APAZONE

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 Search

SMILES

CCCC1C(=O)N2N(C1=O)C3=C(C=CC(C)=C3)N=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
Sources: http://home.intekom.com/pharm/cont_eth/rheumox.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Prostaglandin Synthesis and Regulation 6 Target ID: WP98 Sources: DOI: 10.1007/978-94-009-0713-3_4	Inhibitor 8504	3.0 µM [IC50]
proteoglycan biosynthetic process 3 Target ID: GO:0030166 Sources: DOI: 10.1007/978-94-009-0713-3_4	Activator 1447
interleukin-1 alpha production 2 Target ID: GO:0032610 Sources: DOI: 10.1007/978-94-009-0713-3_4	Inhibitor 8504
Xanthine dehydrogenase 33 Target ID: CHEMBL1929 Sources: DOI: 10.1007/978-94-009-0713-3_4	Inhibitor 8504	15.0 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 320 Sources: http://home.intekom.com/pharm/cont_eth/rheumox.html	Primary	Withdrawn	Rheumox Approved Use Rheumox is usually prescribed for people with rheumatoid arthritis
Osteoarthritis 157 Sources: http://home.intekom.com/pharm/cont_eth/rheumox.html	Primary	Withdrawn	Rheumox Approved Use It is indicated for use in the treatment of osteo-arthritis
Gout 28 Sources: http://home.intekom.com/pharm/cont_eth/rheumox.html	Primary	Withdrawn	Rheumox Approved Use Rheumox is usually prescribed for people with acute gouty inflammation of the joints.

PubMed

Title	Date	PubMed
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.	2015-01-05	25455453
Acute renal failure associated with acute pyelonephritis and consumption of non-steroidal anti-inflammatory drugs.	1986-01-11	3080108

Patents

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 `Wed Apr 02 07:52:38 GMT 2025` Edited by `admin` on `Wed Apr 02 07:52:38 GMT 2025`
Record UNII	K2VOT966ZI
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

APAZONE

Official Name

English

AZAPROPAZONE

Preferred 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

(±)-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