Cefixime

Cefixime: Cefixime

Systematic (IUPAC) name

(6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxy
methoxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia-
1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Clinical data

Trade names Suprax

AHFS/Drugs.com monograph

MedlinePlus a690007

Pregnancy cat. B

Legal status ?

Routes Oral

Pharmacokinetic data

Bioavailability 40% to 50%

Protein binding Approximately 60%

Half-life Variable
Average 3 to 4 hours

Excretion Renal and biliary

Identifiers

CAS number 79350-37-1^Y

ATC code J01DD08

PubChem CID 5362065

DrugBank APRD00583

ChemSpider 4514923^Y

UNII 97I1C92E55^Y

KEGG D00258^Y

ChEBI CHEBI:472657^Y

ChEMBL CHEMBL1541^Y

Chemical data

Formula C₁₆H₁₅N₅O₇S₂

Mol. mass 453.452 g/mol

SMILES eMolecules & PubChem

InChI

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^Y
Key:OKBVVJOGVLARMR-QSWIMTSFSA-N^Y

Y(what is this?) (verify)

Cefixime is an oral third generation cephalosporin antibiotic. Cefixime is a cephalosporin antibiotic used to treat infections caused by bacteria such as pneumonia; bronchitis; gonorrhea; and ear, lung, throat, and urinary tract infections. Antibiotics will not work for colds, flu, or other viral infections.

It was sold under the trade name Suprax in the USA until 2003 when it was taken off the market by drug manufacturer Wyeth after its patent expired. The oral suspension form of "Suprax" was re-launched by Lupin in the USA.

Cefixime API is manufactured by many pharmaceutical companies the world over. The major manufacturers are based in India.

References

http://www.nlm.nih.gov/medlineplus/druginfo/meds/a690007.html

v · d · eAntibacterials: cell envelope antibiotics (J01C-J01D)

Intracellular
inhibit peptidoglycan subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin) • DADAL/AR inhibitors (Cycloserine) • bactoprenol inhibitors (Bacitracin)

Glycopeptide
inhibit PG chain elongation: Vancomycin^# (Oritavancin, Telavancin) • Teicoplanin (Dalbavancin) • Ramoplanin

β-lactams/
(inhibit PBP
cross-links)

Penicillins/
(penams)

Extended sp.

aminopenicillins: Amoxicillin^# • Ampicillin^# (Pivampicillin, Hetacillin, Bacampicillin, Metampicillin, Talampicillin) • Epicillin

carboxypenicillins: Carbenicillin (Carindacillin) • Ticarcillin • Temocillin

ureidopenicillins: Azlocillin • Piperacillin • Mezlocillin
other: Mecillinam (Pivmecillinam) • Sulbenicillin

Narrow sp.

β-lactamase sensitive

Benzylpenicillin (G)^#: Clometocillin • Benzathine benzylpenicillin^# • Procaine benzylpenicillin^# • Azidocillin • Penamecillin
Phenoxymethylpenicillin (V)^#: Propicillin • Benzathine phenoxymethylpenicillin • Pheneticillin

β-lactamase resistant

Cloxacillin^# (Dicloxacillin, Flucloxacillin) • Oxacillin • Meticillin • Nafcillin

Penems

Faropenem

Carbapenems

Biapenem • Ertapenem • antipseudomonal (Doripenem • Imipenem • Meropenem) • Panipenem

Cephalosporins/
(cephems)

1st (P Ec K)

Cefazolin^# • Cefacetrile • Cefadroxil • Cefalexin • Cefaloglycin • Cefalonium • Cefaloridine • Cefalotin • Cefapirin • Cefatrizine • Cefazedone • Cefazaflur • Cefradine • Cefroxadine • Ceftezole

2nd (H E N)

Cefaclor • Cefamandole • Cefminox • Cefonicid • Ceforanide • Cefotiam • Cefprozil • Cefbuperazone • Cefuroxime • Cefuzonam • cephamycin (Cefoxitin, Cefotetan, Cefmetazole) • carbacephem (Loracarbef)

3rd

Cefixime^# • Ceftriaxone^# • antipseudomonal (Ceftazidime^# • Cefoperazone) • Cefcapene • Cefdaloxime • Cefdinir • Cefditoren • Cefetamet • Cefmenoxime • Cefodizime • Cefotaxime • Cefpimizole • Cefpiramide • Cefpodoxime • Cefsulodin • Cefteram • Ceftibuten • Ceftiolene • Ceftizoxime • oxacephem (Flomoxef, Latamoxef ^‡)

4th (antips-)

Cefepime • Cefozopran • Cefpirome • Cefquinome

5th

Ceftobiprole • Ceftaroline fosamil

Veterinary

Ceftiofur • Cefquinome • Cefovecin

Monobactams

Aztreonam • Tigemonam • Carumonam • Tabtoxin

β-lactamase inh.

penam (Sulbactam, Tazobactam) • clavam (Clavulanic acid)

Combinations

Amoxicillin/clavulanic acid^# • Imipenem/cilastatin^# • Ampicillin/flucloxacillin • Ampicillin/sulbactam (Sultamicillin) • Piperacillin/tazobactam

Other
polymyxins/detergent (Colistin, Polymyxin B) • depolarizing (Daptomycin) • hydrolyze NAM-NAG (Lysozyme) • Gramicidin

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: BAC

bact (clas)

gr+f/gr+a(t)/gr-p(c)/gr-o

drug(J1p, w, n, m, vacc)

Categories:
Cephalosporin antibiotics
Thiazoles

Cefixime

Systematic (IUPAC) name
(6R,7R)-7-{[2-(2-amino-1,3-thiazol-4-yl)-2-(carboxy methoxyimino)acetyl]amino}-3-ethenyl-8-oxo-5-thia- 1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Suprax
AHFS/Drugs.com	monograph
MedlinePlus	a690007
Pregnancy cat.	B
Legal status	?
Routes	Oral
Pharmacokinetic data
Bioavailability	40% to 50%
Protein binding	Approximately 60%
Half-life	Variable Average 3 to 4 hours
Excretion	Renal and biliary
Identifiers
CAS number	79350-37-1^Y
ATC code	J01DD08
PubChem	CID 5362065
DrugBank	APRD00583
ChemSpider	4514923^Y
UNII	97I1C92E55^Y
KEGG	D00258^Y
ChEBI	CHEBI:472657^Y
ChEMBL	CHEMBL1541^Y
Chemical data
Formula	C₁₆H₁₅N₅O₇S₂
Mol. mass	453.452 g/mol
SMILES	eMolecules & PubChem
InChI 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^Y Key:OKBVVJOGVLARMR-QSWIMTSFSA-N^Y
Y(what is this?) (verify)

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Céfixime — Général Nom IUPAC Acide (6R,7R) 7 ({(2E) 2 (2 amino 1,3 thiazol 4 yl) 2 [(carboxyméthoxy)imino]acétyl}amino) 3 éthényl 8 oxo 5 thia 1 azabicyclo[4.2.0]oct 2 ène 2 carboxylique … Wikipédia en Français
cefixime — noun An oral cephalosporin antibiotic used to treat gonorrhea, tonsillitis, pharyngitis and otitis media … Wiktionary
cefixime — cef·ix·ime .sef iks .ēm n a semisynthetic cephalosporin antibiotic C16H15N5O7S2 that is administered orally and is effective esp. against gram negative bacteria and streptococci * * * ce·fix·ime (sə fikґsēm) [USP] a semisynthetic, third … Medical dictionary
cefixime — An antibiotic drug used to treat infection. It belongs to the family of drugs called cephalosporins … English dictionary of cancer terms
Cephalosporin — See also: Discovery and development of cephalosporins Core structure of the cephalosporins … Wikipedia
Cefixim — Strukturformel Allgemeines Freiname Cefixim Andere Namen … Deutsch Wikipedia
Curcumin — IUPAC name (1E,6E) 1,7 bis (4 hydroxy 3 methoxyphenyl) 1,6 heptadiene 3,5 dione … Wikipedia
Nectar Lifesciences — Limited Type Public Traded as BSE: 532649 … Wikipedia
Discovery and development of cephalosporins — Cephalosporins are a broad class of bactericidal antibiotics that include the β lactam ring and share a structural similarity and mechanism of action with other β lactam antibiotics (e.g. penicillins, carbapenems and aztreonam).[1] The… … Wikipedia
Ampicillin — Systematic (IUPAC) name (2S,5R,6R) 6 ([(2R) 2 amino 2 phenylace … Wikipedia

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Cefixime

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