CEFIXIME

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15N5O7S2.3H2O
Molecular Weight	507.495
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=IPYWNMVPZOAFOQ-NABDTECSSA-N

InChI=1S/C16H15N5O7S2.3H2O/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7;;;/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27);3*1H2/b20-9-;;;/t10-,14-;;;/m1.../s1

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf | https://www.drugbank.ca/drugs/DB00671

Cefixime, an antibiotic, is a third-generation cephalosporin like ceftriaxone and cefotaxime. Cefixime is highly stable in the presence of beta-lactamase enzymes. As a result, many organisms resistant to penicillins and some cephalosporins due to the presence of beta-lactamases, may be susceptible to cefixime. The antibacterial effect of cefixime results from inhibition of mucopeptide synthesis in the bacterial cell wall. Like all beta-lactam antibiotics, cefixime binds to specific penicillin-binding proteins (PBPs) located inside the bacterial cell wall, causing the inhibition of the third and last stage of bacterial cell wall synthesis. Cell lysis is then mediated by bacterial cell wall autolytic enzymes such as autolysins; it is possible that cefixime interferes with an autolysin inhibitor. Cefixime is sold under the brand name Suprax, indicated for the treatment of: Uncomplicated Urinary Tract Infections Otitis Media Pharyngitis and Tonsillitis Acute Exacerbations of Chronic Bronchitis Uncomplicated Gonorrhea (cervical/urethral)

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/16940068 \| https://www.ncbi.nlm.nih.gov/pubmed/19528266 \| https://www.ncbi.nlm.nih.gov/pubmed/20093260	Inhibitor 8297		9.91 pM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 205 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8429	SUPRAX Approved Use To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date 1989
Otitis media 41 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8429	SUPRAX Approved Use To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date 1989
Pharyngitis 31 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8429	SUPRAX Approved Use To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date 1989
Chronic bronchitis 51 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8429	SUPRAX Approved Use To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date 1989
Gonorrhea 30 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8429	SUPRAX Approved Use To reduce the development of drug resistant bacteria and maintain the effectiveness of cefixime for oral suspension USP and other antibacterial drugs, cefixime for oral suspension USP should be used only to treat infections that are proven or strongly suspected to be caused by susceptible bacteria. When culture and susceptibility information are available, they should be considered in selecting or modifying antimicrobial therapy. In the absence of such data, local epidemiology and susceptibility patterns may contribute to the empiric selection of therapy. Cefixime is a cephalosporin antibacterial indicated in the treatment of adults and pediatric patients six months of age or older with the following infections when caused by susceptible isolates of the designated bacteria: Cefixime is a cephalosporin antibacterial drug indicated for Uncomplicated Urinary Tract Infections (1.1) Otitis Media (1.2) Pharyngitis and Tonsillitis (1.3) Acute Exacerbations of Chronic Bronchitis (1.4) Uncomplicated Gonorrhea (cervical/urethral) (1.5) 1.1 Uncomplicated Urinary Tract Infections Uncomplicated Urinary Tract Infections caused by Escherichia coli and Proteus mirabilis. 1.2 Otitis Media Otitis Media caused by Haemophilus influenzae, Moraxella catarrhalis, and Streptococcus pyogenes. (Efficacy for Streptococcus pyogenes in this organ system was studied in fewer than 10 infections.) Note: For patients with otitis media caused by Streptococcus pneumoniae, overall response was approximately 10% lower for cefixime than for the comparator. Launch Date 1989

C_max

Value	Dose	Co-administered	Analyte	Population
4.74 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CEFIXIME ANHYDROUS serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
34.9 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CEFIXIME ANHYDROUS serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CEFIXIME ANHYDROUS serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
35% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		CEFIXIME ANHYDROUS serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2079371/	unhealthy, adult n = 37 Health Status: unhealthy Condition: ENT-infections Age Group: adult Sex: unknown Population Size: 37 Sources: https://pubmed.ncbi.nlm.nih.gov/2079371/	Other AEs: Perioral dermatitis... Other AEs: Perioral dermatitis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/2079371/
8 mg/kg 1 times / day multiple, oral Recommended Dose: 8 mg/kg, 1 times / day Route: oral Route: multiple Dose: 8 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2188437/	unhealthy, children n = 61 Health Status: unhealthy Condition: urinary tract infections Age Group: children Sex: unknown Population Size: 61 Sources: https://pubmed.ncbi.nlm.nih.gov/2188437/	Sources: https://pubmed.ncbi.nlm.nih.gov/2188437/

AEs

AE	Significance	Dose	Population
Perioral dermatitis	1 patient	200 mg 2 times / day steady, oral Recommended Dose: 200 mg, 2 times / day Route: oral Route: steady Dose: 200 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/2079371/	unhealthy, adult n = 37 Health Status: unhealthy Condition: ENT-infections Age Group: adult Sex: unknown Population Size: 37 Sources: https://pubmed.ncbi.nlm.nih.gov/2079371/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587 activator 80		inhibitor 1852 activator 23

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 72 CYP2B6 810 CYP2C8/9 44 CYP2C19 1478 CYP2E1 882

Drug as perpetrator

Target	Modality	Activity
CYP1A 121	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP1A 121	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2B6 1001	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2B6 1001	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C19 1553	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C19 1553	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C8/9 44	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C8/9 44	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2D6 1891	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2E1 970	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2E1 970	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP3A4 1925	activator 214 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP3A4 1925	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no

Sourcing

Vendor/Aggregator	ID	URL
AK Scientific	K403
Alfa Chemistry	ACM97164562
BOC Sciences	97164-56-2
BioSynth	J-501698
Capot Chemical	13762
Hairui	HR131072
Hangzhou Yuhao Chemical Technology	RT14390
Hangzhou Yuhao Chemical Technology	RT14399
MolPort	MolPort-003-927-336
MolPort	MolPort-023-220-345
Molnova	M15976
TargetMol	T0932
Toronto Research Chemicals	C242800
Toronto Research Chemicals	C242820
Toronto Research Chemicals	Z438000
ZINC	ZINC000012503147	http://zinc15.docking.org/substances/ZINC000012503147
eMolecules	45919056
eMolecules	93409772
eNovation Chemicals	D767114
mcule	MCULE-2478205578

PubMed

Title	Date	PubMed
Double-blind comparison of cefixime and cefaclor in the treatment of acute otitis media in children.	1991	1957129
[Clinical evaluation of cefixime in pediatric respiratory tract infections].	1991 Jan	2041146
5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group.	1995	8537138
[Benign intracranial hypertension after treatment with pefloxacin].	1998 Aug	9759304
Nephrotic syndrome following cefixime therapy in a 10-month-old girl: spontaneous resolution without corticosteroid treatment.	1999 Oct	10528699
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center.	2004 Oct	15466073
The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime.	2007 Apr	17509176
Diagnostic evaluation of hypersensitivity reactions to beta-lactam antibiotics in a large population of children.	2014 Feb	24329898
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

Adults: 400 mg daily Children: 8 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

A mosaic penicillin-binding protein 2 (PBP 2) was found in a single isolate that exhibited the highest cefixime MIC (0.5 mg/L).

Name

Type

Language

CEFIXIME

Official Name

English

CEFIXIME [USP-RS]

Common Name

English

FK 027

Code

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, 7(SUP 2)-(Z)-(O-(CARBOXYMETHYL)OXIME)TRIHYDRATE

Common Name

English

SUPRAX

Brand Name

English

CEFIXIME [USAN]

Common Name

English

CITROPEN

Brand Name

English

FR-17027

Code

English

CEFIXIME TRIHYDRATE [MI]

Common Name

English

FK-027

Code

English

CEFIXIME HYDRATE [JAN]

Common Name

English

CEPHORAL

Brand Name

English

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

Common Name

English

CEFIXIME TRIHYDRATE

Common Name

English

CEFIXIME [MART.]

Common Name

English

CEFIXIME HYDRATE

Common Name

English

CL-284635

Code

English

CEFIXIME [USP MONOGRAPH]

Common Name

English

FR 17027

Code

English

CL 284,635

Code

English

CEFIXIME [VANDF]

Common Name

English

CEFIXIME [ORANGE BOOK]

Common Name

English

CEFIXIME [EP MONOGRAPH]

Common Name

English

Cefixime trihydrate [WHO-DD]

Common Name

English

Classification Tree Code System Code

LIVERTOX

NBK548666