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Cefluprenam

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Cefluprenam
Names

IUPAC name (6R,7R)-3-[(E)-3-[(2-amino-2-oxoethyl)-ethyl-methylazaniumyl]prop-1-enyl]-7-[[(2Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-(fluoromethoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
Other names Antibiotic E 1077
Identifiers
CAS Number	116853-25-9^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL2074822^N
ChemSpider	5020189^N
KEGG	D01054^Y
PubChem CID	6536774
UNII	098633Q42P^Y
CompTox Dashboard (EPA)	DTXSID001029568
InChI InChI=1S/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1^N Key: XAKKNLNAJBNLPC-MAYKBZFQSA-N^N InChI=1/C20H25FN8O6S2/c1-3-29(2,7-11(22)30)6-4-5-10-8-36-18-13(17(32)28(18)14(10)19(33)34)24-16(31)12(26-35-9-21)15-25-20(23)37-27-15/h4-5,13,18H,3,6-9H2,1-2H3,(H5-,22,23,24,25,27,30,31,33,34)/b5-4+,26-12-/t13-,18-,29?/m1/s1 Key: XAKKNLNAJBNLPC-MAYKBZFQBE
SMILES O=C2N1/C(=C(/C=C/C[N+](CC(=O)N)(CC)C)CS[C@@H]1[C@@H]2NC(=O)C(=N\OCF)/c3nc(sn3)N)C([O-])=O
Properties
Chemical formula	C₂₀H₂₅FN₈O₆S₂
Molar mass	556.59 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is ^YN ?) Infobox references

Cefluprenam is a fourth generation cephalosporin.^[1] It was patented in 2008 by now defunct Cubist Pharmaceuticals.^[2] A 1997 clinical trial illustrated that Cefluprenam is highly effective against bacterial pneumonia.^[3]

References[edit]

^ PubChem. "Cefluprenam". pubchem.ncbi.nlm.nih.gov. Retrieved 2022-08-03.

^ EU patent 2379580B1, Pearson, Lee Andre; Metcalf, A. Chester & Li, Jing, "Novel antibacterial agents for the treatment of gram positive infections", published 2011-10-26, issued 2013-10-23

^ Shimada, K.; Ohmichi, M.; Sasaki, H.; Watanabe, A.; Sato, K.; Nagai, K.; Konishi, K.; Ohta, T.; Matsuura, Y.; Ikeda, H.; Igarashi, K. (August 1997). "[Usefulness of 7 day therapy with cefluprenam in the management of respiratory tract infections]". Kansenshogaku Zasshi. The Journal of the Japanese Association for Infectious Diseases. 71 (8): 770–787. doi:10.11150/kansenshogakuzasshi1970.71.770. ISSN 0387-5911. PMID 9311195.

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

Beta-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)

β-lactamase resistant
(2nd generation)

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

β-lactamase inhibitors

Combinations

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

This systemic antibiotic-related article is a stub. You can help Wikipedia by expanding it.

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Retrieved from "https://en.wikipedia.org/w/index.php?title=Cefluprenam&oldid=1172411390" Categories: ●Cephalosporin antibiotics ●Thiadiazoles ●Quaternary ammonium compounds ●Acetamides ●Organofluorides ●Antibiotic stubs Hidden categories: ●Articles with changed EBI identifier ●Articles with changed ChemSpider identifier ●Articles with changed InChI identifier ●Articles containing unverified chemical infoboxes ●Chembox image size set ●Articles with short description ●Short description matches Wikidata ●All stub articles ●This page was last edited on 26 August 2023, at 22:36 (UTC). ●Text is available under the Creative Commons Attribution-ShareAlike License 4.0; additional terms may apply. By using this site, you agree to the Terms of Use and Privacy Policy. Wikipedia® is a registered trademark of the Wikimedia Foundation, Inc., a non-profit organization. ●Privacy policy ●About Wikipedia ●Disclaimers ●Contact Wikipedia ●Code of Conduct ●Developers ●Statistics ●Cookie statement ●Mobile view