N -methyl glucamine antimonate

Structural formula
	Possible structural formula (without considering the stereochemistry ), see also structure
General
Surname	N -methyl glucamine antimonate
other names	Meglumine antimonate; Meglumine [trioxoantimonate (V)];
Molecular formula	C 7 H 18 NO 8 Sb
External identifiers / databases
EC number	205-108-3
ECHA InfoCard	100.004.645
PubChem	64953
Wikidata	Q2757969
Drug information
ATC code	P01 CB01 ; Q P51AB01 ;
properties
Molar mass	365.98 g · mol -1
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

N -methylglucamine antimonate is a drug that is used in the treatment of all forms of leishmaniasis . It was added to the World Health Organization 's Essential Medicines List in 1988. In Germany and Switzerland there are no approvals fordrugs containing N- methylglucamine antimonate.

Presentation and extraction

The compound can be prepared by reacting N -methylglucamine with antimony pentachloride or potassium hexahydroxyantimonate in an aqueous medium.

Chemical properties

structure

The structure of the present antimony (V) complex could not be elucidated for a long time. Investigations with current analytical methods suggest that N -methylglucamine antimonate is present as a mixture of different polymeric and zwitterionic structures, the composition in the solid state being different from that in solution.

Clinical information

N -methylglucamine antimonate is not absorbed and is therefore administered parenterally ( intramuscularly , subcutaneously ). It has to be used for weeks. This can result in considerable costs, especially for pets. The drug is quite toxic and side effects include vomiting , myalgia , headache , arthralgia, and thrombocytopenia , among others . In dogs , the administration leads to an improvement in clinical symptoms, but a relapse cannot be ruled out. In advanced leishmaniasis with pronounced liver damage and existing renal insufficiency, the prognosis is unfavorable and treatment should be avoided.

pharmacology

The mechanism of action is unclear. An inhibition of glycolysis is being discussed . Long-term therapy can lead to the development of resistance . The metabolism takes place over three stages and takes place mainly in the liver. Excretion takes place renally .

Trade names

Glucantime

Aventis produces Glucantime in the order of 5 million ampoules per year.

Web links

Entry on meglumine antimonate at Vetpharm, accessed on January 9, 2013.

Individual evidence

↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b ^c H. Frey, W. Löscher u. a .: Textbook of pharmacology and toxicology for veterinary medicine . 3. Edition. Enke 2009. ISBN 978-3-8304-1079-9 , p. 403.
↑ Demicheli, D .; Ochoa, R .; Lula, IS; Gozzo, FC; Eberlin, MN; Frézard, F .: Pentavalent organoantimonial derivatives: two simple and efficient synthetic methods for meglumine antimonate . In: Appl Organomet Chem . 17 (2003) 226-231, doi : 10.1002 / aoc.425 .
Jump up ↑ Frézard F, Demicheli C, Ribeiro PR: Pentavalent Antimonials: New Perspectives for Old Drugs . (pdf) In: Molecules . 14, No. 7, 2009, pp. 2317-2336. doi : 10.3390 / molecules14072317 . PMID 19633606 .
↑ Frézard et al .: New insights into the chemical structure and composition of the pentavalent antimonial drugs, meglumine antimonate and sodium stibogluconate. In: J. Inorg. Biochem. 102 (2008) 656-665. doi : 10.1016 / j.jinorgbio.2007.10.010
↑ CJ Estler, H. Schmidt: Pharmakologie und Toxikologie . 6th edition. Schattauer. ISBN 978-3794522958 , p. 855.
↑ C. Riera et al. a .: Serological and parasitological follow-up in dogs experimentally infected with Leishmania infantum and treated with meglumine antimoniate. In: Veterinary Parasitology 1999 84 (1-2): 33-47.
↑ T. Herdegen: Short textbook pharmacology and toxicology Georg Thieme Verlag. Stuttgart 2013. ISBN 978-3131422934 .
↑ Jasmin Ryczak: Active ingredients for the treatment of leishmaniasis. Antimony and more In: Pharmakologie Unserer Zeit 2009 38, 538-544.
↑ Registration number: 323471 . DPMAregister, accessed on January 8, 2013.
↑ Sanofi-Aventis reaffirms its commitment to ensure access to medicines in the "southern countries" with a policy of tiered drug prices depending on the population's income (German translation) ( Memento from March 4, 2016 in the Internet Archive ), Aventis press release from 15 April 2005.

[NV-1] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[Frey-2] H. Frey, W. Löscher u. a .: Textbook of pharmacology and toxicology for veterinary medicine . 3. Edition. Enke 2009. ISBN 978-3-8304-1079-9 , p. 403.

[Frezard1-3] Demicheli, D .; Ochoa, R .; Lula, IS; Gozzo, FC; Eberlin, MN; Frézard, F .: Pentavalent organoantimonial derivatives: two simple and efficient synthetic methods for meglumine antimonate . In: Appl Organomet Chem . 17 (2003) 226-231, doi : 10.1002 / aoc.425 .

[4] Jump up ↑ Frézard F, Demicheli C, Ribeiro PR: Pentavalent Antimonials: New Perspectives for Old Drugs . (pdf) In: Molecules . 14, No. 7, 2009, pp. 2317-2336. doi : 10.3390 / molecules14072317 . PMID 19633606 .

[5] Frézard et al .: New insights into the chemical structure and composition of the pentavalent antimonial drugs, meglumine antimonate and sodium stibogluconate. In: J. Inorg. Biochem. 102 (2008) 656-665. doi : 10.1016 / j.jinorgbio.2007.10.010

[6] CJ Estler, H. Schmidt: Pharmakologie und Toxikologie . 6th edition. Schattauer. ISBN 978-3794522958 , p. 855.

[7] C. Riera et al. a .: Serological and parasitological follow-up in dogs experimentally infected with Leishmania infantum and treated with meglumine antimoniate. In: Veterinary Parasitology 1999 84 (1-2): 33-47.

[8] T. Herdegen: Short textbook pharmacology and toxicology Georg Thieme Verlag. Stuttgart 2013. ISBN 978-3131422934 .

[9] Jasmin Ryczak: Active ingredients for the treatment of leishmaniasis. Antimony and more In: Pharmakologie Unserer Zeit 2009 38, 538-544.

[10] Registration number: 323471 . DPMAregister, accessed on January 8, 2013.

[11] Sanofi-Aventis reaffirms its commitment to ensure access to medicines in the "southern countries" with a policy of tiered drug prices depending on the population's income (German translation) ( Memento from March 4, 2016 in the Internet Archive ), Aventis press release from 15 April 2005.