Oxyclozanide

Last updated
Oxyclozanide
Oxyclozanide.png
Names
Preferred IUPAC name
2,3,5-Trichloro-N-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.017.186 OOjs UI icon edit-ltr-progressive.svg
KEGG
PubChem CID
UNII
  • InChI=1S/C13H6Cl5NO3/c14-4-1-6(16)11(20)8(2-4)19-13(22)9-10(18)5(15)3-7(17)12(9)21/h1-3,20-21H,(H,19,22) X mark.svgN
    Key: JYWIYHUXVMAGLG-UHFFFAOYSA-N X mark.svgN
  • InChI=1/C13H6Cl5NO3/c14-4-1-6(16)11(20)8(2-4)19-13(22)9-10(18)5(15)3-7(17)12(9)21/h1-3,20-21H,(H,19,22)
    Key: JYWIYHUXVMAGLG-UHFFFAOYAW
  • C1=C(C=C(C(=C1Cl)O)NC(=O)C2=C(C(=CC(=C2Cl)Cl)Cl)O)Cl
Properties
C13H6Cl5NO3
Molar mass 401.45 g·mol−1
Pharmacology
QP52AG06 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Oxyclozanide is a salicylanilide anthelmintic. It is used in the treatment and control of fascioliasis in ruminants mainly domestic animals such as cattle, sheep, and goats. It mainly acts by uncoupling of oxidative phosphorylation in flukes. [1] Along with niclosamide, another tapeworm drug, it has been recently found to display "strong in vivo and in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA)". [2]

Sometimes alluded to as "Pentaclosamide": CN101891646.

Related Research Articles

<span class="mw-page-title-main">Phenothiazine</span> Heterocyclic compound containing a ring of four carbon, one nitrogen and one sulfur atom

Phenothiazine, abbreviated PTZ, is an organic compound that has the formula S(C6H4)2NH and is related to the thiazine-class of heterocyclic compounds. Derivatives of phenothiazine are highly bioactive and have widespread use and rich history. The derivatives chlorpromazine and promethazine revolutionized the fields of psychiatry and allergy treatment, respectively. An earlier derivative, methylene blue, was one of the first antimalarial drugs, and derivatives are under investigation as possible anti-infective drugs. Phenothiazine is a prototypical pharmaceutical lead structure in medicinal chemistry.

<i>Staphylococcus aureus</i> Species of Gram-positive bacterium

Staphylococcus aureus is a Gram-positive spherically shaped bacterium, a member of the Bacillota, and is a usual member of the microbiota of the body, frequently found in the upper respiratory tract and on the skin. It is often positive for catalase and nitrate reduction and is a facultative anaerobe that can grow without the need for oxygen. Although S. aureus usually acts as a commensal of the human microbiota, it can also become an opportunistic pathogen, being a common cause of skin infections including abscesses, respiratory infections such as sinusitis, and food poisoning. Pathogenic strains often promote infections by producing virulence factors such as potent protein toxins, and the expression of a cell-surface protein that binds and inactivates antibodies. S. aureus is one of the leading pathogens for deaths associated with antimicrobial resistance and the emergence of antibiotic-resistant strains, such as methicillin-resistant S. aureus (MRSA), is a worldwide problem in clinical medicine. Despite much research and development, no vaccine for S. aureus has been approved.

Methicillin-resistant <i>Staphylococcus aureus</i> Bacterium responsible for difficult-to-treat infections in humans

Methicillin-resistant Staphylococcus aureus (MRSA) is a group of Gram-positive bacteria that are genetically distinct from other strains of Staphylococcus aureus. MRSA is responsible for several difficult-to-treat infections in humans. It caused more than 100,000 deaths attributable to antimicrobial resistance in 2019.

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

Methicillin (USAN), also known as meticillin (INN), is a narrow-spectrum β-lactam antibiotic of the penicillin class.

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

Fusidic acid, sold under the brand names Fucidin among others, is an antibiotic that is often used topically in creams and eyedrops but may also be given systemically as tablets or injections. The global problem of advancing antimicrobial resistance has led to a renewed interest in its use recently.

Vancomycin-resistant <i>Staphylococcus aureus</i> Antibiotica resistant bacteria

Vancomycin-resistant Staphylococcus aureus (VRSA) are strains of Staphylococcus aureus that have become resistant to the glycopeptide antibiotic vancomycin.

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

Niclosamide, sold under the brand name Niclocide among others, is an anthelmintic medication used to treat tapeworm infestations, including diphyllobothriasis, hymenolepiasis, and taeniasis. It is not effective against other worms such as flukes or roundworms. It is taken by mouth.

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

Sultamicillin, sold under the brand name Unasyn among others, is an oral form of the penicillin antibiotic combination ampicillin/sulbactam. It is used for the treatment of bacterial infections of the upper and lower respiratory tract, the kidneys and urinary tract, skin and soft tissues, among other organs. It contains esterified ampicillin and sulbactam.

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

Dicloxacillin is a narrow-spectrum β-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible (non-resistant) Gram-positive bacteria. It is active against beta-lactamase-producing organisms such as Staphylococcus aureus, which would otherwise be resistant to most penicillins. Dicloxacillin is available under a variety of trade names including Diclocil (BMS).

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

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

Tefibazumab is a humanized monoclonal antibody for the treatment of severe infections with Staphylococcus aureus. Possible indications include the treatment of S. aureus in a phase 2a patients with cystic fibrosis and of methicillin-resistant S. aureus.

<span class="mw-page-title-main">Oritavancin</span> Pharmaceutical drug

Oritavancin, sold under the brand name Orbactiv among others, is a semisynthetic glycopeptide antibiotic medication for the treatment of serious Gram-positive bacterial infections. Its chemical structure as a lipoglycopeptide is similar to vancomycin.

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

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.

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

Ceftobiprole (Zevtera/Mabelio) is a fifth-generation cephalosporin for the treatment of hospital-acquired pneumonia and community-acquired pneumonia. It is marketed by Basilea Pharmaceutica in the United Kingdom, Germany, Switzerland and Austria under the trade name Zevtera, in France and Italy under the trade name Mabelio. Like other cephalosporins, ceftobiprole exerts its antibacterial activity by binding to important penicillin-binding proteins and inhibiting their transpeptidase activity which is essential for the synthesis of bacterial cell walls. Ceftobiprole has high affinity for penicillin-binding protein 2a of methicillin-resistant Staphylococcus aureus strains and retains its activity against strains that express divergent mecA gene homologues. Ceftobiprole also binds to penicillin-binding protein 2b in Streptococcus pneumoniae (penicillin-intermediate), to penicillin-binding protein 2x in Streptococcus pneumoniae (penicillin-resistant), and to penicillin-binding protein 5 in Enterococcus faecalis.

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

Telavancin is a bactericidal lipoglycopeptide for use in MRSA or other Gram-positive infections. Telavancin is a semi-synthetic derivative of vancomycin.

mecA is a gene found in bacterial cells which allows them to be resistant to antibiotics such as methicillin, penicillin and other penicillin-like antibiotics.

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

Arbekacin (INN) is a semisynthetic aminoglycoside antibiotic which was derived from kanamycin. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus (MRSA). Arbekacin was originally synthesized from dibekacin in 1973 by Hamao Umezawa and collaborators. It has been registered and marketed in Japan since 1990 under the trade name Habekacin. Arbekacin is no longer covered by patent and generic versions of the drug are also available under such trade names as Decontasin and Blubatosine.

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

Salicylanilide is a chemical compound which is the amide of salicylic acid and aniline. It is classified as both a salicylamide and an anilide.

<i>Staphylococcus</i> Genus of Gram-positive bacteria

Staphylococcus is a genus of Gram-positive bacteria in the family Staphylococcaceae from the order Bacillales. Under the microscope, they appear spherical (cocci), and form in grape-like clusters. Staphylococcus species are facultative anaerobic organisms.

<span class="mw-page-title-main">Anthelmintic</span> Antiparasitic drugs that expel parasitic worms (helminths) from the body

Anthelmintics or antihelminthics are a group of antiparasitic drugs that expel parasitic worms (helminths) and other internal parasites from the body by either stunning or killing them and without causing significant damage to the host. They may also be called vermifuges or vermicides. Anthelmintics are used to treat people who are infected by helminths, a condition called helminthiasis. These drugs are also used to treat infected animals.

References

[3]

  1. CID 16779 from PubChem
  2. Rajamuthiah, Rajmohan; Fuchs, Beth Burgwyn; Conery, Annie L.; Kim, Wooseong; Jayamani, Elamparithi; Kwon, Bumsup; Ausubel, Frederick M.; Mylonakis, Eleftherios (2015). "Repurposing Salicylanilide Anthelmintic Drugs to Combat Drug Resistant Staphylococcus aureus". PLOS ONE. 10 (4): e0124595. doi: 10.1371/journal.pone.0124595 . PMC   4405337 . PMID   25897961.
  3. Oxyclozanide MSDS