Propicillin
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Mixture of diastereomers - the stereocenter in the side chain is marked with an asterisk * | |||||||||||||||||||
General | |||||||||||||||||||
Surname | Propicillin | ||||||||||||||||||
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Molar mass | 378.44 g mol −1 | ||||||||||||||||||
Physical state |
firmly |
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As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Propicillin is an organic chemical compound belonging to the group of β-lactam antibiotics , more precisely the semisynthetic β-lactam antibiotics. It is one of the penicillin derivatives and is used in the form of the monopotassium salt . It was patented by Beecham (now GlaxoSmithKline ) in 1961 . Similar to benzylpenicillin (penicillin G), it is effective against some gram-positive bacteria.
properties
The effect of propicillin is less strong than that of penicillin G. Propicillin can be administered orally due to its good absorbability and stability to acids. Opposite β-lactamases however, it is sensitive.
Manufacturing
For the synthesis of propicillin, 6-aminopenicillanic acid is acylated on the primary amino group (NH 2 ) . For the acylation, ( RS ) -2-phenoxybutyric acid is used in combination with isobutyl chloroformate in the presence of triethylamine . Propicillin is formed as a mixture of diastereomers .
Isomers and salts
Name and synonyms | CAS number | Molecular formula | Molar mass [g · mol ‑1 ] |
Database links |
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Levopropicillin
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3736-12-07 | C 18 H 22 N 2 O 5 S | 378.44 |
PubChem : 172994 |
Propicillin potassium
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1245-44-9 | C 18 H 21 KN 2 O 5 S. | 416.53 |
PubChem : 23682190 |
Levopropicillin Potassium
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4803-44-5 | C 18 H 21 KN 2 O 5 S. | 416.53 |
PubChem : 23674237 |
Isopropicillin
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4780-24-9 | C 18 H 22 N 2 O 5 S | 378.44 |
PubChem : 3038477 |
Individual evidence
- ↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
- ↑ a b c d Entry on propicillin. In: Römpp Online . Georg Thieme Verlag, accessed on March 26, 2020.
- ↑ a b Martha Windholz, Susan Budavari, Lorraine Y. Stroumtos, Margaret Noether Done: The Merck Index An Encyclopedia of Chemicals and Drugs Vol. 14, Merck & Co., INC., Whitehouse Station, NJ, USA, 2006, ISBN 978 -0-911910-00-1 , p. 1344.
- ↑ JS van der Hoeven, CW van den Kieboom: Effects of propicillin on mixed continuous cultures of periodontal bacteria. In: Antimicrobial Agents and Chemotherapy , Volume 45, No. 9, 09.1991, pp. 1717-1720, doi: 10.1128 / AAC.35.9.1717 .
- ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009) ISBN 978-3-13-558405-8 , p. 772; also online with biannual additions and updates.