CEPHRADINE ANHYDROUS

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 Search

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
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
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	15244036
[Tryptase and fatal anaphylaxic reaction].	2002 Aug	12608287
Regression of mucosa-associated lymphoid tissue lymphoma of the bladder after antibiotic therapy.	2002 Feb 1	11821481
[Empirical therapy of peritonitis in peritoneal dialysis patients--it is reasonable to use a new therapeutic schedule?].	2002 Nov	12621757
Prolonged intestinal absorption of cephradine with chitosan-coated ethylcellulose microparticles in rats.	2002 Nov	12419970
Treatments for symptomatic urinary tract infections during pregnancy.	2003	14583949
Uptake of dipeptide and beta-lactam antibiotics by the basolateral membrane vesicles prepared from rat kidney.	2003 Jan 10	12507756
Sensitive determination of a beta-lactam antibiotic, cefaclor by liquid chromatography with chemiluminescence detection.	2003 Jan 15	12485718
An interrupted time series analysis of parenteral antibiotic use in Colombia.	2003 Oct	14568634
Re: "Methicillin-resistant Staphylococcus aureus in children with cystic fibrosis: an eradication protocol" Solis et al. (Pediatr Pulmonol 2003;36: 189-195).	2004 Sep	15274111
Purification and characterization of inducible cephalexin synthesizing enzyme in Gluconobacter oxydans.	2005 Mar	15784972
[Bacterial pathogens and resistance patterns in community acquired pediatric urinary tract infection: experience of 152 cases].	2006 Apr	16613703
Controlled drug delivery system based on magnetic hollow spheres/polyelectrolyte multilayer core-shell structure.	2006 Sep-Oct	17048538
Development of intestinal bifidobacteria and lactobacilli in breast-fed neonates.	2007 Oct	17507117
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
[Prophylactic use of antibiotics in selective colorectal operation: a randomized controlled trial].	2008 Jan 15	18509971
Aeromonas salmonicida peritonitis after eating fish in a patient undergoing CAPD.	2008 May-Jun	18474929
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.	2009	20140078
High macrolide resistance in Streptococcus pyogenes strains isolated from children with pharyngitis in China.	2009 May	19360846
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
A survey of the management of urinary tract infection in children in primary care and comparison with the NICE guidelines.	2010 Jan 26	20102638

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 `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

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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

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