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23325-78-2 | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-, hydrate (1:1), (6R,7R)-
CAS No: 23325-78-2 Catalog No: AG002MUS MDL No:MFCD08141797
Product Description
Catalog Number:
AG002MUS
Chemical Name:
5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-, hydrate (1:1), (6R,7R)-
CAS Number:
23325-78-2
Molecular Formula:
C16H19N3O5S
Molecular Weight:
365.4042
MDL Number:
MFCD08141797
IUPAC Name:
(6R,7R)-7-[[(2R)-2-amino-2-phenylacetyl]amino]-3-methyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;hydrate
InChI:
InChI=1S/C16H17N3O4S.H2O/c1-8-7-24-15-11(14(21)19(15)12(8)16(22)23)18-13(20)10(17)9-5-3-2-4-6-9;/h2-6,10-11,15H,7,17H2,1H3,(H,18,20)(H,22,23);1H2/t10-,11-,15-;/m1./s1
InChI Key:
AVGYWQBCYZHHPN-CYJZLJNKSA-N
SMILES:
N[C@H](c1ccccc1)C(=O)N[C@@H]1C(=O)N2[C@@H]1SCC(=C2C(=O)O)C.O
EC Number:
239-773-6
UNII:
OBN7UDS42Y
Properties
Complexity:
600
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
2
Defined Atom Stereocenter Count:
3
Defined Bond Stereocenter Count:
0
Exact Mass:
365.105g/mol
Formal Charge:
0
Heavy Atom Count:
25
Hydrogen Bond Acceptor Count:
7
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
365.404g/mol
Monoisotopic Mass:
365.105g/mol
Rotatable Bond Count:
4
Topological Polar Surface Area:
139A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
Literature
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| Bullous necrotizing fixed drug eruption in an infant. | Pediatric dermatology 20040101 |
| Detection and characterization of beta-lactam resistance in Bacillus cereus PTCC 1015. | TheScientificWorldJournal 20040101 |
| Bullous pemphigoid in a patient with psoriasis and possible drug reaction: a case report. | Connecticut medicine 20040101 |
| [Immunomodulating, antioxidant and hepatoprotective effects of immobilized dosage forms of rifampicin and cephalexin]. | Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] 20040101 |
| [Interaction of aminoglycosides and the other antibiotic on selected bacterial strains]. | Medycyna doswiadczalna i mikrobiologia 20040101 |
| [Means of purification of cephalexin with a view to therapeutic use]. | Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi 20040101 |
| Histological examinations of chief and parietal cells of the rat gastric glands after experimental administration of cephalexin and ethanol. | Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101 |
| The influence of experimental administration of ethanol and cephalexin on stomach mucous barrier of rat. | Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20040101 |
| Iguana bite-induced hypersensitivity reaction. | Archives of dermatology 20031201 |
| Group G streptococcus--a rare cause of osteomyelitis simulating bone tumour: a case report. | Journal of orthopaedic surgery (Hong Kong) 20031201 |
| Linear lesions on the face. | American family physician 20031201 |
| In vitro antimicrobial susceptibility of Escherichia coli isolates from clinical bovine mastitis in Finland and Israel. | Journal of dairy science 20031201 |
| Cephalexin: a channel hydrate. | Acta crystallographica. Section C, Crystal structure communications 20031101 |
| Urinary tract infection. | The New England journal of medicine 20031023 |
| Short term therapy for uncomplicated urinary tract infection today. Clinical outcome upholds the theories. | International journal of antimicrobial agents 20031001 |
| Antimicrobial drug susceptibility of Staphylococcus aureus strains isolated from bovine and ovine mammary glands. | Journal of dairy science 20031001 |
| Herpes simplex virus prophylaxis with famciclovir in patients undergoing aesthetic facial CO2 laser resurfacing. | Cutis 20031001 |
| Thrombotic thrombocytopenic purpura after cephalosporin administration: a possible relationship. | Transfusion 20030901 |
| Hydroxypropyl methylcellulose based cephalexin extended release tablets: influence of tablet formulation, hardness and storage on in vitro release kinetics. | Chemical & pharmaceutical bulletin 20030801 |
| Combination effects of cephalexin and gentamicin on Edwardsiella tarda and Streptococcus iniae. | International journal of antimicrobial agents 20030701 |
| A complication of an unusual sexual practice. | Southern medical journal 20030701 |
| Type-I hypersensitivity to ceftriaxone and cross-reactivity with cefalexin and ampicillin. | Allergy 20030601 |
| Intestinal absorption of cephalexin in diabetes mellitus model rats. | European journal of pharmaceutical sciences : official journal of the European Federation for Pharmaceutical Sciences 20030601 |
| [Impact of non-target gene mutations and reduced permeability of outer membrane on quinolone resistance and multiple antibiotic resistance in Escherichia coli]. | Hunan yi ke da xue xue bao = Hunan yike daxue xuebao = Bulletin of Hunan Medical University 20030601 |
| Hormonal regulation of dipeptide transporter (PepT1) in Caco-2 cells with normal and anoxia/reoxygenation management. | World journal of gastroenterology 20030415 |
| Inhibition of cell division blocks the synthesis of the second nitrogenase (Nif2) in the cyanobacterium Anabaena variabilis. | FEMS microbiology letters 20030214 |
| Group A streptococcal hydrocele infection and sepsis in a renal transplant recipient. | The Canadian journal of urology 20030201 |
| Residue persistence in sheep milk following antibiotic therapy. | Veterinary journal (London, England : 1997) 20030101 |
| A 'Fine' chemical industry for life science products: green solutions to chemical challenges. | Advances in biochemical engineering/biotechnology 20030101 |
| Effects of an ethyl lactate shampoo in conjunction with a systemic antibiotic in the treatment of canine superficial bacterial pyoderma in an open-label, nonplacebo-controlled study. | Veterinary therapeutics : research in applied veterinary medicine 20030101 |
| [Effect of ozone on antibiotic sensitivity of microorganisms]. | Stomatologiia 20030101 |
| Conjugation of penicillin acylase with the reactive copolymer of N-isopropylacrylamide: a step toward a thermosensitive industrial biocatalyst. | Biotechnology progress 20030101 |
| Efficacy of cephalexin two vs. three times daily vs. cefadroxil once daily for streptococcal tonsillopharyngitis. | Clinical pediatrics 20030101 |
| Neonatal suppurative parotitis: a case report. | Clinical pediatrics 20030101 |
| Arachnid envenomation from the brown recluse spider. | Clinical pediatrics 20030101 |
| Comparison of micellar electrokinetic chromatography, liquid chromatography, and microbiologic assay for analysis of cephalexin in oral suspensions. | Journal of AOAC International 20030101 |
| Enzyme distribution derived from macroscopic particle behavior of an industrial immobilized penicillin-G acylase. | Biotechnology progress 20030101 |
| Histological changes of white rat kidney after experimental administration of ethanol and cephalexin. | Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20030101 |
| Orbital abscess following uncomplicated phacoemulsification cataract surgery. | Clinical & experimental ophthalmology 20021201 |
| Antibiotic-associated maculopapular reaction. | The Annals of pharmacotherapy 20021201 |
| Novel S-benzylisothiourea compound that induces spherical cells in Escherichia coli probably by acting on a rod-shape-determining protein(s) other than penicillin-binding protein 2. | Bioscience, biotechnology, and biochemistry 20021201 |
| High-dose antibiotic therapy is superior to a 3-drug combination of prostanoids and lipid A derivative in protecting irradiated canines. | Journal of radiation research 20021201 |
| Modelling of the enzymatic kinetically controlled synthesis of cephalexin: influence of diffusion limitation. | Biotechnology and bioengineering 20021105 |
| Influence of a new prophylactic antibiotic therapy on the incidence of liver abscesses after chemoembolization treatment of liver tumors. | Journal of vascular and interventional radiology : JVIR 20021101 |
| In vitro and in situ evidence for the contribution of Labrasol and Gelucire 44/14 on transport of cephalexin and cefoperazone by rat intestine. | European journal of pharmaceutics and biopharmaceutics : official journal of Arbeitsgemeinschaft fur Pharmazeutische Verfahrenstechnik e.V 20021101 |
| Integrated reactor concepts for the enzymatic kinetic synthesis of cephalexin. | Biotechnology and bioengineering 20021020 |
| Selective antibiotic use to prevent postoperative wound infection after external dacryocystorhinostomy. | Ophthalmic plastic and reconstructive surgery 20020901 |
| Advantages of using non-isothermal bioreactors for the enzymatic synthesis of antibiotics: the penicillin G acylase as enzyme model. | Biotechnology and bioengineering 20020805 |
| A two-step, one-pot enzymatic synthesis of cephalexin from D-phenylglycine nitrile. | Biotechnology and bioengineering 20020805 |
| Prophylactic antibiotics in cirrhotics with upper gastrointestinal hemorrhage: a prospective, controlled trial. | Zhonghua yi xue za zhi = Chinese medical journal; Free China ed 20020801 |
| Comparison of several methods used for the determination of cephalosporins. Analysis of cephalexin in pharmaceutical samples. | Journal of pharmaceutical and biomedical analysis 20020701 |
| Update on prosthetic joints, dental treatment, and antibiotic prophylaxis. | Dentistry today 20020701 |
| Pharmacokinetics of cephalexin in the horse after intravenous and intramuscular administration of two formulations. | Veterinary journal (London, England : 1997) 20020701 |
| Generalized pustules in a healthy woman. | Journal of drugs in dermatology : JDD 20020701 |
| The effect of tablet formulation and hardness on in vitro release of cephalexin from Eudragit L100 based extended release tablets. | Biological & pharmaceutical bulletin 20020401 |
| Salmonella mastitis in a child. | Clinical pediatrics 20020401 |
| Emergence of new pathogens in CF: the devil we know or the devil we don't know? | The Journal of pediatrics 20020301 |
| Antibiotic prophylaxis in infants and young children with cystic fibrosis: a randomized controlled trial. | The Journal of pediatrics 20020301 |
| [Improvement of efficacy of the bacteriological diagnosis in whooping cough]. | Klinicheskaia laboratornaia diagnostika 20020201 |
| [Studies on enzymatic synthesis of cephalexin by immobilized penicillin acylase by polyacrylonitrile fibres]. | Wei sheng wu xue bao = Acta microbiologica Sinica 20020201 |
| Comparison of bidirectional cephalexin transport across MDCK and caco-2 cell monolayers: interactions with peptide transporters. | Pharmaceutical research 20020101 |
| [Pharmacokinetics of cephalexin from two oral formulations in dogs]. | Berliner und Munchener tierarztliche Wochenschrift 20020101 |
| A comparison of the efficacy and safety of mupirocin cream and cephalexin in the treatment of secondarily infected eczema. | Clinical and experimental dermatology 20020101 |
| Determination of cephalexin in oral suspensions by micellar electrokinetic chromatography. | Journal of capillary electrophoresis and microchip technology 20020101 |
| Effect of cephalexin on the pharmacokinetics of metformin in healthy human volunteers. | Drug metabolism and drug interactions 20020101 |
| Enzyme reaction engineering: effect of methanol on the synthesis of antibiotics catalyzed by immobilized penicillin G acylase under isothermal and non-isothermal conditions. | Biotechnology progress 20020101 |
| Analgesic effect of meloxicam in canine acute dermatitis--a pilot study. | Acta veterinaria Scandinavica 20020101 |
| Histological changes in the pancreas of white rats after administering cephalexin and ethanol. | Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101 |
| Ultrastructural changes of pancreas of white rats after experimental administration of ethanol and cephalexin. | Annales Universitatis Mariae Curie-Sklodowska. Sectio D: Medicina 20020101 |
| Concentration-dependent preferences of absorptive and excretive transport cause atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. | Research communications in molecular pathology and pharmacology 20020101 |
| PepT1-mediated epithelial transport of dipeptides and cephalexin is enhanced by luminal leptin in the small intestine. | The Journal of clinical investigation 20011115 |
| Consensus statement on management of antenatally detected hydronephrosis. | Indian pediatrics 20011101 |
| Introduction of recirculatory analysis into portal and systemic concentration difference method. | Biological & pharmaceutical bulletin 20011101 |
| CF and antistaphylococcal prophylaxis. | Thorax 20011001 |
| Outpatient management of low-velocity gunshot-induced fractures. | Orthopedics 20011001 |
| Equal allergenic potency of beta-lactam antibiotics produced by chemical or enzymatic manufacturing--mouse IgE test. | International archives of allergy and immunology 20011001 |
| Invasive group A streptococcus in two siblings: a case for antibiotic prophylaxis of close contacts. | Canada communicable disease report = Releve des maladies transmissibles au Canada 20010901 |
| Cephalexin tolerated despite delayed aminopenicillin reactions. | Allergy 20010801 |
| Special feature: picture of the month. | Archives of pediatrics & adolescent medicine 20010601 |
| Modeling of the enzymatic kinetic synthesis of cephalexin--influence of substrate concentration and temperature. | Biotechnology and bioengineering 20010505 |
| Bullous pemphigoid induced by cephalexin. | The Australasian journal of dermatology 20010501 |
| Probing the penicillin sidechain selectivity of recombinant deacetoxycephalosporin C synthase. | Cellular and molecular life sciences : CMLS 20010501 |
| Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales. | The Journal of antimicrobial chemotherapy 20010301 |
| Mutations in DnaA protein suppress the growth arrest of acidic phospholipid-deficient Escherichia coli cells. | The EMBO journal 20010301 |
| Antibiotic prophylaxis for full-face laser resurfacing: is it necessary? | Archives of dermatology 20010301 |
| Take a 2nd look at your first impression. | JEMS : a journal of emergency medical services 20010301 |
| Drug inhibition of Gly-Sar uptake and hPepT1 localization using hPepT1-GFP fusion protein. | AAPS pharmSci 20010301 |
| Bioaugmentation and treatment of cephalexin drug-based pharmaceutical effluent in an upflow anaerobic fluidized bed system. | Bioresource technology 20010201 |
| Roles of Escherichia coli histone-like protein HU in DNA replication: HU-beta suppresses the thermosensitivity of dnaA46ts. | Biochimie 20010201 |
| Effects of ceramic component on cephalexin release from bioactive bone cement consisting of Bis-GMA/TEGDMA resin and bioactive glass ceramics. | Bio-medical materials and engineering 20010101 |
| Severe anaphylaxis after a chlorhexidine bath. | Journal of the American Academy of Dermatology 19990501 |
| Human dipeptide transporter, hPEPT1, stably transfected into Chinese hamster ovary cells. | Pharmaceutical research 19961101 |
| A large population-based follow-up study of trimethoprim-sulfamethoxazole, trimethoprim, and cephalexin for uncommon serious drug toxicity. | Pharmacotherapy 19950101 |
| Acute interstitial nephritis and non-oliguric renal failure after cefaclor treatment. | Klinische Wochenschrift 19860317 |
| Cholestatic jaundice and hematuria due to hypersensitivity to cefaclor in a child. | Journal of toxicology. Clinical toxicology 19830301 |
| Ototoxicity associated with cephalexin in two patients with renal failure. | Lancet (London, England) 19821120 |
| Cephalosporin-induced cholestatic jaundice. | Lancet (London, England) 19820807 |
| Cefroxadine (CGP-9000), an orally active cephalosporin. | Antimicrobial agents and chemotherapy 19800701 |
| Cephalexin-related nephropathy. | JAMA 19751110 |
| Cephalexin nephrotoxicity. Reversible nonoliguric acute renal failure and hepatotoxicity associated with cephalexin therapy. | JAMA 19740715 |
| Relative nephrotoxicity of cephalosporin antibiotics in an animal model. | Canadian Medical Association journal 19720909 |
| Acute intravascular haemolysis associated with cephalexin therapy. | Postgraduate medical journal 19720301 |
| Cephalexin dosage in general practice assessed by double-blind trial. | Current medical research and opinion 19720101 |
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