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Details

Stereochemistry RACEMIC
Molecular Formula C19H23NO.ClH
Molecular Weight 317.8536
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BLARCAMESINE HYDROCHLORIDE

SMILES

CN(C)CC1CCOC1(c2ccccc2)c3ccccc3.Cl

InChI

InChIKey=FEQOLYDPQKHFTD-UHFFFAOYSA-N
InChI=1S/C19H23NO.ClH/c1-20(2)15-18-13-14-21-19(18,16-9-5-3-6-10-16)17-11-7-4-8-12-17;/h3-12,18H,13-15H2,1-2H3;1H

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H23NO
Molecular Weight 281.3927
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: description was created based on several sources, including: http://en.pharmacodia.com/web/drug/1_1897.html | http://adisinsight.springer.com/drugs/800033840 | https://en.wikipedia.org/wiki/ANAVEX2-73 | http://www.alzforum.org/therapeutics/anavex-2-73

ANAVEX 2-73 is an orally available drug candidate developed to potentially modify Alzheimer’s. This drug is in Phase II trials for Alzheimer's disease and Rett syndrome, phase I trials for epilepsy and in preclinical trials for multiple sclerosis and Parkinson's disease. ANAVEX 2-73 is a sigma-1 receptor agonist, which also has micromolar affinities for muscarinic M1–M4 receptors, the sodium channel site 2 and NMDAreceptors. Observed adverse events at doses above the maximum tolerated single dose (60 mg) included headache and dizziness, which were moderate in severity and reversible.

Originator

Sources: Farmaco (1996), 51, (1), 19-26http://www.anavex.com/about-us/overview/
Curator's Comment:: https://www.google.com/patents/US20140228375

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
860.0 nM [IC50]
8.0 µM [IC50]
5.1 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
5 mg 1 times / day multiple, intravenous (total daily dose)
Highest studied dose
Dose: 5 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 5 mg, 1 times / day
Sources:
unhealthy, ADULT
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
60 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
healthy, ADULT
n = 22
Health Status: healthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
Other AEs: Dizziness, headache...
55 mg 1 times / day multiple, oral
MTD
Dose: 55 mg, 1 times / day
Route: oral
Route: multiple
Dose: 55 mg, 1 times / day
Sources:
healthy, ADULT
n = 22
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
AEs

AEs

AESignificanceDosePopulation
Dizziness moderate
60 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
healthy, ADULT
n = 22
Health Status: healthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
headache moderate
60 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 60 mg, 1 times / day
Route: oral
Route: multiple
Dose: 60 mg, 1 times / day
Sources:
healthy, ADULT
n = 22
Health Status: healthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
PubMed

PubMed

TitleDatePubMed
[Anticonvulsant and forced swim anti-immobility effects of tetrahydro-N, N-dimethyl-2,2-diphenyl-3-furanemethanamine (AE37): common action mechanism?].
2002 Mar
Anti-amnesic and neuroprotective potentials of the mixed muscarinic receptor/sigma 1 (σ1) ligand ANAVEX2-73, a novel aminotetrahydrofuran derivative.
2011 Aug
Blockade of Tau hyperphosphorylation and Aβ₁₋₄₂ generation by the aminotetrahydrofuran derivative ANAVEX2-73, a mixed muscarinic and σ₁ receptor agonist, in a nontransgenic mouse model of Alzheimer's disease.
2013 Aug
Mitochondrial protection by the mixed muscarinic/σ1 ligand ANAVEX2-73, a tetrahydrofuran derivative, in Aβ25-35 peptide-injected mice, a nontransgenic Alzheimer's disease model.
2014
Alzheimer's Association International Conference on Alzheimer's Disease 2015 (AAIC 2015) (July 18-23, 2015 - Washington, D.C., USA).
2015 Jul
Protection by sigma-1 receptor agonists is synergic with donepezil, but not with memantine, in a mouse model of amyloid-induced memory impairments.
2016 Jan 1
Patents

Sample Use Guides

30-50 mg Anavex2-73 hard gelatin capsule orally once daily for 52 weeks.
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:40:17 UTC 2021
Edited
by admin
on Sat Jun 26 13:40:17 UTC 2021
Record UNII
1M49V1PBPL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BLARCAMESINE HYDROCHLORIDE
USAN  
Official Name English
ANA001-HCl
Code English
ANAVEX2-73 HYDROCHLORIDE
Code English
AE-37 HYDROCHLORIDE
Code English
BLARCAMESINE HYDROCHLORIDE [USAN]
Common Name English
ANAVEX 2-73 HYDROCHLORIDE
Code English
ANAVEX-2-73 HYDROCHLORIDE
Code English
3-FURANMETHANAMINE, TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-, HYDROCHLORIDE (1:1)
Systematic Name English
TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-3-FURANMETHANAMINE HYDROCHLORIDE
Systematic Name English
RAC-C-((3R)-2,2-DIPHENYLOXOLAN-3-YL)-N,N-DIMETHYLMETHANAMINE HYDROCHLORIDE
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 520816
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
FDA ORPHAN DRUG 524416
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C171847
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
PRIMARY
CAS
195615-84-0
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
PRIMARY
PUBCHEM
46932299
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
PRIMARY
EVMPD
SUB197745
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
PRIMARY
FDA UNII
1M49V1PBPL
Created by admin on Sat Jun 26 13:40:17 UTC 2021 , Edited by admin on Sat Jun 26 13:40:17 UTC 2021
PRIMARY
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