Cefaparole

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Cefaparole
Cefaparole.svg
Identifiers
  • (6R,7R)-7-{[(2R)-2-Amino-2-(4-hydroxyphenyl)acetyl]amino}-3-{[(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
ECHA InfoCard 100.052.097 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C19H19N5O5S3
Molar mass 493.57 g·mol−1
3D model (JSmol)
  • Cc1nnc(s1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)[C@@H](c4ccc(cc4)O)N)SC2)C(=O)O
  • InChI=1S/C19H19N5O5S3/c1-8-22-23-19(32-8)31-7-10-6-30-17-13(16(27)24(17)14(10)18(28)29)21-15(26)12(20)9-2-4-11(25)5-3-9/h2-5,12-13,17,25H,6-7,20H2,1H3,(H,21,26)(H,28,29)/t12-,13-,17-/m1/s1
  • Key:SBUCDZYLTRYMFG-PBFPGSCMSA-N

Cefaparole (cephaparole) is a cephem antibiotic of the cephalosporin subclass [1] that was never marketed.

Related Research Articles

Beta-lactamase Class of enzymes

Beta-lactamases, (β-lactamases) are enzymes produced by bacteria that provide multi-resistance to beta-lactam antibiotics such as penicillins, cephalosporins, cephamycins, monobactams and carbapenems (ertapenem), although carbapenems are relatively resistant to beta-lactamase. Beta-lactamase provides antibiotic resistance by breaking the antibiotics' structure. These antibiotics all have a common element in their molecular structure: a four-atom ring known as a beta-lactam (β-lactam) ring. Through hydrolysis, the enzyme lactamase breaks the β-lactam ring open, deactivating the molecule's antibacterial properties.

Cephalosporin 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.

Ceftriaxone Chemical compound

Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. These include middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease. It is also sometimes used before surgery and following a bite wound to try to prevent infection. Ceftriaxone can be given by injection into a vein or into a muscle.

Cefalexin 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 beta-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.

Cefprozil

Cefprozil is a second-generation cephalosporin antibiotic. It can be used to treat ear infections, skin infections, and other bacterial infections. It comes as a tablet and as a liquid suspension.

Carbapenem Class of highly effective antibiotic agents

Carbapenems are a class of very effective antibiotic agents most commonly used for the treatment of severe bacterial infections. This class of antibiotics is usually reserved for known or suspected multidrug-resistant (MDR) bacterial infections. Similar to penicillins and cephalosporins, carbapenems are members of the beta lactam class of antibiotics, which kill bacteria by binding to penicillin-binding proteins, thus inhibiting bacterial cell wall synthesis. However, these agents individually exhibit a broader spectrum of activity compared to most cephalosporins and penicillins. Furthermore, carbapenems are typically unaffected by emerging antibiotic resistance, even to other beta-lactams.

Cefotaxime

Cefotaxime is an antibiotic used to treat a number of bacterial infections in human, other animals and plant tissue culture. Specifically in human it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

Cefdinir 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.

Cefpiramide

Cefpiramide is a third-generation cephalosporin antibiotic.

Cefquinome

Cefquinome is a fourth-generation cephalosporin with pharmacological and antibacterial properties valuable in the treatment of coliform mastitis and other infections. It is only used in veterinary applications.

Cefditoren Chemical to treat skin infections

Cefditoren also known as cefditoren pivoxil is a broad-spectrum antibiotic, taken by mouth to treat pneumonia and other infections. It is a third-generation oral cephalosporin with a broad spectrum of activity against bacterial pathogens, including both Gram-positive and Gram-negative bacteria, and it is effective against some antibiotic-resistant bacteria because it is not susceptible to hydrolysis by many common beta-lactamases. The United States Food and Drug Administration approved cefditoren pivoxil for adults and adolescents in 2001. In 2018 Zuventus Healthcare received approval for cefditoren pivoxil dry powder for suspension for the treatment of mild to moderate infection in children which are caused by susceptible strains of the designated microorganisms.

Cefodizime

Cefodizime is a 3rd generation cephalosporin antibiotic with broad spectrum activity against aerobic gram positive and gram negative bacteria. Clinically, it has been shown to be effective against upper and lower respiratory tract infections, urinary tract infections, and gonorrhea. Cefodizime is a bactericidal antibiotic that targets penicillin-binding proteins (PBPs) 1A/B, 2, and 3 resulting in the eventual death of the bacterial cell. In vivo experimental models of infection showed that bacterial clearance by this drug is at least as effective compared with other 3rd generation cephalosporins. It has similar adverse effect profile to other 3rd generation cephalosporins as well, mainly being limited to gastrointestinal or dermatological side effects.

Latamoxef Chemical compound

Latamoxef is an oxacephem antibiotic usually grouped with the cephalosporins. In oxacephems such as latamoxef, the sulfur atom of the cephalosporin core is replaced with an oxygen atom.

Cefroxadine

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

Cephaloridine

Cephaloridine is a first-generation semisynthetic derivative of antibiotic cephalosporin C. It is a Beta lactam antibiotic, like penicillin. Its chemical structure contains 3 cephems, 4 carboxyl groups and three pyridinium methyl groups.

Cefonicid Chemical compound

Cefonicide is a cephalosporin antibiotic.

Cefazaflur Cephalosporin antibiotic

Cefazaflur (INN) is a first-generation cephalosporin antibiotic.

Cephalosporins are a broad class of bactericidal antibiotics that include the β-lactam ring and share a structural similarity and mechanism of action with other β-lactam antibiotics. The cephalosporins have the ability to kill bacteria by inhibiting essential steps in the bacterial cell wall synthesis which in the end results in osmotic lysis and death of the bacterial cell. Cephalosporins are widely used antibiotics because of their clinical efficiency and desirable safety profile.

Cephalosporin C Chemical compound

Cephalosporin C is an antibiotic of the cephalosporin class. It was isolated from a fungus of the genus Acremonium and first characterized in 1961. Although not a very active antibiotic itself, synthetic analogs of cephalosporin C, such as cefalotin, became some of the first marketed cephalosporin antibiotic drugs.

Ceftolozane/tazobactam 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.

References

  1. Yamada H, Jimpo K, Tobiki H, Komatsu T, Noguchi H, Irie K, Nakagome T (May 1983). "New broad-spectrum cephalosporins with anti-pseudomonal activity. I. Synthesis and antibacterial activity of 7 beta-[D-2-[(4-hydroxy-1,5-naphthyridine-3-carbonylamino)- and (4-hydroxypyridine-3-carbonylamino)]-2-(4-hydoxyphenyl)acetamido] cephalosporins". The Journal of Antibiotics. 36 (5): 522–31. doi: 10.7164/antibiotics.36.522 . PMID   6409868.