Identification

Name
Droxicam
Accession Number
DB09215
Type
Small Molecule
Groups
Withdrawn
Description

Droxicam is a non-steroidal anti-inflammatory drug of the oxicam class. A prodrug of Piroxicam, it is used for the relief of pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.

Structure
Thumb
Synonyms
Not Available
Categories
UNII
F24ADO1E2D
CAS number
90101-16-9
Weight
Average: 357.34
Monoisotopic: 357.04194164
Chemical Formula
C16H11N3O5S
InChI Key
OEHFRZLKGRKFAS-UHFFFAOYSA-N
InChI
InChI=1S/C16H11N3O5S/c1-18-13-14(10-6-2-3-7-11(10)25(18,22)23)24-16(21)19(15(13)20)12-8-4-5-9-17-12/h2-9H,1H3
IUPAC Name
8-methyl-5-(pyridin-2-yl)-3-oxa-9λ⁶-thia-5,8-diazatricyclo[8.4.0.0²,⁷]tetradeca-1(14),2(7),10,12-tetraene-4,6,9,9-tetrone
SMILES
CN1C2=C(OC(=O)N(C2=O)C2=CC=CC=N2)C2=CC=CC=C2S1(=O)=O

Pharmacology

Indication

Droxicam is an NSAID previously used for the treatment of inflammation and rheumatoid arthritis [4].

Pharmacodynamics

Droxicam is a prodrug of Piroxicam [1]. Droxicam administration produces anti-inflammatory, antirheumatic, analgesic, and antipyretic effects similar to Piroxicam.

Mechanism of action

Droxicam is converted to Piroxicam via hydrolysis of the ester group in the intestine [2]. Droxicam administration inhibits the synthesis of prostaglandins by cyclooxygenase enzymes [1].

TargetActionsOrganism
AProstaglandin G/H synthase 1
inhibitor
Human
AProstaglandin G/H synthase 2
inhibitor
Human
Absorption

Tmax of 7 h. Bioavailability equivalent to Piroxicam which is thought to be completely absorbed in humans based on data from rabbits [2].

Volume of distribution

Data not available for prodrug. See Piroxicam for information on the active compound.

Protein binding

Data not available for prodrug. See Piroxicam for information on the active compound.

Metabolism

Converted to Piroxicam via ester hydrolysis [2].

Route of elimination

Data not available for prodrug. See Piroxicam for information on the active compound.

Half life

Data not available for prodrug. See Piroxicam for information on the active compound.

Clearance

Data not available for prodrug. See Piroxicam for information on the active compound.

Toxicity

Exposure to Droxicam is associated with significantly increased risk of hepatic toxicity resulting in its withdrawal from the market [3].

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(4R)-limoneneThe risk or severity of adverse effects can be increased when (4R)-limonene is combined with Droxicam.
16-BromoepiandrosteroneThe risk or severity of adverse effects can be increased when Droxicam is combined with 16-Bromoepiandrosterone.
19-norandrostenedioneThe risk or severity of adverse effects can be increased when Droxicam is combined with 19-norandrostenedione.
5-androstenedioneThe risk or severity of adverse effects can be increased when Droxicam is combined with 5-androstenedione.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Droxicam is combined with Abciximab.
AcebutololDroxicam may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Droxicam.
AcemetacinThe risk or severity of adverse effects can be increased when Droxicam is combined with Acemetacin.
AcenocoumarolDroxicam may increase the anticoagulant activities of Acenocoumarol.
AcetaminophenDroxicam may decrease the excretion rate of Acetaminophen which could result in a higher serum level.
Food Interactions
Not Available

References

General References
  1. Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [PubMed:3278945]
  2. Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [PubMed:8162655]
  3. Lapeyre-Mestre M, de Castro AM, Bareille MP, Del Pozo JG, Requejo AA, Arias LM, Montastruc JL, Carvajal A: Non-steroidal anti-inflammatory drug-related hepatic damage in France and Spain: analysis from national spontaneous reporting systems. Fundam Clin Pharmacol. 2006 Aug;20(4):391-5. doi: 10.1111/j.1472-8206.2006.00416.x. [PubMed:16867024]
  4. WHO: Droxicam [Link]
External Links
KEGG Drug
D07267
PubChem Compound
65679
PubChem Substance
310265122
ChemSpider
59108
ChEBI
76133
ChEMBL
CHEMBL1213420
PharmGKB
PA166049182
Wikipedia
Droxicam
ATC Codes
M01AC04 — Droxicam
MSDS
Download (263 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0319 mg/mLALOGPS
logP1.75ALOGPS
logP1.23ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)0.92ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area96.88 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity88.19 m3·mol-1ChemAxon
Polarizability33.9 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as benzothiazines. These are organic compounds containing a benzene fused to a thiazine ring (a six-membered ring with four carbon atoms, one nitrogen atom and one sulfur atom).
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Benzothiazines
Sub Class
Not Available
Direct Parent
Benzothiazines
Alternative Parents
Pyridines and derivatives / Organosulfonamides / Benzenoids / Heteroaromatic compounds / Lactams / Oxacyclic compounds / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds
show 2 more
Substituents
Benzothiazine / Pyridine / Benzenoid / Organosulfonic acid amide / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Heteroaromatic compound / Lactam / Oxacycle / Azacycle
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotricyclic compound, pyridines, ring assembly (CHEBI:76133)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Droxicam is converted to Piroxicam which acts on the target.
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Involved in the constitutive production of prostanoids in particular in the stomach and platelets. In gas...
Gene Name
PTGS1
Uniprot ID
P23219
Uniprot Name
Prostaglandin G/H synthase 1
Molecular Weight
68685.82 Da
References
  1. Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [PubMed:3278945]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Droxicam is converted to Piroxicam which acts on the target.
General Function
Prostaglandin-endoperoxide synthase activity
Specific Function
Converts arachidonate to prostaglandin H2 (PGH2), a committed step in prostanoid synthesis. Constitutively expressed in some tissues in physiological conditions, such as the endothelium, kidney and...
Gene Name
PTGS2
Uniprot ID
P35354
Uniprot Name
Prostaglandin G/H synthase 2
Molecular Weight
68995.625 Da
References
  1. Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [PubMed:3278945]

Drug created on October 21, 2015 10:02 / Updated on October 01, 2018 14:48