U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Molecular Formula C19H23NO
Molecular Weight 281.392
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
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
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Agonist
2662
Sigma non-opioid intracellular receptor 1
26
Target ID: Q99720|||Q7Z653
Gene ID: 10280.0
Gene Symbol: SIGMAR1
Target Organism: Homo sapiens (Human)
Agonist
2662
Agonist
2662
 860.0 nM [IC50]
Modulator
822
 8.0 µM [IC50]
Modulator
822
 5.1 µM [IC50]
Modulator
822
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Phase II
1144
Unknown

Approved Use

Unknown
Primary
Phase II
1144
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
Anti-amnesic and neuroprotective potentials of the mixed muscarinic receptor/sigma 1 (σ1) ligand ANAVEX2-73, a novel aminotetrahydrofuran derivative.
2011 Aug
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 Thu Jul 06 21:23:23 UTC 2023
Edited
by admin
on Thu Jul 06 21:23:23 UTC 2023
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 [WHO-DD]
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 Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
Code System Code Type Description
INN
11031
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
USAN
FG-91
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
PUBCHEM
9882189
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
NCI_THESAURUS
C171846
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
EVMPD
SUB197746
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
SMS_ID
100000183265
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
CAS
195615-83-9
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
EPA CompTox
DTXSID60941344
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
FDA UNII
9T210MMZ3F
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
WIKIPEDIA
Blarcamesine
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
PRIMARY
DRUG BANK
DB05592
Created by admin on Thu Jul 06 21:23:24 UTC 2023 , Edited by admin on Thu Jul 06 21:23:24 UTC 2023
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
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966