CEPHRADINE DIHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19N3O4S.2H2O
Molecular Weight	385.435
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.O.[H][C@]12SCC(C)=C(N1C(=O)[C@H]2NC(=O)[C@H](N)C3=CCC=CC3)C(O)=O

InChI

InChIKey=HBKDHIDYMXXJLI-OEDJVVDHSA-N

InChI=1S/C16H19N3O4S.2H2O/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);2*1H2/t10-,11-,15-;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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

Description
Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=69176
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19015345 \| https://www.ncbi.nlm.nih.gov/pubmed/7592463 \| https://www.ncbi.nlm.nih.gov/pubmed/6373702	Inhibitor 8297		30.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=69176	Curative	Approved 8429	VELOSEF '125' Approved Use Cephradine 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 Date 1.46102403E11
Otitis media 41 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=69176	Curative	Approved 8429	VELOSEF '125' Approved Use Cephradine 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 Date 1.46102403E11
Skin and skin structure infections 80 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=69176	Curative	Approved 8429	VELOSEF '125' Approved Use Cephradine 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 Date 1.46102403E11
Urinary tract infections 205 Sources: https://dailymed.nlm.nih.gov/dailymed/archives/fdaDrugInfo.cfm?archiveid=69176	Curative	Approved 8429	VELOSEF '125' Approved Use Cephradine 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 Date 1.46102403E11

C_max

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

T_1/2

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

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00ILYH
A2B Chem	AI67465
AA Blocks	AA00ILF1
AK Scientific	6526AH
AK Scientific	6527AH
AK Scientific	E914
AbovChem LLC	HY-B1156
Ambeed	A114890
Angene	AGN-PC-0RHN84
AstaTech	C74975
BLD Pharm	BD46333
BOC Sciences	38821-53-3
Bosche Scientific	C2321
Chem Scene	CS-4608
Chem-Impex International	14312
Compound Cloud	38103
Enamine	EN300-6479201
Fluorochem	493329
Hangzhou APIChem Technology	AC-1409
Hangzhou Yuhao Chemical Technology	RT19741
KeyOrganics	AS-75158
Lab Network	LN01268780
Lab Seeker	SC-13473
MedChem Express	HY-B1156
MolPort	MolPort-003-940-846
MolPort	MolPort-039-140-513
Norris Pharm	NSZB-A200423
Ryan Scientific	Sodium_ceftiofur
Sigma Aldrich	C0690000
Sigma Aldrich	C0690000\|SIAL
Sigma Aldrich	C8395
Sigma Aldrich	C8395\|SIGMA
Sigma Aldrich	Y0000568
StruChem	SC-13473
TargetMol	T0199
Tetrahedron	TS64686
Toronto Research Chemicals	C261800
W&J PharmaChem	100988
ZINC	ZINC000003830515	http://zinc15.docking.org/substances/ZINC000003830515
eMolecules	536524
mcule	MCULE-5616371730

PubMed

Title	Date	PubMed
Cutaneous vasculitis due to ciprofloxacin.	1992 Jul 4	1638195
Synthesis and antibacterial activity of cephradine metal complexes: part I complexes with magnesium, calcium, chromium and manganese.	2003 Jan	16414567
Molecularly imprinted solid phase extraction-pulsed elution-mass spectrometry for determination of cephalexin and alpha-aminocephalosporin antibiotics in human serum.	2004 Nov 15	15522521
Synthesis and antibacterial activity of cephradine metal complexes : part II complexes with cobalt, copper, zinc and cadmium.	2005 Jan	16431381
Systemic and local antibiotic prophylaxis in the prevention of Staphylococcus epidermidis graft infection.	2005 Oct 21	16242027
Properties and active substance release kinetics from gelatin-alginate matrices.	2006	17190292
[Bacterial pathogens and resistance patterns in community acquired pediatric urinary tract infection: experience of 152 cases].	2006 Apr	16613703
Increasing single and multi-antibiotic resistance in Shigella species isolated from shigellosis patients in Sana'a, Yemen.	2006 Aug	16883444
Microplate assay for inhibitors of the transpeptidase activity of PBP1b of Escherichia coli.	2006 Dec	17092918
Crystal form of cephradine.	2006 Feb	16526284
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	16137854
Chemiluminescence flow-injection analysis of beta-lactam antibiotics using the luminol-permanganate reaction.	2006 Jul-Aug	16791833
Controlled drug delivery system based on magnetic hollow spheres/polyelectrolyte multilayer core-shell structure.	2006 Sep-Oct	17048538
Characterization of beta-lactamases from urinary isolates of Escherichia coli in Tehran.	2007 Apr	18051951
Cephradine antacids interaction studies.	2007 Jul	17545100
Determination of beta-lactam antibiotics in milk using micro-flow chemiluminescence system with on-line solid phase extraction.	2007 Jun 5	17512825
[Genotypes of Staphylococcus aureus strains with methicillin resistant phenotype].	2007 May	17657328
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	17854115
A comprehensive in vitro and in silico analysis of antibiotics that activate pregnane X receptor and induce CYP3A4 in liver and intestine.	2008 Aug	18505790
Effects of treatment with antimicrobial agents on the human colonic microflora.	2008 Dec	19337440
Human case of Rickettsia felis infection, Taiwan.	2008 Dec	19046543
Characteristics of Streptococcus pyogenes strains isolated from Chinese children with scarlet fever.	2008 Dec	18691162
Plasmid-mediated quinolone resistance in Salmonella enterica, United Kingdom.	2008 Feb	18258138
Biomimetic apatite coatings on titanium coprecipitated with cephradine and salviae miltlorrhizae.	2008 Feb	17635037
[Prophylactic use of antibiotics in selective colorectal operation: a randomized controlled trial].	2008 Jan 15	18509971
Pharmacokinetic study of cephradine in Pakistani healthy male volunteers.	2008 Oct	18930862
Studies on diseased freshwater prawn Macrobrachium rosenbergii infected with Vibrio vulnificus.	2008 Sep 1	19266922
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.	2009	20140078
Adverse drug reactions in hospital in-patients: a prospective analysis of 3695 patient-episodes.	2009	19209224
Antibiotic susceptibility of thermo-tolerant Escherichia coli 2 isolated from drinking water of Khairpur City, Sindh, Pakistan.	2009 Apr 15	19634491
A study of the chemiluminescence behavior of cephalosporins with luminol and its analytical application.	2009 Aug	19702549
[Analysis of multiple cephalosporins in blood and urine by HPLC].	2009 Dec	20225621
[Kneading and dispersing manipulation in treatment of early-stage acute mastitis: a randomized controlled trial].	2009 Dec	20015432
Rapid and simple method for determination of cephradine in human plasma using liquid chromatography-tandem mass spectrometry (LC-MS/MS): application to the bioequivalence study.	2009 Dec 1	19854118
[Study of cefadroxil and cephradine charge transfer process by fluorescence quenching method].	2009 Feb	19445223
Antibiotics for mastitis in breastfeeding women.	2009 Jan 21	19160255
Antibiotic susceptibility pattern of Staphylococcus epidermidis.	2009 Jul	19623137
Lack of interaction between the peptidomimetic substrates captopril and cephradine.	2009 Mar	19246733
High macrolide resistance in Streptococcus pyogenes strains isolated from children with pharyngitis in China.	2009 May	19360846
[Microcalorimetric investigation of two cephalosporins on colon bacteria activity].	2009 Oct	20055136
[Antibiotic consumption and antimicrobial susceptibility evolution in the Centro Hospitalario Pereira Rossell in methicillin resistant Staphylococcus aureus era].	2009 Oct	19915749
Study on the binding behavior of lysozyme with cephalosporin analogues by fluorescence spectroscopy.	2009 Sep	19343485
Traumatic optic neuropathy accompanying orbital grease gun injury.	2010 Apr	20379466
Colorimetric detection of cephradine in pharmaceutical formulations via fluorosurfactant-capped gold nanoparticles.	2010 Apr 15	20188984
Avian colibacillosis and salmonellosis: a closer look at epidemiology, pathogenesis, diagnosis, control and public health concerns.	2010 Jan	20195435
Selective densitometric determination of four alpha-aminocephalosporins using ninhydrin reagent.	2010 Jan	20056040
A survey of the management of urinary tract infection in children in primary care and comparison with the NICE guidelines.	2010 Jan 26	20102638
Uropathogen resistance to antibiotic prophylaxis in urinary tract infections.	2010 Jun	20370510
Rate of conversion and complications of laparoscopic cholecystectomy in a tertiary care center in Saudi Arabia.	2010 Mar-Apr	20220265
Rhinoscleroma: case report.	2010 Sep-Oct	20015775

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

MIC 90 of Cephradine standard powder against 25 clinical isolates of S. aureus was 2048 ug/ml.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:26:22 UTC 2023` Edited by `admin` on `Fri Dec 15 15:26:22 UTC 2023`
Record UNII	56PPJ9MMPE
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEPHRADINE DIHYDRATE

Common Name

English

CEPHRADINE DIHYDRATE [MI]

Common Name

English

(6R,7R)-7-((R)-2-AMINO-2-(1,4-CYCLOHEXADIEN-1-YL)ACETAMIDO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID DIHYDRATE

Systematic Name

English

CEFRADINE DIHYDRATE

Common Name

English

SQ 22022

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C357