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

Molecular Formula	C16H15N5O7S2
Molecular Weight	453.45
Charge	0
Count

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

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 234 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 8504		9.91 pM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8583	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 42 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8583	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 8583	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 52 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2012/203195Orig1s000Lbl.pdf	Curative	Approved 8583	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 8583	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	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
3.696 μg/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/202091Orig1s000ClinPharmR.pdf#page=23	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.837 μg/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/202091Orig1s000ClinPharmR.pdf#page=23	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.74 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CEFIXIME serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.68 mg/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CEFIXIME serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
0.69 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.13 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1.95 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	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
30.211 μg × h/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/202091Orig1s000ClinPharmR.pdf#page=23	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
15.864 μg × h/mL OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/202091Orig1s000ClinPharmR.pdf#page=23	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
34.9 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CEFIXIME serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
49.5 mg × h/L DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CEFIXIME serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.32 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
8.66 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
14.99 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	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
3.479 h OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/202091Orig1s000ClinPharmR.pdf#page=23	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.461 h OTHER GOV'T https://www.accessdata.fda.gov/drugsatfda_docs/nda/2013/202091Orig1s000ClinPharmR.pdf#page=23	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
3.5 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CEFIXIME serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
4.2 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12	400 mg 1 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	CEFIXIME serum	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.54 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.38 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.29 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/3693588/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	CEFIXIME serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

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
35% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/202091s009lbl.pdf#page=12			CEFIXIME serum	Homo sapiens

Doses

Dose	Population	Adverse events
800 mg 3 times / day multiple, oral Highest studied dose Dose: 800 mg, 3 times / day Route: oral Route: multiple Dose: 800 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/29624558/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M+F Food Status: FASTED Sources: https://pubmed.ncbi.nlm.nih.gov/29624558/	Sources: https://pubmed.ncbi.nlm.nih.gov/29624558/
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/	Disc. AE: Diarrhea, Vomiting... Other AEs: Nausea... AEs leading to discontinuation/dose reduction: Diarrhea (2.5%) Vomiting (0.8%) Increased urinary frequency (0.8%) Other AEs: Nausea (0.8%) Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/
400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	Disc. AE: Hypersensitivity, Diarrhea, Clostridium difficile... AEs leading to discontinuation/dose reduction: Hypersensitivity Diarrhea, Clostridium difficile Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
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 Health Status: unhealthy Age Group: adult Sex: unknown 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 Health Status: unhealthy Age Group: children Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/2188437/	Sources: https://pubmed.ncbi.nlm.nih.gov/2188437/

AEs

AE	Significance	Dose	Population
Nausea	0.8%	400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/
Increased urinary frequency	0.8% Disc. AE	400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/
Vomiting	0.8% Disc. AE	400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/
Diarrhea	2.5% Disc. AE	400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/8451674/
Diarrhea, Clostridium difficile	Disc. AE	400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
Hypersensitivity	Disc. AE	400 mg 1 times / day multiple, oral Recommended Dose: 400 mg, 1 times / day Route: oral Route: multiple Dose: 400 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/202091s005,203195s006lbl.pdf
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 Health Status: unhealthy Age Group: adult Sex: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/2079371/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 activator 150		inhibitor 2507 activator 25

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 70 CYP2B6 926 CYP2C8/9 42 CYP2C19 2057 CYP2E1 1060

Drug as perpetrator

Target	Modality	Activity
CYP1A 122	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP1A 122	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2B6 1160	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2B6 1160	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C19 2141	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C19 2141	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C8/9 42	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2C8/9 42	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2D6 2546	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2E1 1146	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP3A4 2633	activator 342 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/14709907/	no

Sourcing

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

PubMed

Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015-05-18	25811541
Diagnostic evaluation of hypersensitivity reactions to beta-lactam antibiotics in a large population of children.	2014-02	24329898
Investigation of the role of oligopeptide transporter PEPT1 and sodium/glucose cotransporter SGLT1 in intestinal absorption of their substrates using small GTP-binding protein Rab8-null mice.	2009-03	19074526
The treatment of pharyngeal gonorrhoea with a single oral dose of cefixime.	2007-04	17509176
IgE antibodies to betalactams: relationship between the triggering hapten and the specificity of the immune response.	2006-08	16867046
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center.	2004-10	15466073
Nephrotic syndrome following cefixime therapy in a 10-month-old girl: spontaneous resolution without corticosteroid treatment.	1999-10	10528699
[Benign intracranial hypertension after treatment with pefloxacin].	1998-08	9759304
5-day cefixime therapy for bacterial pharyngitis and/or tonsillitis: comparison with 10-day penicillin V therapy. Cefixime Study Group.	1995	8537138
Cefixime compared with amoxicillin for treatment of acute otitis media.	1991-07	1906097
[Clinical evaluation of cefixime in pediatric respiratory tract infections].	1991-01	2041146
Double-blind comparison of cefixime and cefaclor in the treatment of acute otitis media in children.	1991	1957129

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).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:56:37 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:37 GMT 2025`
Record UNII	97I1C92E55
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFIXIME TRIHYDRATE

Preferred Name

English

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 [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