Main menu Navigation ●Main page ●Contents ●Current events ●Random article ●About Wikipedia ●Contact us ●Donate Contribute ●Help ●Learn to edit ●Community portal ●Recent changes ●Upload file

●Create account ●Log in ●Create account ● Log in Pages for logged out editors learn more ●Contributions ●Talk

(Top) 1 Synthesis 2 References

Cefteram

●العربية ●Español ●فارسی ●Српски / srpski ●Srpskohrvatski / српскохрватски ●Tiếng Việt ●中文 Edit links ●Article ●Talk ●Read ●Edit ●View history Tools Actions ●Read ●Edit ●View history General ●What links here ●Related changes ●Upload file ●Special pages ●Permanent link ●Page information ●Cite this page ●Get shortened URL ●Download QR code ●Wikidata item Print/export ●Download as PDF ●Printable version Appearance From Wikipedia, the free encyclopedia

Cefteram
Clinical data

AHFS/Drugs.com	International Drug Names
ATC code	J01DD18 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Identifiers
IUPAC name (6R,7R)-7-([(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino)-3-[(5-methyltetrazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number	82547-58-8
PubChem CID	6537431
ChemSpider	4576594
UNII	74CQ4Q3N63
KEGG	D07655
ChEMBL	ChEMBL2105953
CompTox Dashboard (EPA)	DTXSID7048821
Chemical and physical data
Formula	C₁₆H₁₇N₉O₅S₂
Molar mass	479.49 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)Cn4nc(nn4)C)C(=O)O

Cefteram (INN) is a third-generation cephalosporin antibiotic.^[1]

Synthesis

[edit]

The reaction of 7-aminocephalosporanic acid (1) with the methyl-substituted tetrazole (2) gives the intermediate (3). Protection with diazodiphenylmethane (4) produces (5). Amide formation with the thiazole carboxylic acid (6) gives (7), which is deprotected with trifluoroacetic acid to yield cefteram.^[2]^[3]

[edit]

^ Yamaguchi K, Ohno A, Takahashi S, Hayashi M, Yamanaka K, Hirakata Y, Mitsuyama J (January 1998). "[In vitro antibacterial activities of cefteram and other beta-lactam agents against recent clinical isolates]". The Japanese Journal of Antibiotics. 51 (1): 11–25. PMID 9557273.

^ "Cefteram". chemdrug.com. Retrieved 2024-07-03.

^ US patent 4489072, Hiroshi Sadaki, et al., issued 1984-12-18, assigned to Toyama Chemical Co Ltd

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)

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^‡

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

Combinations

Insert into bacterial cell wall causing perforation and depolarization: Daptomycin
Surfactin

Other

Intracellular

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

Other

^‡Withdrawn from market

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