Amiselimod phosphate

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H31F3NO6P
Molecular Weight	457.4215
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCCCOC1=C(C=C(CCC(N)(CO)COP(O)(O)=O)C=C1)C(F)(F)F

InChI

InChIKey=OFRUGVQKZMGHHH-UHFFFAOYSA-N

InChI=1S/C19H31F3NO6P/c1-2-3-4-5-6-11-28-17-8-7-15(12-16(17)19(20,21)22)9-10-18(23,13-24)14-29-30(25,26)27/h7-8,12,24H,2-6,9-11,13-14,23H2,1H3,(H2,25,26,27)

HIDE SMILES / InChI

Molecular Formula	C19H31F3NO6P
Molecular Weight	457.4215
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27921320 | https://www.ncbi.nlm.nih.gov/pubmed/27714763 | https://www.mssociety.org.uk/ms-research/treatments-in-the-pipeline/MT-1303

Amiselimod (MT-1303) is a selective sphingosine 1-phosphate 1 (S1P1 ) receptor modulator which is currently being developed for the treatment of various autoimmune diseases. Unlike some other S1P receptor modulators, amiselimod seemed to show a favourable cardiac safety profile in preclinical, phase I and II studies. Amiselimod may be potentially useful for treatment of multiple sclerosis; inflammatory diseases; autoimmune diseases; psoriasis and inflammatory bowel diseases. Amiselimod is currently being developed by Mitsubishi Tanabe Pharma Corporation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sphingosine 1-phosphate receptor 3 Target ID: CHEMBL2363041 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27714763 \| https://www.ncbi.nlm.nih.gov/pubmed/27543447	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Multiple sclerosis 104 Sources: https://www.mssociety.org.uk/ms-research/treatments-in-the-pipeline/MT-1303 https://multiplesclerosisnewstoday.com/amiselimod-mt-1303-for-rrms	Primary	Phase II 1132	Unknown Approved Use Unknown
Crohn's disease 42 Sources: http://adisinsight.springer.com/drugs/800028902	Primary	Phase II 1132	Unknown Approved Use Unknown
Plaque psoriasis 16 Sources: http://adisinsight.springer.com/drugs/800028902	Primary	Phase II 1132	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	UGT 192 CYP4F2 3 CYP4F3B 3 CYP4F12 3 Sphingosine kinases 3

Drug as victim

Target	Modality	Activity
CYP3A4 1737	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30231665/	minor
CYP4F12 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30231665/	yes
CYP4F2 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30231665/	yes
CYP4F3B 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30231665/	yes
Sphingosine kinases 3	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30231665/	yes
UGT 192	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30231665/	yes

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00GURQ	https://www.1pchem.com/search?query=1P00GURQ
AChemBlock	O34167	http://www.achemblock.com/catalogsearch/result/?q=O34167
BLD Pharm	BD764620	http://www.bldpharm.com/search/Search.html?keyword=BD764620
Cayman Chemical	20970	http://www.caymanchem.com/app/template/Product.vm/catalog/20970
Chem Scene	CS-5972	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5972
ChemShuttle	141238	https://www.chemshuttle.com/catalogsearch/result/?q=141238
ChemShuttle	186193	https://www.chemshuttle.com/catalogsearch/result/?q=186193
Excenen	EX-A1426	http://www.excenen.com/searchresultlist.php?id=EX-A1426
Excenen	EX-A1427	http://www.excenen.com/searchresultlist.php?id=EX-A1427
Lab Network	LN01344129	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01344129
MedChem Express	HY-16734A	https://www.medchemexpress.com/search.html?q=HY-16734A&ft=&fa=&fp=
MolPort	MolPort-044-561-788	https://www.molport.com/shop/molecule-link/MolPort-044-561-788
Molnova	M16743	https://www.molnova.com/en/serch-list.html?keywords=M16743
MuseChem	I005600	https://www.musechem.com/product/I005600.html
ShangHai Biochempartner	BCP18775	http://www.biochempartner.com/search_BCP18775
eMolecules	104447473	https://orderbb.emolecules.com/search/#?query=104447473
eMolecules	222564916	https://orderbb.emolecules.com/search/#?query=222564916
eMolecules	303448456	https://orderbb.emolecules.com/search/#?query=303448456
mcule	MCULE-2136007073	https://mcule.com/MCULE-2136007073/
mcule	MCULE-8850038517	https://mcule.com/MCULE-8850038517/

PubMed

Title	Date	PubMed
Amiselimod, a novel sphingosine 1-phosphate receptor-1 modulator, has potent therapeutic efficacy for autoimmune diseases, with low bradycardia risk.	2017 Jan	27714763
Evaluation and Optimization of in silico designed Sphingosine-1-Phosphate (S1P) Receptor Subtype 1 Modulators for the Management of Multiple Sclerosis.	2017 Mar	28356890
Cardiac effects of amiselimod compared with fingolimod and placebo: results of a randomised, parallel-group, phase I study in healthy subjects.	2017 May	27921320
Two-year results from a phase 2 extension study of oral amiselimod in relapsing multiple sclerosis.	2018 Oct	28911260

Patents

Sample Use Guides

In Vivo Use Guide

A total of 81 healthy subjects aged 18-55 years were equally randomized to receive amiselimod 0.4 mg, amiselimod 0.8 mg, placebo or fingolimod 0.5 mg once daily for 28 days.

Route of Administration: Oral

In Vitro Use Guide

HEK293 cells or HCMs were plated onto 48-well culture plates, cultured overnight and then incubated with 100 nmol/L of amiselimod for 3–12 h.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:48:36 GMT 2023` Edited by `admin` on `Sat Dec 16 19:48:36 GMT 2023`
Record UNII	QL6WNR6C4D
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

Amiselimod phosphate

Common Name

English

Amiselimod-P

Common Name

English

2-Amino-4-(4-heptyloxy-3-trifluoromethylphenyl)-2-[(phosphonooxy)methyl]butanol

Systematic Name

English

1,3-Propanediol, 2-amino-2-[2-[4-(heptyloxy)-3-(trifluoromethyl)phenyl]ethyl]-, 1-(dihydrogen phosphate)

Systematic Name

English

Code System Code Type Description

PUBCHEM

23581980

Created by admin on Sat Dec 16 19:48:36 GMT 2023 , Edited by admin on Sat Dec 16 19:48:36 GMT 2023

PRIMARY

FDA UNII

QL6WNR6C4D

Created by admin on Sat Dec 16 19:48:36 GMT 2023 , Edited by admin on Sat Dec 16 19:48:36 GMT 2023

PRIMARY

CAS

942398-85-8

Created by admin on Sat Dec 16 19:48:36 GMT 2023 , Edited by admin on Sat Dec 16 19:48:36 GMT 2023

PRIMARY

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					G72T8FL60W

SPHINGOSINE 1-PHOSPHATE RECEPTOR 1

TARGET->MODULATOR

Amount:

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					358M5150LY

AMISELIMOD

PRODRUG -> METABOLITE ACTIVE

Amount:

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					QL6WNR6C4D

Amiselimod phosphate

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27921320 | https://www.ncbi.nlm.nih.gov/pubmed/27714763 | https://www.mssociety.org.uk/ms-research/treatments-in-the-pipeline/MT-1303

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

Approved Use

Overview

OverviewOther

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27921320 | https://www.ncbi.nlm.nih.gov/pubmed/27714763 | https://www.mssociety.org.uk/ms-research/treatments-in-the-pipeline/MT-1303