Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H18N3O4S.Na |
| Molecular Weight | 371.387 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CCC=CC3)C([O-])=O
InChI
InChIKey=LSEIVBOQBUBVGP-CYJZLJNKSA-M
InChI=1S/C16H19N3O4S.Na/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;/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23);/q;+1/p-1/t10-,11-,15-;/m1./s1
| Molecular Formula | C16H18N3O4S |
| Molecular Weight | 348.397 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | Na |
| Molecular Weight | 22.9898 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/cephradine.html | http://www.medicinenet.com/cephradine-oral/article.htm | https://www.ncbi.nlm.nih.gov/pubmed/4684646
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/mtm/cephradine.html | http://www.medicinenet.com/cephradine-oral/article.htm | https://www.ncbi.nlm.nih.gov/pubmed/4684646
Cephradine is a semisynthetic cephalosporin antibiotic. Cephradine is active against the following organisms in vitro: Group A beta-hemolytic streptococci; Staphylococci, including coagulase-positive, coagulase-negative, and penicillinase-producing strains; Streptococcus pneumoniae (formerly Diplococcus pneumoniae); Escherichia coli; Proteus mirabilis; Klebsiella species; Hemophilus influenza. It works by stopping the growth of bacteria. It is used to treat a wide variety of bacterial infections (e.g., skin, ear, respiratory and urinary tract infections). Pseudomembranous colitis has been reported in patients receiving cephradine both orally and intravenously. Diarrhea generally starts 1 to 16 days after starting cephradine therapy. Gastrointestinal side effects have included nausea, vomiting. Hypersensitivity reactions have included rash, urticaria, pruritus, and joint pain. Bacteriostats may interfere with the bactericidal action of cephalosporins in acute infection; other agents, e.g., aminoglycosides, colistin, polymyxins, vancomycin, may increase the possibility of nephrotoxicity.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
| 30.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | VELOSEF '125' Approved UseCephradine is indicated in the treatment of the following infections: RESPIRATORY TRACT INFECTIONS (e.g., tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia). OTITIS MEDIA caused by group A beta-hemolytic streptococci, S. pneumoniae (formerly D. pneumoniae), H. influenzae, and staphylococci. SKIN AND SKIN STRUCTURE INFECTIONS caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. URINARY TRACT INFECTIONS, including prostatitis, caused by E. coli, P. mirabilis, Klebsiella species, and enterococci (S. faecalis). Launch Date1974 |
|||
| Curative | VELOSEF '125' Approved UseCephradine is indicated in the treatment of the following infections: RESPIRATORY TRACT INFECTIONS (e.g., tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia). OTITIS MEDIA caused by group A beta-hemolytic streptococci, S. pneumoniae (formerly D. pneumoniae), H. influenzae, and staphylococci. SKIN AND SKIN STRUCTURE INFECTIONS caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. URINARY TRACT INFECTIONS, including prostatitis, caused by E. coli, P. mirabilis, Klebsiella species, and enterococci (S. faecalis). Launch Date1974 |
|||
| Curative | VELOSEF '125' Approved UseCephradine is indicated in the treatment of the following infections: RESPIRATORY TRACT INFECTIONS (e.g., tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia). OTITIS MEDIA caused by group A beta-hemolytic streptococci, S. pneumoniae (formerly D. pneumoniae), H. influenzae, and staphylococci. SKIN AND SKIN STRUCTURE INFECTIONS caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. URINARY TRACT INFECTIONS, including prostatitis, caused by E. coli, P. mirabilis, Klebsiella species, and enterococci (S. faecalis). Launch Date1974 |
|||
| Curative | VELOSEF '125' Approved UseCephradine is indicated in the treatment of the following infections: RESPIRATORY TRACT INFECTIONS (e.g., tonsillitis, pharyngitis, and lobar pneumonia) caused by group A beta-hemolytic streptococci and S. pneumoniae (formerly D. pneumonia). OTITIS MEDIA caused by group A beta-hemolytic streptococci, S. pneumoniae (formerly D. pneumoniae), H. influenzae, and staphylococci. SKIN AND SKIN STRUCTURE INFECTIONS caused by staphylococci (penicillin-susceptible and penicillin-resistant) and beta-hemolytic streptococci. URINARY TRACT INFECTIONS, including prostatitis, caused by E. coli, P. mirabilis, Klebsiella species, and enterococci (S. faecalis). Launch Date1974 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
17.7 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/848940/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHRADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
27.5 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/848940/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHRADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.61 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/848940/ |
500 mg single, oral dose: 500 mg route of administration: Oral experiment type: SINGLE co-administered: |
CEPHRADINE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cutaneous vasculitis due to ciprofloxacin. | 1992 Jul 4 |
|
| Synthesis and antibacterial activity of cephradine metal complexes: part I complexes with magnesium, calcium, chromium and manganese. | 2003 Jan |
|
| Synthesis and antibacterial activity of cephradine metal complexes : part II complexes with cobalt, copper, zinc and cadmium. | 2005 Jan |
|
| Systemic and local antibiotic prophylaxis in the prevention of Staphylococcus epidermidis graft infection. | 2005 Oct 21 |
|
| Properties and active substance release kinetics from gelatin-alginate matrices. | 2006 |
|
| [Bacterial pathogens and resistance patterns in community acquired pediatric urinary tract infection: experience of 152 cases]. | 2006 Apr |
|
| Increasing single and multi-antibiotic resistance in Shigella species isolated from shigellosis patients in Sana'a, Yemen. | 2006 Aug |
|
| A case of inadvertent anterior chamber and corneal stromal injection with antibiotics during cataract operation. | 2006 Dec |
|
| Microplate assay for inhibitors of the transpeptidase activity of PBP1b of Escherichia coli. | 2006 Dec |
|
| Crystal form of cephradine. | 2006 Feb |
|
| A specific and rapid HPLC assay for the determination of cefroxadine in human plasma and its application to pharmacokinetic study in Korean. | 2006 Feb 13 |
|
| Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction. | 2006 Jul-Aug |
|
| Controlled drug delivery system based on magnetic hollow spheres/polyelectrolyte multilayer core-shell structure. | 2006 Sep-Oct |
|
| Characterization of beta-lactamases from urinary isolates of Escherichia coli in Tehran. | 2007 Apr |
|
| Cephradine antacids interaction studies. | 2007 Jul |
|
| Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. | 2007 Jul 15 |
|
| Determination of beta-lactam antibiotics in milk using micro-flow chemiluminescence system with on-line solid phase extraction. | 2007 Jun 5 |
|
| [Genotypes of Staphylococcus aureus strains with methicillin resistant phenotype]. | 2007 May |
|
| Development of intestinal bifidobacteria and lactobacilli in breast-fed neonates. | 2007 Oct |
|
| Use of SDS micelles for improving sensitivity, resolution, and speed in the analysis of beta-lactam antibiotics in environmental waters by SPE and CE. | 2007 Sep |
|
| Quantitative prediction of oral absorption of PEPT1 substrates based on in vitro uptake into Caco-2 cells. | 2008 Apr 16 |
|
| A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine. | 2008 Aug |
|
| Human case of Rickettsia felis infection, Taiwan. | 2008 Dec |
|
| Characteristics of Streptococcus pyogenes strains isolated from Chinese children with scarlet fever. | 2008 Dec |
|
| Cranial osteomyelitis: a late complication of a dental infection. | 2008 Dec |
|
| Plasmid-mediated quinolone resistance in Salmonella enterica, United Kingdom. | 2008 Feb |
|
| Risk of major bleeding during concomitant use of antibiotic drugs and coumarin anticoagulants. | 2008 Feb |
|
| Biomimetic apatite coatings on titanium coprecipitated with cephradine and salviae miltlorrhizae. | 2008 Feb |
|
| [Prophylactic use of antibiotics in selective colorectal operation: a randomized controlled trial]. | 2008 Jan 15 |
|
| Aeromonas salmonicida peritonitis after eating fish in a patient undergoing CAPD. | 2008 May-Jun |
|
| Pharmacokinetic study of cephradine in Pakistani healthy male volunteers. | 2008 Oct |
|
| Studies on diseased freshwater prawn Macrobrachium rosenbergii infected with Vibrio vulnificus. | 2008 Sep 1 |
|
| Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations. | 2009 |
|
| Adverse drug reactions in hospital in-patients: a prospective analysis of 3695 patient-episodes. | 2009 |
|
| Antibiotic susceptibility of thermo-tolerant Escherichia coli 2 isolated from drinking water of Khairpur City, Sindh, Pakistan. | 2009 Apr 15 |
|
| [Analysis of multiple cephalosporins in blood and urine by HPLC]. | 2009 Dec |
|
| [Kneading and dispersing manipulation in treatment of early-stage acute mastitis: a randomized controlled trial]. | 2009 Dec |
|
| [Study of cefadroxil and cephradine charge transfer process by fluorescence quenching method]. | 2009 Feb |
|
| Antibiotics for mastitis in breastfeeding women. | 2009 Jan 21 |
|
| Antibiotic susceptibility pattern of Staphylococcus epidermidis. | 2009 Jul |
|
| Lack of interaction between the peptidomimetic substrates captopril and cephradine. | 2009 Mar |
|
| [Microcalorimetric investigation of two cephalosporins on colon bacteria activity]. | 2009 Oct |
|
| [Antibiotic consumption and antimicrobial susceptibility evolution in the Centro Hospitalario Pereira Rossell in methicillin resistant Staphylococcus aureus era]. | 2009 Oct |
|
| Traumatic optic neuropathy accompanying orbital grease gun injury. | 2010 Apr |
|
| Colorimetric detection of cephradine in pharmaceutical formulations via fluorosurfactant-capped gold nanoparticles. | 2010 Apr 15 |
|
| Avian colibacillosis and salmonellosis: a closer look at epidemiology, pathogenesis, diagnosis, control and public health concerns. | 2010 Jan |
|
| Selective densitometric determination of four alpha-aminocephalosporins using ninhydrin reagent. | 2010 Jan |
|
| A survey of the management of urinary tract infection in children in primary care and comparison with the NICE guidelines. | 2010 Jan 26 |
|
| Uropathogen resistance to antibiotic prophylaxis in urinary tract infections. | 2010 Jun |
|
| Rate of conversion and complications of laparoscopic cholecystectomy in a tertiary care center in Saudi Arabia. | 2010 Mar-Apr |
Patents
Sample Use Guides
For respiratory tract infections (other than lobar pneumonia) and skin and skin structure infections, the usual dose is 250 mg every 6 hours or 500 mg every 12 hours.
For lobar pneumonia, the usual dose is 500 mg every 6 hours or 1 g every 12 hours.
For uncomplicated urinary tract infections, the usual dose is 500 mg every 12 hours. In more serious urinary tract infections, including prostatitis, 500 mg every 6 hours or 1 g every 12 hours may be administered.
Larger doses (up to 1 g every 6 hours) may be given for severe or chronic infections.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
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| Record UNII |
04FRJ20XNF
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| Record Status |
Validated (UNII)
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| Record Version |
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