Pivmecillinam

Structural formula
General
Non-proprietary name	Pivmecillinam
other names	2,2-Dimethylpropanoyloxymethyl (2 S , 5 R , 6 R ) -6 - [(azepan-1-ylmethylene) amino] -3,3-dimethyl-7-oxo-4-thia-1-azabicyclo [3.2.0 ] heptane-2-carboxylate ( IUPAC ) ; Amdinocillin Pivoxil ( USAN ) ;
Molecular formula	C 21 H 33 N 3 O 5 S
External identifiers / databases
EC number	251-276-6
ECHA InfoCard	100,046,600
PubChem	115163
ChemSpider	16735658
DrugBank	DB01605
Wikidata	Q418086
Drug information
ATC code	J01 CA09
Drug class	β-lactam antibiotics
properties
Molar mass	439.57 g · mol -1 (base); 476.04 g · mol -1 (hydrochloride);
Melting point	118.5-119.5 ° C (base); 172-173 ° C (hydrochloride);
pK s value	8.9
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	3020 mg kg −1 ( LD 50 , mouse , oral , hydrochloride) ; 9500 mg kg −1 ( LD 50 , rat , oral , hydrochloride) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Pivmecillinam is a semi-synthetic, antibiotic active substance from the group of β-lactam antibiotics , which was patented by LEO Pharma in 1971 . The compound is used almost exclusively as a hydrochloride .

application

Pivmecillinam has been used for decades, especially in the Scandinavian countries, to treat uncomplicated urinary tract infections . Since 2010, due to the favorable resistance situation, it has also been recommended in the German-language S3 guideline for the treatment of urinary tract infections as the first choice for the treatment of uncomplicated cystitis . The drug has been available on the German market since 2016 and approved for men and women aged 18 and over. It is particularly effective against gram-negative pathogens.

Mode of action

The bacteriostatic effect of Pivmecillinam based (somewhat different from other β-lactam antibiotics) on the blocking of penicillin - binding protein 2 (PBP2). This prevents the formation of a new cell wall in the case of bacteria in the dividing phase.

Trade names

Selexid (A), X-Systo (D), Pivmelam (D)

Web links

Pivmecillinam - a new penicillin derivative for oral use , ZCT issue 2, 1985

Individual evidence

↑ ^a ^b ^c ^d ^e ^f Entry on Pivmecillinam. In: Römpp Online . Georg Thieme Verlag, accessed on July 24, 2019.
↑ ^a ^b ^c Entry on pivotmecillinam in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ 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 Drugs in Japan Vol. 6 , p. 632, 1982.
^ Wagenlehner, Florian ME; Hoyme, Udo; Kaase, Martin; Five piece, Reinhard; Naber, Kurt G .; Schmiemann, Guido: Clinical Guideline Uncomplicated Urinary Tract Infections (2011). In: Dtsch Arztebl Int 2011; 108 (24): 415-423. Retrieved June 20, 2011 .
↑ technical information X Systo. Retrieved June 30, 2017 .
↑ New, HC: Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use . In: Pharmacotherapy . 1985 Jan-Feb; 5 (1): 1-10. PMID 3885172 .

[rol-1] ↑ ^a ^b ^c ^d ^e ^f Entry on Pivmecillinam. In: Römpp Online . Georg Thieme Verlag, accessed on July 24, 2019.

[chemid-2] Entry on pivotmecillinam in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[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.

[dij-4] Drugs in Japan Vol. 6 , p. 632, 1982.

[5] Wagenlehner, Florian ME; Hoyme, Udo; Kaase, Martin; Five piece, Reinhard; Naber, Kurt G .; Schmiemann, Guido: Clinical Guideline Uncomplicated Urinary Tract Infections (2011). In: Dtsch Arztebl Int 2011; 108 (24): 415-423. Retrieved June 20, 2011 .

[6] technical information X Systo. Retrieved June 30, 2017 .

[7] New, HC: Amdinocillin: a novel penicillin. Antibacterial activity, pharmacology and clinical use . In: Pharmacotherapy . 1985 Jan-Feb; 5 (1): 1-10. PMID 3885172 .