Pivmecillinam

Jump to: navigation, search
Pivmecillinam
Pivmecilinam Wiki Str.png
Clinical data
AHFS/Drugs.comMicromedex Detailed Consumer Information
Pregnancy
category
  • US: B (No risk in non-human studies)

  • Appears safe in pregnancy[1]
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityLow
Protein binding5 to 10% (as mecillinam)
MetabolismPivmecillinam is hydrolyzed to mecillinam
Elimination half-life1 to 3 hours
ExcretionRenal and biliary, mostly as mecillinam
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC21H33N3O5S
Molar mass439.569 g/mol
3D model (JSmol)
 ☒N☑Y (what is this?)  (verify)

WikiDoc Resources for Pivmecillinam

Articles

Most recent articles on Pivmecillinam

Most cited articles on Pivmecillinam

Review articles on Pivmecillinam

Articles on Pivmecillinam in N Eng J Med, Lancet, BMJ

Media

Powerpoint slides on Pivmecillinam

Images of Pivmecillinam

Photos of Pivmecillinam

Podcasts & MP3s on Pivmecillinam

Videos on Pivmecillinam

Evidence Based Medicine

Cochrane Collaboration on Pivmecillinam

Bandolier on Pivmecillinam

TRIP on Pivmecillinam

Clinical Trials

Ongoing Trials on Pivmecillinam at Clinical Trials.gov

Trial results on Pivmecillinam

Clinical Trials on Pivmecillinam at Google

Guidelines / Policies / Govt

US National Guidelines Clearinghouse on Pivmecillinam

NICE Guidance on Pivmecillinam

NHS PRODIGY Guidance

FDA on Pivmecillinam

CDC on Pivmecillinam

Books

Books on Pivmecillinam

News

Pivmecillinam in the news

Be alerted to news on Pivmecillinam

News trends on Pivmecillinam

Commentary

Blogs on Pivmecillinam

Definitions

Definitions of Pivmecillinam

Patient Resources / Community

Patient resources on Pivmecillinam

Discussion groups on Pivmecillinam

Patient Handouts on Pivmecillinam

Directions to Hospitals Treating Pivmecillinam

Risk calculators and risk factors for Pivmecillinam

Healthcare Provider Resources

Symptoms of Pivmecillinam

Causes & Risk Factors for Pivmecillinam

Diagnostic studies for Pivmecillinam

Treatment of Pivmecillinam

Continuing Medical Education (CME)

CME Programs on Pivmecillinam

International

Pivmecillinam en Espanol

Pivmecillinam en Francais

Business

Pivmecillinam in the Marketplace

Patents on Pivmecillinam

Experimental / Informatics

List of terms related to Pivmecillinam

Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Pivmecillinam (INN) or amdinocillin pivoxil (USAN, trade names Selexid, Penomax and Coactabs) is an orally active prodrug of mecillinam, an extended-spectrum penicillin antibiotic. Pivmecillinam is the pivaloyloxymethyl ester of mecillinam. Neither drug is available in the United States.[2]

Pivmecillinam is only considered to be active against Gram-negative bacteria, and is used primarily in the treatment of lower urinary tract infections. In the Nordic countries, it has been widely used in that indication since the 1970s. It has been proposed as the first-line drug of choice for empirical treatment of acute cystitis.[1][3] It has also been used to treat paratyphoid fever.[4]

Adverse effects

The adverse effect profile of pivmecillinam is similar to that of other penicillins. The most common side effects of mecillinam use are rash and gastrointestinal upset, including nausea and vomiting.[1][5]

Prodrugs that release pivalic acid when broken down by the body — such as pivmecillinam, pivampicillin and cefditoren pivoxil — have long been known to deplete levels of carnitine.[6][7] This is not due to the drug itself, but to pivalate, which is mostly removed from the body by forming a conjugate with carnitine. Although short-term use of these drugs can cause a marked decrease in blood levels of carnitine,[8] it is unlikely to be of clinical significance;[7] long-term use, however, appears problematic and is not recommended.[7][9][10]

References

  1. 1.0 1.1 1.2 Nicolle LE (August 2000). "Pivmecillinam in the treatment of urinary tract infections". J Antimicrob Chemother. 46 (Suppl A): 35–39. doi:10.1093/jac/46.suppl_1.35. PMID 10969050.
  2. Pham P, Bartlett JG (August 28, 2008). "Amdinocillin (Mecillinam)". Point-of-Care Information Technology ABX Guide. Johns Hopkins University. Retrieved on August 31, 2008. Freely available with registration.
  3. Graninger W (October 2003). "Pivmecillinam—therapy of choice for urinary tract infection". Int J Antimicrob Agents. 22. Suppl 2: 73–8. doi:10.1016/S0924-8579(03)00235-8. PMID 14527775.
  4. Tanphaichitra D, Srimuang S, Chiaprasittigul P, Menday P, Christensen OE (1984). "The combination of pivmecillinam and pivampicillin in the treatment of enteric fever". Infection. 12 (6): 381–3. doi:10.1007/BF01645219. PMID 6569851.
  5. "Selexid Tablets". electronic Medicines Compendium. June 5, 2008. Retrieved on August 31, 2008.
  6. Holme E, Greter J, Jacobson CE; et al. (August 1989). "Carnitine deficiency induced by pivampicillin and pivmecillinam therapy". Lancet. 2 (8661): 469–73. doi:10.1016/S0140-6736(89)92086-2. PMID 2570185.
  7. 7.0 7.1 7.2 Brass EP (December 2002). "Pivalate-generating prodrugs and carnitine homeostasis in man". Pharmacol Rev. 54 (4): 589–98. doi:10.1124/pr.54.4.589. PMID 12429869.
  8. Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I (June 1995). "Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration—a risk irrespective of age". Biochem. Mol. Med. 55 (1): 77–9. doi:10.1006/bmme.1995.1036. PMID 7551831.
  9. Holme E, Jodal U, Linstedt S, Nordin I (September 1992). "Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children". Scand J Clin Lab Invest. 52 (5): 361–72. doi:10.3109/00365519209088371. PMID 1514015.
  10. Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N (September 2007). "Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid". Pediatrics. 120 (3): e739–41. doi:10.1542/peds.2007-0339. PMID 17724113.
Pivmecilinam Active.png

Template:Beta-lactam antibiotics


Linked-in.jpg