Meloxicam

Structural formula
General
Non-proprietary name	Meloxicam
other names	4-Hydroxy-2-methyl- N - (5-methyl-2-thiazolyl) -2 H -1,2-benzothiazine-3-carboxamide-1,1-dioxide ( IUPAC ); Meloxicamum ( Latin );
Molecular formula	C 14 H 13 N 3 O 4 S 2
Brief description	Light yellow powder
External identifiers / databases
EC number	615-253-8
ECHA InfoCard	100.113.257
PubChem	54677470
DrugBank	DB00814
Wikidata	Q414028
Drug information
ATC code	M01 AC06 M01 AC56 (combinations);
Drug class	non-steroidal anti-inflammatory drug
Mechanism of action	Cyclooxygenase inhibitors
properties
Molar mass	351,40 g · mol -1
Physical state	firmly
Melting point	254 ° C
pK s value	4.08
solubility	practically insoluble in water (7.15 mg l −1 at 25 ° C)
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances danger
H and P phrases	H: 301
	P: 301 + 310
Toxicological data	84 mg kg −1 ( LD 50 , rat , oral ) ; 470 mg kg −1 ( LD 50 , mouse , oral ) ; 320 mg kg −1 ( LD 50 , rabbit , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Meloxicam is a drug, more precisely a nonsteroidal anti-inflammatory drug (NSAID, NSAID) from the group of oxicams . It is a light yellow powder that is almost insoluble in water.

Extraction

The synthesis starting from saccharin is described in the literature.

pharmacology

Mechanism of action

Like all nonsteroidal anti-inflammatory drugs, meloxicam inhibits cyclooxygenases (COX), whereby it has a slightly selective COX-2 effect and therefore less severe side effects , which occur primarily with compounds with a COX-1 preference.

Meloxicam also reduces the migration of leukocytes into areas of inflammation . The platelet aggregation is only slightly inhibited.

Meloxicam can be used both orally and subcutaneously . It is quickly absorbed . The plasma protein binding is 99.4 percent, the plasma half-life 15–20 hours. The degradation takes place in the liver via the enzyme CYP2C9 , excretion via the bile and kidneys , i.e. via feces and urine .

Indications

Meloxicam is mainly used for chronic joint diseases ( arthritis , arthrosis ), as it accumulates in the synovial fluid . It can also be used for other painful processes ( gout , Bechterew's disease , rheumatism ) and for pain therapy before and after operations.

The agent should not be used in diseases of the gastric or intestinal mucosa , kidney failure , blood clotting disorders and children or very young animals (<6 weeks). The drug is contraindicated in late pregnancy or gestation .

Side effects

Like all NSAIDs, meloxicam can cause gastrointestinal disorders ( ulcer , loss of appetite , diarrhea , vomiting ), blood clotting and kidney function. Intolerance reactions or skin changes can also occur.

Environmental relevance

Since the use of diclofenac for the preventive treatment of cattle in South Asia has led to a decline in three species of vulture ( Gyps bengalensis , Gyps indicus , Gyps tenuirostris ) by more than 95%, meloxicam, which is non-toxic for vultures, is partly used.

Trade names

Monopreparations in human medicine: Mobec (D), Mobic (A), Mobicox (CH), Movalis (A), Loxitan (GR), numerous generics (D, A)

Veterinary medicine: Acticam , Animeloxan , Contacera , Emdocan , Flexicam (except trade), Inflacam , Loxicom , Melosolute , Melosus , Melovem , Meloxidolor , Meloxidyl , Meloxivet , Meloxoral , Metacam , Novem , Recocam , Rheumocam , Vetoxicam (except trade), Vexxocam , Zeleris

Web links

Entry on meloxicam at Vetpharm

Individual evidence

↑ Scientific assessment report of the European Medicines Agency from April 2010 on Loxicom ( PDF ), accessed on June 27, 2020.

↑ ^a ^b ^c ^d ^e ^f Entry on meloxicam in the DrugBank of the University of Alberta .

↑ ^a ^b Datasheet Meloxicam-d ₃ from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).

^ Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .

↑ Mutschler, Ernst: drug effects. Pharmacology, clinical pharmacology, toxicology. 10th edition. Stuttgart. 2013.

↑ G. E Swan, R. Cuthbert, M. Quevedo, R. E Green, D. J Pain, P. Bartels, A. A Cunningham, N. Duncan, A. A Meharg, J Lindsay Oaks, J. Parry- Jones, S. Shultz, M.A. Taggart, G. Verdoorn, K. Wolter: Toxicity of diclofenac to Gyps vultures . In: Biology Letters . 2, No. 2, 2006, pp. 279-282. doi : 10.1098 / rsbl.2005.0425 . PMID 17148382 . PMC 1618889 (free full text).

^ Rachel Becker: Cattle drug threatens thousands of vultures . In: Nature . 2016, doi : 10.1038 / nature.2016.19839 .

↑ Michael Hopkin: Switching vet drug could save vultures . In: news @ nature . 2006, doi : 10.1038 / news060130-2 .

↑ Gerry Swan, Vinasan Naidoo, Richard Cuthbert, Rhys E Green, Deborah J Pain, Devendra Swarup, Vibhu Prakash, Mark Taggart, Lizette Bekker, Devojit Das, Jörg Diekmann, Maria Diekmann, Elmarié Killian, Andy Meharg, Ramesh Chandra Patra, Mohini Saini, Kerri Wolter, Georgina Mace : Removing the Threat of Diclofenac to Critically Endangered Asian Vultures . In: PLoS Biology . tape 4 , no. 3 , 2006, p. e66 , doi : 10.1371 / journal.pbio.0040066 .

↑ Proprietary Medicinal Products Register of AGES , accessed on February 16 2016th

[epar-1] Scientific assessment report of the European Medicines Agency from April 2010 on Loxicom ( PDF ), accessed on June 27, 2020.

[DrugBank-2] ↑ ^a ^b ^c ^d ^e ^f Entry on meloxicam in the DrugBank of the University of Alberta .

[Sigma-3] Datasheet Meloxicam-d ₃ from Sigma-Aldrich , accessed on May 13, 2017 ( PDF ).

[A._Kleemann-4] Axel Kleemann , Jürgen Engel, Bernd Kutscher and Dietmar Reichert: Pharmaceutical Substances , 4th edition (2000), Thieme-Verlag Stuttgart, ISBN 978-1-58890-031-9 .

[5] Mutschler, Ernst: drug effects. Pharmacology, clinical pharmacology, toxicology. 10th edition. Stuttgart. 2013.

[6] G. E Swan, R. Cuthbert, M. Quevedo, R. E Green, D. J Pain, P. Bartels, A. A Cunningham, N. Duncan, A. A Meharg, J Lindsay Oaks, J. Parry- Jones, S. Shultz, M.A. Taggart, G. Verdoorn, K. Wolter: Toxicity of diclofenac to Gyps vultures . In: Biology Letters . 2, No. 2, 2006, pp. 279-282. doi : 10.1098 / rsbl.2005.0425 . PMID 17148382 . PMC 1618889 (free full text).

[7] Rachel Becker: Cattle drug threatens thousands of vultures . In: Nature . 2016, doi : 10.1038 / nature.2016.19839 .

[8] Michael Hopkin: Switching vet drug could save vultures . In: news @ nature . 2006, doi : 10.1038 / news060130-2 .

[9] Gerry Swan, Vinasan Naidoo, Richard Cuthbert, Rhys E Green, Deborah J Pain, Devendra Swarup, Vibhu Prakash, Mark Taggart, Lizette Bekker, Devojit Das, Jörg Diekmann, Maria Diekmann, Elmarié Killian, Andy Meharg, Ramesh Chandra Patra, Mohini Saini, Kerri Wolter, Georgina Mace : Removing the Threat of Diclofenac to Critically Endangered Asian Vultures . In: PLoS Biology . tape 4 , no. 3 , 2006, p. e66 , doi : 10.1371 / journal.pbio.0040066 .

[asp-10] Proprietary Medicinal Products Register of AGES , accessed on February 16 2016th