Pivmecillinam Hydrochloride

(BANM, rINNM)
Synonyms: Hidrocloruro de pivmecilinam; Pivmecilinam-hydrochlorid; Pivmecilinamo hidrochloridas; Pivmécillinam, Chlorhydrate de; Pivmecillinám-hidroklorid; Pivmecillinamhydroklorid; Pivmecillinami hydrochloridum; Pivmesillinaamihydrokloridi.
Cyrillic synonym: Пивмециллинама Гидрохлорид.

💊 Chemical information

Chemical formula: C21H33N3O5S,HCl = 476.0.
CAS — 32887-03-9.
ATC — J01C A08.
ATC Vet — QJ01CA08.

Pharmacopoeias.

In Eur. and Jpn.

Ph. Eur. 6.2

(Pivmecillinam Hydrochloride). A white or almost white crystalline powder. Freely soluble in water, in dehydrated alcohol, and in methyl alcohol; slightly soluble in acetone. A 10% solution in water has a pH of 2.8 to 3.8. Store at a temperature of 2° to 8°. Protect from light.

💊 Adverse Effects and Precautions

As for Benzylpenicillin. Pivaloyloxymethyl esters such as pivmecillinam have been associated with the induction of carnitine deficiency (see Pivampicillin, above).

Administration.

Oesophageal injury has been associated rarely with pivmecillinam tablets.1,2 Patients are advised to take them during a meal, while sitting or standing, and with at least half a glass of water.3
1. Committee on Safety of Medicines. Pivmecillinam and oesophageal injury. Current Problems 19 1987. Available at: http://www.mhra.gov.uk/home/idcplg?IdcService=GET_FILE& dDocName=CON2024426&RevisionSelectionMethod= LatestReleased (accessed 22/07/08
2. Mortimer Ö, Wiholm B-E. Oesophageal injury associated with pivmecillinam tablets. Eur J Clin Pharmacol 1989; 37: 605–7
3. Anonymous. CSM warning on pivmecillinam. Pharm J 1987; 238: 443.

Porphyria.

Pivmecillinam has been associated with acute attacks of porphyria and is considered unsafe in porphyric patients.

💊 Interactions

💊 Antimicrobial Action

Pivmecillinam has the antimicrobial activity of mecil-
linam to which it is hydrolysed in vivo.

💊 Pharmacokinetics

Pivmecillinam is well absorbed from the gastrointestinal tract and is rapidly hydrolysed to the active drug mecillinam, pivalic acid, and formaldehyde. The presence of food in the stomach does not appear to have a significant effect on absorption. Peak plasma concentrations of mecillinam of 5 micrograms/mL have been achieved 1 to 2 hours after a 400-mg dose of pivmecillinam. About 45% of a dose may be excreted in the urine as mecillinam, mainly within the first 6 hours.
1. Heikkilä A, et al. The pharmacokinetics of mecillinam and pivmecillinam in pregnant and non-pregnant women. Br J Clin Pharmacol 1992; 33; 629–33.

💊 Uses and Administration

Pivmecillinam is the pivaloyloxymethyl ester of mecillinam, to which it is hydrolysed after oral dosage. It is used in the treatment of urinary-tract infections. Doses of pivmecillinam have often been expressed in a confusing manner since no differentiation has been made between the hydrochloride, used in tablets, and the base, used in suspensions for oral use. Pivmecillinam 1.35 g and pivmecillinam hydrochloride 1.46 g are each equivalent to about 1 g of mecillinam. Pivmecillinam should preferably be taken with food (see also Administration, under Adverse Effects and Precautions, above). In acute uncomplicated cystitis, the initial adult dose is 400 mg orally followed by 200 mg three times daily for 8 doses. In chronic or recurrent bacteriuria, 400 mg may be given 3 or 4 times daily. The dose for children (weighing less than 40 kg) with urinary-tract infections is 20 to 40 mg/kg daily in 3 or 4 divided doses. Pivmecillinam has been given with other beta lactams, particularly pivampicillin, to extend the spectrum of antimicrobial activity to Gram-positive organisms and because of reported synergism against Gramnegative bacteria in vitro. For parenteral use, mecillinam is given.
1. Nicolle LE. Pivmecillinam in the treatment of urinary tract infections. J Antimicrob Chemother 2000; 46 (suppl S1): 35–9.

💊 Preparations

Proprietary Preparations

Austria: Selexid; Belg.: Selexid†; Canad.: Selexid†; Denm.: Selexid; Fin.: Selexid; Fr.: Selexid; Norw.: Selexid; NZ: Selexid; Port.: Selecid†; Swed.: Selexid; UK: Selexid.
Published May 08, 2019.