Panipenem

Panipenem
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01DH55 (WHO) (with betamipron)
Identifiers
IUPAC name (5R,6S)-3-{[(3S)-1-ethanimidoylpyrrolidin-3-yl]sulfanyl}- 6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene- 2-carboxylic acid
CAS Number	87726-17-8^Y
PubChem CID	72015
ChemSpider	16736434^N
UNII	W9769W09JF
KEGG	D01048
ChEMBL	ChEMBL339323^N
CompTox Dashboard (EPA)	DTXSID20868982
Chemical and physical data
Formula	C₁₅H₂₁N₃O₄S
Molar mass	339.41 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@H]([C@@H]1[C@H]2CC(=C(N2C1=O)C(=O)O)S[C@H]3CCN(C3)C(=N)C)O
InChI InChI=1S/C15H21N3O4S/c1-7(19)12-10-5-11(13(15(21)22)18(10)14(12)20)23-9-3-4-17(6-9)8(2)16/h7,9-10,12,16,19H,3-6H2,1-2H3,(H,21,22)/t7-,9+,10-,12-/m1/s1^N Key:TYMABNNERDVXID-DLYFRVTGSA-N^N
^NY (what is this?) (verify)

Panipenem (INN) is a carbapenem antibiotic used in combination with betamipron.^[1] It is not used in the United States.^{[citation needed]}

References

^ Goa KL, Noble S (2003). "Panipenem/betamipron". Drugs. 63 (9): 913–25, discussion 926. doi:10.2165/00003495-200363090-00005. PMID 12678575. S2CID 263994230.

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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