LASMIDITAN HYDROCHLORIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H18F3N3O2.ClH
Molecular Weight	413.821
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CN1CCC(CC1)C(=O)C2=CC=CC(NC(=O)C3=C(F)C=C(F)C=C3F)=N2

InChI

InChIKey=YBTPRLDGGGYWIP-UHFFFAOYSA-N

InChI=1S/C19H18F3N3O2.ClH/c1-25-7-5-11(6-8-25)18(26)15-3-2-4-16(23-15)24-19(27)17-13(21)9-12(20)10-14(17)22;/h2-4,9-11H,5-8H2,1H3,(H,23,24,27);1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C19H18F3N3O2
Molecular Weight	377.3603
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20855361 | https://www.ncbi.nlm.nih.gov/mesh/67554777 | https://www.ncbi.nlm.nih.gov/pubmed/31340760

LASMIDITAN is a serotonin (5-HT) receptor agonist without vasoconstrictor activity, which selectively binds to the 5-HT(1F) receptor subtype. It is under development for the treatment of migraine.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 1f (5-HT1f) receptor 15 Target ID: CHEMBL1805 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20855361	Agonist 2752		2.1 nM [Ki]

C_max

Value	Dose	Analyte	Population
526.15 ng/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT03465436	400 mg single, oral dose: 400 mg route of administration: oral experiment type: single co-administered:	LASMIDITAN plasma	Homo sapiens population: healthy age: sex: food status:
322.8 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/29563831/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LASMIDITAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
394.7 ng/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/29563831/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LASMIDITAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

AUC

Value	Dose	Analyte	Population
3189.08 ng*h/mL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT03465436	400 mg single, oral dose: 400 mg route of administration: oral experiment type: single co-administered:	LASMIDITAN plasma	Homo sapiens population: healthy age: sex: food status:
1892 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/29563831/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LASMIDITAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2244 ng × h/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/29563831/	200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered:	LASMIDITAN serum	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	inhibitor 2438 substrate 1193 inducer 440	inhibitor 2507 substrate 1388	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
P-gp 1741 BCRP 910 OCT1 620 CYP1A2 2153 CYP2A6 879 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP2E1 1060 CYP3A 227 FMO3 3 MATE1 415 MATE2 267 OCT2 779 OAT1 725 OAT3 747 OATP1B1 1079 OATP1B3 961	P-gp 2052 CYP1A2 1197 CYP2A6 626 CYP2B6 776 CYP2C8 810 CYP2C19 1119 CYP2E1 729	CYP3A 142 CYP1A2 832

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
FMO3 3	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	low
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	low
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	low
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	low
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	low
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	low
OCT1 656	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 8, 18	low	no (co-administration study) Comment: "when administered with sumatriptan, no change in sumatriptan PK was observed; '""low potential of interactions""" Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8; https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 8, 18
CYP2A6 911	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2E1 1146	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no	no (co-administration study) Comment: administered with caffeine, daily dosing of lasmiditan did not alter PK of caffeine Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no	no (co-administration study) Comment: administered with caffeine, daily dosing of lasmiditan did not alter PK of caffeine Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no	no (co-administration study) Comment: administered with tolbutamide, daily dosing of lasmiditan did not alter the PK of tolbutamide. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no	no (co-administration study) Comment: administered with tolbutamide, daily dosing of lasmiditan did not alter the PK of tolbutamide. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0
CYP3A 317	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no	no (co-administration study) Comment: administered with midazolam, daily dosing of lasmiditan did not alter PK of midazolam Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no	no (co-administration study) Comment: administered with midazolam, daily dosing of lasmiditan did not alter PK of midazolam Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=37 Page: 37.0	yes [IC50 85 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=37; https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 37, 8	yes [Ki 20.7 uM]
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=16 Page: 16.0	yes
MATE1 416	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	yes
MATE2 267	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0	yes

Drug as victim

Target	Modality	Activity
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2A6 626	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2B6 776	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2C8 810	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP2E1 729	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/211280s000lbl.pdf#page=8 Page: 8.0	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/211280Orig1s000ClinPharmR.pdf#page=18 Page: 18.0

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY113432	https://www.001chemical.com/chem/439239-90-4
AA Blocks	AA00DB3R	https://www.aablocks.com/goods/Goods/detail?id=AA00DB3R
Aaron Chemicals	AR00DBVJ	http://www.aaronchem.com/439239-90-4
abcr GmbH	AB479695	http://www.abcr.com/shop/en/AB479695
AbMole Bioscience	M10160	http://www.abmole.com/products/lasmiditan.html
AbMole Bioscience	M5214	http://www.abmole.com/products/lasmiditan.html
Achemo Scientific Limited	AC-105121	http://www.achemo.com/search/?Keyword=439239-90-4
Achemtek	0104-035885	http://www.achemtek.com/439239-90-4
Adooq BioScience	A14198	https://www.adooq.com/lasmiditan.html
AK Scientific, Inc. (AKSCI)	6063AB	http://www.aksci.com/item_detail.php?cat=6063AB
Ambinter	Amb22233527	http://www.ambinter.com/reference/22233527
Angel Pharmatech	AG-11845	http://www.angelpharmatech.com/439239-90-4.html
Angene	AGN-PC-00CM98	http://www.angenechemical.com/productshow/AGN-PC-00CM98.html
ApexBio Technology	B1058	http://www.apexbt.com/lasmiditan.html
Ark Pharma Scientific Limited	A-1201	http://www.arkpharmtech.com/product/33152.html
Aurora Fine Chemicals LLC	A13.105.806	http://online.aurorafinechemicals.com/info?ID=A13.105.806
BioChemPartner	BCP04734	http://www.biochempartner.com/439239-90-4-BCP04734
BioCrick	BCC4077	http://www.biocrick.com/Lasmiditan-BCC4077.html
Boerchem	BC600589	http://www.boerchem.com/?product_43424.html
Chem Scene	CS-2032	http://www.chemscene.com/439239-90-4.html
Chemspace	CSSB00015188126	https://chem-space.com/CSSB00015188126
Clearsynth	CS-MM-09003	https://www.clearsynth.com/en/CSMM09003.html
DC Chemicals	DC7710	http://www.dcchemicals.com/product_show-Lasmiditan_COL_144_LY573144_.html
eNovation Chemicals	D501949	http://www.enovationchem.com/productDetails.asp?productID=D501949
eNovation Chemicals	Y1012792	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y1012792
Excenen	EX-A1300	http://www.excenen.com/searchresultlist.php?id=439239-90-4
Excenen	EX-A1653	http://www.excenen.com/searchresultlist.php?id=439239-90-4
Lab Network	LN00188248	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00188248
Matrix Scientific	90054	https://www.matrixscientific.com/090054.html
MedChem Express	HY-14861	https://www.medchemexpress.com/lasmiditan.html
Molcore	MC113432	https://www.molcore.com/product/439239-90-4
Selleck Chemicals	S5064	http://www.selleckchem.com/products/lasmiditan.html
Smolecule	S532530	http://www.smolecule.com/products/s532530
Synblock Inc	SB19007	http://www.synblock.com/product/439239-90-4.html
THE BioTek	bt-272592	https://www.thebiotek.com/product/inhibitors/bt-272592
THE BioTek	bt-341446	https://www.thebiotek.com/product/others/bt-341446

PubMed

Title	Date	PubMed
Acute treatment of migraine with the selective 5-HT1F receptor agonist lasmiditan--a randomised proof-of-concept trial.	2010-10	20855362
Preclinical pharmacological profile of the selective 5-HT1F receptor agonist lasmiditan.	2010-10	20855361
Molecule of the month. Lasmiditan hydrochloride.	2010-09	20862397

Patents

Sample Use Guides

In Vitro Use Guide

Lasmiditan in vitro binding studies show a Ki value of 2.21 nM at the 5-HT(1F) serotonin receptor, compared with Ki values of 1043 nM and 1357 nM at the 5-HT(1B) and 5-HT(1D) receptors, respectively. Lasmiditan did not contract rabbit saphenous vein rings, a surrogate assay for human coronary artery constriction, at concentrations up to 100 uM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 11:22:13 GMT 2025` Edited by `admin` on `Wed Apr 02 11:22:13 GMT 2025`
Record UNII	H7A23C6P5F
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

2,4,6-TRIFLUORO-N-(6-(1-METHYLPIPERIDINE-4-CARBONYL)PYRIDIN-2-YL)BENZAMIDE HYDROCHLORIDE

Preferred Name

English

LASMIDITAN HYDROCHLORIDE

Common Name

English

BENZAMIDE, 2,4,6-TRIFLUORO-N-(6-((1-METHYL-4-PIPERIDINYL)CARBONYL)-2-PYRIDINYL)-, HYDROCHLORIDE (1:1)

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID901350570

Created by admin on Wed Apr 02 11:22:13 GMT 2025 , Edited by admin on Wed Apr 02 11:22:13 GMT 2025

PRIMARY

PUBCHEM

17980336

Created by admin on Wed Apr 02 11:22:13 GMT 2025 , Edited by admin on Wed Apr 02 11:22:13 GMT 2025

PRIMARY

CAS

613677-28-4

Created by admin on Wed Apr 02 11:22:13 GMT 2025 , Edited by admin on Wed Apr 02 11:22:13 GMT 2025

PRIMARY

FDA UNII

H7A23C6P5F

Created by admin on Wed Apr 02 11:22:13 GMT 2025 , Edited by admin on Wed Apr 02 11:22:13 GMT 2025

PRIMARY

Related Record Type Details


					760I9WM792

LASMIDITAN

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					760I9WM792

LASMIDITAN

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/20855361 | https://www.ncbi.nlm.nih.gov/mesh/67554777 | https://www.ncbi.nlm.nih.gov/pubmed/31340760

CNS Activity

Originator

Approval Year

Targets

Cmax

AUC

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20855361 | https://www.ncbi.nlm.nih.gov/mesh/67554777 | https://www.ncbi.nlm.nih.gov/pubmed/31340760

C_max

Drug as perpetrator