Droxicam

Identification

Generic Name
Droxicam
DrugBank Accession Number
DB09215
Background

Droxicam is an oxicam non-steroidal anti-inflammatory drug and a prodrug of Piroxicam. It is used to reduce pain and inflammation in musculoskeletal disorders such as rheumatoid arthritis and osteoarthritis.

Type
Small Molecule
Groups
Withdrawn
Structure
Weight
Average: 357.34
Monoisotopic: 357.04194164
Chemical Formula
C16H11N3O5S
Synonyms
  • Droxicam

Pharmacology

Indication

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

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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
Humans
AProstaglandin G/H synthase 2
inhibitor
Humans
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.

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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.

Adverse Effects
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Toxicity

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

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbacavirDroxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
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.
Food Interactions
Not Available

Categories

ATC Codes
M01AC04 — Droxicam
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzothiazine / Heteroaromatic compound / Hydrocarbon derivative / Lactam / Organic nitrogen compound / Organic oxide / Organic oxygen compound
show 8 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
organic heterotricyclic compound, pyridines, ring assembly (CHEBI:76133)
Affected organisms
Not Available

Chemical Identifiers

UNII
F24ADO1E2D
CAS number
90101-16-9
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

References

General References
  1. Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [Article]
  2. Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [Article]
  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. [Article]
  4. WHO: Droxicam [Link]
KEGG Drug
D07267
PubChem Compound
65679
PubChem Substance
310265122
ChemSpider
59108
RxNav
23687
ChEBI
76133
ChEMBL
CHEMBL1213420
ZINC
ZINC000000597502
PharmGKB
PA166049182
Wikipedia
Droxicam
MSDS
Download (263 KB)

Clinical Trials

Clinical Trials
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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

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-MSsplash10-0006-2933000000-5f186fed75038151cdf4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-91550487eceb97eba160
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0090000000-f19d9e45e3aad522345c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0009000000-48a4b1e99e0b6c5f9169
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gbc-0192000000-80c5fdfbbf0330f8080b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-052f-0094000000-6dd766e9c3938f50c1ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-1974000000-f6d51294151a177b0dcd
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-188.4340837
predicted
DarkChem Lite v0.1.0
[M-H]-169.82092
predicted
DeepCCS 1.0 (2019)
[M+H]+189.4874837
predicted
DarkChem Lite v0.1.0
[M+H]+172.17892
predicted
DeepCCS 1.0 (2019)
[M+Na]+188.9678837
predicted
DarkChem Lite v0.1.0
[M+Na]+178.48854
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
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. [Article]
Kind
Protein
Organism
Humans
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. [Article]

Drug created at October 21, 2015 16:02 / Updated at February 21, 2021 18:52