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SML0681

Sigma-Aldrich

Febrifugine dihydrochloride

≥95% (HPLC)

Synonym(s):

3-[3-[(2R,3S)-3-Hydroxy-2-piperidinyl]-2-oxopropyl]-4(3H)-quinazolinone dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C16H19N3O3 · 2HCl
CAS Number:
Molecular Weight:
374.26
UNSPSC Code:
51111800
PubChem Substance ID:
NACRES:
NA.77

Quality Level

Assay

≥95% (HPLC)

form

powder

optical activity

[α]/D 10 to 15°, c = 1 in H2O

storage condition

desiccated

color

off-white to gray-brown

solubility

H2O: 15 mg/mL, clear

storage temp.

−20°C

SMILES string

O=C1C2=CC=CC=C2N=CN1CC(C[C@@H]3[C@@H](O)CCCC3)=O.C

InChI

1S/C17H20N2O3.CH4/c20-13(9-12-5-1-4-8-16(12)21)10-19-11-18-15-7-3-2-6-14(15)17(19)22;/h2-3,6-7,11-12,16,21H,1,4-5,8-10H2;1H4/t12-,16+;/m1./s1

Biochem/physiol Actions

Febrifugine dihydrochloride exhibits strong antimalarial activity against Plasmodium falciparum, the most insidious malaria causative agent. The adverse effects of febrifugine include diarrhoea, vomiting and liver toxicity.[1]
Febrifugine is an antimalarial, the active component of the Chinese herb Chang Shan. Recent studies indicate that its mechanism of action is as an inhibitor of prolyl-transfer RNA synthetase (ProRS).

Pictograms

Exclamation mark

Signal Word

Warning

Hazard Statements

Precautionary Statements

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The chemistry and biology of febrifugine and halofuginone.
McLaughlin N P, et al.
Bioorganic & Medicinal Chemistry, 22(7), 1993-2004 (2014)

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