Biapenem - Misplaced Pages

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Biapenem
Clinical data

Trade names	Omegacin
AHFS/Drugs.com	International Drug Names
Routes of administration	IV
ATC code	J01DH05 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (4R,5S,6S)-3-(6,7-dihydro-5H- pyrazolo triazol-8- ium-6-ylsulfanyl)- 6-(1-hydroxyethyl)- 4-methyl-7-oxo-1-azabicyclohept-2- ene-2-carboxylate
CAS Number	120410-24-4
PubChem CID	71339
ChemSpider	64442
UNII	YR5U3L9ZH1
ChEBI	CHEBI:3089
ChEMBL	ChEMBL285347
CompTox Dashboard (EPA)	DTXSID5046435
Chemical and physical data
Formula	C₁₅H₁₈N₄O₄S
Molar mass	350.39 g·mol
3D model (JSmol)	Interactive image
SMILES CC1C2C(C(=O)N2C(=C1SC3CN4C=NC=4C3)C(=O))C(C)O
InChI InChI=1S/C15H18N4O4S/c1-7-11-10(8(2)20)14(21)19(11)12(15(22)23)13(7)24-9-3-17-5-16-6-18(17)4-9/h5-11,20H,3-4H2,1-2H3/t7-,8-,10-,11-/m1/s1 Key:MRMBZHPJVKCOMA-YJFSRANCSA-N
(verify)

Biapenem (INN) is a carbapenem antibiotic. It has in vitro activity against anaerobes. 1-β-methyl-carbapenem antibiotic. Approved in Japan in 2001.

References

Aldridge KE, Morice N, Schiro DD (April 1994). "In vitro activity of biapenem (L-627), a new carbapenem, against anaerobes". Antimicrob. Agents Chemother. 38 (4): 889–93. doi:10.1128/aac.38.4.889. PMC 284564. PMID 8031067.

External links

(in Japanese) Omegacin

Antibacterials active on the cell wall and envelope (J01C-J01D)

β-lactams
(inhibit synthesis
of peptidoglycan
layer of bacterial
cell wall by binding
to and inhibiting
PBPs, a group of
D-alanyl-D-alanine
transpeptidases)

Penicillins (Penams)

Narrow
spectrum

β-lactamase sensitive (1st generation)	Benzylpenicillin (G) Benzathine benzylpenicillin Procaine benzylpenicillin Phenoxymethylpenicillin (V) Propicillin Pheneticillin Azidocillin Clometocillin Penamecillin
β-lactamase resistant (2nd generation)	Cloxacillin (Dicloxacillin Flucloxacillin) Oxacillin Nafcillin Methicillin

Extended
spectrum

Aminopenicillins (3rd generation)	Amoxicillin Ampicillin (Pivampicillin Hetacillin Bacampicillin Lenampicillin Metampicillin Talampicillin) Epicillin
Carboxypenicillins (4th generation)	Ticarcillin Carbenicillin / Carindacillin Temocillin
Ureidopenicillins (4th generation)	Piperacillin Azlocillin Mezlocillin
Other	Mecillinam (Pivmecillinam) Sulbenicillin

Carbapenems / Penems

Cephems
Cephalosporins
Cephamycins
Carbacephems

1st generation	Cefazolin Cefalexin Cefadroxil Cefapirin Cefazedone Cefazaflur Cefradine Cefroxadine Ceftezole Cefaloglycin Cefacetrile Cefalonium Cefaloridine Cefalotin Cefatrizine
2nd generation	Cefaclor Cefprozil Cefuroxime Cefuroxime axetil Cefamandole Cefonicid Ceforanide Cefuzonam Cephamycin (Cefoxitin Cefotetan Cefminox Cefbuperazone Cefmetazole) Carbacephem (Loracarbef)
3rd generation	Cefixime Ceftriaxone Cefotaxime Antipseudomonal (Ceftazidime Cefoperazone) Cefdinir Cefcapene Cefdaloxime Ceftizoxime Cefmenoxime Cefpiramide Cefpodoxime Ceftibuten Cefditoren Cefotiam Cefetamet Cefodizime Cefpimizole Cefsulodin Cefteram Ceftiolene Oxacephem (Flomoxef Latamoxef)
4th generation	Cefepime Cefozopran Cefpirome Cefquinome
5th generation	Ceftaroline fosamil Ceftolozane Ceftobiprole
Siderophore	Cefiderocol
Veterinary	Ceftiofur Cefquinome Cefovecin

Monobactams

β-lactamase inhibitors

Combinations

Polypeptides

Lipopeptides	Insert into bacterial cell wall causing perforation and depolarization: Daptomycin Surfactin
Other	Inhibits PG elongation and crosslinking: Ramoplanin

Intracellular

Inhibit PG subunit synthesis and transport: NAM synthesis inhibition (Fosfomycin)
DADAL/AR inhibitors (Cycloserine)
bactoprenol inhibitors (Bacitracin)

Other

WHO-EM
Withdrawn from market
Clinical trials:
- Phase III
- Never to phase III

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