Cefapirin

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Cefapirin
Cefapirin.svg
Clinical data
AHFS/Drugs.com International Drug Names
MedlinePlus a601206
Routes of
administration
Intravenous, intramuscular
ATC code
Legal status
Legal status
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.040.409 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C17H17N3O6S2
Molar mass 423.46 g·mol−1
3D model (JSmol)
  • O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)CSc3ccncc3)COC(=O)C)C(=O)O
  • InChI=1S/C17H17N3O6S2/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25)/t13-,16-/m1/s1 Yes check.svgY
  • Key:UQLLWWBDSUHNEB-CZUORRHYSA-N Yes check.svgY
   (verify)

Cefapirin (INN, also spelled cephapirin) is an injectable, first-generation cephalosporin antibiotic. It is marketed under the trade name Cefadyl. Production for use in humans has been discontinued in the United States. [1]

It also has a role in veterinary medicine as Metricure, an intrauterine preparation, and combined with prednisolone in Mastiplan, an intramammary preparation. Both are licensed in cattle.[ citation needed ]

Synthesis

Cephapirin synthesis: U.S. Patent 3,422,100 U.S. Patent 3,503,967 U.S. Patent 3,578,661 Cephapirin synthesis.svg
Cephapirin synthesis: U.S. Patent 3,422,100 U.S. Patent 3,503,967 U.S. Patent 3,578,661

In one of the syntheses, 7-aminocephalosporanic acid (7-ACA) is reacted with bromoacetyl chloride to give the amide. The halo group is then displaced by 4-thiopyridine. [2]

Related Research Articles

<span class="mw-page-title-main">Beta-lactamase</span> 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.

<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">Ceftriaxone</span> 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.

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

Ceftazidime, sold under the brand name Fortaz among others, is a third-generation cephalosporin antibiotic useful for the treatment of a number of bacterial infections. Specifically it is used for joint infections, meningitis, pneumonia, sepsis, urinary tract infections, malignant otitis externa, Pseudomonas aeruginosa infection, and vibrio infection. It is given by injection into a vein, muscle, or eye.

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

Cefpodoxime is an oral, third-generation cephalosporin antibiotic available in the US in various generic preparations. It is active against both Gram-positive and Gram-negative organisms with notable exceptions including Pseudomonas aeruginosa, Enterococcus, and Bacteroides fragilis. It is typically used to treat acute otitis media, pharyngitis, sinusitis, and gonorrhea. It also finds use as oral continuation therapy when intravenous cephalosporins are no longer necessary for continued treatment.

<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">Cefquinome</span> Chemical compound

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.

<span class="mw-page-title-main">Latamoxef</span> 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.

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

Cefmetazole is a cephamycin antibiotic, usually grouped with the second-generation cephalosporins.

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

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.

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

Cefonicide is a cephalosporin antibiotic.

In enzymology, a glutaryl-7-aminocephalosporanic-acid acylase (EC 3.5.1.93) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">Cefazaflur</span> Cephalosporin antibiotic

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

Hebei Zhongrun Pharmaceutical Co., Ltd is one of China's largest producers of bulk antibiotic active pharmaceutical ingredients. CSPC Zhongrun produces both penicillin and cephalosporin series API.

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

Talampicillin is a beta lactam antibiotic from the penicillin family. It is an acid stable prodrug that was administered orally. It is not approved by the FDA for use in the United States. It should be avoided in Liver diseases

<span class="mw-page-title-main">7-ACA</span> Chemical compound

7-ACA is the core chemical structure for the synthesis of cephalosporin antibiotics and intermediates. It can be obtained by chemoenzymatic hydrolysis of cephalosporin C.

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.

<span class="mw-page-title-main">Cephalosporin C</span> 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.

References

  1. "CEFADYL". U.S. Food and Drug Administration.
  2. 1 2 Crast LB, Graham RG, Cheney LC (December 1973). "Synthesis of cephapirin and related cephalosporins from 7-(alpha-bromoacetamido)cephalosporanic acid". Journal of Medicinal Chemistry. 16 (12): 1413–5. doi:10.1021/jm00270a025. PMID   4148798.