CEFIXIME ANHYDROUS

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15N5O7S2
Molecular Weight	453.45
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

SMILES

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=OKBVVJOGVLARMR-QSWIMTSFSA-N

InChI=1S/C16H15N5O7S2/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)/b20-9-/t10-,14-/m1/s1

HIDE SMILES / InChI

Description

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	Inhibitor 8,504		9.91 pM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Urinary tract infections 207	Curative	Approved 8,583	SUPRAX
Otitis media 42	Curative	Approved 8,583	SUPRAX
Pharyngitis 31	Curative	Approved 8,583	SUPRAX
Chronic bronchitis 52	Curative	Approved 8,583	SUPRAX
Gonorrhea 30	Curative	Approved 8,583	SUPRAX

C_max

Value	Dose	Analyte	Population
4.74 mg/L	400 mg 1 times / day steady-state, oral	CEFIXIME ANHYDROUS serum	Homo sapiens
3.696 μg/mL	200 mg single, oral	CEFIXIME plasma	Homo sapiens
1.837 μg/mL	200 mg single, oral	CEFIXIME plasma	Homo sapiens
4.74 mg/L	400 mg 1 times / day steady-state, oral	CEFIXIME serum	Homo sapiens
5.68 mg/L	400 mg 1 times / day steady-state, oral	CEFIXIME serum	Homo sapiens
0.69 μg/mL	50 mg single, oral	CEFIXIME serum	Homo sapiens
1.13 μg/mL	100 mg single, oral	CEFIXIME serum	Homo sapiens
1.95 μg/mL	200 mg single, oral	CEFIXIME serum	Homo sapiens

AUC

Value	Dose	Analyte	Population
34.9 mg × h/L	400 mg 1 times / day steady-state, oral	CEFIXIME ANHYDROUS serum	Homo sapiens
30.211 μg × h/mL	200 mg single, oral	CEFIXIME plasma	Homo sapiens
15.864 μg × h/mL	200 mg single, oral	CEFIXIME plasma	Homo sapiens
34.9 mg × h/L	400 mg 1 times / day steady-state, oral	CEFIXIME serum	Homo sapiens
49.5 mg × h/L	400 mg 1 times / day steady-state, oral	CEFIXIME serum	Homo sapiens
5.32 μg × h/mL	50 mg single, oral	CEFIXIME serum	Homo sapiens
8.66 μg × h/mL	100 mg single, oral	CEFIXIME serum	Homo sapiens
14.99 μg × h/mL	200 mg single, oral	CEFIXIME serum	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.5 h	400 mg 1 times / day steady-state, oral	CEFIXIME ANHYDROUS serum	Homo sapiens
3.479 h	200 mg single, oral	CEFIXIME plasma	Homo sapiens
3.461 h	200 mg single, oral	CEFIXIME plasma	Homo sapiens
3.5 h	400 mg 1 times / day steady-state, oral	CEFIXIME serum	Homo sapiens
4.2 h	400 mg 1 times / day steady-state, oral	CEFIXIME serum	Homo sapiens
2.54 h	50 mg single, oral	CEFIXIME serum	Homo sapiens
2.38 h	100 mg single, oral	CEFIXIME serum	Homo sapiens
2.29 h	200 mg single, oral	CEFIXIME serum	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
35%	400 mg 1 times / day steady-state, oral		CEFIXIME ANHYDROUS serum	Homo sapiens
35%			CEFIXIME serum	Homo sapiens

Doses

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Dose	Population	Adverse events
800 mg 3 times / day multiple, oral Highest studied dose	healthy, ADULT
400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Diarrhea, Vomiting... Other AEs: Nausea...
400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Hypersensitivity, Diarrhea, Clostridium difficile...
200 mg 2 times / day steady, oral Recommended	unhealthy, adult	Other AEs: Perioral dermatitis...
8 mg/kg 1 times / day multiple, oral Recommended	unhealthy, children

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AEs

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AE	Significance	Dose	Population
Nausea	0.8%	400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
Increased urinary frequency	0.8% Disc. AE	400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
Vomiting	0.8% Disc. AE	400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
Diarrhea	2.5% Disc. AE	400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT
Diarrhea, Clostridium difficile	Disc. AE	400 mg 1 times / day multiple, oral Recommended	unhealthy, ADULT

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 activator 150		inhibitor 2,507 activator 25

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A 70 CYP2B6 926 CYP2C8/9 42 CYP2C19 2,057 CYP2E1 1,060

Drug as perpetrator

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Target	Modality	Activity
CYP1A 122	activator 342	no
CYP1A 122	inhibitor 4,027	no
CYP2B6 1,160	activator 342	no
CYP2B6 1,160	inhibitor 4,027	no
CYP2C19 2,141	activator 342	no

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
AK Scientific	K403
Alfa Chemistry	ACM97164562
BioSynth	J-501698
BOC Sciences	97164-56-2
Capot Chemical	13762

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PubMed

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Title	Date	PubMed
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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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).

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Name

Type

Language

CEFIXIME ANHYDROUS

Common Name

English

ANHYDROUS CEFIXIME

Preferred Name

English

Cefixime [WHO-DD]

Common Name

English

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

Systematic Name

English

CEFIXIME [MI]

Common Name

English

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Classification Tree

Code System

Code

Third-generation cephalosporins

WHO-ATC

J01DD08

Established Pharmacologic Class

NDF-RT

N0000175488

Cephalosporins, Oral

LIVERTOX

NBK548358

Cephalosporins

LIVERTOX

NBK548666

beta-Lactams

NDF-RT

N0000011161

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Code System

Code

Type

Description

EVMPD

SUB07395MIG

PRIMARY

EPA CompTox

DTXSID7022754

PRIMARY

EVMPD

SUB70432

PRIMARY

MERCK INDEX

m3195

PRIMARY

DRUG BANK

DB00671

PRIMARY

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ACTIVE MOIETY


					XZ7BG04GJX

CEFIXIME ANHYDROUS

SALT/SOLVATE (PARENT)


					97I1C92E55

CEFIXIME

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator