157, PMID 19655290 , PMC 3550397 (free full text).

[ntp-1] ↑ ^a ^b ^c ^d ^e ^f Entry on Carbromal in the Hazardous Substances Data Bank , accessed on November 18, 2014.

[Römpp-2] Entry on Carbromal. In: Römpp Online . Georg Thieme Verlag, accessed on November 18, 2014.

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[ChemIDplus-4] Entry on Carbromal in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[Roth/Fenner-5] H. J. Roth, H. Fenner: Medicines. Thieme, Stuttgart a. New York, 1988. p. 272.

[6] Hermann Druckrey, Eva Müller, Margarete Stuhlmann: The Influence of the Sedative Effects by Antipyretics and Caffeine. In: Naunyn-Schmiedebergs Archive for Experimental Pathology and Pharmacology. 185, 1937, p. 221, doi : 10.1007 / BF01925281 .

[7] bioassay of Carbromal for possible carcinogenicity. In: National Cancer Institute carcinogenesis technical report series. Volume 173, 1979, pp. 1-135, PMID 12799690 .

[8] P. Borrie: A purpuric drug eruption caused by carbromal. In: British medical journal. Vol. 1, No. 4914, March 1955, pp. 645-646, PMID 13230580 , PMC 2061381 (free full text).

[9] HW Buck, JC Mitchell: Dermatitis Medicamentosa Caused by Diethyl Bromacetyl Carbamide (Carbromal). In: Canadian Medical Association journal. Vol. 89, No. 9, August 1963, p. 419, PMID 20327677 , PMC 1921693 (free full text).

[10] M. Steel, JM Johnstone: Addiction to carbromal. In: British medical journal. Volume 2, number 5143, August 1959, p. 118, PMID 13671224 , PMC 1989911 (free full text).

[11] D. Lugassy, L. Nelson: Case files of the medical toxicology fellowship at the New York City poison control: bromism: forgotten, but not gone. In: Journal of medical toxicology: official journal of the American College of Medical Toxicology. Volume 5, Number 3, September 2009, pp. 151-157, PMID 19655290 , PMC 3550397 (free full text).