CEFDINIR, (E)-

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

SMILES

[H][C@]12SCC(C=C)=C(N1C(=O)[C@H]2NC(=O)C(=N\O)\C3=CSC(N)=N3)C(O)=O

InChI

InChIKey=RTXOFQZKPXMALH-RWFJUVPESA-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

Molecular Formula	C14H13N5O5S2
Molecular Weight	395.414
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

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
Myeloperoxidase 6	Inhibitor 8,297
Bacterial penicillin-binding protein 233	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Community-acquired pneumonia 47	Curative	Approved 8,429	CEFDINIR
Acute exacerbations of chronic bronchitis 3	Curative	Approved 8,429	CEFDINIR
Acute maxillary sinusitis 10	Curative	Approved 8,429	CEFDINIR
Pharyngitis 31	Curative	Approved 8,429	CEFDINIR
Tonsillitis 36	Curative	Approved 8,429	CEFDINIR
Uncomplicated skin and skin-structure infections 21	Curative	Approved 8,429	CEFDINIR

C_max

Value	Dose	Analyte	Population
1 μg/mL	200 mg single, oral	CEFDINIR plasma	Homo sapiens
1.55 μg/mL	300 mg single, oral	CEFDINIR plasma	Homo sapiens
2.15 μg/mL	400 mg single, oral	CEFDINIR plasma	Homo sapiens
2.35 μg/mL	600 mg single, oral	CEFDINIR plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
4.08 μg × h/mL	200 mg single, oral	CEFDINIR plasma	Homo sapiens
6.53 μg × h/mL	300 mg single, oral	CEFDINIR plasma	Homo sapiens
8.83 μg × h/mL	400 mg single, oral	CEFDINIR plasma	Homo sapiens
9.84 μg × h/mL	600 mg single, oral	CEFDINIR plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.43 h	200 mg single, oral	CEFDINIR plasma	Homo sapiens
1.46 h	300 mg single, oral	CEFDINIR plasma	Homo sapiens
1.43 h	400 mg single, oral	CEFDINIR plasma	Homo sapiens
1.5 h	600 mg single, oral	CEFDINIR plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
39%	200 mg single, oral		CEFDINIR plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
600 mg 1 times / day multiple, oral Recommended	unhealthy n = 5093	Disc. AE: Diarrhea, Nausea...
600 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Allergic reaction, Hypersensitivity reaction...

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AEs

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AE	Significance	Dose	Population
Rash	0.4% Disc. AE	600 mg 1 times / day multiple, oral Recommended	unhealthy n = 5093
Diarrhea	Disc. AE	600 mg 1 times / day multiple, oral Recommended	unhealthy n = 5093
Nausea	Disc. AE	600 mg 1 times / day multiple, oral Recommended	unhealthy n = 5093
Allergic reaction	Disc. AE	600 mg 1 times / day multiple, oral Recommended	unhealthy
Pseudomembranous colitis	Disc. AE	600 mg 1 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCTN2 66 PEPT1 20 PEPT2 10 OAT1 599 OAT3 642 CYP2B6 810 CYP 111	OAT3 339 CYP 270	CYP 76

Drug as perpetrator

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Target	Modality	Activity
CYP 147	inducer 1,573	no
CYP 147	inhibitor 3,277	no
CYP2B6 1,001	inhibitor 3,277	no
PEPT1 22	inhibitor 3,277	weak [Ki 11900 uM]
PEPT2 12	inhibitor 3,277	weak [Ki 20100 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
CYP 270	substrate 3,367	no
OAT3 339	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:3485	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:3485
ChemicalBook	CB7483101	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB7483101
MolPort	MolPort-002-885-812	https://www.molport.com/shop/molecule-link/MolPort-002-885-812
Selleck Chemicals	Cefdinir(Omnicef)	http://www.selleckchem.com/products/Cefdinir(Omnicef).html
ZINC	ZINC000003927198	http://zinc15.docking.org/substances/ZINC000003927198

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PubMed

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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

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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).

Substance Class	Chemical
Record UNII	61G2M33IGF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFDINIR, (E)-

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.(E)))-

Common Name

English

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

Common Name

English

E-CEFDINIR

Common Name

English

(6R ,7R )-7-((E)-2-(2-AMINOTHIAZOL-4-YL-)-2-(HYDROXYIMINO)ACETAMIDO)-8-OXO-3-VINYL-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID

Common Name

English

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Code System

Code

Type

Description

CAS

178601-88-2

PRIMARY

FDA UNII

61G2M33IGF

PRIMARY

PUBCHEM

6399253

PRIMARY

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Related Record

Type

Details


					CI0FAO63WC

CEFDINIR

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

RELATIONSHIP_AMOUNT [<0.7] WEIGHT PERCENT (limits)

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator