Cefoxitin

Structural formula
General
Surname	Cefoxitin
other names	3- (Carbamoyloxymethyl) -7 α -methoxy-7 β - [2- (2-thienyl) -acetamido] -3-cephem-4-carboxylic acid; (6 R , 7 S ) - {[(aminocarbonyl) oxy] methyl} -7-methoxy-8-oxo-7 - [(2-thienylacetyl) amino] -5-thia-1-azabicyclo [4.2.0] oct -2-en-2-carboxylic acid;
Molecular formula	C 16 H 17 N 3 O 7 S 2
External identifiers / databases
EC number	252-641-2
ECHA InfoCard	100,047,841
PubChem	441199
ChemSpider	389981
DrugBank	DB01331
Wikidata	Q2353907
Drug information
ATC code	J01 DC01 Q J01DC01
Drug class	β-lactam antibiotic
Mechanism of action	Inhibition of septum formation and cell wall synthesis
properties
Molar mass	427.45 g mol −1
Physical state	firmly
Melting point	149-150 ° C
solubility	Very soluble in acetone , soluble in aq. NaHCO 3 solution, very sparingly soluble in water
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Sodium salt Caution
H and P phrases	H: 317
	P: 280-302 + 352-333 + 313
Toxicological data	> 10 g kg −1 ( LD 50 , rat , oral ) ; 8.98 g kg −1 ( LD 50 , rat , iv ) ; > 10 g kg −1 ( LD 50 , mouse , oral ) ; 5.1 g kg −1 ( LD 50 , mouse , iv ) ;
	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.

[MERCK_Index-1] 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.

[Alfa-2] ta sheet Cefoxitin sodium, 92.7-97% from AlfaAesar, accessed on March 31, 2020 ( PDF )(JavaScript required) .

[Römpp-3] ↑ ^a ^b ^c ^d ^e entry on cefoxitin. In: Römpp Online . Georg Thieme Verlag, accessed on March 27, 2020.

[4] 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.

[5] 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.

[6] 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.

[Kleemann-7] 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.

[8] 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 .

[9] European Pharmacopoeia, 8th edition, Grundwerk 2014, p. 2710.