PRAVADOLINE MALEATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H26N2O3.C4H4O4
Molecular Weight	494.5363
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

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	No
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	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2243340 | https://www.ncbi.nlm.nih.gov/pubmed/2175798 | DOI: 10.1038/clpt.1989.17 | https://www.ncbi.nlm.nih.gov/pubmed/8365586

Pravadoline is the anti-nociceptive agent, which has analgesic efficacy against 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

Targets

Primary Target	Pharmacology	Potency
prostaglandin biosynthetic process 23 Target ID: GO:0001516 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2243340	Inhibitor 8297	4.9 µM [IC50]
Cannabinoid CB1 receptor 85 Target ID: CHEMBL3571 Sources: Reggio, P. H. (2008) The Cannabinoid Receptors, page 54, retrieved from: https://books.google.ru/books?id=kiicCpjCInEC \| https://www.ncbi.nlm.nih.gov/pubmed/8450470 \| https://www.ncbi.nlm.nih.gov/pubmed/9857088 \| https://www.ncbi.nlm.nih.gov/pubmed/7636873	Binding Agent 1064	2511.0 nM [Ki]
Prostaglandin G/H synthase (cyclooxygenase) 4 Target ID: CHEMBL2111349 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2243340	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24259678	Primary	Basic research	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2243340 https://www.ncbi.nlm.nih.gov/pubmed/2175798	Primary	Phase II 1132	Unknown Approved Use Unknown
Inflammation 102 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2243340	Primary	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	NO11881	https://www.001chemical.com/chem/search?q=NO11881
A2B Chem	AC83575	http://a2bchem.com/prod/AC83575
AK Scientific	W9553	https://aksci.com/item_detail.php?cat=W9553
Achemo Scientific Limited	AC-63875	http://www.achemo.com/search/?Keyword=AC-63875
AstaTech	26395	http://astatechinc.com/CPSResult.php?CRNO=26395
Axon MedChem	1523	https://www.axonmedchem.com/product/1523
BOC Sciences	92623-83-1	http://www.bocsci.com/description.asp?cas=92623-83-1
Capot Chemical	25261	https://www.capotchem.com/search.do?q=25261
Cayman Chemical	10006973	http://www.caymanchem.com/app/template/Product.vm/catalog/10006973
Combi-Blocks	QB-3503	http://www.combi-blocks.com/cgi-bin/find.cgi?QB-3503
Hairui	HR147698	http://www.hairuichem.com/en/product/search.do?q=HR147698
KeyOrganics	DS-1893	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=DS-1893
Lab Network	LN00188504	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00188504
Matrix Scientific	90817	http://www.matrixscientific.com/090817.html
MolPort	MolPort-018-616-283	https://www.molport.com/shop/molecule-link/MolPort-018-616-283
Molcore	CS11881	http://www.molcore.com/CatCS11881.html
MuseChem	R050563	https://www.musechem.com/product/R050563.html
Oakwood	213740	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=213740
Toronto Research Chemicals	P701180	https://www.trc-canada.com/product-detail/?CatNum=P701180
Wonderchem	WD04DZ3	http://www.wonder-chem.com/search.html?text=WD04DZ3
eNovation Chemicals	D641458	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D641458&searchbtn.x=0&searchbtn.y=0

PubMed

Title	Date	PubMed
		252160220
Pravadoline and aminoalkylindole (AAI) analogues: actions which suggest a receptor interaction.	1989 Dec	2611534
Pravadoline: profile in isolated tissue preparations.	1990 Dec	2175798
Aminoalkylindole binding in rat cerebellum: selective displacement by natural and synthetic cannabinoids.	1993 Mar	8450470
Effects of the cannabinoid CB1 receptor antagonist rimonabant on distinct measures of impulsive behavior in rats.	2007 Jul	17387457

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 `Fri Dec 15 15:03:39 UTC 2023` Edited by `admin` on `Fri Dec 15 15:03:39 UTC 2023`
Record UNII	2DH4X8278M
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PRAVADOLINE MALEATE

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