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Details

Stereochemistry ACHIRAL
Molecular Formula C19H23N3O3
Molecular Weight 341.4042
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of COLURACETAM

SMILES

CC1=C(C)C2=C(NC(=O)CN3CCCC3=O)C4=C(CCCC4)N=C2O1

InChI

InChIKey=PSPGQHXMUKWNDI-UHFFFAOYSA-N
InChI=1S/C19H23N3O3/c1-11-12(2)25-19-17(11)18(13-6-3-4-7-14(13)20-19)21-15(23)10-22-9-5-8-16(22)24/h3-10H2,1-2H3,(H,20,21,23)

HIDE SMILES / InChI

Molecular Formula C19H23N3O3
Molecular Weight 341.4042
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

Coluracetam (code name BCI-540; formerly MKC-231) is a nootropic agent of the racetam family. It was initially developed and tested by the Mitsubishi Tanabe Pharma Corporation for Alzheimer's disease. After the drug failed to reach endpoints in its clinical trials it was in-licensed by BrainCells Inc for investigations into major depressive disorder (MDD). Like most racetam compounds, Coluracetam increases choline uptake, but it also increases uptake in damaged neurons. Specifically, Coluracetam interacts with the HACU process, which is responsible for absorbing choline into the neurons. This increased uptake occurs during the Acetylcholine synthesis process. Since Coluracetam improves choline preservation during this process, a larger amount is converted into Acetylcholine. This results in increased memory, attention and alertness. It is important to note here, that these benefits were only seen in subjects with previously impaired neurons, not in subjects with normally functioning neurons. Coluracetam is also shown to improve AMPA potentiation, which is a process that triggers cognitive function and alertness. Although Coluracetam interacts with choline transporters as well, there isn’t enough evidence to explain why or how this interaction occurs, or what occurs after the interaction. Coluracetam has been in phase II clinical trials for the treatment of major depression and anxiety. However, this research has been discontinued.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
2.0 nM [Kd]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
A dosage of 240mg (split into three daily doses of 80mg) was useful in treating major depression co-morbid with GAD (generalized anxiety disorder).
Route of Administration: Oral
In Vitro Use Guide
Incubation of synaptosomes with MKC-231 (Coluracetam) (10(-8) M) significantly increased Vmax without significant change in the Km of AF64A-treated rats
Substance Class Chemical
Record UNII
V6FL6O5GR7
Record Status Validated (UNII)
Record Version