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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 of RS-127445

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
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
9.5 null [pKi]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
500 mg single, oral (unknown)
Studied dose
Dose: 500 mg
Route: oral
Route: single
Dose: 500 mg
Sources:
healthy
n = 6
Health Status: healthy
Sex: M
Food Status: FASTED
Population Size: 6
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Characterization of the contractile 5-hydroxytryptamine receptor in the renal artery of the normotensive rat.
2004 Apr
Role of serotonin via 5-HT2B receptors in the reinforcing effects of MDMA in mice.
2009 Nov 23
The central serotonin 2B receptor: a new pharmacological target to modulate the mesoaccumbens dopaminergic pathway activity.
2010 Sep 1
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can aslo be used i.p. https://www.ncbi.nlm.nih.gov/pubmed/20003079
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
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 UTC 2023
Edited
by admin
on Fri Dec 15 15:41:33 UTC 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
Created by admin on Fri Dec 15 15:41:33 UTC 2023 , Edited by admin on Fri Dec 15 15:41:33 UTC 2023
PRIMARY
CAS
199864-87-4
Created by admin on Fri Dec 15 15:41:33 UTC 2023 , Edited by admin on Fri Dec 15 15:41:33 UTC 2023
PRIMARY
PUBCHEM
196968
Created by admin on Fri Dec 15 15:41:33 UTC 2023 , Edited by admin on Fri Dec 15 15:41:33 UTC 2023
PRIMARY
EPA CompTox
DTXSID60941960
Created by admin on Fri Dec 15 15:41:33 UTC 2023 , Edited by admin on Fri Dec 15 15:41:33 UTC 2023
PRIMARY
FDA UNII
0JAU3P8OBM
Created by admin on Fri Dec 15 15:41:33 UTC 2023 , Edited by admin on Fri Dec 15 15:41:33 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
ANTAGONIST
Ki
Related Record Type Details
ACTIVE MOIETY