U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H19N3O4S
Molecular Weight 349.405
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHRADINE ANHYDROUS

SMILES

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

InChI

InChIKey=RDLPVSKMFDYCOR-UEKVPHQBSA-N
InChI=1S/C16H19N3O4S/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)/t10-,11-,15-/m1/s1

HIDE SMILES / InChI

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
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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
Curative
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
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
17.7 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
27.5 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.61 h
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

PubMed

TitleDatePubMed
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
Regression of mucosa-associated lymphoid tissue lymphoma of the bladder after antibiotic therapy.
2002 Feb 1
[Empirical therapy of peritonitis in peritoneal dialysis patients--it is reasonable to use a new therapeutic schedule?].
2002 Nov
Prolonged intestinal absorption of cephradine with chitosan-coated ethylcellulose microparticles in rats.
2002 Nov
Treatments for symptomatic urinary tract infections during pregnancy.
2003
Uptake of dipeptide and beta-lactam antibiotics by the basolateral membrane vesicles prepared from rat kidney.
2003 Jan 10
Sensitive determination of a beta-lactam antibiotic, cefaclor by liquid chromatography with chemiluminescence detection.
2003 Jan 15
An interrupted time series analysis of parenteral antibiotic use in Colombia.
2003 Oct
Re: "Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: an eradication protocol" Solis et al. (Pediatr Pulmonol 2003;36: 189-195).
2004 Sep
Purification and characterization of inducible cephalexin synthesizing enzyme in Gluconobacter oxydans.
2005 Mar
[Bacterial pathogens and resistance patterns in community acquired pediatric urinary tract infection: experience of 152 cases].
2006 Apr
Controlled drug delivery system based on magnetic hollow spheres/polyelectrolyte multilayer core-shell structure.
2006 Sep-Oct
Development of intestinal bifidobacteria and lactobacilli in breast-fed neonates.
2007 Oct
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
[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
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.
2009
High macrolide resistance in Streptococcus pyogenes strains isolated from children with pharyngitis in China.
2009 May
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
A survey of the management of urinary tract infection in children in primary care and comparison with the NICE guidelines.
2010 Jan 26
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
In Vitro Use Guide
Sources: DOI: 10.5897/IJPS11.057
MIC 90 of Cephradine standard powder against 25 clinical isolates of S. aureus was 2048 ug/ml.
Substance Class Chemical
Created
by admin
on Sat Dec 16 17:07:46 GMT 2023
Edited
by admin
on Sat Dec 16 17:07:46 GMT 2023
Record UNII
9YA6SX5S4D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEPHRADINE ANHYDROUS
Common Name English
Cefradine [WHO-DD]
Common Name English
cefradine [INN]
Common Name English
CEFRADINE [EP MONOGRAPH]
Common Name English
CEFRADINE [JAN]
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-((AMINO-1,4-CYCLOHEXADIEN-1-YLACETYL)AMINO)-3-METHYL-8-OXO-, (6R-(6.ALPHA.,7.BETA.(R*)))-
Common Name English
CEFRADINE
INN  
Official Name English
(6R,7R)-7-(((2R)-2-AMINO-2-CYCLOHEXA-1,4-DIEN-1-YLACETYL)AMINO)-3-METHYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
NSC-756672
Code English
CEFRADINE [MART.]
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
Systematic Name English
CEPHRADINE [MI]
Common Name English
CEPHRADINE [HSDB]
Common Name English
Classification Tree Code System Code
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
WHO-VATC QJ01DB09
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
LIVERTOX NBK547862
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NCI_THESAURUS C357
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
LIVERTOX NBK548666
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000175488
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
WHO-ATC J01DB09
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
LIVERTOX NBK548358
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
NDF-RT N0000011161
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID4022785
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
254-137-8
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
FDA UNII
9YA6SX5S4D
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
DRUG CENTRAL
576
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
INN
3119
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
SMS_ID
100000092817
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
CHEBI
3547
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
MERCK INDEX
m3255
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY Merck Index
HSDB
3216
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
NCI_THESAURUS
C76181
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
WIKIPEDIA
CEFRADINE
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
PUBCHEM
38103
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
DRUG BANK
DB01333
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
ChEMBL
CHEMBL1604
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
NSC
756672
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
CAS
38821-53-3
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
EVMPD
SUB07417MIG
Created by admin on Sat Dec 16 17:07:48 GMT 2023 , Edited by admin on Sat Dec 16 17:07:48 GMT 2023
PRIMARY
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