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PIVMECILLINAM

CAS No.:
32886-97-8
Catalog Number:
AG00C0EG
Molecular Formula:
C21H33N3O5S
Molecular Weight:
439.5688
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Product Description
Catalog Number:
AG00C0EG
Chemical Name:
PIVMECILLINAM
CAS Number:
32886-97-8
Molecular Formula:
C21H33N3O5S
Molecular Weight:
439.5688
MDL Number:
MFCD01694516
IUPAC Name:
2,2-dimethylpropanoyloxymethyl (2S,5R,6R)-6-(azepan-1-ylmethylideneamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
InChI:
InChI=1S/C21H33N3O5S/c1-20(2,3)19(27)29-13-28-18(26)15-21(4,5)30-17-14(16(25)24(15)17)22-12-23-10-8-6-7-9-11-23/h12,14-15,17H,6-11,13H2,1-5H3/t14-,15+,17-/m1/s1
InChI Key:
NPGNOVNWUSPMDP-HLLBOEOZSA-N
SMILES:
O=C([C@@H]1N2C(=O)[C@H]([C@H]2SC1(C)C)/N=C/N1CCCCCC1)OCOC(=O)C(C)(C)C
EC Number:
251-276-6
UNII:
1WAM1OQ30B
Properties
Complexity:
710  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
439.214g/mol
Formal Charge:
0
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
439.571g/mol
Monoisotopic Mass:
439.214g/mol
Rotatable Bond Count:
8  
Topological Polar Surface Area:
114A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
3.1  
Literature
Title Journal
Maternal use of cystitis medication and childhood epilepsy in a danish population-based cohort. Paediatric and perinatal epidemiology 20121101
Efficacy of pivmecillinam for treatment of lower urinary tract infection caused by extended-spectrum β-lactamase-producing Escherichia coli and Klebsiella pneumoniae. Microbial drug resistance (Larchmont, N.Y.) 20120401
Maternal use of antibiotics and the risk of orofacial clefts: a nationwide cohort study. Pharmacoepidemiology and drug safety 20120301
French results of the ARESC study: clinical aspects and epidemiology of antimicrobial resistance in female patients with cystitis. Implications for empiric therapy. Medecine et maladies infectieuses 20120201
Maternal use of antibiotics, hospitalisation for infection during pregnancy, and risk of childhood epilepsy: a population-based cohort study. PloS one 20120101
Antimicrobials in urogenital infections. International journal of antimicrobial agents 20111201
Ciprofloxacin safety in paediatrics: a systematic review. Archives of disease in childhood 20110901
[Urinary tract infections]. Der Internist 20110901
A multi-center randomized trial to assess the efficacy of gatifloxacin versus ciprofloxacin for the treatment of shigellosis in Vietnamese children. PLoS neglected tropical diseases 20110801
Uncomplicated urinary tract infections. Deutsches Arzteblatt international 20110601
[Clinical efficacy of tebipenem pivoxil treatment in children with pneumonia, who had no relief despite having administered oral beta-lactam antibiotics]. The Japanese journal of antibiotics 20110601
Bacterial characteristics of importance for recurrent urinary tract infections caused by Escherichia coli. Danish medical bulletin 20110401
[National S3 guideline on uncomplicated urinary tract infection: recommendations for treatment and management of uncomplicated community-acquired bacterial urinary tract infections in adult patients]. Der Urologe. Ausg. A 20110201
Inequality in quality? Regional and educational differences in treatment with fluoroquinolone in urinary tract infection of 236,376 Swedish patients. BMJ quality & safety 20110101
[Uncomplicated urinary tract infection and treatment]. Aktuelle Urologie 20110101
Use of prescribed drugs among primiparous women: an 11-year population-based study in Denmark. Clinical epidemiology 20110101
Urinary tract infections in women: etiology and treatment options. International journal of general medicine 20110101
Characteristics of Escherichia coli causing persistence or relapse of urinary tract infections: phylogenetic groups, virulence factors and biofilm formation. Virulence 20110101
Prevention of urinary tract infections in nursing homes: lack of evidence-based prescription? BMC geriatrics 20110101
Antibiotic resistance in primary care in Austria - a systematic review of scientific and grey literature. BMC infectious diseases 20110101
[Update on current care guidelines: urinary tract infections]. Duodecim; laaketieteellinen aikakauskirja 20110101
Rising prevalence of antimicrobial resistance in urinary tract infections during pregnancy: necessity for exploring newer treatment options. Journal of laboratory physicians 20110101
Shigella spp. antimicrobial drug resistance, Papua New Guinea, 2000-2009. Emerging infectious diseases 20101101
How are antibacterials used in nursing homes? Results from a point-prevalence prescription study in 44 Norwegian nursing homes. Pharmacoepidemiology and drug safety 20101001
Antibiotics for the treatment of dysentery in children. International journal of epidemiology 20100401
Molecular characterisation of trimethoprim resistance in Escherichia coli and Klebsiella pneumoniae during a two year intervention on trimethoprim use. PloS one 20100101
Valproate-induced hyperammonemic encephalopathy enhanced by topiramate and phenobarbitone: a case report and an update. Annals of Indian Academy of Neurology 20100101
Different antibiotic regimens for treating asymptomatic bacteriuria in pregnancy. The Cochrane database of systematic reviews 20100101
Existing data sources for clinical epidemiology: Aarhus University Prescription Database. Clinical epidemiology 20100101
[Oral antibiotic treatment of urinary tract infections in children]. Tidsskrift for den Norske laegeforening : tidsskrift for praktisk medicin, ny raekke 20090625
Pivmecillinam versus sulfamethizole for short-term treatment of uncomplicated acute cystitis in general practice: a randomized controlled trial. Scandinavian journal of primary health care 20090101
Effects of treatment with antimicrobial agents on the human colonic microflora. Therapeutics and clinical risk management 20081201
Zinc supplementation in the management of shigellosis in malnourished children in Bangladesh. European journal of clinical nutrition 20080701
Risk of miscarriage for pregnant users of pivmecillinam: a population-based case-control study. APMIS : acta pathologica, microbiologica, et immunologica Scandinavica 20080401
Diagnosis-prescribing surveys in 2000, 2002 and 2005 in Swedish general practice: consultations, diagnosis, diagnostics and treatment choices. Scandinavian journal of infectious diseases 20080101
Usefulness and problems of the urinary tract infection criteria for evaluating drug efficacy for complicated urinary tract infections. Journal of infection and chemotherapy : official journal of the Japan Society of Chemotherapy 20071001
Increasing spectrum in antimicrobial resistance of Shigella isolates in Bangladesh: resistance to azithromycin and ceftriaxone and decreased susceptibility to ciprofloxacin. Journal of health, population, and nutrition 20070601
Antimicrobial resistance among enterobacteriaceae causing uncomplicated urinary tract infections in Mauritius: consequences of past misuse of antibiotics. Journal of chemotherapy (Florence, Italy) 20070401
Clinical and bacteriological outcome of different doses and duration of pivmecillinam compared with placebo therapy of uncomplicated lower urinary tract infection in women: the LUTIW project. Scandinavian journal of primary health care 20070101
Successful treatment of ctx-m ESBL producing Escherichia coli relapsing pyelonephritis with long term pivmecillinam. Scandinavian journal of infectious diseases 20070101
Hypocarnitinaemia induced by sodium pivalate in the rat is associated with left ventricular dysfunction and impaired energy metabolism. Drugs in R&D 20060101
New media for the semiselective isolation and enumeration of Xanthomonas campestris pv. mangiferaeindicae, the causal agent of mango bacterial black spot. Journal of applied microbiology 20050101
Science review: carnitine in the treatment of valproic acid-induced toxicity - what is the evidence? Critical care (London, England) 20050101
Hyperammonemic encephalopathy induced by a combination of valproate and pivmecillinam. Acta neurologica Scandinavica 20040401
Antimicrobial resistance in Escherichia coli in urine samples from children and adults: a 12 year analysis. Acta paediatrica (Oslo, Norway : 1992) 20040401
Urinary concentrations and urine ex-vivo effect of mecillinam and sulphamethizole. Clinical microbiology and infection : the official publication of the European Society of Clinical Microbiology and Infectious Diseases 20040101
Management of urinary tract infections in primary care: a repeated 1-week diagnosis-prescribing study in five counties in Sweden in 2000 and 2002. Scandinavian journal of infectious diseases 20040101
The natural course of uncomplicated lower urinary tract infection in women illustrated by a randomized placebo controlled study. Scandinavian journal of infectious diseases 20040101
Pivmecillinam and adverse birth and neonatal outcomes: a population-based cohort study. Scandinavian journal of infectious diseases 20040101
[Is repeat antibiotic prescription following treatment with sulfonamide or pivmecillinam a valid method for assessment of therapeutic failure in urinary infection?]. Ugeskrift for laeger 20031103
[Sulfamethizole versus pivmecillinam in urinary tract infections]. Ugeskrift for laeger 20031103
Pivmecillinam--therapy of choice for lower urinary tract infection. International journal of antimicrobial agents 20031001
[Prescriptions of a new antibiotic following treatment with sulfamethizole or pivmecillinam]. Ugeskrift for laeger 20030922
Empirical treatment of acute cystitis in women. International journal of antimicrobial agents 20030701
Best pharmacological practice: urinary tract infections. Expert opinion on pharmacotherapy 20030501
Symptomatic vaginal candidiasis after pivmecillinam and norfloxacin treatment of acute uncomplicated lower urinary tract infection. International journal of antimicrobial agents 20021001
Treatment failures after antibiotic therapy of uncomplicated urinary tract infections. A prescription database study. Scandinavian journal of primary health care 20020601
[Urinary antimicrobial prophylaxis]. Archives de pediatrie : organe officiel de la Societe francaise de pediatrie 20020501
[Is new prescription of antibiotics after treatment with sulfonamide or pivmecillinam a validated method for assessment of treatment failure?]. Ugeskrift for laeger 20020211
Three days of pivmecillinam or norfloxacin for treatment of acute uncomplicated urinary infection in women. Scandinavian journal of infectious diseases 20020101
[Repeat antibiotic prescriptions following treatment with sulfonamide or pivmecillinam. A survey of prescriptions among women aged 15-50 years in the county of Nordjylland]. Ugeskrift for laeger 20011231
Hyperimmune bovine colostrum in the treatment of shigellosis in children: a double-blind, randomized, controlled trial. Acta paediatrica (Oslo, Norway : 1992) 20011201
Effect of perorally administered pivmecillinam on the normal oropharyngeal, intestinal and skin microflora. Journal of chemotherapy (Florence, Italy) 20010601
Use of antibiotics to treat bacteriuria of pregnancy in the Nordic countries. Which antibiotics are appropriate to treat bacteriuria of pregnancy? International journal of antimicrobial agents 20010401
Birth outcome and risk of neonatal hypoglycaemia following in utero exposure to pivmecillinam: a population-based cohort study with 414 exposed pregnancies. Scandinavian journal of infectious diseases 20010101
Effect of beta-lactam prodrugs on human intestinal microflora. Scandinavian journal of infectious diseases. Supplementum 19860101
Pivmecillinam (selexid). Drug and therapeutics bulletin 19781222
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