Bacampicillin

Structural formula
	Mixture of diastereomers - the stereocenter in the side chain is marked with an asterisk *
General
Surname	Bacampicillin
other names	(2 S , 5 R , 6 R ) -6 - {[(2 R ) -aminophenylacetyl] amino} -3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0] heptane-2 -carboxylic acid 1 - [(ethoxycarbonyl) oxy] ethyl ester; 6 - [( R ) -2-Amino-2-phenylacetamido] penicillanic acid [1- (ethoxycarbonyloxy) ethyl] ester; 1'-ethoxycarbonyloxyethyl 6- ( D -α-aminophenylacetamido) penicillanate; (2 S , 5 R , 6 R ) -6 - [( R ) - (2-Amino-2-phenylacetamido)] -3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0 ] heptane-2-carboxylic acid ester with ( RS ) -ethyl-1-hydroxyethyl carbonate;
Molecular formula	C 21 H 27 N 3 O 7 S
External identifiers / databases
PubChem	441397
ChemSpider	390135
DrugBank	DB01602
Wikidata	Q2878140
Drug information
ATC code	J01 CA06
Drug class	β-lactam antibiotic
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	465.52 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	8529 mg kg −1 ( LD 50 , mouse , oral ) ; 16 mg kg −1 ( LD 50 , mouse , ip ) ; 9475 mg kg −1 ( LD 50 , mouse , sc ) ; 184 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 .

Bacampicillin is a drug from the group of broad-spectrum penicillins , more precisely the aminopenicillins . It was first patented by Astra in 1972 . The antibiotic is used in the form of the hydrochloride . It works against both aerobic and anaerobic bacteria, which is why it is used, for example, to treat inflammatory diseases of the pelvic organs.

Manufacturing

Bacampicillin, the 1- (ethoxycarbonyloxy) ethyl ester of ampicillin, is made from the sodium salt of azidocillin . This also requires α-chlorodiethyl carbonate, hydrogen and a palladium catalyst.

application

Bacampicillin can be given orally (such as tablets). The drug is considered to be well tolerated. It found, inter alia use in acute otitis media (otitis media). Bacampicillin is the absorption ester of ampicillin and, after almost complete absorption, quickly hydrolyzes into the effective form. The resistance of bacteria to ampicillin, which is often observed, is based on an ampicillin resistance gene which is localized on a plasmid .

Individual evidence

^ A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances (Online) . Thieme, Stuttgart, test date April 6, 2020.
↑ 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 ^e entry on bacampicillin. In: Römpp Online . Georg Thieme Verlag, accessed on April 2, 2020.
^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006, ISBN 978-0-911910-00-1 , pp. 158.
↑ K. Grafford, E. Guttorm, G. Kristensen, T. Philipsen, A. Selnes: Bacampicillin in the treatment of pelvic inflammatory disease: A study of two dosage regimens . In: Infection, 1980, Vol. 8, No. 6, pp. 290-292, doi: 10.10077 / BF01640921 .
↑ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009) ISBN 978-3-13-558405-8 , pp. 69-70; also online with biannual additions and updates.
^ S. Virtanen, E.-A. Lahikainen: Ampicillin concentrations in middle ear effusions in acute otitis media after administration of bacampicillin . In: Infection, 1979, Vol. 7, pp. S472-S474, doi: 10.1007 / BF01659775 .
↑ A. Heimdahl, C. Nord, K. Weilander: Effect of bacampicillin on human mouth, throat and colon flora . In: Infection, 1979, Vol. 7, pp. 446-451, doi: 10.1007 / BF01659768 .
↑ E. Mutschler : Medicinal Effects , 7th Edition, WVG Stuttgart, 1996. P. 667.
↑ Medical history: first ampicillin resistance emerged in cattle breeding , aerzteblatt.de, December 1, 2017.

[Pharmaceutical_Substances-1] A. Kleemann , J. Engel, B. Kutscher, D. Reichert: Pharmaceutical Substances (Online) . Thieme, Stuttgart, test date April 6, 2020.

[NV-2] 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-3] ↑ ^a ^b ^c ^d ^e entry on bacampicillin. In: Römpp Online . Georg Thieme Verlag, accessed on April 2, 2020.

[MERCK_Index-4] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006, ISBN 978-0-911910-00-1 , pp. 158.

[5] K. Grafford, E. Guttorm, G. Kristensen, T. Philipsen, A. Selnes: Bacampicillin in the treatment of pelvic inflammatory disease: A study of two dosage regimens . In: Infection, 1980, Vol. 8, No. 6, pp. 290-292, doi: 10.10077 / BF01640921 .

[Kleemann-6] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009) ISBN 978-3-13-558405-8 , pp. 69-70; also online with biannual additions and updates.

[7] S. Virtanen, E.-A. Lahikainen: Ampicillin concentrations in middle ear effusions in acute otitis media after administration of bacampicillin . In: Infection, 1979, Vol. 7, pp. S472-S474, doi: 10.1007 / BF01659775 .

[8] A. Heimdahl, C. Nord, K. Weilander: Effect of bacampicillin on human mouth, throat and colon flora . In: Infection, 1979, Vol. 7, pp. 446-451, doi: 10.1007 / BF01659768 .

[9] E. Mutschler : Medicinal Effects , 7th Edition, WVG Stuttgart, 1996. P. 667.

[10] Medical history: first ampicillin resistance emerged in cattle breeding , aerzteblatt.de, December 1, 2017.