| 词条 | Pivmecillinam |
| 释义 |
| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 437135864 | IUPAC_name = 2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-[(azepan-1-ylmethylene)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate | image = Pivmecillinam.svg | image2 = Pivmecillinam-3D-balls.png | tradename = | Drugs.com = {{drugs.com|CONS|pivmecillinam}} | pregnancy_AU = | pregnancy_US = B | pregnancy_category = Appears safe in pregnancy[1] | legal_AU = | legal_CA = | legal_UK = | legal_US = | legal_status = Rx-only | routes_of_administration = Oral | bioavailability = Low | protein_bound = 5 to 10% (as mecillinam) | metabolism = Pivmecillinam is hydrolyzed to mecillinam | elimination_half-life = 1 to 3 hours | excretion = Renal and biliary, mostly as mecillinam | CAS_number_Ref = {{cascite|correct|??}} | CAS_number = 32886-97-8 | CAS_supplemental = | ATC_prefix = J01 | ATC_suffix = CA08 | ATC_supplemental = | ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL = 1650818 | PubChem = 36272 | DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank = | ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} | ChemSpiderID = 33356 | UNII_Ref = {{fdacite|correct|FDA}} | UNII = 1WAM1OQ30B | KEGG_Ref = {{keggcite|correct|kegg}} | KEGG = D02889 | C=21 | H=33 | N=3 | O=5 | S=1 | molecular_weight = 439.569 g/mol | smiles = CC1(C(N2C(S1)C(C2=O)N=CN3CCCCCC3)C(=O)OCOC(=O)C(C)(C)C)C }}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.[1] 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.[2][3] It has also been used to treat paratyphoid fever and shigellosis.[4] Activity{{See also|Mecillinam}}Adverse effects{{see also|Beta-lactam antibiotic#Adverse effects|l1=Beta-lactam antibiotic: 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.[2][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] References1. ^{{cite web |url=http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html |title=Amdinocillin (Mecillinam) |vauthors=Pham P, Bartlett JG |date=August 28, 2008 |work=Point-of-Care Information Technology ABX Guide |publisher=Johns Hopkins University |deadurl=yes |archiveurl=https://web.archive.org/web/20090204193527/http://prod.hopkins-abxguide.org/antibiotics/antibacterial/pcn_others/amdinocillin__mecillinam_.html |archivedate=February 4, 2009 |df= }} Retrieved on August 31, 2008. Freely available with registration. {{Beta-lactam antibiotics}}2. ^1 2 {{cite journal |author=Nicolle LE |title=Pivmecillinam in the treatment of urinary tract infections |journal=J Antimicrob Chemother |volume=46 |issue= Suppl A|pages=35–39 |date=August 2000 |pmid=10969050 |doi= 10.1093/jac/46.suppl_1.35|url=http://jac.oxfordjournals.org/cgi/pmidlookup?view=long&pmid=10969050}} 3. ^{{cite journal |author=Graninger W |title=Pivmecillinam—therapy of choice for urinary tract infection |journal=Int J Antimicrob Agents |volume=Suppl 2 |issue= |pages=73–8 |series=22 |date=October 2003 |pmid=14527775 |doi= 10.1016/S0924-8579(03)00235-8|url=http://linkinghub.elsevier.com/retrieve/pii/S0924857903002358}} 4. ^{{cite journal |vauthors=Tanphaichitra D, Srimuang S, Chiaprasittigul P, Menday P, Christensen OE |title=The combination of pivmecillinam and pivampicillin in the treatment of enteric fever |journal=Infection |volume=12 |issue=6 |pages=381–3 |year=1984 |pmid=6569851 |doi= 10.1007/BF01645219|url=}} 5. ^{{cite web |url=http://emc.medicines.org.uk/emc/assets/c/html/DisplayDoc.asp?DocumentID=2566 |title=Selexid Tablets |date=June 5, 2008 |publisher=electronic Medicines Compendium}} Retrieved on August 31, 2008. 6. ^{{cite journal |vauthors=Holme E, Greter J, Jacobson CE, etal |title=Carnitine deficiency induced by pivampicillin and pivmecillinam therapy |journal=Lancet |volume=2 |issue=8661 |pages=469–73 |date=August 1989 |pmid=2570185 |doi= 10.1016/S0140-6736(89)92086-2|url=http://linkinghub.elsevier.com/retrieve/pii/S0140-6736(89)92086-2}} 7. ^1 2 {{cite journal |author=Brass EP |title=Pivalate-generating prodrugs and carnitine homeostasis in man |journal=Pharmacol Rev |volume=54 |issue=4 |pages=589–98 |date=December 2002 |pmid=12429869 |doi= 10.1124/pr.54.4.589|url=http://pharmrev.aspetjournals.org/cgi/pmidlookup?view=long&pmid=12429869}} 8. ^{{cite journal |vauthors=Abrahamsson K, Holme E, Jodal U, Lindstedt S, Nordin I |title=Effect of short-term treatment with pivalic acid containing antibiotics on serum carnitine concentration—a risk irrespective of age |journal=Biochem. Mol. Med. |volume=55 |issue=1 |pages=77–9 |date=June 1995 |pmid=7551831 |doi= 10.1006/bmme.1995.1036|url=http://linkinghub.elsevier.com/retrieve/pii/S1077315085710368}} 9. ^{{cite journal |vauthors=Holme E, Jodal U, Linstedt S, Nordin I |title=Effects of pivalic acid-containing prodrugs on carnitine homeostasis and on response to fasting in children |journal=Scand J Clin Lab Invest |volume=52 |issue=5 |pages=361–72 |date=September 1992 |pmid=1514015 |doi= 10.3109/00365519209088371|url=}} 10. ^{{cite journal |vauthors=Makino Y, Sugiura T, Ito T, Sugiyama N, Koyama N |title=Carnitine-associated encephalopathy caused by long-term treatment with an antibiotic containing pivalic acid |journal=Pediatrics |volume=120 |issue=3 |pages=e739–41 |date=September 2007 |pmid=17724113 |doi=10.1542/peds.2007-0339}} 3 : Penicillins|Azepanes|Prodrugs |
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