NAV

Bimoclomol

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Bimoclomol
DrugBank Accession Number
DB06258
Background

Bimoclomol is an investigational drug that induces stress proteins and has cytoprotective effects.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 297.781
Monoisotopic: 297.124404606
Chemical Formula
C14H20ClN3O2
Synonyms
  • Bimoclomol
External IDs
  • ABT-822
  • BRLP-42
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Pharmacology

Indication

Investigated for use/treatment in neuropathy (diabetic) and wounds.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Bimoclomol binds to HSF-1 and induces a prolonged binding of HSF-1 to the respective DNA elements. Since HSF-1 does not bind to DNA in the absence of stress, the bimoclomol-induced extension of HSF-1/DNA interaction may contribute to the chaperone co-induction of bimoclomol observed previously. These findings indicate that bimoclomol may be of value in targeting HSF-1 so as to induce up-regulation of protective Hsp-s in a non-stressful manner and for therapeutic benefit.

TargetActionsOrganism
UHeat shock factor protein 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Not Available
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as pyridines and derivatives. These are compounds containing a pyridine ring, which is a six-member aromatic heterocycle which consists of one nitrogen atom and five carbon atoms.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Not Available
Direct Parent
Pyridines and derivatives
Alternative Parents
Piperidines / Heteroaromatic compounds / Trialkylamines / Secondary alcohols / 1,2-aminoalcohols / Azacyclic compounds / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
1,2-aminoalcohol / Alcohol / Amine / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Organic nitrogen compound / Organic oxygen compound / Organochloride
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
9IYF14814M
CAS number
130493-03-7
InChI Key
NMOVJBAGBXIKCG-VKAVYKQESA-N
InChI
InChI=1S/C14H20ClN3O2/c15-14(12-5-4-6-16-9-12)17-20-11-13(19)10-18-7-2-1-3-8-18/h4-6,9,13,19H,1-3,7-8,10-11H2/b17-14-
IUPAC Name
(Z)-N-[2-hydroxy-3-(piperidin-1-yl)propoxy]pyridine-3-carbonimidoyl chloride
SMILES
OC(CO\N=C(/Cl)C1=CN=CC=C1)CN1CCCCC1

References

General References
  1. Hargitai J, Lewis H, Boros I, Racz T, Fiser A, Kurucz I, Benjamin I, Vigh L, Penzes Z, Csermely P, Latchman DS: Bimoclomol, a heat shock protein co-inducer, acts by the prolonged activation of heat shock factor-1. Biochem Biophys Res Commun. 2003 Aug 1;307(3):689-95. [Article]
PubChem Compound
9576891
ChemSpider
7851332
ChEMBL
CHEMBL2104595

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.488 mg/mLALOGPS
logP1.39ALOGPS
logP1.57Chemaxon
logS-2.8ALOGPS
pKa (Strongest Acidic)14Chemaxon
pKa (Strongest Basic)9.14Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area57.95 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity79.44 m3·mol-1Chemaxon
Polarizability31.88 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9858
Blood Brain Barrier+0.9139
Caco-2 permeable-0.563
P-glycoprotein substrateSubstrate0.5426
P-glycoprotein inhibitor IInhibitor0.8807
P-glycoprotein inhibitor IIInhibitor0.9459
Renal organic cation transporterInhibitor0.753
CYP450 2C9 substrateNon-substrate0.7797
CYP450 2D6 substrateNon-substrate0.792
CYP450 3A4 substrateNon-substrate0.5626
CYP450 1A2 substrateNon-inhibitor0.7449
CYP450 2C9 inhibitorNon-inhibitor0.8563
CYP450 2D6 inhibitorNon-inhibitor0.6451
CYP450 2C19 inhibitorNon-inhibitor0.6087
CYP450 3A4 inhibitorNon-inhibitor0.8036
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8354
Ames testNon AMES toxic0.5607
CarcinogenicityNon-carcinogens0.801
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5800 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.759
hERG inhibition (predictor II)Inhibitor0.7706
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0002-9420000000-e98978d10ed7c54f14c2
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-259ddbd5923546e35f9a
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-1390000000-8975b96e322aa6321b2f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-001l-9540000000-495501b0b6300fb7594e
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-5920000000-7461db73b4003afdb7a0
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9130000000-edc6e9c98262fe26c4cb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-01si-5920000000-f96df4dbd40c77e4773c
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-168.53322
predicted
DeepCCS 1.0 (2019)
[M+H]+170.89124
predicted
DeepCCS 1.0 (2019)
[M+Na]+176.98439
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Heat shock factor protein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcriptional repressor activity, rna polymerase ii core promoter proximal region sequence-specific binding
Specific Function
DNA-binding protein that specifically binds heat shock promoter elements (HSE) and activates transcription. In higher eukaryotes, HSF is unable to bind to the HSE unless the cells are heat shocked.
Gene Name
HSF1
Uniprot ID
Q00613
Uniprot Name
Heat shock factor protein 1
Molecular Weight
57259.87 Da
References
  1. Hargitai J, Lewis H, Boros I, Racz T, Fiser A, Kurucz I, Benjamin I, Vigh L, Penzes Z, Csermely P, Latchman DS: Bimoclomol, a heat shock protein co-inducer, acts by the prolonged activation of heat shock factor-1. Biochem Biophys Res Commun. 2003 Aug 1;307(3):689-95. [Article]

Drug created at March 19, 2008 16:19 / Updated at February 21, 2021 18:52