DECLOPRAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C13H20ClN3O
Molecular Weight	269.77
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCNC(=O)C1=CC=C(N)C(Cl)=C1

InChI

InChIKey=YEYAKZXEBSVURO-UHFFFAOYSA-N

InChI=1S/C13H20ClN3O/c1-3-17(4-2)8-7-16-13(18)10-5-6-12(15)11(14)9-10/h5-6,9H,3-4,7-8,15H2,1-2H3,(H,16,18)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9482687
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/10226556 |http://www.prnewswire.com/news-releases/oxigene-initiates-phase-ii-trials-for-declopramide-an-apoptosis-inducing-and-nf-kappa-beta-inhibiting-cancer-drug-candidate-76239792.html | http://adisinsight.springer.com/drugs/800007055

Declopramide is an apoptosis inducer. Also, it inhibits NFkappaB activation by inhibition of IkappaBbeta breakdown. In preclinical research, Declopramide demonstrated strong antitumor properties. It had been in phase II clinical trials for the treatment of colorectal cancer. However, this research has been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 3 (5-HT3) receptor 59 Target ID: CHEMBL2094116 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10194550	Binding Agent 1064
I-kappaB kinase/NF-kappaB signaling 4 Target ID: GO:0007249 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10576654	Inhibitor 8297
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10576654 \| http://www.prnewswire.com/news-releases/oxigene-initiates-phase-ii-trials-for-declopramide-an-apoptosis-inducing-and-nf-kappa-beta-inhibiting-cancer-drug-candidate-76239792.html	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Inflammatory bowel disease 19 Sources: http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=15507 http://www.evaluategroup.com/Universal/View.aspx?type=Story&id=25314	Primary	Preclinical	Unknown Approved Use Unknown
Colorectal cancer 101 Sources: http://www.prnewswire.com/news-releases/oxigene-initiates-phase-ii-trials-for-declopramide-an-apoptosis-inducing-and-nf-kappa-beta-inhibiting-cancer-drug-candidate-76239792.html	Primary	Phase II 1132	Unknown Approved Use Unknown
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9482687 https://www.ncbi.nlm.nih.gov/pubmed/10226556	Primary	Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00H1P7	https://www.1pchem.com/search?query=1P00H1P7
A2B Chem	AH94555	http://a2bchem.com/prod/AH94555
Alfa Chemistry	ACM891601	http://www.alfa-chemistry.com/search.aspx?q=ACM891601
Chemspace	CSC001171102	https://chem-space.com/CSC001171102
Enamine	BBV-38940910	http://www.enaminestore.com/catalog/BBV-38940910
Enamine	EN300-1425545	https://www.enaminestore.com/catalog/EN300-1425545
MolPort	MolPort-004-952-397	https://www.molport.com/shop/molecule-link/MolPort-004-952-397
MuseChem	I006416	https://www.musechem.com/product/I006416.html
Selena	SEL12375801
eMolecules	276807381	https://orderbb.emolecules.com/search/#?query=276807381

PubMed

Title	Date	PubMed
Mechanism of action for N-substituted benzamide-induced apoptosis.	2002 Mar 18	11953831
Pharmacokinetics and splenic accumulation of N-acetylamino-3-chloro-N-(2-diethylamino-ethyl) benzamide after a single administration to rats.	2004 Oct	15386479

Patents

Sample Use Guides

In Vivo Use Guide

Rat: 50 mg/kg 3 times per day

Route of Administration: Other

In Vitro Use Guide

Human monocytic cells (THP-1) were exposed to 3-chloroprocainamide (3-CPA) at doses 0.2, 1 and 5 mM just before 5 h stimulation with LPS to induce cytokine production. In this experiment, dose dependent inhibition of TNFalpha was paralleled by an equivalent inhibition of IL-1B, IL-6 and IL-8.

Name

Type

Language

DECLOPRAMIDE

Official Name

English

4-AMINO-3-CHLORO-N-(2-(DIETHYLAMINO)ETHYL)BENZAMIDE

Systematic Name

English

declopramide [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C798