Isoxicam

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Isoxicam
Accession Number
DB08942
Type
Small Molecule
Groups
Withdrawn
Description

Isoxicam is a non-steroidal anti-inflammatory drug that is not marketed in the United States.

Structure
Thumb
Synonyms
  • isoxicamo
External IDs
W 8495
International/Other Brands
Maxicam
Categories
UNII
8XU734C4NG
CAS number
34552-84-6
Weight
Average: 335.335
Monoisotopic: 335.057591231
Chemical Formula
C14H13N3O5S
InChI Key
YYUAYBYLJSNDCX-UHFFFAOYSA-N
InChI
InChI=1S/C14H13N3O5S/c1-8-7-11(16-22-8)15-14(19)12-13(18)9-5-3-4-6-10(9)23(20,21)17(12)2/h3-7,18H,1-2H3,(H,15,16,19)
IUPAC Name
4-hydroxy-2-methyl-N-(5-methyl-2,3-dihydro-1,2-oxazol-3-ylidene)-1,1-dioxo-2H-1λ⁶,2-benzothiazine-3-carboxamide
SMILES
CN1C(C(=O)N=C2NOC(C)=C2)=C(O)C2=CC=CC=C2S1(=O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Isoxicam is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Isoxicam is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Isoxicam is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Isoxicam is combined with 4-hydroxycoumarin.
AbacavirIsoxicam 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 Isoxicam is combined with Abciximab.
AcarboseIsoxicam may decrease the excretion rate of Acarbose which could result in a higher serum level.
AcebutololIsoxicam may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Isoxicam.
AcemetacinThe risk or severity of adverse effects can be increased when Isoxicam is combined with Acemetacin.
Food Interactions
Not Available

References

General References
  1. Fenner H: Comparative biochemical pharmacology of the oxicams. Scand J Rheumatol Suppl. 1987;65:97-101. [PubMed:3500509]
  2. DiPasquale G, Rassaert C, Richter R, Welaj P, Gingold J, Singer R: The anti=inflammatory properties of isoxicam (4-hydroxy-2methyl-N-(5-methyl-3isoxolyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide). Agents Actions. 1975 Aug;5(3):256-63. [PubMed:1236641]
  3. Evaluation of the Characteristics of Safety Withdrawal of Prescription Drugs from Worldwide Pharmaceutical Markets-1960 to 1999 [Link]
External Links
KEGG Drug
D04639
PubChem Compound
54677972
PubChem Substance
310264909
ChemSpider
10442695
ChEBI
76163
ChEMBL
CHEMBL53292
PharmGKB
PA166049183
HET
ICD
Wikipedia
Isoxicam
PDB Entries
4m10

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 Solubility0.336 mg/mLALOGPS
logP0.6ALOGPS
logP-0.085ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)4.46ChemAxon
pKa (Strongest Basic)-0.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area108.3 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity94.9 m3·mol-1ChemAxon
Polarizability32.24 Å3ChemAxon
Number of Rings3ChemAxon
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 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
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0hi2-4920000000-6d8f0aecb48174d3dfd1

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
Alpha amino acids and derivatives / Organosulfonamides / Benzenoids / 1,2-thiazines / Vinylogous acids / Isoxazoles / Heteroaromatic compounds / N-acylimines / Oxacyclic compounds / Azacyclic compounds
show 4 more
Substituents
Alpha-amino acid or derivatives / Benzothiazine / Ortho-thiazine / Organosulfonic acid amide / Benzenoid / Azole / Isoxazole / Organic sulfonic acid or derivatives / Organosulfonic acid or derivatives / Vinylogous acid
show 14 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
monocarboxylic acid amide, isoxazoles, benzothiazine (CHEBI:76163)

Drug created on May 26, 2014 16:17 / Updated on November 02, 2018 06:56