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Details

Stereochemistry ACHIRAL
Molecular Formula C23H26N2O3.C4H4O4
Molecular Weight 494.5363
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PRAVADOLINE MALEATE

SMILES

OC(=O)\C=C/C(O)=O.COC1=CC=C(C=C1)C(=O)C2=C(C)N(CCN3CCOCC3)C4=C2C=CC=C4

InChI

InChIKey=DOYGKOLTUWPTGK-BTJKTKAUSA-N
InChI=1S/C23H26N2O3.C4H4O4/c1-17-22(23(26)18-7-9-19(27-2)10-8-18)20-5-3-4-6-21(20)25(17)12-11-24-13-15-28-16-14-24;5-3(6)1-2-4(7)8/h3-10H,11-16H2,1-2H3;1-2H,(H,5,6)(H,7,8)/b;2-1-

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C23H26N2O3
Molecular Weight 378.4641
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Pravadoline is the anti-nociceptive agent, which has analgesic efficacy against the postoperative pain in humans. Pravadoline inhibits the enzyme cyclooxygenase, but in contrast to cyclooxygenase-inhibiting NSAIDs does not produce gastrointestinal irritation. Pravadoline inhibited the synthesis of prostaglandins in mouse brain both in vitro and ex vivo. Pravadoline demonstrated only weak anti-inflammatory activity relative to its anti-nociceptive potency. Single doses of pravadoline were safe and effective in humans, without serious adverse events. Single oral administration of pravadoline maleate induced acute tubular necrosis in male and female beagle dogs.

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Pravadoline and aminoalkylindole (AAI) analogues: actions which suggest a receptor interaction.
1989 Dec
Pravadoline: profile in isolated tissue preparations.
1990 Dec
Pharmacology of pravadoline: a new analgesic agent.
1990 Nov
Nephrotoxicity of pravadoline maleate (WIN 48098-6) in dogs: evidence of maleic acid-induced acute tubular necrosis.
1993 Jul
Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids.
1993 Mar
Aminoalkylindoles: structure-activity relationships of novel cannabinoid mimetics.
1995 Aug 4
Effects of the cannabinoid CB1 receptor antagonist rimonabant on distinct measures of impulsive behavior in rats.
2007 Jul
Combined antiproliferative effects of the aminoalkylindole WIN55,212-2 and radiation in breast cancer cells.
2014 Feb
Patents

Sample Use Guides

In Vivo Use Guide
200, 400 or 800 mg single dose
Route of Administration: Oral
In Vitro Use Guide
Pravadoline (10 and 100 uM) reduced PGE2 content in guinea pig ileum (P < .05).
Substance Class Chemical
Created
by admin
on Tue Oct 22 06:05:37 UTC 2019
Edited
by admin
on Tue Oct 22 06:05:37 UTC 2019
Record UNII
2DH4X8278M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRAVADOLINE MALEATE
USAN  
USAN  
Official Name English
METHANONE, (4-METHOXYPHENYL)(2-METHYL-1-(2-(4-MORPHOLINYL)ETHYL)-1H-INDOL-3-YL)-, (Z)-2-BUTENEDIOATE (1:1)
Systematic Name English
WIN 48,098-6
Code English
PRAVADOLINE MALEATE [USAN]
Common Name English
WIN-48098-6
Code English
P-METHOXYPHENYL 2-METHYL-1-(2-MORPHOLINOETHYL)INDOL-3-YL KETONE MALEATE (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Tue Oct 22 06:05:37 UTC 2019 , Edited by admin on Tue Oct 22 06:05:37 UTC 2019
Code System Code Type Description
CAS
92623-84-2
Created by admin on Tue Oct 22 06:05:37 UTC 2019 , Edited by admin on Tue Oct 22 06:05:37 UTC 2019
PRIMARY
ChEMBL
CHEMBL13178
Created by admin on Tue Oct 22 06:05:37 UTC 2019 , Edited by admin on Tue Oct 22 06:05:37 UTC 2019
PRIMARY
PUBCHEM
9957393
Created by admin on Tue Oct 22 06:05:37 UTC 2019 , Edited by admin on Tue Oct 22 06:05:37 UTC 2019
PRIMARY
MESH
C062767
Created by admin on Tue Oct 22 06:05:37 UTC 2019 , Edited by admin on Tue Oct 22 06:05:37 UTC 2019
PRIMARY
NCI_THESAURUS
C81065
Created by admin on Tue Oct 22 06:05:37 UTC 2019 , Edited by admin on Tue Oct 22 06:05:37 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY