NAV

Azapropazone

Identification

Generic Name
Azapropazone
DrugBank Accession Number
DB07402
Background

Not Available

Type
Small Molecule
Groups
Withdrawn
Structure
3D
Similar Structures
Weight
Average: 298.3397
Monoisotopic: 298.14297584
Chemical Formula
C16H18N4O2
Synonyms
  • 1,2-Dihydro-3-dimethylamino-7-methyl-1,2-(propylmalonyl)-1,2,4-benzotriazine
  • 3-Dimethylamino-7-methyl-1,2-(n-propylmalonyl)-1,2-dihydro-1,2,4-benzotriazine
  • 5-(Dimethylamino)-9-methyl-2-propyl-1H-pyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2H)-dione
  • Apazone
  • Azapropazon
  • Azapropazona
  • Azapropazone
  • Azapropazonum
External IDs
  • AHR 3018
  • AHR-3018
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofGout flares••••••••••••••••••• ••••••
Treatment ofMuscle inflammation••••••••••••••••••• ••••••
Treatment ofNeuralgia, sciatic••••••••••••••••••• ••••••
Treatment ofPain caused by orthopedic surgeries••••••••••••••••••• ••••••
Treatment ofPain, inflammatory caused by orthopedic surgeries••••••••••••••••••• ••••••
Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

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.
DrugInteraction
Integrate drug-drug
interactions in your software
AbacavirAzapropazone 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 Azapropazone is combined with Abciximab.
AcebutololAzapropazone may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Azapropazone.
AcemetacinThe risk or severity of adverse effects can be increased when Azapropazone is combined with Acemetacin.
Food Interactions
Not Available

Products

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International/Other Brands
Rheumox (Amdipharm Mercury Company Limited)

Categories

ATC Codes
M01AX04 — Azapropazone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as aminotriazines. These are organic compounds containing an amino group attached to a triazine ring.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Triazines
Sub Class
Aminotriazines
Direct Parent
Aminotriazines
Alternative Parents
Pyrazolidinones / Benzenoids / 1,3-dicarbonyl compounds / 1,2,4-triazines / Guanidines / Carboxylic acid hydrazides / Propargyl-type 1,3-dipolar organic compounds / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 1 more
Substituents
1,2,4-triazine / 1,3-dicarbonyl compound / Amino-1,2,4-triazine / Aminotriazine / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid hydrazide
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
K2VOT966ZI
CAS number
13539-59-8
InChI Key
WOIIIUDZSOLAIW-NSHDSACASA-N
InChI
InChI=1S/C16H18N4O2/c1-5-6-11-14(21)19-13-9-10(2)7-8-12(13)17-16(18(3)4)20(19)15(11)22/h5,7-9,11H,1,6H2,2-4H3/t11-/m0/s1
IUPAC Name
(4S)-7-(dimethylamino)-12-methyl-4-(prop-2-en-1-yl)-2,6,8-triazatricyclo[7.4.0.0^{2,6}]trideca-1(13),7,9,11-tetraene-3,5-dione
SMILES
[H][C@@]1(CC=C)C(=O)N2N(C1=O)C1=CC(C)=CC=C1N=C2N(C)C

References

Synthesis Reference

Molnar, I., Wagner-Jauregg,T., Jahn, U. and Mixich, G.; US. Patent 3,349,088; October 24, 1967; assigned to Siegfried AG, Switzerland Molnar, I.,Wagner-Jauregg,T., Jahn, U. and Mixich, G.; US. Patent 3,482,024; December 2, 1969; assigned to Siegfried AG.

General References
Not Available
KEGG Drug
D02966
PubChem Compound
46937068
PubChem Substance
99443873
ChemSpider
25056860
RxNav
1029
ChEBI
38010
ZINC
ZINC000033821211
PDBe Ligand
AZQ
Wikipedia
Azapropazone
PDB Entries
2bx8 / 2bxi / 2bxk

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)187Molnar, I., Wagner-Jauregg,T., Jahn, U. and Mixich, G.; US. Patent 3,349,088; October 24, 1967; assigned to Siegfried AG, Switzerland Molnar, I.,Wagner-Jauregg,T., Jahn, U. and Mixich, G.; US. Patent 3,482,024; December 2, 1969; assigned to Siegfried AG.
Predicted Properties
PropertyValueSource
Water Solubility0.641 mg/mLALOGPS
logP0.92ALOGPS
logP2.16Chemaxon
logS-2.7ALOGPS
pKa (Strongest Acidic)5.5Chemaxon
pKa (Strongest Basic)4.32Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area56.22 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity85.69 m3·mol-1Chemaxon
Polarizability31.94 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9389
Caco-2 permeable+0.5728
P-glycoprotein substrateNon-substrate0.5961
P-glycoprotein inhibitor IInhibitor0.8281
P-glycoprotein inhibitor IIInhibitor0.6484
Renal organic cation transporterNon-inhibitor0.7843
CYP450 2C9 substrateNon-substrate0.8218
CYP450 2D6 substrateNon-substrate0.8107
CYP450 3A4 substrateSubstrate0.6289
CYP450 1A2 substrateInhibitor0.5528
CYP450 2C9 inhibitorNon-inhibitor0.8735
CYP450 2D6 inhibitorNon-inhibitor0.9188
CYP450 2C19 inhibitorNon-inhibitor0.8614
CYP450 3A4 inhibitorNon-inhibitor0.8273
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.725
Ames testAMES toxic0.5466
CarcinogenicityNon-carcinogens0.8321
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.4784 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7311
hERG inhibition (predictor II)Non-inhibitor0.8171
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0006-9270000000-535beb50ed73bcf5626b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-36d972d4ad671c557a5b
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-006t-4090000000-d4d0ad97c73668915f57
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-5ba47f836e733b642495
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-81a39f25cea6b6529cb0
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0gbc-6790000000-bdbbab4af20f17e99d5d
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ox-7790000000-8cf0fc9928cda5514cf1
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]-167.67708
predicted
DeepCCS 1.0 (2019)
[M+H]+170.03508
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.67297
predicted
DeepCCS 1.0 (2019)

Carriers

Details1. Serum albumin
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at September 15, 2010 21:21 / Updated at June 12, 2020 17:42