RS-127445

Details

Stereochemistry	ACHIRAL
Molecular Formula	C17H16FN3
Molecular Weight	281.3274
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C1=NC(N)=NC(=C1)C2=CC=C(F)C3=CC=CC=C23

InChI

InChIKey=ZZZQXCUPAJFVBN-UHFFFAOYSA-N

InChI=1S/C17H16FN3/c1-10(2)15-9-16(21-17(19)20-15)13-7-8-14(18)12-6-4-3-5-11(12)13/h3-10H,1-2H3,(H2,19,20,21)

HIDE SMILES / InChI

Molecular Formula	C17H16FN3
Molecular Weight	281.3274
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/10455251 | https://www.ncbi.nlm.nih.gov/pubmed/16517693
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11575715

RS-127445 is a selective; high affinity; orally bioavailable serotonin 5-HT2B receptor antagonist. RS-127445 was found to have a nanomolar affinity for the 5-HT2B receptor (pKi = 9.5 /-0.1) and 1,000 fold selectivity for this receptor as compared to numerous other receptors and ion channel binding sites. RS-127445 potently antagonized 5-HT-evoked formation of inositol phosphates (pK(B) = 9.5 /-0.1) and 5-HT-evoked increases in intracellular calcium (pIC50 = 10.4 /-0.1). RS-127445 also blocked 5-HT-evoked contraction of rat isolated stomach fundus (pA2 = 9.5 /-1.1) and ( /-)alpha-methyl-5-HT-mediated relaxation of the rat jugular vein (pA2 = 9.9 /-0.3). RS-127445 (MT-500) was being developed for the prophylactic treatment of migraine. POZEN acquired MT-500 from Roche in November 1999 and assumed full responsibility for its development for migraine prophylaxis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin 2b (5-HT2b) receptor 60 Target ID: CHEMBL1833 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10455251 \| https://www.ncbi.nlm.nih.gov/pubmed/16517693	Antagonist 2778		9.5 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Migraine 103 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11575715	Preventing		Phase I 428	Unknown Approved Use Unknown
Anxiety 267 Sources: http://adisinsight.springer.com/drugs/800012581	Primary		Preclinical	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
500 mg single, oral (unknown) Studied dose Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/11117368	healthy n = 6 Health Status: healthy Sex: M Food Status: FASTED Population Size: 6 Sources: https://pubmed.ncbi.nlm.nih.gov/11117368	Sources: https://pubmed.ncbi.nlm.nih.gov/11117368

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY113539	https://www.001chemical.com/chem/search?q=DY113539
001 Chemical	DY114930	https://www.001chemical.com/chem/search?q=DY114930
001 Chemical	DY115067	https://www.001chemical.com/chem/search?q=DY115067
1PlusChem LLC	1P002CUZ	https://www.1pchem.com/search?query=1P002CUZ
1PlusChem LLC	1P002CV0	https://www.1pchem.com/search?query=1P002CV0
A2B Chem	AB09179	http://a2bchem.com/prod/AB09179
AChemBlock	10757	http://www.achemblock.com/catalogsearch/result/?q=10757
AK Scientific	0270AB	https://aksci.com/item_detail.php?cat=0270AB
AK Scientific	W4227	https://aksci.com/item_detail.php?cat=W4227
AK Scientific	X7621	https://aksci.com/item_detail.php?cat=X7621
Achemo Scientific Limited	AC-83896	http://www.achemo.com/search/?Keyword=AC-83896
Alfa Chemistry	11747	http://www.alfa-chemistry.com/search.aspx?q=11747
Alfa Chemistry	AFI199864863	http://www.alfa-chemistry.com/search.aspx?q=AFI199864863
Angene	AGN-PC-0MVG89	http://www.angenechemical.com/productshow/AGN-PC-0MVG89.html
Angene	AGN-PC-0WH8K5	http://www.angenechemical.com/productshow/AGN-PC-0WH8K5.html
ApexBio Technology	A3778	https://www.apexbt.com/catalogsearch/result/?q=A3778
ApexBio Technology	B7848	https://www.apexbt.com/catalogsearch/result/?q=B7848
AstaTech	C73789	http://astatechinc.com/CPSResult.php?CRNO=C73789
BOC Sciences	199864-86-3	http://www.bocsci.com/description.asp?cas=199864-86-3
BOC Sciences	199864-87-4	http://www.bocsci.com/description.asp?cas=199864-87-4
Chem Scene	CS-0852	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0852
ChemShuttle	141607	https://www.chemshuttle.com/catalogsearch/result/?q=141607
Lab Network	LN00188812	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00188812
Lab Network	LN00198877	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00198877
Lab Seeker	SC-85611	http://www.labseeker.com/search.php?keywords=SC-85611&category=0
Matrix Scientific	90895	http://www.matrixscientific.com/090895.html
Matrix Scientific	97301	http://www.matrixscientific.com/097301.html
Matrix Scientific	98588	http://www.matrixscientific.com/098588.html
MedChem Express	HY-15419	https://www.medchemexpress.com/search.html?q=HY-15419&ft=&fa=&fp=
MolPort	MolPort-019-879-337	https://www.molport.com/shop/molecule-link/MolPort-019-879-337
MolPort	MolPort-021-804-999	https://www.molport.com/shop/molecule-link/MolPort-021-804-999
Molcore	MC113539	http://www.molcore.com/CatMC113539.html
Molcore	MC114930	http://www.molcore.com/CatMC114930.html
Molcore	MC115067	http://www.molcore.com/CatMC115067.html
Molnova	M17415	https://www.molnova.com/en/serch-list.html?keywords=M17415
MuseChem	R056332	https://www.musechem.com/product/R056332.html
Oakwood	213329	http://www.oakwoodchemical.com/ProductsList.aspx?txtSearch=213329
PI Chemicals	PI-35964	http://www.pipharm.com/catalog_products/PI-35964.html
Selleck Chemicals	S2698	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2698
ShangHai Biochempartner	BCP000451	http://www.biochempartner.com/search_BCP000451
ShangHai Biochempartner	BCP02714	http://www.biochempartner.com/search_BCP02714
Synchem UG and Co KG	s037b	https://www.synchem.de/?s=s037b&post_type=product
TargetMol	T6973	https://www.targetmol.com/search?keyword=T6973
Tocris	2993	https://www.tocris.com/search.php?Type=QuickSearch&Value=2993
Toronto Research Chemicals	E895013	https://www.trc-canada.com/product-detail/?CatNum=E895013
Toronto Research Chemicals	R700930	https://www.trc-canada.com/product-detail/?CatNum=R700930
Wonderchem	WD05J8B	http://www.wonder-chem.com/search.html?text=WD05J8B
eMolecules	24587970	https://orderbb.emolecules.com/search/#?query=24587970
eMolecules	300112263	https://orderbb.emolecules.com/search/#?query=300112263
eMolecules	37153218	https://orderbb.emolecules.com/search/#?query=37153218
eMolecules	44690009	https://orderbb.emolecules.com/search/#?query=44690009
eMolecules	44845589	https://orderbb.emolecules.com/search/#?query=44845589
eNovation Chemicals	D754000	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D754000&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-3886555485	https://mcule.com/MCULE-3886555485/
mcule	MCULE-4836692954	https://mcule.com/MCULE-4836692954/

PubMed

Title	Date	PubMed
RS-127445: a selective, high affinity, orally bioavailable 5-HT2B receptor antagonist.	1999 Jul	10455251
Role of serotonin via 5-HT2B receptors in the reinforcing effects of MDMA in mice.	2009 Nov 23	19956756

Patents

Sample Use Guides

In Vivo Use Guide

Rats: oral administration of a selective, high affinity 5-HT(2B)receptor antagonist, RS-127445, significantly inhibited visceral hypersensitivity provoked by restraint stress (35 to 74% inhibition at 1 to 10 mg kg(-1)).

Route of Administration: Oral

In Vitro Use Guide

RS-127445 (0.3-3nM) potently inhibited the 5-HT evoked increase in the formation of inositol phosphates in HEK-293 cells expressing the human 5-HT2B receptors, producing parallel rightward shifts in the concentration response curves of 5-HT.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:41:33 GMT 2023` Edited by `admin` on `Fri Dec 15 15:41:33 GMT 2023`
Record UNII	0JAU3P8OBM
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

RS-127445

Code

English

2-PYRIMIDINAMINE, 4-(4-FLUORO-1-NAPHTHALENYL)-6-(1-METHYLETHYL)-

Systematic Name

English

2-AMINO-4-(4-FLUORONAPHTHYL-1-YL)-6-ISOPROPYLPYRIMIDINE

Common Name

English

RS-127,445

Code

English

MT-500

Code

English

Code System Code Type Description

WIKIPEDIA

RS-127445