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Merck
CN

SML3015

Arimoclomol maleate

≥98% (HPLC)

Synonym(s):

(+)-(R)-N-[2-Hydroxy-3-(1-piperidinyl)propoxy]pyridine-1-oxide-3-carboximidoyl chloride, maleate salt, (R)-3-(Chloro(2-hydroxy-3-(piperidin-1-yl)propoxyimino)methyl)pyridine 1-oxide, maleate salt, Anti-neurodegeneration agent 1, BRX 220, BRX-220, BRX220, N-[(2R)-2-Hydroxy-3-(1-piperidinyl)propoxy]-3-pyridinecarboximidoyl chloride 1-oxide, maleate salt, maleate salt

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About This Item

Empirical Formula (Hill Notation):
C14H20ClN3O3 · C4H4O4
CAS Number:
289893-26-1
Molecular Weight:
429.85
MDL number:
MFCD28143527
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

H2O: 2 mg/mL, clear

storage temp.

2-8°C

SMILES string

Cl/C(C1=CC=C[N+]([O-])=C1)=N\OC[C@@H](CN2CCCCC2)O.O=C(O)/C=C\C(O)=O

InChI

1S/C14H20ClN3O3.C4H4O4/c15-14(12-5-4-8-18(20)9-12)16-21-11-13(19)10-17-6-2-1-3-7-17;5-3(6)1-2-4(7)8/h4-5,8-9,13,19H,1-3,6-7,10-11H2;1-2H,(H,5,6)(H,7,8)/b;2-1-/t13-;/m1./s1

InChI key

OHUSJUJCPWMZKR-FEGZNKODSA-N

Biochem/physiol Actions

Arimoclomol is an orally available, CNS-penetrant coinducer of heat shock proteins (HSPs), notably HSP70, that exhibits in vivo efficay in disease models of diabetes, Gaucher disease (GD), sporadic inclusion body myositis (sIBM), and neurological disorders, including amyotrophic lateral sclerosis (ALS) and Niemann-Pick disease type C1 (NPC1). Note: arimoclomol maleate and citrate salt forms are known as BRX-220 and BRX-345, respectively.
Orally available, CNS-penetrant coinducer of heat shock proteins (HSPs), notably HSP70 (HSP72), with in vivo ALS, GD, NPC1, and sIBM therapeutic efficacy.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000468844
0000468844
0000455941
0000455942
0000455942

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B Kalmar et al.
Experimental neurology, 176(1), 87-97 (2002-07-03)
Heat shock proteins (hsps) are induced in a variety of cells following periods of stress, where they promote cell survival. In this study, we examined the effect of upregulating hsp expression by treatment with BRX-220, a co-inducer of hsps, on
Dairin Kieran et al.
Nature medicine, 10(4), 402-405 (2004-03-23)
Amyotrophic lateral sclerosis (ALS) is a fatal neurodegenerative condition in which motoneurons of the spinal cord and motor cortex die, resulting in progressive paralysis. This condition has no cure and results in eventual death, usually within 1-5 years of diagnosis.
Zoltán Rakonczay et al.
Free radical biology & medicine, 32(12), 1283-1292 (2002-06-12)
Nontoxic heat shock protein (HSP) inducer compounds open up promising therapeutic possibilities by activating one of the natural and highly conserved defense mechanisms of the organism. In the present experiments, we examined the effects of a HSP coinducer drug-candidate, BRX-220
Mhoriam Ahmed et al.
Science translational medicine, 8(331), 331ra41-331ra41 (2016-03-25)
Sporadic inclusion body myositis (sIBM) is the commonest severe myopathy in patients more than 50 years of age. Previous therapeutic trials have targeted the inflammatory features of sIBM but all have failed. Because protein dyshomeostasis may also play a role
Bernadett Kalmar et al.
Journal of neurochemistry, 107(2), 339-350 (2008-08-05)
Amyotrophic lateral sclerosis (ALS) is a progressive neurodegenerative disorder characterized by motoneuron degeneration, resulting in muscle paralysis and death, typically within 1-5 years of diagnosis. Although the pathogenesis of ALS remains unclear, there is evidence for the involvement of proteasome
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