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Details

Stereochemistry ABSOLUTE
Molecular Formula C35H47N5O6
Molecular Weight 633.7776
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BI-44370

SMILES

CC1=CC(C[C@@H](OC(=O)N2CCC(CC2)N3CCC4=C(NC3=O)C=CC=C4)C(=O)N5CCC(CC5)N6CCOCC6)=CC(C)=C1O

InChI

InChIKey=HTLWMOKBJQKDIJ-WJOKGBTCSA-N
InChI=1S/C35H47N5O6/c1-24-21-26(22-25(2)32(24)41)23-31(33(42)38-12-8-28(9-13-38)37-17-19-45-20-18-37)46-35(44)39-14-10-29(11-15-39)40-16-7-27-5-3-4-6-30(27)36-34(40)43/h3-6,21-22,28-29,31,41H,7-20,23H2,1-2H3,(H,36,43)/t31-/m1/s1

HIDE SMILES / InChI

Molecular Formula C35H47N5O6
Molecular Weight 633.7776
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

BI 44370 was developed as a calcitonin gene-related peptide receptor antagonist for the treatment of acute migraine attacks. In spite of the positive results from the phase II clinical trials, the BI-44370 study has been discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
Calcitonin gene-related peptide (CGRP) receptor antagonists in the treatment of migraine.
2010 Jul
New Agents for Acute Treatment of Migraine: CGRP Receptor Antagonists, iNOS Inhibitors.
2012 Feb
Review of dose-response curves for acute antimigraine drugs: triptans, 5-HT1F agonists and CGRP antagonists.
2015
Patents

Sample Use Guides

BI 44370 TA (50 mg, 200 mg, and 400 mg) Administered Orally Once During an Acute Migraine Attack of Moderate or Severe Intensity
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 11:18:58 UTC 2023
Edited
by admin
on Sat Dec 16 11:18:58 UTC 2023
Record UNII
7L3WOA232W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BI-44370
Code English
BI44370
Code English
BI 44370 TA
Code English
J3.353.239C
Code English
BI-44370-BS
Code English
1-PIPERIDINECARBOXYLIC ACID, 4-(1,2,4,5-TETRAHYDRO-2-OXO-3H-1,3-BENZODIAZEPIN-3-YL)-, (1R)-1-((4-HYDROXY-3,5-DIMETHYLPHENYL)METHYL)-2-(4-(4-MORPHOLINYL)-1-PIPERIDINYL)-2-OXOETHYL ESTER
Systematic Name English
4-(2-OXO-1,2,4,5-TETRAHYDRO-3H-1,3-BENZODIAZEPINE-3-YL)PIPERIDINE-1-CARBOXYLIC ACID (R)-.ALPHA.-((4-MORPHOLINOPIPERIDINO)CARBONYL)-3,5-DIMETHYL-4-HYDROXYPHENETHYL ESTER
Systematic Name English
Code System Code Type Description
CAS
866086-05-7
Created by admin on Sat Dec 16 11:18:58 UTC 2023 , Edited by admin on Sat Dec 16 11:18:58 UTC 2023
PRIMARY
PUBCHEM
23654987
Created by admin on Sat Dec 16 11:18:58 UTC 2023 , Edited by admin on Sat Dec 16 11:18:58 UTC 2023
PRIMARY
CLINICAL_TRIALS.GOV
BI-44370
Created by admin on Sat Dec 16 11:18:58 UTC 2023 , Edited by admin on Sat Dec 16 11:18:58 UTC 2023
PRIMARY Official Title: A Randomised, Double-blind, Placebo- and Active Comparator-controlled, Five Parallel Groups Study to Investigate the Efficacy and Safety of BI 44370 TA (50 mg, 200 mg, and 400 mg) Administered Orally Once During an Acute Migraine Attack of Moderate or Severe IntensityPurpose: The objective of this trial is to assess the safety, tolerability, and efficacy of three doses of BI 44370 TA in the treatment of patients with an acute migraine attack and headache pain of moderate or severe intensity, compared to placebo and an active comparator.
FDA UNII
7L3WOA232W
Created by admin on Sat Dec 16 11:18:58 UTC 2023 , Edited by admin on Sat Dec 16 11:18:58 UTC 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
RESULTS: The primary endpoint, pain-free after two hours, was reached by significantly more subjects in the BI44370TA 400mg (20/73=27.4%) and eletriptan 40mg (24/69=34.8%) groups compared to placebo (6/70=8.6%, p=.0016), but not by subjects in the BI 44370 TA 200mg group (14/65=21.5%). The effect of 50mg BI44370TA (5/64=7.8%) was similar to that of placebo. Analysis of secondary endpoints supported the conclusion from the primary analysis. The frequency of adverse events was low in all groups. CONCLUSION: Efficacy of BI 44370 TA was shown in a dose-dependent manner in the treatment of acute migraine attacks.
ACTIVE MOIETY
Originator: Boehringer Ingelheim; Class: Antimigraine; Mechanism of Action: Calcitonin gene-related peptide receptor antagonist; Highest Development Phase: Discontinued for Migraine