Loracarbef

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Loracarbef

Systematic (IUPAC) name
(6R,7S)-7-[[(2S)-2-amino-2-phenylacetyl]amino]-3-chloro-8-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Clinical data
Trade names	Lorabid
AHFS/Drugs.com	monograph
MedlinePlus	a601206
Legal status	?
Pharmacokinetic data
Protein binding	25%
Identifiers
CAS number	76470-66-1^Y
ATC code	J01DC08
PubChem	CID 5284584
DrugBank	DB00447
ChemSpider	4447634^Y
UNII	W72I5ZT78Z^N
KEGG	D08143^Y
ChEMBL	CHEMBL1013^N
Chemical data
Formula	C₁₆H₁₆Cl N₃O₄
Mol. mass	349.769 g/mol
SMILES Cl\C3=C(/C(=O)O)N2C(=O)[C@@H](NC(=O)[C@@H](c1ccccc1)N)[C@H]2CC3.O
InChI InChI=1S/C16H16ClN3O4.H2O/c17-9-6-7-10-12(15(22)20(10)13(9)16(23)24)19-14(21)11(18)8-4-2-1-3-5-8;/h1-5,10-12H,6-7,18H2,(H,19,21)(H,23,24);1H2/t10-,11-,12+;/m1./s1^Y Key:GPYKKBAAPVOCIW-HSASPSRMSA-N^Y= ^Y= ^Y
N (what is this?) (verify)

Loracarbef is an antibiotic.^[1] Its use was discontinued in 2006.^{[citation needed]} It is a carbacephem, but it is sometimes grouped together with the second-generation cephalosporin antibiotics. It was marketed under the trade name Lorabid. Loracarbef is a synthetic "carba" analogue of cefaclor, and is more stable chemically. Diarrhea is the most common adverse effect with Loracarbef. Side effects are more frequently seen with children under the age of twelve. It received FDA approval in 1991.

References

↑ Biedenbach DJ, Jones RN (February 1994). "Predictive accuracy of disk diffusion test for Proteus vulgaris and Providencia species against five newer orally administered cephalosporins, cefdinir, cefetamet, cefprozil, cefuroxime, and loracarbef". J. Clin. Microbiol. 32 (2): 559–62. PMC 263078. PMID 8150976.

External links

RxList.com - Loracarbef

Antibacterials: 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.

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

Cephalosporins/Cephamycins
(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

β-lactamase inh.

Combinations

Other

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

^#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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