Basic information
- CAS
5330-29-0- Standard SMILES
CCN(CC)CCCCCCNc1cc(OC)cc2c(C)ccnc12- InChIKey
RVAKDGYPIVSYEU-UHFFFAOYSA-N- Molecular formula
- C21H33N3O
- Average molar mass
- 343.5 g/mol
- Monoisotopic mass
- 343.26236269
Overview
Sitamaquine (WR-6026) is an orally active 8-aminoquinoline analog in development by the Walter Reed Army Institute, in collaboration with GlaxoSmithKline (formerly SmithKline Beecham), for the potential treatment of visceral leishmaniasis.
Names & identifiers
- Preferred name
- Sitamaquine
- IUPAC
- N',N'-diethyl-N-(6-methoxy-4-methylquinolin-8-yl)hexane-1,6-diamine
- English name
- SITAMAQUINE,N,N-DIETHYL-N'-(6-METHOXY-4-METHYL-QUINOLIN-8-YL)-HEXANE-1,6-DIAMINE
- Molecular formula
- C21H33N3O
- Molecular weight
- 343.51
Names & synonyms
Sitamaquine57695-04-2Sitamaquina5AIJ4TGC6BWR 60268-((6-(Diethylamino)hexyl)amino)-6-methoxy-4-methylquinolineDTXSID70206395sitamaquinumsitamaquine hydrochlorideRefChem:886376DTXCID70128886N-(6-(diethylamino)hexyl)-6-methoxy-4-methylquinolin-8-amine
Show more names
6-METHOXY-8-(6-DIETHYLAMINOHEXYLAMINO)-4-METHYLQUINOLINEN-[6-(Diethylamino)hexyl]-4-methyl-6-methoxyquinoline-8-amineN,N-Diethyl-N'-(6-methoxy-4-methylquinolin-8-yl)-1,6-hexanediamine1,6-Hexanediamine, N1,N1-diethyl-N6-(6-methoxy-4-methyl-8-quinolinyl)-
WR-6026WR6026N',N'-diethyl-N-(6-methoxy-4-methylquinolin-8-yl)hexane-1,6-diamineWR 6026 dihydrochlorideMMV000063SITAMAQUINE,N,N-DIETHYL-N'-(6-METHOXY-4-METHYL-QUINOLIN-8-YL)-HEXANE-1,6-DIAMINE1,6-Hexanediamine, N,N-diethyl-N'-(6-methoxy-4-methyl-8-quinolinyl)-NSC2452
Database identifiers
- CAS
5330-29-0、57695-04-2
Properties
Computed structural properties
- XLogP
- 4.7
- Topological polar surface area
- 37.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 11
- Heavy atoms
- 25
- Formal charge
- 0
- Complexity
- 348
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
Physicochemical properties
- Boiling point
- 0.05 · bp0.05 190-200°
- Density
- 1.033 · 1.033±0.06 g/cm3(Predicted)
- pka
- 10.56 · 10.56±0.25(Predicted)
- FDA UNII
- 5 AIJ4TGC6B · 5AIJ4TGC6B
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H301 (100%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P272, P280, P301+P316, P302+P352, P305+P354+P338, P317, P321, P330, P333+P317, P362+P364, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 3 (100%)
Chemistry & industry
Pharmacology
Mechanism of Action
The mechanism of plasmodicidal action of sitamaquine is not completely understood. Like other quinoline derivatives, it is thought to inhibit heme polymerase activity. This results in accumulation of free heme, which is toxic to the parasites.
Upstream & downstream products
Upstream raw materials
Suppliers2 total
北京华美互利生物化工010-56205725 · [email protected]
TargetMol 中国（陶术生物）400-821-0310 15002144251 · [email protected]
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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