Cefamandolnafat

Structural formula
General
Non-proprietary name	Cefamandolnafat (INNm)
other names	Sodium [(6 R , 7 R ) -7 - {[(2 R ) -2- (formyloxy) -2-phenylacetyl] amino} -3 - {[(1-methyl-1H-tetrazol-5-yl) sulfanyl ] methyl} -8-oxo-5-thia-1-azabicyclo [4.2.0] oct-2-ene-2-carboxylate]; Cefamandol formate sodium salt;
Molecular formula	C 19 H 17 N 6 NaO 6 S 2
External identifiers / databases
EC number	255-877-4
ECHA InfoCard	100.050.780
PubChem	23665731
ChemSpider	4447584
DrugBank	DB14725
Wikidata	Q27106102
Drug information
ATC code	J01 DA07
Drug class	β-lactam antibiotic
Mechanism of action	Inhibition of cell wall synthesis
properties
Molar mass	512.5 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
Toxicological data	3915 mg kg −1 ( LD 50 , mouse , iv ) ; 2562 mg kg −1 ( LD 50 , rat , iv ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Cefamandolnafate is the international non-proprietary name (INN) of the sodium salt of the formic acid ester of cefamandol . Since cefamandolnafate is hydrolyzed very quickly in the blood plasma , it is a prodrug of the drug cefamandol.

properties

Cefamandolnafate is a white to almost white, odorless powder. It is easily soluble in water, but only with difficulty in methanol. It occurs as a mixture with cefamandol sodium and sodium carbonate.

synthesis

If cefamandol is reacted with formic acid to form formate and then the sodium salt of 2-ethylhexanoic acid is added in acetone , cefamandolnafate is formed.

storage

The substance must be tightly closed, protected from light and moisture. A safety lock is also necessary for sterile substances. In addition, depending on how it is stored, it can be used within 24 hours to a maximum of 4 days after production.

stability

In solids with a water content of less than 0.1%, hydrolysis does not occur . The rate of hydrolysis increases with rising temperatures (over 50 ° C) and higher water content. At high temperatures and extreme pH values, the molecule splits.

Decomposition products

1-methyl-1H- tetrazole -5-thiol
Lactam
Mandelic acid

Individual evidence

↑ ^a ^b ^c data sheet Cefamandol nafate from Sigma-Aldrich , accessed on April 8, 2020 ( PDF ).
↑ ^a ^b ^c ^d ^e ^f Entry on Cefamandol. In: Römpp Online . Georg Thieme Verlag, accessed on April 1, 2020.
^ 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.
↑ European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, ISBN 978-3-7692-3962-1 , pp. 2000–2002.
↑ 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 8, 2020 ( PDF ).

[Römpp-2] ↑ ^a ^b ^c ^d ^e ^f Entry on Cefamandol. In: Römpp Online . Georg Thieme Verlag, accessed on April 1, 2020.

[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.

[EuropäischesArzneibuch-4] European Pharmacopoeia , Deutscher Apotheker Verlag Stuttgart, 6th edition, 2008, ISBN 978-3-7692-3962-1 , pp. 2000–2002.

[Kleemann-5] 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.

[6] 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 .