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Details

Stereochemistry RACEMIC
Molecular Formula C16H20N4O2
Molecular Weight 300.3556
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of APAZONE

SMILES

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

InChI

InChIKey=MPHPHYZQRGLTBO-UHFFFAOYSA-N
InChI=1S/C16H20N4O2/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

HIDE SMILES / InChI
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Withdrawn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Withdrawn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Withdrawn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 16:27:20 GMT 2023
Edited
by admin
on Sat Dec 16 16:27:20 GMT 2023
Record UNII
K2VOT966ZI
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
APAZONE
MI   USAN  
USAN  
Official Name English
APAZONE, (±)-
Common Name English
AZAPROPAZONE [MART.]
Common Name English
APAZONE [MI]
Common Name English
CINNOPROPAZONE
Common Name English
NSC-102824
Code English
1H-PYRAZOLO(1,2-A)(1,2,4)BENZOTRIAZINE-1,3(2H)-DIONE, 5-(DIMETHYLAMINO)-9-METHYL-2-PROPYL-
Systematic Name English
APAZONE [USAN]
Common Name English
5-(Dimethylamino)-9-methyl-2-propyl-1H-pyrazolo[1,2-a][1,2,4]benzotriazine-1,3(2H)-dione
Systematic Name English
5-DIMETHYLAMINO-9-METHYL-2-PROPYLPYRAZOLO(1,2-A)(1,2,4)BENZOTRIAZINE-1,3(2H)-DIONE
Systematic Name English
azapropazone [INN]
Common Name English
AZAPROPAZONE
INN   MART.   WHO-DD  
INN  
Official Name English
(±)-APAZONE
Common Name English
MI-85
Code English
Azapropazone [WHO-DD]
Common Name English
AHR-3018
Code English
Classification Tree Code System Code
WHO-VATC QM01AX04
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
WHO-ATC M01AX04
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
NCI_THESAURUS C257
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
Code System Code Type Description
INN
2276
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
FDA UNII
K2VOT966ZI
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
EVMPD
SUB05638MIG
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
MESH
D001032
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
NSC
102824
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
NCI_THESAURUS
C73074
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
CAS
13539-59-8
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
ChEMBL
CHEMBL1565476
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
DRUG CENTRAL
266
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
WIKIPEDIA
AZAPROPAZONE
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
ECHA (EC/EINECS)
236-913-8
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
DRUG BANK
DB07402
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
RXCUI
1029
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID6045408
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
CHEBI
38010
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
LACTMED
Apazone
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
MERCK INDEX
m1983
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY Merck Index
PUBCHEM
26098
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
SMS_ID
100000086076
Created by admin on Sat Dec 16 16:27:21 GMT 2023 , Edited by admin on Sat Dec 16 16:27:21 GMT 2023
PRIMARY
Related Record Type Details
Structure of APAZONE, (S)-
ENANTIOMER -> RACEMATE
Structure of APAZONE, (R)-
ENANTIOMER -> RACEMATE
Structure of APAZONE DIHYDRATE
SOLVATE->ANHYDROUS
Related Record Type Details
Structure of APAZONE
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