FEBRIFUGINE DIHYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H19N3O3.2ClH
Molecular Weight	374.262
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of FEBRIFUGINE DIHYDROCHLORIDE

Structure Search

SMILES

Cl.Cl.O[C@H]1CCCN[C@@H]1CC(=O)CN2C=NC3=CC=CC=C3C2=O

InChI

InChIKey=RDUHYEILHQUTIR-AMTWEWDESA-N

InChI=1S/C16H19N3O3.2ClH/c20-11(8-14-15(21)6-3-7-17-14)9-19-10-18-13-5-2-1-4-12(13)16(19)22;;/h1-2,4-5,10,14-15,17,21H,3,6-9H2;2*1H/t14-,15+;;/m1../s1

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C16H19N3O3
Molecular Weight	301.3404
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://wiredspace.wits.ac.za/bitstream/handle/10539/1743/01chapter1.pdf
Curator's Comment: description was created based on several sources, including: Weici Tang, Gerhard Eisenbrand (2013) "Chinese Drugs of Plant Origin", p.455-457 Retrieved from https://books.google.ru/books?id=xmHwCAAAQBAJ

The alkaloids febrifugine was originally isolated from the roots of the Chinese shrub Dichroa febrifuga. Febrifugine showed an antimalarial activity 50-100 times higher than that of quinine. Febrifugine acts by causing an increase in NO production during the immunological response - increased production of NO by febrifugine plays an important role in host defense against malaria infection in mice. Also, febrifugine are known to inhibit prolyl-tRNA synthetase of malaria parasite Plasmodium falciparum.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Proline--tRNA ligase 2 Target ID: Q8I5R7 Gene ID: 811187.0 Gene Symbol: proRS Target Organism: Plasmodium falciparum (isolate 3D7) Sources: https://www.ncbi.nlm.nih.gov/pubmed/22327401 \| https://www.ncbi.nlm.nih.gov/pubmed/25047712 \| https://www.ncbi.nlm.nih.gov/pubmed/25995223	Inhibitor 8297
nitric oxide biosynthetic process 17 Target ID: GO:0006809 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9644055	Activator 1430
Hemozoin formation 2 Target ID: Hemozoin formation Sources: Teng, W.-C. et al. (2016) "Medicinal Plants and Malaria: Applications, Trends, and Prospects", chapter.4.1.3.1 Retrieved from \| https://books.google.ru/books?id=CBXYCwAAQBAJ	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Malaria 95 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10535750 https://www.ncbi.nlm.nih.gov/pubmed/12820231 https://www.ncbi.nlm.nih.gov/pubmed/11009379 https://www.ncbi.nlm.nih.gov/pubmed/9644055	Curative		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Synthesis and antimalarial activity of febrifugine derivatives.	2001 Jun	11411524
Antimalarials: shortages and searches.	2005 Oct	16249521
Effects of limonoids from Cipadessa fruticosa on fall armyworm.	2009 May-Jun	19678552
Dihydroxylation of vinyl sulfones: stereoselective synthesis of (+)- and (-)-febrifugine and halofuginone.	2010 Jan 15	20000346
Synthesis and evaluation of 4-quinazolinone compounds as potential antimalarial agents.	2010 Sep	20538379

Patents

Sample Use Guides

In Vivo Use Guide

dosage range - 50 ug/kg/day - 5.00 mg/kg/day once daily

Route of Administration: Oral

In Vitro Use Guide

Febrifugine exhibits extreme potency against P. falciparum. Its activity is approximately 10-fold that of the effective antimalarial artemisinin, and 25-fold that of the well-known drug (EC50=0.7 nM). chloroquine.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 08:02:58 GMT 2023` Edited by `admin` on `Sat Dec 16 08:02:58 GMT 2023`
Record UNII	K922TFG9SM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FEBRIFUGINE DIHYDROCHLORIDE

Common Name

English

FEBRIFUGINE DIHYDROCHLORIDE [MI]

Common Name

English

4(3H)-QUINAZOLINONE, 3-(3-((2R,3S)-3-HYDROXY-2-PIPERIDINYL)-2-OXOPROPYL)-, HYDROCHLORIDE (1:2)

Systematic Name

English

PROPYLDAZINE HYDROCHLORIDE

Common Name

English

3-(3-((2R,3S)-3-HYDROXY-2-PIPERIDINYL)-2-OXOPROPYL)-4(3H)-QUINAZOLINONE DIHYDROCHLORIDE

Systematic Name

English

2-PROPANOL, 1-((6-HYDRAZINYL-3-PYRIDAZINYL)METHYLAMINO)-, HYDROCHLORIDE (1:2)

Systematic Name

English

FEBRIFUGINE, DIHYDROCHLORIDE

Common Name

English

1-((6-HYDRAZINYL-3-PYRIDAZINYL)METHYLAMINO)-2-PROPANOL

Systematic Name

English

(+)-FEBRIFUGINE DIHYDROCHLORIDE

Common Name

English

Code System Code Type Description

FDA UNII

K922TFG9SM