Azapropazone

Identification

Name
Azapropazone
Accession Number
DB07402
Type
Small Molecule
Groups
Withdrawn
Description
Not Available
Structure
Thumb
Synonyms
  • azapropazona
  • Azapropazone
International/Other Brands
Rheumox (Amdipharm Mercury Company Limited)
Categories
UNII
K2VOT966ZI
CAS number
13539-59-8
Weight
Average: 298.3397
Monoisotopic: 298.14297584
Chemical Formula
C16H18N4O2
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[7.4.0.0²,⁶]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

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
Not Available
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 Azapropazone is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Azapropazone 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 Azapropazone 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 Azapropazone is combined with 4-hydroxycoumarin.
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.
AcarboseAzapropazone may decrease the excretion rate of Acarbose which could result in a higher serum level.
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

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
External Links
PubChem Compound
46937068
PubChem Substance
99443873
ChemSpider
25056860
ChEBI
38010
HET
AZQ
Wikipedia
Azapropazone
ATC Codes
M01AX04 — Azapropazone
PDB Entries
2bx8 / 2bxi / 2bxk

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
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
logP2.08ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)0.52ChemAxon
pKa (Strongest Basic)7.58ChemAxon
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-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 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
Amino-1,2,4-triazine / Aminotriazine / Pyrazolidinone / 1,3-dicarbonyl compound / Benzenoid / 1,2,4-triazine / Pyrazolidine / Carboxylic acid hydrazide / Guanidine / Azacycle
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Carriers

Kind
Protein
Organism
Human
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. [PubMed:10592235]

Drug created on September 15, 2010 15:21 / Updated on November 02, 2018 06:32