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7177-50-6,MFCD00056863
Catalog No.:AA0062DB

7177-50-6 | Nafcillin sodium monohydrate

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1g
≥95%
in stock  
$98.00   $68.00
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5g
≥95%
in stock  
$218.00   $152.00
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10g
≥95%
in stock  
$383.00   $268.00
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25g
≥95%
in stock  
$838.00   $586.00
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  • Technical Information
  • Properties
  • Literature
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA0062DB
Chemical Name:
Nafcillin sodium monohydrate
CAS Number:
7177-50-6
Molecular Formula:
C20H23N2NaO6S
Molecular Weight:
442.4612
MDL Number:
MFCD00056863
SMILES:
CCOc1ccc2c(c1ON[C@@H]1C(=O)N3[C@@H]1SC([C@@H]3C(=O)O[Na])(C)C)cccc2.O
Properties
Properties
 
BP:
714.1°C at 760 mmHg  
Form:
Solid  
MP:
>170°C (dec.)  
Solubility:
H2O: soluble50mg/mL  
Storage:
Inert atmosphere;2-8℃;  

Computed Properties
 
Complexity:
705  
Covalently-Bonded Unit Count:
3  
Defined Atom Stereocenter Count:
3  
Heavy Atom Count:
31  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
2  
Rotatable Bond Count:
5  

Literature

Title: Adverse Events Lead to Drug Discontinuation More Commonly among Patients Who Receive Nafcillin than among Those Who Receive Oxacillin.

Journal: Antimicrobial agents and chemotherapy 20160501

Title: Comparative evaluation of the tolerability of cefazolin and nafcillin for treatment of methicillin-susceptible Staphylococcus aureus infections in the outpatient setting.

Journal: Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20140801

Title: Percutaneous transluminal angioplasty in a patient with vasospasm due to staphylococcal meningitis.

Journal: Journal of neurosurgery 20120701

Title: Possible case of nafcillin-induced acute interstitial nephritis.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20120615

Title: Septic pulmonary embolism in a patient with defibrillator lead endocarditis.

Journal: American journal of respiratory and critical care medicine 20120115

Title: Nafcillin-induced bullous skin eruption with granulocytopenia in a patient with end-stage renal disease.

Journal: Internal medicine (Tokyo, Japan) 20120101

Title: Synergy between vancomycin and nafcillin against Staphylococcus aureus in an in vitro pharmacokinetic/pharmacodynamic model.

Journal: PloS one 20120101

Title: Farnesol decreases biofilms of Staphylococcus epidermidis and exhibits synergy with nafcillin and vancomycin.

Journal: Pediatric research 20111201

Title: Comparative effectiveness of nafcillin or cefazolin versus vancomycin in methicillin-susceptible Staphylococcus aureus bacteremia.

Journal: BMC infectious diseases 20110101

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: Cerebrospinal fluid penetration of high-dose daptomycin in suspected Staphylococcus aureus meningitis.

Journal: The Annals of pharmacotherapy 20101101

Title: Poly(2-hydroxyethyl methacrylate-co-dodecyl methacrylate-co-acrylic acid): synthesis, physico-chemical characterisation and nafcillin carrier.

Journal: Journal of materials science. Materials in medicine 20101001

Title: Thromboembolic events of mitral valve endocarditis.

Journal: Cardiology journal 20100101

Title: Lysostaphin eradicates established Staphylococcus aureus biofilms in jugular vein catheterized mice.

Journal: The Journal of antimicrobial chemotherapy 20090701

Title: Subinhibitory fluoroquinolone exposure selects for reduced beta-lactam susceptibility in methicillin-resistant Staphylococcus aureus and alterations in the SOS-mediated response.

Journal: Research in microbiology 20090401

Title: Case report: diabetic myonecrosis of the neck complicated by infection in an islet transplanted patient.

Journal: Journal of diabetes and its complications 20090101

Title: Epidemiology of community-onset Staphylococcus aureus infections in pediatric patients: an experience at a Children's Hospital in central Illinois.

Journal: BMC infectious diseases 20090101

Title: Nafcillin-loaded PLGA nanoparticles for treatment of osteomyelitis.

Journal: Biomedical materials (Bristol, England) 20080901

Title: Variability in vancomycin use in newborn intensive care units determined from data in an electronic medical record.

Journal: Infection control and hospital epidemiology 20080701

Title: Paraspinal abscess complicated by endocarditis following a facet joint injection.

Journal: European journal of pain (London, England) 20080401

Title: Predominant contribution of rat organic anion transporting polypeptide-2 (Oatp2) to hepatic uptake of beta-lactam antibiotics.

Journal: Pharmaceutical research 20080301

Title: A prickly situation.

Journal: The American journal of medicine 20080301

Title: Role of surface adsorption and porosity features in the molecular recognition ability of imprinted sol-gels.

Journal: Biosensors & bioelectronics 20080227

Title: Identification and species similarity of OATP transporters responsible for hepatic uptake of beta-lactam antibiotics.

Journal: Drug metabolism and pharmacokinetics 20080101

Title: Septicemic arthritis with antibiotic resistance: a case study.

Journal: Clinical laboratory science : journal of the American Society for Medical Technology 20080101

Title: Interaction between warfarin and nafcillin: case report and review of the literature.

Journal: Pharmacotherapy 20071001

Title: Four cases of nafcillin-associated acute interstitial nephritis in one institution.

Journal: Nature clinical practice. Nephrology 20070801

Title: Molecularly imprinted polymers as antibody mimics in automated on-line fluorescent competitive assays.

Journal: Analytical chemistry 20070701

Title: Molecularly imprinted sol-gels for nafcillin determination in milk-based products.

Journal: Journal of agricultural and food chemistry 20070207

Title: Impact of antibiotics on expression of virulence-associated exotoxin genes in methicillin-sensitive and methicillin-resistant Staphylococcus aureus.

Journal: The Journal of infectious diseases 20070115

Title: Sure signs.

Journal: The American journal of medicine 20070101

Title: A passage to injury.

Journal: The American journal of medicine 20060601

Title: Invasive nontypeable Haemophilus influenzae infection in an adult with laryngeal cancer.

Journal: Diagnostic microbiology and infectious disease 20060501

Title: Microsphere-based protease assays and screening application for lethal factor and factor Xa.

Journal: Cytometry. Part A : the journal of the International Society for Analytical Cytology 20060501

Title: Molecular imprinted ormosils for nafcillin recognition by room temperature phosphorescence optosensing.

Journal: Biosensors & bioelectronics 20060315

Title: Pharmaceutical liquid crystals: the relevance of partially ordered systems.

Journal: Journal of pharmaceutical sciences 20050901

Title: Influence of temperature and drug concentration on nafcillin precipitation.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 20050701

Title: An unusual Gram stain finding.

Journal: Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20050601

Title: Evaluation of the efficacy and safety of outpatient parenteral antimicrobial therapy for infections with methicillin-sensitive Staphylococcus aureus.

Journal: Southern medical journal 20050601

Title: Dermatoses of pregnancy update.

Journal: Journal of the American Academy of Dermatology 20050501

Title: Chronic Staphylococcus aureus infection leading to pyogenic granuloma and preventing socket re-epithelialization after orbital exenteration.

Journal: Ophthalmic plastic and reconstructive surgery 20050501

Title: Community-acquired methicillin-resistant Staphylococcus aureus prostatic abscess.

Journal: Urology 20041001

Title: Pharmacodynamics of telavancin (TD-6424), a novel bactericidal agent, against gram-positive bacteria.

Journal: Antimicrobial agents and chemotherapy 20040801

Title: Drug-induced lupus erythematosus secondary to nafcillin: the first reported case.

Journal: Rheumatology international 20040701

Title: Assessment of molecularly imprinted sol-gel materials for selective room temperature phosphorescence recognition of nafcillin.

Journal: Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20040505

Title: Continuous antibiotic prophylaxis and cerebral spinal fluid infection in patients with intracranial pressure monitors.

Journal: Neurocritical care 20040101

Title: 28-year-old man with recurrent fever.

Journal: Mayo Clinic proceedings 20030701

Title: Evidence of an interaction between nifedipine and nafcillin in humans.

Journal: British journal of clinical pharmacology 20030601

Title: Case study: submandibular mass in a premature infant.

Journal: Seminars in pediatric infectious diseases 20030401

Title: Metastatic intracranial abscesses of bronchopulmonary origin.

Journal: The Pediatric infectious disease journal 20030301

Title: Effect of disruption of Staphylococcus aureus PBP4 gene on resistance to beta-lactam antibiotics.

Journal: Microbial drug resistance (Larchmont, N.Y.) 20030101

Title: Haemophilus aphrophilus endocarditis after tongue piercing.

Journal: Emerging infectious diseases 20020801

Title: Delayed intracranial migration of cervical sublaminar and interspinous wires and subsequent cerebellar abscess. Case report.

Journal: Journal of neurosurgery 20020701

Title: Higher occurrence of hepatotoxicity and rash in patients treated with oxacillin, compared with those treated with nafcillin and other commonly used antimicrobials.

Journal: Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20020101

Title: Adsorption of an amphiphilic penicillin onto human serum albumin: characterisation of the complex.

Journal: Biophysical chemistry 20010830

Title: Comparative evaluation of oral levofloxacin and parenteral nafcillin in the treatment of experimental methicillin-susceptible Staphylococcus aureus osteomyelitis in rabbits.

Journal: The Journal of antimicrobial chemotherapy 20010801

Title: Isolated septic arthritis caused by penicillin-resistant Streptococcus pneumoniae.

Journal: Southern medical journal 20010401

Title: Parinaud's oculoglandular syndrome attributable to an encounter with a wild rabbit.

Journal: American journal of ophthalmology 20010201

Title: Possible role of cellular immunity: a case of cellulitis.

Journal: Clinical infectious diseases : an official publication of the Infectious Diseases Society of America 20010101

Title: Adverse drug reactions in home care patients receiving nafcillin or oxacillin.

Journal: American journal of health-system pharmacy : AJHP : official journal of the American Society of Health-System Pharmacists 19970515

Title: Case-control study of the association between intraoperative administration of nafcillin and acute postoperative development of azotemia.

Journal: Journal of the American Veterinary Medical Association 19960401

Title: Nafcillin-associated hepatotoxicity. Report of a case and review of the literature.

Journal: Digestive diseases and sciences 19960101

Title: Suspected nafcillin-induced interstitial nephritis.

Journal: The Annals of pharmacotherapy 19930201

Title: Hepatic and renal dysfunction following nafcillin administration.

Journal: The Annals of pharmacotherapy 19920101

Title: Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase.

Journal: The Biochemical journal 19920101

Title: Venous irritation from the use of a nafcillin sodium 2 g i.v. minibag product.

Journal: American journal of hospital pharmacy 19901201

Title: Ciprofloxacin therapy of experimental endocarditis caused by methicillin-susceptible or methicillin-resistant Staphylococcus aureus.

Journal: Antimicrobial agents and chemotherapy 19880501

Title: Intraventricular nafcillin-induced seizures in a neonate.

Journal: Pediatric neurology 19880101

Title: Bacteriological efficacy of nafcillin and vancomycin alone or combined with rifampicin or amikacin in experimental meningitis due to methicillin-susceptible or -resistant Staphylococcus aureus.

Journal: The Japanese journal of antibiotics 19850801

Title: Acute interstitial nephritis associated with mezlocillin, nafcillin, and gentamicin treatment for Pseudomonas infection.

Journal: Archives of internal medicine 19850701

Title: Cefotaxime compared with nafcillin plus tobramycin for serious bacterial infections. A randomized, double-blind trial.

Journal: Annals of internal medicine 19841001

Title: Hepatic dysfunction following nafcillin and cephalothin therapy in a patient with a history of oxacillin hepatitis.

Journal: Clinical pharmacy 19830101

Title: Community-acquired methicillin-resistant Staphylococcus aureus endocarditis in the Detroit Medical Center.

Journal: Annals of internal medicine 19820901

Title: Antigen-specific desensitization of patients allergic to penicillin.

Journal: The Journal of allergy and clinical immunology 19820601

Title: Nafcillin-tolerant Staphylococcus epidermidis endocarditis.

Journal: JAMA 19820101

Title: Efficacy of ampicillin plus a beta-lactamase inhibitor (CP-45,899) in experimental endocarditis due to Staphylococcus aureus.

Journal: The Journal of infectious diseases 19810901

Title: Comparative toxicities of methicillin and nafcillin.

Journal: American journal of diseases of children (1960) 19810101

Title: Nafcillin-induced interstitial nephritis.

Journal: JAMA 19801212

Title: Absence of nafcillin-associated nephritis. A prospective analysis of 210 patients.

Journal: The Western journal of medicine 19801201

Title: Nafcillin, pseudoproteinuria, and hypokalemic alkalosis.

Journal: The Journal of pediatrics 19801101

Title: Synergistic action of nafcillin and ampicillin against ampicillin-resistant Haemophilus influenzae type b bacteremia and meningitis in infant rats.

Journal: Antimicrobial agents and chemotherapy 19800701

Title: Nafcillin-associated hypokalemia.

Journal: JAMA 19790810

Title: Carbenicillin nephrotoxicity.

Journal: Southern medical journal 19780101

Title: Hypokalemia associated with antibiotic treatment. Evidence in children with malignant neoplasms.

Journal: American journal of diseases of children (1960) 19761001

Title: Tan, A.K., et al. Identification of the site of covalent attachment of nafcillin, a reversible suicide inhibitor of beta-lactamase. Biochem J, 1992. 281 ( Pt 1): p. 191-6.

Title: Palmer, D.L., et al. Bacterial wound colonization after broad-spectrum versus narrow-spectrum antibiotics. Ann Thorac Surg, 1995. 59(3): p. 626-31.

Title: Lawrence I. Mortin, et al. Rapid Bactericidal Activity of Daptomycin against Methicillin-Resistant and Methicillin-Susceptible Staphylococcus aureus Peritonitis in Mice as Measured with Bioluminescent Bacteria. Antimicrob Agents Chemother. 2007 May; 51(5): 1787-1794.

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