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Details

Stereochemistry RACEMIC
Molecular Formula C19H23NO
Molecular Weight 281.3927
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BLARCAMESINE

SMILES

CN(C)CC1CCOC1(c2ccccc2)c3ccccc3

InChI

InChIKey=BOTHKNZTGGXFEQ-UHFFFAOYSA-N
InChI=1S/C19H23NO/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

HIDE SMILES / InChI
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.

CNS Activity

Originator

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

Approval Year

Unknown
81255
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2451
Sigma non-opioid intracellular receptor 1
23
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Agonist
2451
Agonist
2451
 860.0 nM [IC50]
Modulator
773
 8.0 µM [IC50]
Modulator
773
 5.1 µM [IC50]
Modulator
773
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
Unknown

Approved Use

Unknown
Primary
Phase I
591
Unknown

Approved Use

Unknown
Primary
Phase I
591
Unknown

Approved Use

Unknown
Primary
Phase I
591
Unknown

Approved Use

Unknown
Primary
Phase II
Unknown

Approved Use

Unknown
Primary
Phase II
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Preclinical
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:
https://pubmed.ncbi.nlm.nih.gov/32318621/
unhealthy, ADULT
Health Status: unhealthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M+F
Food Status: FED
Sources:
https://pubmed.ncbi.nlm.nih.gov/32318621/
Sources:
https://pubmed.ncbi.nlm.nih.gov/32318621/
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:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
n = 22
Health Status: healthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
Other AEs: Dizziness, headache...
Other AEs:
Dizziness (moderate)
headache (moderate)
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
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:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
n = 22
Health Status: healthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
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:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
n = 22
Health Status: healthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
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:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
healthy, ADULT
n = 22
Health Status: healthy
Condition: Alzheimer disease
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Population Size: 22
Sources:
https://www.anavex.com/anavex-announces-positive-phase-1-data-for-anavex-2-73-lead-candidate-for-the-treatment-of-alzheimers/
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

Patents

GR99100386
2
US20140228375
2
WO9730983
2

Sample Use Guides

In Vivo Use Guide
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 15:32:15 UTC 2021
Edited
by admin
on Sat Jun 26 15:32:15 UTC 2021
Record UNII
9T210MMZ3F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BLARCAMESINE
INN   USAN  
Official Name English
ANAVEX 2-73
Code English
RAC-1-((3R)-2,2-DIPHENYLOXOLAN-3-YL)-N,N-DIMETHYLMETHANAMINE
Systematic Name English
BLARCAMESINE [INN]
Common Name English
BLARCAMESINE [USAN]
Common Name English
3-FURANMETHANAMINE, TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-
Systematic Name English
TETRAHYDRO-N,N-DIMETHYL-2,2-DIPHENYL-3-FURANMETHANAMINE
Systematic Name English
Code System Code Type Description
INN
11031
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
PUBCHEM
9882189
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
NCI_THESAURUS
C171846
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
EVMPD
SUB197746
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
CAS
195615-83-9
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
FDA UNII
9T210MMZ3F
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
DRUG BANK
DB05592
Created by admin on Sat Jun 26 15:32:15 UTC 2021 , Edited by admin on Sat Jun 26 15:32:15 UTC 2021
PRIMARY
Related Record Type Details
SIGMA NON-OPIOID INTRACELLULAR RECEPTOR 1
TARGET -> AGONIST
MUSCARINIC ACETYLCHOLINE RECEPTOR M1
TARGET->MODULATOR
Structure of BLARCAMESINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of BLARCAMESINE
ACTIVE MOIETY
NIH
NCATS
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