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Basic information
- CAS
90101-16-9- Standard SMILES
CN1c2c(oc(=O)n(-c3ccccn3)c2=O)-c2ccccc2S1(=O)=O- InChIKey
OEHFRZLKGRKFAS-UHFFFAOYSA-N- Molecular formula
- C16H11N3O5S
- Average molar mass
- 357.3 g/mol
- Monoisotopic mass
- 357.04194163
Names & identifiers
- Preferred name
- Droxicam
- IUPAC
- 5-methyl-6,6-dioxo-3-pyridin-2-yl-[1,3]oxazino[5,6-c][1,2]benzothiazine-2,4-dione
- English name
- Droxicam
- Molecular formula
- C16H11N3O5S
- Molecular weight
- 357.34
Names & synonyms
Droxicam90101-16-9DroxicamumF24ADO1E2DDTXSID70238035CHEBI:76133RefChem:1358475-methyl-3-(2-pyridyl)-2H,5H-1,3-oxazino(5,6-c)(1,2)benzothiazine-2,4(3H)dione-6,6-dioxideDTXCID90160526M01AC048-methyl-5-(pyridin-2-yl)-3-oxa-9??-thia-5,8-diazatricyclo(8.4.0.02,?)tetradeca-1(14),2(7),10,12-tetraene-4,6,9,9-tetrone5-Methyl-3-(pyridin-2-yl)benzo[5,6][1,2]thiazino[3,4-e][1,3]oxazine-2,4(3H,5H)-dione 6,6-dioxide
Show more names
E-318DroxarDobenamDroxicam USP/EP/BP5-Methyl-3-(2-pyridyl)-2H,5H-1,3-oxazino[5,6-c][1,2]benzothiazine-2,4(3H)-dione 6,6-dioxide
Droxicam [INN]C16H11N3O5SE-3128MFCD008660325-methyl-6,6-dioxo-3-pyridin-2-yl-[1,3]oxazino[5,6-c][1,2]benzothiazine-2,4-dioneOmbolanDroxicam (INN)5-Methyl-3-(pyridin-2-yl)benzo[5,6][1,2]thiazino-[3,4-e][1,3]oxazine-2,4(3H,5H)-dione 6,6-dioxide
Database identifiers
- CAS
90101-16-9
Properties
Computed structural propertiesFilling in
- XLogP
- 1.2
- Topological polar surface area
- 105 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 1
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 741
Physicochemical properties
- Melting point
- 259 · 259-261°
- Boiling point
- 554.7 · 554.7±60.0 °C(Predicted)
- Density
- 1.68 · 1.68±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- DMSO (Slightly), Methanol (Slightly, Heated)
- pka
- 3.8 · 3.80±0.19(Predicted)
- form
- Solid
- color
- Off-White to Pale Yellow
- CAS DataBase Reference
- 90101 · 90101-16-9
- FDA UNII
- 24 ADO1E2D · F24ADO1E2D
- ATC code
- 1 AC04 · M01AC04
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H332-H335
- Precautionary statements
- 261 · P261-P280-P305+P351+P338
- Toxicity
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Droxicam
vMost-DILI-concern
8
Withdrawn
DOI:10.1016/j.drudis.2016.02.015
Safety data
- Toxicity
- LD50 orally in male, female mice, and male, female rats: 6192, 8841, 1434, 1994 mg/kg (Soler, 1986)
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H302-H315-H319-H332-H335
- Precautionary statements
- P261-P280-P305+P351+P338
Chemistry & industry
Pharmacology
ATC Code
M - Musculo-skeletal system；M01 - Antiinflammatory and antirheumatic products；M01A - Antiinflammatory and antirheumatic products, non-steroids；M01AC - Oxicams；M01AC04 - Droxicam
QM - Musculo-skeletal system；QM01 - Antiinflammatory and antirheumatic products；QM01A - Antiinflammatory and antirheumatic products, non-steroids；QM01AC - Oxicams；QM01AC04 - Droxicam
Protein BindingData not available for prodrug. See [DB00554] for information on the active compound.
PharmacodynamicsDroxicam is a prodrug of [DB00554]. Droxicam administration produces anti-inflammatory, antirheumatic, analgesic, and antipyretic effects similar to [DB00554].
Mechanism of ActionDroxicam is converted to [DB00554] via hydrolysis of the ester group in the intestine. Droxicam administration inhibits the synthesis of prostaglandins by cyclooxygenase enzymes.
Biological Half-LifeData not available for prodrug. See [DB00554] for information on the active compound.
Metabolism/MetabolitesConverted to [DB00554] via ester hydrolysis.
MeSH Pharmacological Classification
Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects.
Absorption, Distribution and Excretion
Tmax of 7 h. Bioavailability equivalent to [DB00554] which is thought to be completely absorbed in humans based on data from rabbits.
Related reactions
2 records
Compound notes
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