Propicillin

Structural formula
	Mixture of diastereomers - the stereocenter in the side chain is marked with an asterisk *
General
Surname	Propicillin
other names	(2 S , 5 R , 6 R ) -3,3-Dimethyl-7-oxo-6 - [(1-oxo-2-phenoxybutyl) amino] -4-thia-1-azabicyclo [3.2.0] -heptane -2-carboxylic acid; 6- (α-phenoxybutyramido) penicillanic acid; [( RS ) -1-phenoxypropyl] penicillin; α-phenoxypropyl penicillin;
Molecular formula	C 18 H 22 N 2 O 5 S; C 18 H 21 KN 2 O 5 S (potassium salt) ;
External identifiers / databases
EC number	208-995-5
ECHA InfoCard	100.008.178
PubChem	92879
ChemSpider	58550
Wikidata	Q7250320
Drug information
ATC code	J01 CE03
Drug class	β-lactam antibiotic
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	378.44 g mol −1
Physical state	firmly
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	5 g kg −1 ( LD 50 , rat , oral ) ; 292 mg kg −1 ( LD 50 , mouse , iv ) ;
	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
Levopropicillin (2 S , 5 S , 6 S ) -3,3-Dimethyl-7-oxo-6 - [( S ) -2-phenoxybutanamido] -4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid 6- (L-α-phenoxybutyramido) penicillanic acid (-) - (1-Phenoxypropyl) penicillin	3736-12-07	C ₁₈ H ₂₂ N ₂ O ₅ S	378.44	PubChem : 172994 UNII : EVM0146RSP
Propicillin potassium (2 S , 5 S , 6 S ) -3,3-Dimethyl-7-oxo-6- (2-phenoxybutanamido) -4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid potassium salt	1245-44-9	C ₁₈ H ₂₁ KN ₂ O ₅ S.	416.53	PubChem : 23682190 UNII: 75RXW2P83Y Wikidata: Q27114769
Levopropicillin Potassium Lilly 38389 P 248	4803-44-5	C ₁₈ H ₂₁ KN ₂ O ₅ S.	416.53	PubChem : 23674237 UNII: 2IY8ZC06FM
Isopropicillin (2 S , 5 S , 6 S ) -3,3-Dimethyl-6- (1-methyl-2-phenoxypropanamido) -7-oxo-4-thia-1-aza-bicyclo [3.2.0] heptane-2 -carboxylic acid Lilly 33332	4780-24-9	C ₁₈ H ₂₂ N ₂ O ₅ S	378.44	PubChem : 3038477 UNII: 05T9139TJW

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.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Römpp-2] Entry on propicillin. In: Römpp Online . Georg Thieme Verlag, accessed on March 26, 2020.

[Merck-3] 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.

[4] 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 .

[Kleemann-5] 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.