CEPHRADINE MONOHYDRATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19N3O4S.H2O
Molecular Weight	367.42
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VHNPSPMQGXQSET-CYJZLJNKSA-N

InChI=1S/C16H19N3O4S.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;/h2-3,6,10-11,15H,4-5,7,17H2,1H3,(H,18,20)(H,22,23);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 1974
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 1974
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 1974
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 1974

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
Capillary electrophoresis study on the micellization and critical micelle concentration of sodium dodecyl sulfate. Influence of solubilized solutes.	2001 Jul 27	11521911
Factors associated with antibiotic resistance in coliform organisms from community urinary tract infection in Wales.	2001 Mar	11222563
Clinical significance and epidemiology of NO-1, an unusual bacterium associated with dog and cat bites.	2002 Feb	11897069
Regression of mucosa-associated lymphoid tissue lymphoma of the bladder after antibiotic therapy.	2002 Feb 1	11821481
Prolonged intestinal absorption of cephradine with chitosan-coated ethylcellulose microparticles in rats.	2002 Nov	12419970
Antimicrobial resistance pattern of Escherichia coli causing urinary tract infections, and that of human fecal flora, in the southeast of Iran.	2002 Summer	12118516
Effect of composition on the physicochemical properties and active substance release from gelatin-alginate sponge.	2003	15058110
Do cell culture conditions influence the carrier-mediated transport of peptides in Caco-2 cell monolayers?	2003 Aug	12907294
Synthesis and antibacterial activity of cephradine metal complexes: part I complexes with magnesium, calcium, chromium and manganese.	2003 Jan	16414567
Comparison of the effect of detergent versus hypochlorite cleaning on environmental contamination and incidence of Clostridium difficile infection.	2003 Jun	12818583
Treatment of breast abscesses with sonographically guided aspiration, irrigation, and instillation of antibiotics.	2003 Oct	14500237
Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: An eradication protocol.	2003 Sep	12910579
Variation of peptide transporter (PepT1 and HPT1) expression in Caco-2 cells as a function of cell origin.	2004 Jul	15176063
Determination of ceftriaxone in cerebrospinal fluid by ion-pair liquid chromatography.	2005 Mar-Apr	15859068
Microplate assay for inhibitors of the transpeptidase activity of PBP1b of Escherichia coli.	2006 Dec	17092918
Development of intestinal bifidobacteria and lactobacilli in breast-fed neonates.	2007 Oct	17507117
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
Human case of Rickettsia felis infection, Taiwan.	2008 Dec	19046543
Cranial osteomyelitis: a late complication of a dental infection.	2008 Dec	18486999
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
[Analysis of multiple cephalosporins in blood and urine by HPLC].	2009 Dec	20225621
Antibiotics for mastitis in breastfeeding women.	2009 Jan 21	19160255
Traumatic optic neuropathy accompanying orbital grease gun injury.	2010 Apr	20379466
Selective densitometric determination of four alpha-aminocephalosporins using ninhydrin reagent.	2010 Jan	20056040
Uropathogen resistance to antibiotic prophylaxis in urinary tract infections.	2010 Jun	20370510

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 15:34:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:34:57 GMT 2023`
Record UNII	FUC0D71IZN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEPHRADINE MONOHYDRATE

Common Name

English

CEPHRADINE MONOHYDRATE [MI]

Common Name

English

Cefradine monohydrate [WHO-DD]

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 MONOHYDRATE

Systematic Name

English

CEFRADINE MONOHYDRATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357