Cefixime

Also known as CL-284635, FK-027, FR-17027, cefixime anhydrous, (−)-cefixime, suprax

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

In the Vinony graph

Within Vinony's link graph, Cefixime is referenced by 213 other articles, and connects out to antibiotic, ceftolozane/tazobactam and penicillin binding proteins.

It is catalogued under topics including Cephalosporin antibiotics, Dermatoxins and Drugboxes which contain changes to verified fields.

Its subject is documented across 30 Wikipedia language editions.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.verifiedrevid: 460023156
Drug.image: Cefixime skeletal structure.svg
Drug.image_class: skin-invert-image
Drug.image2: Cefixime ball-and-stick model from xtal 2013.png
Drug.image_class2: bg-transparent
Drug.tradename: Suprax, others
Drug.MedlinePlus: a690007
Drug.DailyMedID: Cefixime
Drug.routes_of_administration: By mouth
Drug.ATC_prefix: J01
Drug.ATC_suffix: DD08
Drug.legal_CA: Rx-only
Drug.legal_UK: POM
Drug.legal_US: Rx-only
Drug.legal_status: Rx-only
Drug.bioavailability: 30 to 50%

via Wikipedia infobox

Chemical data

Formula: C16H15N5O7S2
Molecular weight: 453.5 g/mol
IUPAC name: (6R,7R)-7-[[(2Z)-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
SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
InChIKey: OKBVVJOGVLARMR-QSWIMTSFSA-N
XLogP: -0.7
Polar surface area: 238 Å²
H-bond donors: 4
H-bond acceptors: 12
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1989
Admin. routes: oral
Indications: Otitis media, infection, neoplasm, osteomyelitis

via ChEMBL · EBI

Wikidata facts

Subclass of: cephalosporin antibiotic
Mass: 453.04128982000003
Has use: medication

Show 9 more facts

chemical formula: C₁₆H₁₅N₅O₇S₂
subject has role: enzyme inhibitor
medical condition treated: otitis media
canonical SMILES: C=CC1=C(N2C(C(C2=O)NC(=O)C(=NOCC(=O)O)C3=CSC(=N3)N)SC1)C(=O)O
isomeric SMILES: C=CC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OCC(=O)O)/C3=CSC(=N3)N)SC1)C(=O)O
World Health Organisation international non-proprietary name: cefixime
NCI Thesaurus ID: C1100
defined daily dose: 0.4
Commons category: Cefixime