arimoclomol   Click here for help

GtoPdb Ligand ID: 8271

Synonyms: BRX-220 | BRX220
Compound class: Synthetic organic
Comment: Arimoclomol is an oral therapeutic candidate for the treatment of amyotrophic lateral sclerosis (ALS). Arimoclomol may be delivered as the citrate salt (BRX-345 with PubChem CID 72710735)
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 72
Molecular weight 313.12
XLogP 2.49
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OC(CN1CCCCC1)CON=C(c1ccc[n+](c1)[O-])Cl
Isomeric SMILES O[C@H](CN1CCCCC1)CO/N=C(/c1ccc[n+](c1)[O-])\Cl
InChI InChI=1S/C14H20ClN3O3/c15-14(12-5-4-8-18(20)9-12)16-21-11-13(19)10-17-6-2-1-3-7-17/h4-5,8-9,13,19H,1-3,6-7,10-11H2/b16-14-/t13-/m1/s1
InChI Key SGEIEGAXKLMUIZ-XUVDNFPMSA-N
References
1. Benn SC, Brown Jr RH. (2004)
Putting the heat on ALS.
Nat Med, 10 (4): 345-7. [PMID:15057226]
2. Brown IR. (2007)
Heat shock proteins and protection of the nervous system.
Ann N Y Acad Sci, 1113: 147-58. [PMID:17656567]
3. Kalmar B, Burnstock G, Vrbová G, Urbanics R, Csermely P, Greensmith L. (2002)
Upregulation of heat shock proteins rescues motoneurones from axotomy-induced cell death in neonatal rats.
Exp Neurol, 176 (1): 87-97. [PMID:12093085]
4. Kalmar B, Greensmith L. (2009)
Activation of the heat shock response in a primary cellular model of motoneuron neurodegeneration-evidence for neuroprotective and neurotoxic effects.
Cell Mol Biol Lett, 14 (2): 319-35. [PMID:19183864]
5. Kalmar B, Greensmith L, Malcangio M, McMahon SB, Csermely P, Burnstock G. (2003)
The effect of treatment with BRX-220, a co-inducer of heat shock proteins, on sensory fibers of the rat following peripheral nerve injury.
Exp Neurol, 184 (2): 636-47. [PMID:14769355]
6. Kalmar B, Novoselov S, Gray A, Cheetham ME, Margulis B, Greensmith L. (2008)
Late stage treatment with arimoclomol delays disease progression and prevents protein aggregation in the SOD1 mouse model of ALS.
J Neurochem, 107 (2): 339-50. [PMID:18673445]
7. Kieran D, Kalmar B, Dick JR, Riddoch-Contreras J, Burnstock G, Greensmith L. (2004)
Treatment with arimoclomol, a coinducer of heat shock proteins, delays disease progression in ALS mice.
Nat Med, 10 (4): 402-5. [PMID:15034571]