Ambazone
This article needs more primary sources. (October 2013) |
Names | |
---|---|
IUPAC name
[4-(2-(Diaminomethylidene)hydrazinyl)phenyl]iminothiourea
| |
Other names
2-[4-[(aminoiminomethyl)hydrazono]-2,5-cyclohexadien-1-ylidene]-Hydrazinecarbothioamide; (4-Oxo-2,5-cyclohexadien-1-ylideneamino)guanidine thiosemicarbazone; 1,4-Benzoquinone amidinohydrazone thiosemicarbazone; Ambazon; Anginon; Benzoquinone guanylhydrazone thiosemicarbazone; Faringosept; Guanothiazon; Inversal; Inversal; Ivertol; N-Guanidino-N'-thioureido-p-benzoquinonediimide; Primal; p-Benzoquinone amidinohydrazone thiosemicarbazone;Faringosept (TN); Ambazone (INN); OAMBAZONE; Ambazonum [INN-Latin]; Ambazona [INN-Spanish]; Ambazone [INN:BAN:DCF]; CCRIS 1926; MLS001240207
| |
Identifiers | |
3D model (
JSmol ) |
|
ChEMBL | |
ChemSpider | |
ECHA InfoCard
|
100.007.922 |
EC Number |
|
KEGG | |
PubChem CID
|
|
UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
Properties | |
C8H11N7S | |
Molar mass | 237.28 g/mol |
Appearance | Dark Brown Powder |
0.2 mg/100 ml water | |
Pharmacology | |
R02AA01 (WHO) | |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
|
Ambazone is an oral antiseptic.
Ambazone was patented in 1957 by Bayer under the trade name Iversal, and briefly used in Germany. It is still used in Russia, countries of the former Soviet Union, Poland[2] and Romania. It has not been approved by the United States Food and Drug Administration (FDA).[citation needed]
Synthesis
Ambazone can be obtained in a two step synthetic method, reacting 1,4-benzoquinone with aminoguanidine and thiosemicarbazide.[3][4]
Obtaining a pharmaceutical grade material is difficult due to high amounts of by-products, synthetic intermediates and decomposition products.[5]
Applications
Bacteriostatic action on hemolytic streptococcus, Streptococcus pneumoniae and viridans streptococci.
Physical properties
Through experimental testing ambazone has shown antiseptic properties, along with anti-tumor properties. Ambazone has the following physical characteristics.
Table 1. Physical properties |
---|
Dark brown |
Odorless |
Tasteless |
Powder |
Melting Point 192–194 °C (decomp.)[6] |
Table 2. Solubility | per 100 ml |
---|---|
Water | 0.2 mg |
Methanol | 0.5 mg |
Chloroform | 0.3 mg |
1-butanol | 6.5 mg |
Ethyl acetate | 17 mg |
Acetone | 50 mg |
Ethanol | 85 mg |
Dimethyl formamide | 1.7 g |
sulfoxide | 2.5 g |
Table 3. Uv-Vis | nm |
---|---|
Water | 403 |
Alcohols | 440-445 |
Ethyl acetate | 453 |
Dimethyl sulfoxide | 467 |
Ambazone is prepared by way of solid based crystallization or grinding.
Mode of action
The mode of action for ambazone has been studied extensively and has been shown to react via different methods. Ambazone shows low
Research
The therapeutic properties of ambazone were studied in lab rats and the therapeutic dose was determined to be 60–125 mg/kg of body weight. As stated above, ambazone possesses anti-septic properties shown by its increased activity against gram-positive cocci. Along with anti-septic properties, ambazone has also shown its ability to fight forms of leukemia in lab rats. When administered orally the results showed prolongation of life expectancy and curing of
References
- ^ Ambazone
- ^ "Faringosept tabletki - działanie, dawkowanie, cena, refundacja | Medycyna Praktyczna".
- ^ Patent DE965723: Verfahren zur Herstellung von ondensationsprodukten. Angemeldet am 31. Januar 1953, veröffentlicht am 19. Juni 1957, Anmelder: Bayer AG, Erfinder: Siegfried Petersen, Gerhard Domagk.
- ISBN 978-1-58890-031-9.
- ^ "Patent WO 2005/028431". Archived from the original on 2014-03-31. Retrieved 2014-03-31.
- ^ Marshall Sittig: Pharmaceutical manufacturing encyclopedia. -- 3rd ed. 2007 p. 215