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Details

Stereochemistry RACEMIC
Molecular Formula C16H20N4O2.2H2O
Molecular Weight 336.3862
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APAZONE DIHYDRATE

SMILES

O.O.CCCC1C(=O)N2N(C1=O)C3=CC(C)=CC=C3N=C2N(C)C

InChI

InChIKey=LLMGYOJUHDRDFJ-UHFFFAOYSA-N
InChI=1S/C16H20N4O2.2H2O/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;;/h7-9,11H,5-6H2,1-4H3;2*1H2

HIDE SMILES / InChI
Molecular Formula H2O
Molecular Weight 18.0153
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C16H20N4O2
Molecular Weight 300.3556
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/770078

Azapropazone is a non-steroidal anti-inflammatory drug. It is indicated for use in the treatment of rheumatoid arthritis, osteo-arthritis and gout. Gastro-intestinal disturbances, allergic skin rashes and photosensitivity, headache, vertigo, oedema and kidney impairment may occur. Gastro-intestinal bleeding and angioedema have been reported. Pre-treatment with this drug failed to modify plasma concentrations of phenobarbitone. Brain levels of imipramine or desmethyl imipramine were unaffected 60 minutes after oral administration of imipramine.

CNS Activity

CNS Penetrant
2554
Curator's Comment: Studies on the distribution of the drug revealed that low concentrations were measured in the brain.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Prostaglandin Synthesis and Regulation
6
Target ID: WP98
Sources: DOI: 10.1007/978-94-009-0713-3_4
Inhibitor
8297
 3.0 µM [IC50]
proteoglycan biosynthetic process
3
Target ID: GO:0030166
Sources: DOI: 10.1007/978-94-009-0713-3_4
Activator
1430
interleukin-1 alpha production
2
Target ID: GO:0032610
Sources: DOI: 10.1007/978-94-009-0713-3_4
Inhibitor
8297
Xanthine dehydrogenase
32
Target ID: CHEMBL1929
Sources: DOI: 10.1007/978-94-009-0713-3_4
Inhibitor
8297
 15.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Withdrawn
Rheumox

Approved Use

Rheumox is usually prescribed for people with rheumatoid arthritis
Primary
Withdrawn
Rheumox

Approved Use

It is indicated for use in the treatment of osteo-arthritis
Primary
Withdrawn
Rheumox

Approved Use

Rheumox is usually prescribed for people with acute gouty inflammation of the joints.
PubMed

PubMed

TitleDatePubMed
Acute renal failure associated with acute pyelonephritis and consumption of non-steroidal anti-inflammatory drugs.
1986 Jan 11
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Patents

JP2001525058A
70
JPS62138431A
2

Sample Use Guides

In Vivo Use Guide
The usual dose is 1200 mg per day, given as 600 mg twice daily.
Route of Administration: Oral
In Vitro Use Guide
Azapropazone is an inhibitor of a variety of neutrophil functions (migration, aggregation, superoxide production) at 40-400 ug/ml-1
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:49:17 GMT 2023
Edited
by admin
on Sat Dec 16 05:49:17 GMT 2023
Record UNII
BF18764H96
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APAZONE DIHYDRATE
MI  
Common Name English
1H-PYRAZOLO(1,2-A)(1,2,4)BENZOTRIAZINE-1,3(2H)-DIONE, 5-(DIMETHYLAMINO)-9-METHYL-2-PROPYL-, HYDRATE (1:2)
Systematic Name English
MI-85DI
Code English
Azapropazone dihydrate [WHO-DD]
Common Name English
AZAPROPAZONE DIHYDRATE
WHO-DD  
Common Name English
RHEUMOX
Brand Name English
APAZONE DIHYDRATE [MI]
Common Name English
5-DIMETHYLAMINO-9-METHYL-2-PROPYLPYRAZOLO(1,2-A)(1,2,4)BENZOTRIAZINE-1,3(2H)-DIONE DIHYDRATE
Systematic Name English
PROLIXAN
Brand Name English
Code System Code Type Description
PUBCHEM
90763
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY
MERCK INDEX
m1983
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY Merck Index
CAS
22304-30-9
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022634
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY
EVMPD
SUB00638MIG
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY
FDA UNII
BF18764H96
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY
SMS_ID
100000085328
Created by admin on Sat Dec 16 05:49:17 GMT 2023 , Edited by admin on Sat Dec 16 05:49:17 GMT 2023
PRIMARY
Related Record Type Details
Structure of APAZONE
ANHYDROUS->SOLVATE
Related Record Type Details
Structure of APAZONE
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