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71125-38-7 molecular structure
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4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide

ChemBase ID: 693
Molecular Formular: C14H13N3O4S2
Molecular Mass: 351.40072
Monoisotopic Mass: 351.03474791
SMILES and InChIs

SMILES:
c12c(S(=O)(=O)N(C(=C1O)C(=O)Nc1ncc(s1)C)C)cccc2
Canonical SMILES:
Cc1cnc(s1)NC(=O)C1=C(O)c2ccccc2S(=O)(=O)N1C
InChI:
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)
InChIKey:
ZRVUJXDFFKFLMG-UHFFFAOYSA-N

Cite this record

CBID:693 http://www.chembase.cn/molecule-693.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxamide
IUPAC Traditional name
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1λ6,2-benzothiazine-3-carboxamide
@meloxicam
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-1,1-dioxo-2H-1$l^{6},2-benzothiazine-3-carboxamide
meloxicam
Brand Name
Mobic
Mobicox
Movalis
Movatec
Novo-meloxicam
PHL-meloxicam
PMS-meloxicam
Parocin
Ratio-meloxicam
Tenaron
Metacam
Gen-meloxicam
Dom-meloxicam
Co Meloxicam
Apo-meloxicam
Synonyms
4-Hydroxy-2-methyl-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide 1,1-Dioxide
Mobicox
Movalis
Movatec
Melox
Recoxa
Tenaron
Meloxicam
Mobic
Metacam
Parocin
Meloxicamum [latin]
Meloxicam
4-hydroxy-2-methyl-N-(5-methylthiazol-2-yl)-2H-benzo[e][1,2]thiazine-3-carboxamide 1,1-dioxide
4-hydroxy-2-methyl-N-(5-methyl-1,3-thiazol-2-yl)-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide
CAS Number
71125-38-7
MDL Number
MFCD00868752
PubChem SID
46506624
160964156
PubChem CID
5281106
54677470

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 4.47116  H Acceptors
H Donor LogD (pH = 5.5) 0.53962874 
LogD (pH = 7.4) -0.97548914  Log P 1.6005814 
Molar Refractivity 88.6249 cm3 Polarizability 33.15376 Å3
Polar Surface Area 99.6 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 2.28  LOG S -3.36 
Solubility (Water) 1.54e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
7.15 mg/L expand Show data source
DMSO expand Show data source
Apperance
Light Yellow Solid expand Show data source
Melting Point
240-242°C expand Show data source
Boiling Point
expand Show data source
Hydrophobicity(logP)
1.9 expand Show data source
2.853 expand Show data source
Storage Condition
-20°C expand Show data source
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Mechanism of Action
Cyclooxygenase inhibitor expand Show data source
Prostaglandin antagonist expand Show data source
Purity
95% expand Show data source
95+% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Analgesic expand Show data source
Antiinflammatory agent expand Show data source
Antipyretic expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Selleck Chemicals Selleck Chemicals TRC TRC
MP Biomedicals - 02199147 external link
Non-Steroidal Anti-Inflamantory Drug (N.S.A.I.D). Cyclooxygenase (COX-2) Inhibitor. Used in Osteoarthritis research and to treat pain from rheumatoid arthritis.
DrugBank - DB00814 external link
Item Information
Drug Groups approved
Description Meloxicam is a nonsteroidal anti-inflammatory drug (NSAID) used to relieve the symptoms of arthritis, primary dysmenorrhea, fever; and as an analgesic, especially where there is an inflammatory component. It is closely related to piroxicam. In Europe it is marketed under the brand names Movalis, Melox, and Recoxa. In North America it is generally marketed under the brand name Mobic. In Latin America, the drug is marketed as Tenaron. [Wikipedia]
Indication For symptomatic treatment of arthritis and osteoarthritis.
Pharmacology Meloxicam is an nonsteroidal anti-inflammatory drug (NSAID) with analgesic and antipyretic properties. Prostaglandins are substances that contribute to inflammation of joints. Meloxicam inhibits prostaglandin synthetase (cylooxygenase 1 and 2) and leads to a decrease of the synthesis of prostaglandins, therefore, inflammation is reduced.
Toxicity LD50, Acute: 84 mg/kg (Rat); Oral 470 mg/kg (Mouse); Oral 320 mg/kg (Rabbit)
Affected Organisms
Humans and other mammals
Biotransformation Meloxicam is almost completely metabolized into inactive metabolites by the cytochrome P450 (CYP450) isozymes. CYP2C9 is primarily responsible for metabolism of meloxicam while CYP3A4 plays a minor role. An intermediate metabolite, 5'-hydroxymethyl meloxicam, is further metabolized to 5'-carboxy meloxicam, the major metabolite. Peroxidase activity is thought to produce the two other inactive metabolites of meloxicam.
Absorption Absolute bioavailability = 89%
Half Life 15-20 hours
Protein Binding 99.4% bound, primarily to albumin
Elimination Meloxicam is almost completely metabolized to four pharmacologically inactive metabolites. Meloxicam excretion is predominantly in the form of metabolites, and occurs to equal extents in the urine and feces. Only traces of the unchanged parent compound are excreted in the urine (0.2%) and feces (1.6%). The extent of the urinary excretion was confirmed for unlabeled multiple 7.5 mg doses: 0.5%, 6% and 13% of the dose were found in urine in the form of meloxicam, and the 5'-hydroxymethyl and 5'-carboxy metabolites, respectively.
Distribution * 10 L
Clearance * 8.8 mL/min [Healthy Male Adults (Fed) oral 7.5 mg tablets]
* 9.9 mL/min [Eldery Male (Fed) oral 15 mg capsules]
* 5.1 mL/min [Eldery Female (Fed) oral 15 mg capsules]
* 19 mL/min [Renal Failure (Fasted) oral 15 mg capsules]
* 11 mL/min [Hepatic Insufficiency (Fasted) oral 15 mg capsules]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals - S1734 external link
Research Area: Inflammation
Biological Activity:
Meloxicam (Mobic) is a nonsteroidal anti-inflammatory drug with analgesic and fever reducer effects. Meloxicam inhibits cyclooxygenase (COX), the enzyme responsible for converting arachidonic acid into prostaglandin H2--the first step in the synthesis of prostaglandins, which are mediators of inflammation. Meloxicam has been shown, especially at its low therapeutic dose, selectively to inhibit COX-2 over COX-1. [1]
Toronto Research Chemicals - M216100 external link
Preferential cyclooxygenase (COX-2) inhibitor. Sudoxicam and Meloxicam are nonsteroidal anti-inflammatory drugs (NSAIDs) from the enol-carboxamide class.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  http://en.wikipedia.org/wiki/Meloxicam
  • • Hawkey, C., et al.: Br. J. Rheumatol., 35, Suppl. 1, 1 (1996)
  • • Fleischmann, R., et al.: Expert Opin. Pharmacother., 3, 1501 (1996)
  • • Ger. Pat., 1979, Dr Karl Thomae, 2 756 113; CA, 91, 91656m, (synth, pharmacol)
  • • Busch, U. et al., Drugs Exp. Clin. Res., 1990, 16, 49; 53, (metab)
  • • Tsai, R. et al., Helv. Chim. Acta, 1993, 76, 842, (uv, pKa, props)
  • • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1386
  • • Noble, S. et al., Drugs, 1996, 51, 424
  • • Busch, U. et al., Drug Metab. Dispos., 1998, 26, 576-584, (metab)
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PATENTS

PATENTS

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