Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C16H19N3O4S.C6H14N2O2 |
| Molecular Weight | 495.592 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
NCCCC[C@H](N)C(O)=O.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CCC=CC3)C(O)=O
InChI
InChIKey=NTKRAGMAXIPNKX-SSDGIDNNSA-N
InChI=1S/C16H19N3O4S.C6H14N2O2/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;7-4-2-1-3-5(8)6(9)10/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23);5H,1-4,7-8H2,(H,9,10)/t10-,11-,15-;5-/m10/s1
| Molecular Formula | C6H14N2O2 |
| Molecular Weight | 146.1876 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C16H19N3O4S |
| Molecular Weight | 349.405 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| 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. | 2002 |
|
| [Tryptase and fatal anaphylaxic reaction]. | 2002 Aug |
|
| Effect of composition on the physicochemical properties and active substance release from gelatin-alginate sponge. | 2003 |
|
| Treatments for symptomatic urinary tract infections during pregnancy. | 2003 |
|
| A recirculatory model with enterohepatic circulation by measuring portal and systemic blood concentration difference. | 2003 Apr |
|
| Do cell culture conditions influence the carrier-mediated transport of peptides in Caco-2 cell monolayers? | 2003 Aug |
|
| Synthesis and antibacterial activity of cephradine metal complexes: part I complexes with magnesium, calcium, chromium and manganese. | 2003 Jan |
|
| Comparison of the effect of detergent versus hypochlorite cleaning on environmental contamination and incidence of Clostridium difficile infection. | 2003 Jun |
|
| Symphyseal diastasis and vestibular rupture during spontaneous vaginal delivery. | 2003 Jun |
|
| Concentration-dependent atypical intestinal absorption of cyclic phenylalanylserine: small intestine acts as an interface between the body and ingested compounds. | 2003 Nov |
|
| An interrupted time series analysis of parenteral antibiotic use in Colombia. | 2003 Oct |
|
| Treatment of breast abscesses with sonographically guided aspiration, irrigation, and instillation of antibiotics. | 2003 Oct |
|
| Inhibitory effect of zinc on PEPT1-mediated transport of glycylsarcosine and beta-lactam antibiotics in human intestinal cell line Caco-2. | 2003 Sep |
|
| Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: An eradication protocol. | 2003 Sep |
|
| Microbiology and drug sensitivity patterns of chronic suppurative otitis media. | 2004 Aug |
|
| Preparation and characterization of porous hollow silica nanoparticles for drug delivery application. | 2004 Feb |
|
| Variation of peptide transporter (PepT1 and HPT1) expression in Caco-2 cells as a function of cell origin. | 2004 Jul |
|
| Molecularly imprinted solid phase extraction-pulsed elution-mass spectrometry for determination of cephalexin and alpha-aminocephalosporin antibiotics in human serum. | 2004 Nov 15 |
|
| Multicenter surveillance of antimicrobial resistance of Streptococcus pyogenes, Streptococcus pneumoniae, Haemophilus influenzae, and Moraxella catarrhalis to 14 oral antibiotics. | 2004 Sep |
|
| Re: "Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: an eradication protocol" Solis et al. (Pediatr Pulmonol 2003;36: 189-195). | 2004 Sep |
|
| Nateglinide uptake by a ceftibuten transporter in the rat kidney brush-border membrane. | 2005 Aug 30 |
|
| Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. | 2005 Jan |
|
| H+-dependent transport mechanism of nateglinide in the brush-border membrane of the rat intestine. | 2005 Jan |
|
| Determination of ceftriaxone in cerebrospinal fluid by ion-pair liquid chromatography. | 2005 Mar-Apr |
|
| [Bacterial pathogens and resistance patterns in community acquired pediatric urinary tract infection: experience of 152 cases]. | 2006 Apr |
|
| Crystal form of cephradine. | 2006 Feb |
|
| 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 |
|
| 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 |
|
| Effects of treatment with antimicrobial agents on the human colonic microflora. | 2008 Dec |
|
| 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 |
|
| Risk of major bleeding during concomitant use of antibiotic drugs and coumarin anticoagulants. | 2008 Feb |
|
| [Prophylactic use of antibiotics in selective colorectal operation: a randomized controlled trial]. | 2008 Jan 15 |
|
| 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 |
|
| [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 |
|
| Lack of interaction between the peptidomimetic substrates captopril and cephradine. | 2009 Mar |
|
| High macrolide resistance in Streptococcus pyogenes strains isolated from children with pharyngitis in China. | 2009 May |
|
| [Microcalorimetric investigation of two cephalosporins on colon bacteria activity]. | 2009 Oct |
|
| Study on the binding behavior of lysozyme with cephalosporin analogues by fluorescence spectroscopy. | 2009 Sep |
|
| Traumatic optic neuropathy accompanying orbital grease gun injury. | 2010 Apr |
|
| Selective densitometric determination of four alpha-aminocephalosporins using ninhydrin reagent. | 2010 Jan |
|
| 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
by
admin
on
Edited
Fri Dec 15 15:24:29 GMT 2023
by
admin
on
Fri Dec 15 15:24:29 GMT 2023
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| Record UNII |
41BJN3H129
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| Record Status |
Validated (UNII)
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| Record Version |
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