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Details

Stereochemistry ACHIRAL
Molecular Formula C18H23NO
Molecular Weight 269.3813
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BIFEMELANE

SMILES

CNCCCCOC1=CC=CC=C1CC2=CC=CC=C2

InChI

InChIKey=QSQQPMHPCBLLGX-UHFFFAOYSA-N
InChI=1S/C18H23NO/c1-19-13-7-8-14-20-18-12-6-5-11-17(18)15-16-9-3-2-4-10-16/h2-6,9-12,19H,7-8,13-15H2,1H3

HIDE SMILES / InChI

Molecular Formula C18H23NO
Molecular Weight 269.3813
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Bifemelane is a psychotropic drug, was found to inhibit monoamine oxidase (MAO). It inhibited type A MAO (MAO-A) competitively and type B (MAO-B) noncompetitively and it was a more potent inhibitor of MAO-A than of MAO-B. Bifemelane is an antidepressant and cerebral activator that is used in Japan for the treatment of cerebral infarction patients with depressive symptoms, and in the treatment of senile dementia as well. It also appears to be useful in the treatment of glaucoma.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
4.2 µM [Ki]
46.0 µM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BIFEMELANE
Primary
BIFEMELANE
Primary
BIFEMELANE
Primary
BIFEMELANE

Cmax

ValueDoseCo-administeredAnalytePopulation
7.57 ng/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
18.61 ng/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
13.41 ng/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
3.21 ng/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
46.29 ng × h/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
99.12 ng × h/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
74.26 ng × h/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
20.24 ng × h/mL
50 mg single, oral
BIFEMELANE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.73 h
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
4.69 h
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
4.71 h
50 mg single, oral
BIFEMELANE plasma
Homo sapiens
3.21 h
50 mg single, oral
BIFEMELANE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
150 mg daily in divided doses.
Route of Administration: Oral
In Vitro Use Guide
Bifemelane 10 nM to 1 uM significantly augmented the long-term potentiation in the CA3 region of guinea pig hippocampal slices
Substance Class Chemical
Record UNII
Z4501GN13G
Record Status Validated (UNII)
Record Version