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Details

Stereochemistry RACEMIC
Molecular Formula C19H23NO
Molecular Weight 281.392
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BLARCAMESINE

SMILES

CN(C)CC1CCOC1(C2=CC=CC=C2)C3=CC=CC=C3

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

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
2
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
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2678
Sigma non-opioid intracellular receptor 1
26
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Agonist
2678
Agonist
2678
 860.0 nM [IC50]
Modulator
828
 8.0 µM [IC50]
Modulator
828
 5.1 µM [IC50]
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase I
428
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
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
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
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
Classification Tree Code System Code
FDA ORPHAN DRUG 908022
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
Code System Code Type Description
INN
11031
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
USAN
FG-91
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
PUBCHEM
9882189
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
NCI_THESAURUS
C171846
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
EVMPD
SUB197746
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
SMS_ID
100000183265
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
CAS
195615-83-9
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID60941344
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
FDA UNII
9T210MMZ3F
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
WIKIPEDIA
Blarcamesine
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
DRUG BANK
DB05592
Created by admin on Sat Dec 16 15:51:03 GMT 2023 , Edited by admin on Sat Dec 16 15:51:03 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of BLARCAMESINE
SALT/SOLVATE (PARENT)
Structure of BLARCAMESINE HYDROCHLORIDE
NIH
NCATS
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ACCESSIBILITY
DISCLAIMER
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