Cefoxitin
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Surname | Cefoxitin | |||||||||||||||||||||
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Molecular formula | C 16 H 17 N 3 O 7 S 2 | |||||||||||||||||||||
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Drug information | ||||||||||||||||||||||
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Mechanism of action |
Inhibition of septum formation and cell wall synthesis |
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properties | ||||||||||||||||||||||
Molar mass | 427.45 g mol −1 | |||||||||||||||||||||
Physical state |
firmly |
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Melting point |
149-150 ° C |
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solubility |
Very soluble in acetone , soluble in aq. NaHCO 3 solution, very sparingly soluble in water |
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Toxicological data | ||||||||||||||||||||||
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions . |
Cefoxitin is an organic chemical compound from the group of β-lactam antibiotics , more precisely the cephalosporins . It was patented by Merck & Co. in 1971 and is used in the form of its monosodium salt . The drug works against gram-negative bacteria, which is why it is used, for example, to treat bacterial arthritis .
use
The drug is used to fight gynecological infections with a mild course and without other risk factors. The substance is used as a sequential therapy, which usually involves taking it for 14 days. Doxycycline is taken the next two days . Cefoxitin can also be used to treat bone and joint infections such as tick-borne Lyme disease .
Manufacturing
The synthesis of cefoxitin takes place in a complex process. For this purpose, the cephamycin C obtained by fermentation from Streptomyces species is first mixed with sodium hydroxide solution, tosyl chloride and dicyclohexylamine . Then chloromethyl methyl ether and 2- (2-thienyl) acetyl chloride are added, so that cefoxitin is the product.
Cefoxitin sodium
Cefoxitin sodium is a white to almost white, strongly hygroscopic powder that is very easily soluble in water and not very soluble in ethanol 96%. The melting point is> 160 ° C .
Individual evidence
- ^ A b c The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006, ISBN 978-0-911910-00-1 , P. 318.
- ↑ a b c data sheet Cefoxitin sodium, 92.7-97% from AlfaAesar, accessed on March 31, 2020 ( PDF )(JavaScript required) .
- ↑ a b c d e entry on cefoxitin. In: Römpp Online . Georg Thieme Verlag, accessed on March 27, 2020.
- ↑ D. Adam, K.-F. Bodmann, W. Elies, C. Lebert, K. Naber, K. Simons, F. Vogel, H. Wacha: Oral antibiotics in clinic and practice; Practice-oriented recommendations for antibiotic therapy of mild to moderate bacterial infections in adults in outpatient and inpatient settings. Springer, Heidelsberg, 2009, ISBN 978-3-642-00521-3 , pp. 120-122.
- ↑ D. Adam, K.-F. Bodmann, W. Elies, C. Lebert, K. Naber, K. Simons, F. Vogel, H. Wacha: Oral antibiotics in clinic and practice; Practice-oriented recommendations for antibiotic therapy of mild to moderate bacterial infections in adults in outpatient and inpatient settings. Springer, Heidelsberg, 2009, ISBN 978-3-642-00521-3 , pp. 93-94.
- ↑ D. Adam, K.-F. Bodmann, W. Elies, C. Lebert, K. Naber, K. Simons, F. Vogel, H. Wacha: Oral antibiotics in clinic and practice; practice-oriented recommendations for antibiotic therapy of mild to moderate bacterial infections in adults in outpatient and inpatient settings Area . Springer, Heidelberg, 2009, ISBN 978-3-642-00521-3 , p. 116.
- ^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Active pharmaceutical ingredients: Syntheses; Patents; Applications , Thieme-Verlag Stuttgart, 2. neubear. and exp. Edition (1982) ISBN 313558402X , pp. 173-175.
- ↑ External identifiers or database links for cefoxitin sodium : CAS number: 33564-30-6, EC number: 251-574-6, ECHA InfoCard: 100.046.871 , PubChem : 23667300 , ChemSpider : 390131 , Wikidata : Q27106110 . Molecular formula: C 16 H 16 N 3 NaO 7 S 2 . Molar mass: 449.44 g mol −1 .
- ↑ European Pharmacopoeia, 8th edition, Grundwerk 2014, p. 2710.