Cefonicid

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Cefonicid
Cefonicid.png
Clinical data
AHFS/Drugs.com Micromedex Detailed Consumer Information
MedlinePlus a601206
ATC code
Identifiers
  • (6R,7R)-7-[(2R)-2-hydroxy-2-phenylacetyl)amino]-8-oxo-
    3-{[1-(sulfomethyl)tetrazol-5-yl]sulfanylmethyl}-
    5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
Formula C18H18N6O8S3
Molar mass 542.56 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)[C@H](O)c3ccccc3)CSc4nnnn4CS(=O)(=O)O)C(=O)O
  • InChI=1S/C18H18N6O8S3/c25-13(9-4-2-1-3-5-9)14(26)19-11-15(27)24-12(17(28)29)10(6-33-16(11)24)7-34-18-20-21-22-23(18)8-35(30,31)32/h1-5,11,13,16,25H,6-8H2,(H,19,26)(H,28,29)(H,30,31,32)/t11-,13-,16-/m1/s1 Yes check.svgY
  • Key:DYAIAHUQIPBDIP-AXAPSJFSSA-N Yes check.svgY
   (verify)

Cefonicide (or cefonicid) is a cephalosporin antibiotic. [1]

Contents

It has a density of 1.92g/cm3.

Synthesis

Injectable semi-synthetic cephalosporin antibiotic related to cefamandole, q.v.

Cefonicid synthesis: Cefonicid synthesis.svg
Cefonicid synthesis:

Cefonicid is synthesized conveniently by nucleophilic displacement of the 3-acetoxy moiety of 1 with the appropriately substituted tetrazole thiole 2. The mandelic acid amide C-7 side chain is reminiscent of cefamandole.

See also

Related Research Articles

This is the timeline of modern antimicrobial (anti-infective) therapy. The years show when a given drug was released onto the pharmaceutical market. This is not a timeline of the development of the antibiotics themselves.

<span class="mw-page-title-main">Cephalosporin</span> Class of pharmaceutical drugs

The cephalosporins are a class of β-lactam antibiotics originally derived from the fungus Acremonium, which was previously known as Cephalosporium.

<span class="mw-page-title-main">Cefazolin</span> Antibiotic medication

Cefazolin, also known as cefazoline and cephazolin, is a first-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. Specifically it is used to treat cellulitis, urinary tract infections, pneumonia, endocarditis, joint infection, and biliary tract infections. It is also used to prevent group B streptococcal disease around the time of delivery and before surgery. It is typically given by injection into a muscle or vein.

<span class="mw-page-title-main">Cefuroxime</span> Antibiotic medication

Cefuroxime, sold under the brand name Zinacef among others, is a second-generation cephalosporin antibiotic used to treat and prevent a number of bacterial infections. These include pneumonia, meningitis, otitis media, sepsis, urinary tract infections, and Lyme disease. It is used by mouth or by injection into a vein or muscle.

<span class="mw-page-title-main">Cefalexin</span> Beta-lactam antibiotic

Cefalexin, also spelled cephalexin, is an antibiotic that can treat a number of bacterial infections. It kills gram-positive and some gram-negative bacteria by disrupting the growth of the bacterial cell wall. Cefalexin is a β-lactam antibiotic within the class of first-generation cephalosporins. It works similarly to other agents within this class, including intravenous cefazolin, but can be taken by mouth.

<span class="mw-page-title-main">Cefixime</span> A third generation cephalosporin antibiotic

Cefixime, sold under the brand name Suprax among others, is an antibiotic medication used to treat a number of bacterial infections. These infections include otitis media, strep throat, pneumonia, urinary tract infections, gonorrhea, and Lyme disease. For gonorrhea typically only one dose is required. In the United States it is a second-line treatment to ceftriaxone for gonorrhea. It is taken by mouth.

<span class="mw-page-title-main">Cephem</span> Class of beta-lactam antibiotic

Cephems are a sub-group of β-lactam antibiotics including cephalosporins and cephamycins. It is one of the most common 4-membered ring heterocycle. Produced by actinomycetes, cephamycins were found to display antibacterial activity against a wide range of bacteria, including those resistant to penicillin and cephalosporins. The antimicrobial properties of Cephem include the attachment to certain penicillin-binding proteins that are involved in the production of cell walls of bacteria.

<span class="mw-page-title-main">Cefuroxime axetil</span> Chemical compound

Cefuroxime axetil, sold under the brand name Ceftin among others, is a second generation oral cephalosporin antibiotic.

<span class="mw-page-title-main">Ticarcillin</span> Antibiotic medication

Ticarcillin is a carboxypenicillin. It can be sold and used in combination with clavulanate as ticarcillin/clavulanic acid. Because it is a penicillin, it also falls within the larger class of β-lactam antibiotics. Its main clinical use is as an injectable antibiotic for the treatment of Gram-negative bacteria, particularly Pseudomonas aeruginosa and Proteus vulgaris. It is also one of the few antibiotics capable of treating Stenotrophomonas maltophilia infections.

<span class="mw-page-title-main">Cefepime</span> Fourth-generation Cephalosporin Antibiotic

Cefepime is a fourth-generation cephalosporin antibiotic. Cefepime has an extended spectrum of activity against Gram-positive and Gram-negative bacteria, with greater activity against both types of organism than third-generation agents. A 2007 meta-analysis suggested when data of trials were combined, mortality was increased in people treated with cefepime compared with other β-lactam antibiotics. In response, the U.S. Food and Drug Administration (FDA) performed their own meta-analysis which found no mortality difference.

<span class="mw-page-title-main">Cefradine</span> Chemical compound

Cefradine (INN) or cephradine (BAN) is a first generation cephalosporin antibiotic.

<span class="mw-page-title-main">Cefdinir</span> Chemical compound

Cefdinir, sold under the brand name Omnicef among others, is an antibiotic used to treat pneumonia, otitis media, strep throat, and cellulitis. It is a less preferred option for pneumonia, otitis media, and strep throat which may be used in those with a severe allergy to penicillin. It is taken by mouth.

<span class="mw-page-title-main">Oxacillin</span> Chemical compound

Oxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class developed by Beecham.

<span class="mw-page-title-main">Cefoperazone</span> Antibiotic

Cefoperazone is a third-generation cephalosporin antibiotic, marketed by Pfizer under the name Cefobid. It is one of few cephalosporin antibiotics effective in treating Pseudomonas bacterial infections which are otherwise resistant to these antibiotics.

Nifuroxazide (INN) is an oral nitrofuran antibiotic, patented since 1966 and used to treat colitis and diarrhea in humans and non-humans. It is sold under the brand names Ambatrol, Antinal, Bacifurane, Diafuryl (Turkey), Benol (Pakistan), Pérabacticel (France), Antinal, Diax (Egypt), Nifrozid, Ercefuryl, Erfuzide (Thailand), Endiex (Slovakia), Enterofuryl, Pentofuryl (Germany), Nifuroksazyd Hasco, Nifuroksazyd Polpharma (Poland), Topron, Enterovid, Eskapar (Mexico), Enterocolin, Terracolin (Bolivia), Apazid (Morocco), Nifroxid (Tunisia), Nifural (Indonesia) and Septidiaryl. It is sold in capsule form and also as a suspension.

<span class="mw-page-title-main">Cefamandole</span> Chemical compound

Cefamandole is a second-generation broad-spectrum cephalosporin antibiotic. The clinically used form of cefamandole is the formate ester cefamandole nafate, a prodrug which is administered parenterally. Cefamandole is no longer available in the United States.

<span class="mw-page-title-main">Cefroxadine</span> Chemical compound

Cefroxadine is a cephalosporin antibiotic. It is structurally related to cefalexin, and both drugs share a similar spectrum of activity.

<span class="mw-page-title-main">Cefatrizine</span> Chemical compound

Cefatrizine is a broad-spectrum cephalosporin antibiotic.

<span class="mw-page-title-main">Ceftolozane/tazobactam</span> Antibiotic

Ceftolozane/tazobactam, sold under the brand name Zerbaxa, is a combination antibiotic medication used for the treatment of complicated urinary tract infections and complicated intra-abdominal infections in adults. Ceftolozane is a cephalosporin antibiotic, developed for the treatment of infections with gram-negative bacteria that are resistant to conventional antibiotics. It was studied for urinary tract infections, intra-abdominal infections and ventilator-associated bacterial pneumonia.

<i>SmithKline Corp. v. Eli Lilly & Co.</i>

SmithKline Corp. v. Eli Lilly and Co., 575 F.2d 1056, is a 1978 decision of the United States Court of Appeals for the Third Circuit that first considered the price-discounting practice now termed bundling. Bundling is the setting of the total price of a purchase of several products or services from one seller at a lower level than the sum of the prices of the products or services purchased separately from several sellers. Typically, one of the bundled items is available only from the seller engaging in the bundling, while the other item or items can be obtained from several sellers. The effect of the practice is to divert purchasers who need the primary product to the bundling seller and away from other sellers of only the secondary product. For that reason, the practice may be held an antitrust violation as it was in the SmithKline v. Lilly case, in which the Third Circuit held that Lilly engaged in monopolization in violation of Sherman Act § 2.

References

  1. Saltiel E, Brogden RN (September 1986). "Cefonicid. A review of its antibacterial activity, pharmacological properties and therapeutic use". Drugs. 32 (3): 222–59. doi:10.2165/00003495-198632030-00002. PMID   3530703. S2CID   243051006.
  2. DE 2611270,Berges, David Alan,"Cephalosporin-Derivate [Cephalosporin derivatives]",published 1976-09-30, assigned to SmithKline Corp.
  3. D. A. Berges, U.S. Patent 4,048,311 (1977 to Smith Kline).
  4. U.S. Patent 4,093,723 , U.S. Patent 4,159,373 (1978, 1979 both to Smith Kline).