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Droxicam

Droxicam structure

CAS No:
90101-16-9
Formula:
C16H11N3O5S
Chemical Name:
Droxicam
Synonyms:
2H,5H-1,3-Oxazino[5,6-c][1,2]benzothiazine-2,4(3H)-dione,5-methyl-3-(2-pyridinyl)-,6,6-dioxide;Droxicam;E 318;Ombolan;Droxar;Dobenam;E 3128
Categories:
Active Pharmaceutical Ingredients > Antipyretic Analgesics

Description

ChEBI: An organic heterotricyclic compound that is 2H,5H-[1,3]oxazino[5,6-c][1,2]benzothiazine-2,4(3H)-dione 6,6-dioxide substituted at positions 3 and 5 by pyridin-2-yl and methyl groups respe tively. A prodrug of piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.

Droxicam is an organic heterotricyclic compound that is 2H,5H-[1,3]oxazino[5,6-c][1,2]benzothiazine-2,4(3H)-dione 6,6-dioxide substituted at positions 3 and 5 by pyridin-2-yl and methyl groups respectively. A prodrug of piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis. It has a role as a prodrug, a non-steroidal anti-inflammatory drug, a cyclooxygenase 1 inhibitor, a non-narcotic analgesic, a platelet aggregation inhibitor and a hepatotoxic agent. It is a member of pyridines and an organic heterotricyclic compound. It derives from a piroxicam.|Droxicam is an oxicam non-steroidal anti-inflammatory drug and a prodrug of [DB00554]. It is used to reduce pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.

Droxicam Basic Attributes

Molecular Weight：

357.34

Exact Mass：

357.34

UNII：

F24ADO1E2D

DSSTox ID：

DTXSID70238035

ATC Code：

M - Musculo-skeletal system

Characteristics

PSA：

105

XLogP3：

1.11

Density：

1.7±0.1 g/cm3

Melting Point：

259-261 °C

Boiling Point：

554.7±60.0 °C at 760 mmHg

Flash Point：

289.3±32.9 °C

Refractive Index：

1.748

Toxicity：

LD50 orally in male, female mice, and male, female rats: 6192, 8841, 1434, 1994 mg/kg (Soler, 1986)

Toxicity

Toxicity Summary：

Exposure to Droxicam is associated with significantly increased risk of hepatic toxicity resulting in its withdrawal from the market.

Protein Binding：

Data not available for prodrug. See [DB00554] for information on the active compound.

Drug Information

Drug Indication：

Droxicam is an NSAID previously used for the treatment of inflammation and rheumatoid arthritis.

Pharmacology：

Droxicam is a prodrug of [DB00554]. Droxicam administration produces anti-inflammatory, antirheumatic, analgesic, and antipyretic effects similar to [DB00554].

MeSH：

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. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

Absorption：

Tmax of 7 h. Bioavailability equivalent to [DB00554] which is thought to be completely absorbed in humans based on data from rabbits.|Data not available for prodrug. See [DB00554] for information on the active compound.

Metabolism/Metabolites：

Converted to [DB00554] via ester hydrolysis.

Biological Half-Life：

Data not available for prodrug. See [DB00554] for information on the active compound.

Mechanism of Action：

Droxicam is converted to [DB00554] via hydrolysis of the ester group in the intestine. Droxicam administration inhibits the synthesis of prostaglandins by cyclooxygenase enzymes.

MeSH Entry Terms：

5-methyl-3-(2-pyridyl)-2H,5H-1,3-oxazino(5,6-c)(1,2)benzothiazine-2,4(3H)dione-6,6-dioxide

Droxicam Use and Manufacturing

Methods of Manufacturing

It is obtained by refluxing compound (I) and N-(2-pyridyl) phenyl carbamate in diethylene glycol dimethyl ether.

Uses

It is a prodrug of piroxicam, which is converted into piroxicam in the stomach and works. Used for anti-inflammatory.

Computed Properties

Molecular Weight:357.3
XLogP3:1.2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:1
Exact Mass:357.04194163
Monoisotopic Mass:357.04194163
Topological Polar Surface Area:105
Heavy Atom Count:25
Complexity:741
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes