CEFDINIR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C14H13N5O5S2
Molecular Weight	395.414
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=CS1)C(=N\O)\C(=O)N[C@H]2[C@H]3SCC(C=C)=C(N3C2=O)C(O)=O

InChI

InChIKey=RTXOFQZKPXMALH-GHXIOONMSA-N

InChI=1S/C14H13N5O5S2/c1-2-5-3-25-12-8(11(21)19(12)9(5)13(22)23)17-10(20)7(18-24)6-4-26-14(15)16-6/h2,4,8,12,24H,1,3H2,(H2,15,16)(H,17,20)(H,22,23)/b18-7-/t8-,12-/m1/s1

HIDE SMILES / InChI

Description

Cefdinir is an extended-spectrum, semisynthetic cephalosporin, for oral administration. As with other cephalosporins, bactericidal activity of cefdinir results from inhibition of cell wall synthesis. Cefdinir is stable in the presence of some, but not all, β-lactamase enzymes. Cefdinir is indicated for the treatment of: Community-Acquired Pneumonia, Acute Exacerbations of Chronic Bronchitis, Acute Maxillary Sinusitis, Pharyngitis/Tonsillitis and Uncomplicated Skin and Skin Structure Infections. Side effects include diarrhea, vaginal infections or inflammation, nausea, headache, and abdominal pain. Concomitant administration of 300-mg cefdinir capsules with 30 mL Maalox® TC suspension reduces the rate (Cmax) and extent (AUC) of absorption by approximately 40%. As with other β-lactam antibiotics, probenecid inhibits the renal excretion of cefdinir.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 221	Inhibitor 6625	Sinusitis, Maxillary
Myeloperoxidase 5	Inhibitor 6625

Conditions

Condition	Modality	Targets	Highest Phase	Product
Pharyngitis 45	Primary	Bacterial penicillin-binding protein	Approved 7892	CEFDINIR
Chronic Bronchitis 42	Primary	Bacterial penicillin-binding protein	Approved 7892	CEFDINIR
Tonsillitis 37	Primary	Bacterial penicillin-binding protein	Approved 7892	CEFDINIR
Staphylococcal Skin Infections 86	Primary	Bacterial penicillin-binding protein	Approved 7892	CEFDINIR
Community-Acquired Infections 10	Primary	Bacterial penicillin-binding protein	Approved 7892	CEFDINIR
Sinusitis, Maxillary 6	Primary	Bacterial penicillin-binding protein	Approved 7892	CEFDINIR

PubMed

Title	Date	PubMed
Effect of estrogen administration on activities of testosterone 5alpha-reductase, alkaline phosphatase and arginase in the ventral and the dorsolateral prostates of rats.	1975 Aug	1201739
Successful steroid therapy for cefdinir-induced acute tubulointerstitial nephritis with progressive renal failure.	2001 Feb	11300142
A comparison of 5 days of therapy with cefdinir or azithromycin in children with acute otitis media: a multicenter, prospective, single-blind study.	2005 Jun	16117986
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005 Jun	15962942
Human organic anion transporter hOAT3 is a potent transporter of cephalosporin antibiotics, in comparison with hOAT1.	2005 Oct 1	16098483
A favorable response to steroid therapy in a child with drug-associated acute vanishing bile duct syndrome and skin disorder.	2008 Apr	18377375
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

Patents

Sample Use Guides

In Vivo Use Guide

The total daily dose for all infections is 600 mg. Once-daily dosing for 10 days is as effective as BID dosing. Usual Adult Dose for Pneumonia: 300 mg orally every 12 hours for 10 to 14 days Acute exacerbations of chronic bronchitis: 300 mg orally every 12 hours for 5 to 10 days or 600 mg orally every 24 hours for 10 days Acute maxillary sinusitis: 300 mg orally every 12 hours or 600 mg orally every 24 hours for 10 days

Route of Administration: Oral

In Vitro Use Guide

Cefdinir had a much higher MIC90 against genotypic penicillin-resistant Streptococcus pneumoniae (gPRSP) than cefditoren and cefcapene (8 mg/L cefdinir vs. 1 mg/L cefditoren and cefcapene).

Name

Type

Language

CEFDINIR

Official Name

English

CEFDINIR [JAN]

Common Name

English

CEFDINIR [WHO-DD]

Common Name

English

FK-482

Code

English

CEFDINIR [VANDF]

Common Name

English

CEFDINIR [USP-RS]

Common Name

English

CI-983

Code

English

CEFDINIR [USAN]

Common Name

English

CEFDINIR [INN]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL) (HYDROXYIMINO)ACETYL)AMINO)-3-ETHENYL-8-OXO-, (6R-(6.ALPHA.,7.BETA.(Z)))-

Common Name

English

(6R,7R)-7-(((2Z)-(2-AMINO-4-THIAZOLYL)(HYDROXYIMINO)ACETYL)AMINO)-3-ETHENYL-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID

Systematic Name

English

CEFDINIR [MART.]

Common Name

English

CEFDINIR [ORANGE BOOK]

Common Name

English

CEFZON

Brand Name

English

CEFDINIR ANHYDROUS

Common Name

English

(-)-(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-8-OXO-3-VINYL-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 72-(Z)-OXIME

Common Name

English

CEFDINIR [MI]

Common Name

English

BMY-28488

Code

English

OMNICEF

Brand Name

English

CEFDINIR [USP]

Common Name

English

SYN-7-(2-(2-AMINO-4-THIAZOLYL)-2-HYDROXYIMINOACETAMIDO)-3-VINYL-3-CEPHEM-4-CARBOXYLIC ACID

Common Name

English

FK 482

Code

English

Classification Tree Code System Code

NDF-RT

N0000011161