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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

CC1=C(N2[C@H](SC1)[C@H](NC(=O)[C@H](N)C3=CCC=CC3)C2=O)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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
30.0 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
VELOSEF '125'
Curative
VELOSEF '125'
Curative
VELOSEF '125'
Curative
VELOSEF '125'

Cmax

ValueDoseCo-administeredAnalytePopulation
17.7 μg/mL
500 mg single, oral
CEPHRADINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
27.5 μg × h/mL
500 mg single, oral
CEPHRADINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.61 h
500 mg single, oral
CEPHRADINE plasma
Homo sapiens

Sourcing

PubMed

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
Record UNII
9YA6SX5S4D
Record Status Validated (UNII)
Record Version