MXM

4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide

Created: 2013-08-09
Last modified:  2020-06-05

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Chemical Details

Formal Charge0
Atom Count36
Chiral Atom Count0
Bond Count38
Aromatic Bond Count11
2D diagram of MXM
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Chemical Component Summary

Name4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
SynonymsMeloxicam
Systematic Name (OpenEye OEToolkits)2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-4-oxidanyl-1,1-bis(oxidanylidene)-1$l^{6},2-benzothiazine-3-carboxamide
FormulaC14 H13 N3 O4 S2
Molecular Weight351.401
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs12.01O=C(Nc1ncc(s1)C)C3=C(O)c2ccccc2S(=O)(=O)N3C
SMILESCACTVS3.385CN1C(=C(O)c2ccccc2[S]1(=O)=O)C(=O)Nc3sc(C)cn3
SMILESOpenEye OEToolkits1.7.6Cc1cnc(s1)NC(=O)C2=C(c3ccccc3S(=O)(=O)N2C)O
Canonical SMILESCACTVS3.385 CN1C(=C(O)c2ccccc2[S]1(=O)=O)C(=O)Nc3sc(C)cn3
Canonical SMILESOpenEye OEToolkits1.7.6 Cc1cnc(s1)NC(=O)C2=C(c3ccccc3S(=O)(=O)N2C)O
InChIInChI1.03 InChI=1S/C14H13N3O4S2/c1-8-7-15-14(22-8)16-13(19)11-12(18)9-5-3-4-6-10(9)23(20,21)17(11)2/h3-7,18H,1-2H3,(H,15,16,19)
InChIKeyInChI1.03 ZRVUJXDFFKFLMG-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB00814 
NameMeloxicam
Groups
  • approved
  • vet_approved
DescriptionMeloxicam is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve various types of pain, including pain caused by musculoskeletal conditions, osteoarthritis, and rheumatoid arthritis.[A190189] With a longer half-life than most other NSAIDS, it is a favorable option for those who require once-daily dosing. Meloxicam is available in oral, transdermal, and intravenous formulations. It is a preferential COX-2 inhibitor, purportedly reducing the risk of adverse gastrointestinal tract effects, however, this is a topic of controversy.[A190198,A190201]
Synonyms
  • Méloxicam
  • Meloxicam
  • Meloxicamum
Brand Names
  • Dom-meloxicam
  • Nu-meloxicam
  • Apo-meloxicam
  • NuDroxiPAK M-15
  • Mobicox
IndicationMeloxicam is indicated for the symptomatic treatment of arthritis and osteoarthritis. In addition, it is indicated for the pauciarticular and polyarticular course of Juvenile Rheumatoid Arthritis (JRA) in patients aged 2 years old or above.[L11398] Off-label uses include the treatment of dental or post-surgical pain. In addition to the above, meloxicam has also been studied in the treatment of neuropathic pain. [A190189] Meloxicam, in combination with [bupivacaine], is indicated for postsurgical analgesia in adult patients for up to 72 hours following foot and ankle, small-to-medium open abdominal, and lower extremity total joint arthroplasty surgical procedures.[L34100]
Categories
  • Agents causing hyperkalemia
  • Agents that produce hypertension
  • Amides
  • Analgesics
  • Analgesics, Non-Narcotic
ATC-Code
  • N01BB59
  • M01AC56
  • M01AC06
CAS number71125-38-7

Drug Targets

NameTarget SequencePharmacological ActionActions
Prostaglandin G/H synthase 2MLARALLLCAVLALSHTANPCCSHPCQNRGVCMSVGFDQYKCDCTRTGFY...unknowninhibitor
Prostaglandin G/H synthase 1MSRSLLLWFLLFLLLLPPLPVLLADPGAPTPVNPCCYYPCQHQGICVRFG...unknowninhibitor
6-phosphogluconate dehydrogenase, decarboxylatingMAQADIALIGLAVMGQNLILNMNDHGFVVCAFNRTVSKVDDFLANEAKGT...unknowninhibitor
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknownsubstrate
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL599
PubChem 54677470
ChEMBL CHEMBL599, CHEMBL1741042
ChEBI CHEBI:6741
CCDC/CSD SEDZOQ02, ENICOU01, ENIBUZ, SEDZOQ, SEDZOQ01, EBOLEP, ARIFOX, IDOHAN, FAKJUY, ENICEK, FAKJOS, ENICIO, ENICOU, ENIBOT, ENICAG
COD 4501815, 2008040, 4501817, 4501818, 4501819, 4501814