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Details

Stereochemistry ACHIRAL
Molecular Formula C33H34N2O5
Molecular Weight 538.6335
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of AMELUBANT

SMILES

CCOC(=O)NC(=N)C1=CC=C(OCC2=CC=CC(COC3=CC=C(C=C3)C(C)(C)C4=CC=C(O)C=C4)=C2)C=C1

InChI

InChIKey=SBVYURPQULDJTI-UHFFFAOYSA-N
InChI=1S/C33H34N2O5/c1-4-38-32(37)35-31(34)25-8-16-29(17-9-25)39-21-23-6-5-7-24(20-23)22-40-30-18-12-27(13-19-30)33(2,3)26-10-14-28(36)15-11-26/h5-20,36H,4,21-22H2,1-3H3,(H2,34,35,37)

HIDE SMILES / InChI

Description

Amelubant, its metabolite BIIL 260 (formed by removal of the ethoxycarbonyl protecting group), and its major metabolite BIIL 315 (formed by removal of the protecting group and glucuronidation) had potent in vitro and in vivo Leukotriene B4 receptor antagonistic properties. Amelubant has been in phase II clinical trials by Boehringer Ingelheim for the treatment of cystic fibrosis, chronic obstructive pulmonay disease, bronchial asthma and rheumatoid arthritis. However, this research has been discontinued. In 2002, orphan drug designation was received in E.U. for the treatment of cystic fibrosis. Serious adverse events of Amelubant were characterized by increased presentation of respiratory signs and/or symptoms associated with pulmonary exacerbation and resulted in admission to a hospital and/or administration of IV antibiotics.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.7 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
75, 150 mg once daily for 24 weeks
Route of Administration: Oral
In Vitro Use Guide
Ubiquitous esterases metabolize Amelubant to the active metabolites BIIL 260 and BIIL 315. BIIL 260 and its glucuronide BIIL 315 inhibited LTB4-induced intracellular Ca2+ release in human neutrophils with IC50 values of 0.82 and 0.75 nM/L, respectively.