Cefamandol

Structural formula
General
Non-proprietary name	Cefamandol
other names	7- D -Mandelamido-3 - {[(1-methyl-1 H -tetrazol-5-yl) thio] methyl} -8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene -2-carboxylic acid; (6 R , 7 R ) -7 - {[(2 R ) -2-hydroxy-2-phenylacetyl] amino} -3 - [(1-methyl-tetrazol-5-yl) sulfanylmethyl] -8-oxo-5-thia -1-azabicyclo [4.2.0] oct-2-en-2-carboxylic acid; Cefadol; Cefamondolum; Cephadol;
Molecular formula	C 18 H 18 N 6 O 5 S 2
External identifiers / databases
EC number	252-030-0
ECHA InfoCard	100.047.285
PubChem	456255
ChemSpider	401748
DrugBank	DB01326
Wikidata	Q2601530
Drug information
ATC code	J01 DA07
Drug class	β-lactam antibiotic
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	462.50 g mol −1
Physical state	firmly
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 315-317-319-334-335
	P: 261-280-284-304 + 340-305 + 351 + 338-342 + 311
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cefamandol is a drug from the group of cephalosporins . It was first patented by Lilly in 1972 . For reasons of stability, it is used as the sodium salt of the formic acid ester, cefamandolnafate . Cefamandol works against both gram-positive and gram-negative germs, which is why it is used, for example, to treat chronic bacterial infections of the respiratory tract.

properties

The Cefamandol comes from the second generation of the Cephalosporine. It is more efficient against gram-negative bacteria than the first generation cephalosporins. However, due to its high molecular weight, cefamandol can only pass the blood-liquor barrier with difficulty or not at all, so that effective concentrations can only be set with difficulty.

application

Cefamandol can be used for bacterial infections of the skin, soft tissue and biliary tract. It is also suitable for treating sepsis . If you suffer from a blood clotting disorder, taking it together with vitamin K is recommended. Since the drug is eliminated through the kidneys, the serum levels vary depending on the degree of kidney function. The dose should be adjusted in patients with impaired renal function.

Cefamandol is one of the so-called transitional cephalosporins, which are characterized by increased β-lactamase stability and are given parenterally .

Manufacturing

Cefamandol is produced in a complex synthesis from formic acid , sodium salts and 7-aminocephalosporanic acid , among other things .

1 = 7-aminocephalosporanic acid; 2 = 7-formamidocephalosporanic acid; 3 = 7-amino-3- (1-methyl-1,2,3,4-tetrazol-5-yl) -thiomethyl-3-cefem-4-carboxylic acid; 4 = cefamandole

Finished medicinal products

Mandokef (A)

Individual evidence

↑ ^a ^b ^c data sheet Cefamandol nafate from Sigma-Aldrich , accessed on April 6, 2020 ( PDF ).
↑ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, ISBN 978-3-7692-3962-1 , pp. 2000–2002.
^ 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 , pp. 318.
↑ ^a ^b ^c Entry on Cefamandol. In: Römpp Online . Georg Thieme Verlag, accessed on April 7, 2020.
↑ B. Oellers, O. Müller, K. Fabricius, J. Ungemach: Investigation of the liquor permeability of cefamandol . In: Infection, 1978, Vol. 6, No. 6, pp. 294-296, doi: 10.1007 / BF01641990 .
↑ D. Höffler, D. Moecke, M. Sassmann: Cefamandol: pharmacokinetics with normal and impaired renal function . In: Deutsche Medizinische Wochenschrift, 1978, Vol. 103, No. 34, pp. 1334-1338, doi: 10.1055 / s-0028-1129258 .
↑ Technical information Mandokef 2 g - dry substance for infusion preparation . Astro-Pharma GmbH, Vienna. Status: July 2018.
^ E. Mutschler : Medicinal Effects , 7th Edition, WVG Stuttgart, 1996. P. 669 f.
↑ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009) ISBN 978-3-13-558405-8 , pp. 166-167; also online with biannual additions and updates.
^ Eugene C. Rickard, Gary G. Cooke: Electrochemical Analysis of the Cephalosporin Cefamandole Nafate . In: Journal of Pharmaceutical Sciences, 1977, Vol. 66, No. 3, pp. 379-384, doi: 10.1002 / jps.2600660317 .

[Sigma-1] ta sheet Cefamandol nafate from Sigma-Aldrich , accessed on April 6, 2020 ( PDF ).

[EuropäischesArzneibuch-2] European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, ISBN 978-3-7692-3962-1 , pp. 2000–2002.

[MERCK_Index-3] 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 , pp. 318.

[Römpp-4] Entry on Cefamandol. In: Römpp Online . Georg Thieme Verlag, accessed on April 7, 2020.

[5] B. Oellers, O. Müller, K. Fabricius, J. Ungemach: Investigation of the liquor permeability of cefamandol . In: Infection, 1978, Vol. 6, No. 6, pp. 294-296, doi: 10.1007 / BF01641990 .

[6] D. Höffler, D. Moecke, M. Sassmann: Cefamandol: pharmacokinetics with normal and impaired renal function . In: Deutsche Medizinische Wochenschrift, 1978, Vol. 103, No. 34, pp. 1334-1338, doi: 10.1055 / s-0028-1129258 .

[7] Technical information Mandokef 2 g - dry substance for infusion preparation . Astro-Pharma GmbH, Vienna. Status: July 2018.

[8] E. Mutschler : Medicinal Effects , 7th Edition, WVG Stuttgart, 1996. P. 669 f.

[Kleemann-9] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dieter Reichert: Pharmaceutical Substances , Thieme-Verlag Stuttgart, 5th edition (2009) ISBN 978-3-13-558405-8 , pp. 166-167; also online with biannual additions and updates.

[10] Eugene C. Rickard, Gary G. Cooke: Electrochemical Analysis of the Cephalosporin Cefamandole Nafate . In: Journal of Pharmaceutical Sciences, 1977, Vol. 66, No. 3, pp. 379-384, doi: 10.1002 / jps.2600660317 .