Cabamiquine

Details

Stereochemistry	ACHIRAL
Molecular Formula	C27H31FN4O2
Molecular Weight	462.559
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

FC1=CC2=C(C=C1)N=C(C=C2C(=O)NCCN3CCCC3)C4=CC=C(CN5CCOCC5)C=C4

InChI

InChIKey=BENUHBSJOJMZEE-UHFFFAOYSA-N

InChI=1S/C27H31FN4O2/c28-22-7-8-25-23(17-22)24(27(33)29-9-12-31-10-1-2-11-31)18-26(30-25)21-5-3-20(4-6-21)19-32-13-15-34-16-14-32/h3-8,17-18H,1-2,9-16,19H2,(H,29,33)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26085270
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27809883 | http://adisinsight.springer.com/drugs/800039906

DDD107498 is a compound with a potent and novel spectrum of antimalarial activity against multiple life-cycle stages of the Plasmodium parasite, with good pharmacokinetic properties and an acceptable safety profile. This molecule was developed at the University of Dundee, UK by a research consortium. DDD107498 demonstrates potential to address a variety of clinical needs, including single-dose treatment, transmission blocking and chemoprotection. DDD107498 was developed from a screening programme against blood-stage malaria parasites; its molecular target has been identified as translation elongation factor 2 (eEF2), which is responsible for the GTP-dependent translocation of the ribosome along messenger RNA, and is essential for protein synthesis. Preclinical development is underway in United Kingdom. As at July 2016, no recent reports of development had been identified for preclinical development in Malaria in United Kingdom.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Q8IKW5 (Q8IKW5_PLAF7) 1 Target ID: Q8IKW5 (Q8IKW5_PLAF7) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26085270	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26085270	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
A novel multiple-stage antimalarial agent that inhibits protein synthesis.	2015 Jun 18	26085270
Alternatives to currently used antimalarial drugs: in search of a magic bullet.	2016 Nov 4	27809883

Sample Use Guides

In Vivo Use Guide

mice: 3 mg/kg

Route of Administration: Oral

In Vitro Use Guide

DDD107498 showed excellent activity against 3D7 parasites: 50% effective inhibitory concentration (EC50) 5 1.0 nM (95% confidence interval (CI) 0.8–1.2 nM); EC90 5 2.4 nM (95% CI 2.0–2.9 nM); EC99 5 5.9 nM (95% CI 4.5–7.6 nM), (n 5 39). the ex vivo efficacy of DDD107498 has been shown to be higher than artesunate against P. falciparum (median EC50 = 0.81 nM [range 0.29–3.29 nM]) and P. vivax (median EC50 = 0.51 nM [range 0.25–1.39 nM])

Name

Type

Language

Cabamiquine

Official Name

English

cabamiquine [INN]

Common Name

English

6-fluoro-2-{4-[(morpholin-4-yl)methyl]phenyl}-N-[2-(pyrrolidin-1-yl)ethyl]quinoline-4-carboxamide

Systematic Name

English

CABAMIQUINE [USAN]

Common Name

English

4-Quinolinecarboxamide, 6-fluoro-2-[4-(4-morpholinylmethyl)phenyl]-N-[2-(1-pyrrolidinyl)ethyl]-

Systematic Name

English

MMV121

Code

English

DDD-107498

Code

English

M-5717

Code

English

MMV-121

Code

English

DDD498

Code

English

DDD107498

Code

English

M5717

Code

English

Code System Code Type Description

SMS_ID

300000042071