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Compound Detail

CHEMBL3039520

LASMIDITAN
💊 Approved Drug
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💊 Approved Drug
CN1CCC(C(=O)c2cccc(NC(=O)c3c(F)cc(F)cc3F)n2)CC1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3039520
Name LASMIDITAN
Phase Approved
Structure Type MOL
InChI Key XEDHVZKDSYZQBF-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

COL-144 Lasmiditan LY573144
9
Targets
10
Activities
2
Assay Types
8
PK Parameters
20
Publications
3
Known Names
2
Indications
1
Mechanisms

Molecular Properties

377.4
MW (Da)
3.28
ALogP
4
HBA
1
HBD
62.3
PSA (Ų)
0.83
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 2020
Availability Prescription
Chirality Achiral

Routes of Administration

Oral

Flags

First in Class
USAN Stem -ditan
USAN Year 2012

Extended Properties

Molecular Formula C19H18F3N3O2
MW 377.37
Aromatic Rings 2
Heavy Atoms 27
NP-Likeness -1.44

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Serotonin 1f (5-HT1f) receptor agonist AGONIST 5-hydroxytryptamine receptor 1F ✓ ✓

Indications

Migraine Disorders Substance-Related Disorders

ATC Classification

N02CC08
lasmiditan
Level 1: NERVOUS SYSTEM
Level 2: ANALGESICS

Activity Summary

Ki 9 meas. best 8.66
IC50 1 meas. best 7.06

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
5-hydroxytryptamine receptor 1F
CHEMBL1805
 Ki 8.66 8.66 2.2 1
5-hydroxytryptamine receptor 1F
CHEMBL1805
 IC50 7.06 7.06 87.8 1
5-hydroxytryptamine receptor 1E
CHEMBL2182
 Ki 6.9 6.9 126.9 1
Sigma intracellular receptor 2
CHEMBL4105907
 Ki 6.74 6.74 184.1 1
D(1B) dopamine receptor
CHEMBL1850
 Ki 6.6 6.6 252.7 1
Kappa-type opioid receptor
CHEMBL237
 Ki 6.45 6.45 356.6 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
 Ki 6.2 6.2 632.0 1
5-hydroxytryptamine receptor 1D
CHEMBL1983
 Ki 6.06 6.06 869.4 1
Sigma non-opioid intracellular receptor 1
CHEMBL287
 Ki 5.5 5.5 3132.6 1
5-hydroxytryptamine receptor 7
CHEMBL3155
 Ki 5.27 5.27 5406.9 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 105.0 ng.hr.mL-1 Rattus norvegicus
AUC 386.0 ng.hr.mL-1 Rattus norvegicus
CL 127.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 74.46 nM Rattus norvegicus
Cmax 240.88 nM Rattus norvegicus
F 63.2 % Rattus norvegicus
T1/2 3.12 hr Rattus norvegicus
T1/2 3.38 hr Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
5-hydroxytryptamine receptor 1F Ki = 2.21 nM 8.66 Binding affinity to human 5-HT1F assessed as inhibition constant incubated for 1... 35939391
5-hydroxytryptamine receptor 1F IC50 = 87.84 nM 7.06 Agonist activity at 5HT1F receptor (unknown origin) expressed in HEK293 cells me... 34419891
5-hydroxytryptamine receptor 1E Ki = 126.87 nM 6.9 PDSP Secondary Binding target: HTR1E - Compounds are tested at 10 uM concentrati... -
Sigma intracellular receptor 2 Ki = 184.06 nM 6.74 PDSP Secondary Binding target: TMEM97 - Compounds are tested at 10 uM concentrat... -
D(1B) dopamine receptor Ki = 252.67 nM 6.6 PDSP Secondary Binding target: DRD5 - Compounds are tested at 10 uM concentratio... -
Kappa-type opioid receptor Ki = 356.57 nM 6.45 PDSP Secondary Binding target: OPRK1 - Compounds are tested at 10 uM concentrati... -
Muscarinic acetylcholine receptor M5 Ki = 632.05 nM 6.2 PDSP Secondary Binding target: CHRM5 - Compounds are tested at 10 uM concentrati... -
5-hydroxytryptamine receptor 1D Ki = 869.36 nM 6.06 PDSP Secondary Binding target: HTR1D - Compounds are tested at 10 uM concentrati... -
Sigma non-opioid intracellular receptor 1 Ki = 3132.56 nM 5.5 PDSP Secondary Binding target: SIGMAR1 - Compounds are tested at 10 uM concentra... -
5-hydroxytryptamine receptor 7 Ki = 5406.92 nM 5.27 PDSP Secondary Binding target: HTR7 - Compounds are tested at 10 uM concentratio... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL5724801 Fibroblast 304
- 10.6019/CHEMBL5724801 HEK-293T 304
- 10.6019/CHEMBL5724801 U2OS 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5058577 Fibroblast 304
34419891 10.1016/j.ejmech.2021.113782 ADMET 10
- 10.6019/CHEMBL5058564 Fibroblast 7
- 10.6019/CHEMBL5058564 HEK-293T 5
- 10.6019/CHEMBL5209801 C5a anaphylatoxin chemotactic receptor 1 2
- 10.6019/CHEMBL5209801 Apelin receptor 2
- 10.6019/CHEMBL5209801 Beta-2 adrenergic receptor 2
- 10.6019/CHEMBL5209801 Free fatty acid receptor 4 2
- 10.6019/CHEMBL5209801 Glucose-dependent insulinotropic receptor 2
- 10.6019/CHEMBL5209801 N-formyl peptide receptor 2 2
- 10.6019/CHEMBL5209801 Type-1 angiotensin II receptor 2
- 10.6019/CHEMBL5209801 CX3C chemokine receptor 1 2
- 10.6019/CHEMBL5058564 U2OS 2
34419891 10.1016/j.ejmech.2021.113782 Rattus norvegicus 2
- 10.6019/CHEMBL4495565 SARS-CoV-2 2

Data from ChEMBL 36 via Core Engine