Cefalotin

Cefalotin: Cefalotin

Systematic (IUPAC) name

(6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Clinical data

AHFS/Drugs.com International Drug Names

MedlinePlus a682860

Pregnancy cat. A(AU)

Legal status Prescription Only (S4) (AU) POM (UK)

Routes IV

Pharmacokinetic data

Bioavailability n/a

Protein binding 65 to 80%

Metabolism Hepatic

Half-life 30 minutes to 1 hour

Excretion Renal

Identifiers

CAS number 153-61-7

ATC code J01DB03

PubChem CID 6024

DrugBank APRD00859

ChemSpider 5802^Y

UNII R72LW146E6^Y

KEGG D07635^Y

ChEBI CHEBI:124991^Y

ChEMBL CHEMBL617^Y

Chemical data

Formula C₁₆H₁₆N₂O₆S₂

Mol. mass 396.44 g/mol

SMILES eMolecules & PubChem

InChI

InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1^Y
Key:XIURVHNZVLADCM-IUODEOHRSA-N^Y

Y(what is this?) (verify)

Cefalotin (INN) ( /ˌsɛfəˈloʊtɨn/) or cephalothin (USAN) ( /ˌsɛfəˈloʊθɨn/) is a first-generation cephalosporin antibiotic. It was the first cephalosporin marketed and continues to be widely used. It is an intravenously administered agent with a similar antimicrobial spectrum to cefazolin and the oral agent cefalexin. Cefalotin sodium is commonly marketed under the trade name Keflin (Lilly).

See also

Cephalosporin

Cefalexin

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)

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Cefalotin

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Systematic (IUPAC) name
(6R,7R)-3-[(acetoxy)methyl]-8-oxo-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
AHFS/Drugs.com	International Drug Names
MedlinePlus	a682860
Pregnancy cat.	A(AU)
Legal status	Prescription Only (S4) (AU) POM (UK)
Routes	IV
Pharmacokinetic data
Bioavailability	n/a
Protein binding	65 to 80%
Metabolism	Hepatic
Half-life	30 minutes to 1 hour
Excretion	Renal
Identifiers
CAS number	153-61-7
ATC code	J01DB03
PubChem	CID 6024
DrugBank	APRD00859
ChemSpider	5802^Y
UNII	R72LW146E6^Y
KEGG	D07635^Y
ChEBI	CHEBI:124991^Y
ChEMBL	CHEMBL617^Y
Chemical data
Formula	C₁₆H₁₆N₂O₆S₂
Mol. mass	396.44 g/mol
SMILES	eMolecules & PubChem
InChI InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1^Y Key:XIURVHNZVLADCM-IUODEOHRSA-N^Y
Y(what is this?) (verify)

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Wikipedia

Cefalotin

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