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Withdrawn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

Similar Structures

Weight: Average: 357.34
Monoisotopic: 357.04194164
Chemical Formula: C₁₆H₁₁N₃O₅S

Synonyms

Droxicam

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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings

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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.

Target	Actions	Organism
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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Droxicam
- Piroxicam

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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

Drug	Interaction
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Abacavir	Droxicam may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abciximab	The risk or severity of bleeding and hemorrhage can be increased when Droxicam is combined with Abciximab.
Acebutolol	Droxicam may decrease the antihypertensive activities of Acebutolol.
Aceclofenac	The risk or severity of adverse effects can be increased when Aceclofenac is combined with Droxicam.
Acemetacin	The 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

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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

Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [Article]
Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20. [Article]
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]
WHO: Droxicam [Link]

External Links

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

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Phase	Status	Purpose	Conditions	Count

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

Property	Value	Source
Water Solubility	0.0319 mg/mL	ALOGPS
logP	1.75	ALOGPS
logP	1.23	Chemaxon
logS	-4	ALOGPS
pKa (Strongest Basic)	0.92	Chemaxon
Physiological Charge	0	Chemaxon
Hydrogen Acceptor Count	5	Chemaxon
Hydrogen Donor Count	0	Chemaxon
Polar Surface Area	96.88 Å²	Chemaxon
Rotatable Bond Count	1	Chemaxon
Refractivity	88.19 m³·mol^-1	Chemaxon
Polarizability	33.9 Å³	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-0006-2933000000-5f186fed75038151cdf4
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-91550487eceb97eba160
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0006-0090000000-f19d9e45e3aad522345c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0a4i-0009000000-48a4b1e99e0b6c5f9169
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0gbc-0192000000-80c5fdfbbf0330f8080b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-052f-0094000000-6dd766e9c3938f50c1ca
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-014i-1974000000-f6d51294151a177b0dcd
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å²)	Source type	Source
[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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insights and accelerate drug research.

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Details1. Prostaglandin G/H synthase 1

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

Esteve J, Farre AJ, Roser R: Pharmacological profile of droxicam. Gen Pharmacol. 1988;19(1):49-54. [Article]

Details2. Prostaglandin G/H synthase 2

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

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