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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

InChI key

SNTOTCUGCWLHEZ-KKJWGQAZSA-N

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.
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)

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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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