NAV

Amelubant

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Amelubant
DrugBank Accession Number
DB06248
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 538.644
Monoisotopic: 538.246772203
Chemical Formula
C33H34N2O5
Synonyms
  • Amelubant
  • Carbamic acid, N-[[4-[[3-[[4-[1-(4-hydroxyphenyl)-1-methylethyl]phenoxy]methyl]phenyl]methoxy]phenyl]iminomethyl]-, ethyl ester
External IDs
  • BIIL 284 BS
  • BIIL-284
  • BIIL-284BS
  • LS-49968
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Pharmacology

Indication

Investigated for use/treatment in asthma, chronic obstructive pulmonary disease (COPD), cystic fibrosis, and rheumatoid arthritis.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Amelubant is a long-acting oral Leukotriene B4 (LTB4) receptor antagonist. Amelubant is a prodrug which is metabolized by ubiquitous esterases to BIIL 260 and its glucuronidated metabolite BIIL 315.14. BIIL 260 and BIIL 315.14 interact directly with the LTB4 receptors. LTB4 is a chemotactic factor for immune cells and potentiates the immune response. The G-protein coupled receptors BLT1, (high affinity for LTB4, expressed in most leukocytes) and BLT2 (low affinity for LTB4) are responsible for mediating LTB4's effects.

TargetActionsOrganism
ULeukotriene B4 receptor 2Not AvailableHumans
ULeukotriene B4 receptor 1Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Diphenylmethanes
Direct Parent
Diphenylmethanes
Alternative Parents
Phenylpropanes / Phenoxy compounds / Phenol ethers / Alkyl aryl ethers / 1-hydroxy-2-unsubstituted benzenoids / Propargyl-type 1,3-dipolar organic compounds / Carboximidamides / Carboxamidines / Organic oxides / Hydrocarbon derivatives
show 1 more
Substituents
1-hydroxy-2-unsubstituted benzenoid / Alkyl aryl ether / Amidine / Aromatic homomonocyclic compound / Carbonyl group / Carboximidamide / Carboxylic acid amidine / Diphenylmethane / Ether / Hydrocarbon derivative
show 11 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
E0018IF0K4
CAS number
346735-24-8
InChI Key
SBVYURPQULDJTI-UHFFFAOYSA-N
InChI
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)
IUPAC Name
ethyl N-(4-{[3-({4-[2-(4-hydroxyphenyl)propan-2-yl]phenoxy}methyl)phenyl]methoxy}benzenecarboximidoyl)carbamate
SMILES
CCOC(=O)NC(=N)C1=CC=C(OCC2=CC=CC(COC3=CC=C(C=C3)C(C)(C)C3=CC=C(O)C=C3)=C2)C=C1

References

General References
  1. Diaz-Gonzalez F, Alten RH, Bensen WG, Brown JP, Sibley JT, Dougados M, Bombardieri S, Durez P, Ortiz P, de-Miquel G, Staab A, Sigmund R, Salin L, Leledy C, Polmar SH: Clinical trial of a leucotriene B4 receptor antagonist, BIIL 284, in patients with rheumatoid arthritis. Ann Rheum Dis. 2007 May;66(5):628-32. Epub 2006 Dec 14. [Article]
ChemSpider
8090852
ChEMBL
CHEMBL1742420
ZINC
ZINC000004392964

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentAsthma1
2CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)2
2CompletedTreatmentRheumatoid Arthritis1
1CompletedTreatmentCystic Fibrosis (CF)2
1CompletedTreatmentHealthy Subjects (HS)8

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000101 mg/mLALOGPS
logP6.7ALOGPS
logP7.31Chemaxon
logS-6.7ALOGPS
pKa (Strongest Acidic)8.16Chemaxon
pKa (Strongest Basic)2.62Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area100.87 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity176.93 m3·mol-1Chemaxon
Polarizability60.93 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-4747980000-c245e03540510134c76e
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0005-9201500000-58657a4a3e18d97a7e7b
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-002e-9230000000-e6ddcbf9bd03df1861c2
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0zfs-1219820000-939834f68a3490a1688a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0400-3190400000-2b7e6cfe2c2682a04b01
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kh0-0773960000-073e08fb5910ef4c6e8b
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-231.92043
predicted
DeepCCS 1.0 (2019)
[M+H]+234.316
predicted
DeepCCS 1.0 (2019)
[M+Na]+240.22859
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Leukotriene B4 receptor 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Leukotriene receptor activity
Specific Function
Low-affinity receptor for leukotrienes including leukotriene B4. Mediates chemotaxis of granulocytes and macrophages. The response is mediated via G-proteins that activate a phosphatidylinositol-ca...
Gene Name
LTB4R2
Uniprot ID
Q9NPC1
Uniprot Name
Leukotriene B4 receptor 2
Molecular Weight
41524.35 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Details2. Leukotriene B4 receptor 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Nucleotide binding
Specific Function
Receptor for extracellular ATP > UTP and ADP. The activity of this receptor is mediated by G proteins which activate a phosphatidylinositol-calcium second messenger system. May be the cardiac P2Y r...
Gene Name
LTB4R
Uniprot ID
Q15722
Uniprot Name
Leukotriene B4 receptor 1
Molecular Weight
37556.925 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Drug created at March 19, 2008 16:19 / Updated at May 24, 2023 10:27