NAV

Relacatib

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

Identification

Generic Name
Relacatib
DrugBank Accession Number
DB06367
Background

Not Available

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 540.64
Monoisotopic: 540.20425594
Chemical Formula
C27H32N4O6S
Synonyms
  • Relacatib
External IDs
  • SB 462795
  • SB-462795
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Pharmacology

Indication

Investigated for use/treatment in osteoporosis and bone metastases.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action

Relacatib is a small-molecule drug that inhibits the activity of cathepsin K, an enzyme that appears to be implicated in osteoporosis, osteoarthritis and certain other disorders causing bone degradation.

TargetActionsOrganism
UCathepsin K
inhibitor
Humans
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
Not Available

Interactions

Drug Interactions
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 leucine and derivatives. These are compounds containing leucine or a derivative thereof resulting from reaction of leucine at the amino group or the carboxy group, or from the replacement of any hydrogen of glycine by a heteroatom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Leucine and derivatives
Alternative Parents
N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Pyridinesulfonamides / Benzofurans / 2-heteroaryl carboxamides / Furoic acid and derivatives / Azepanes / Organosulfonamides / N-acyl amines / Benzenoids
show 9 more
Substituents
2-heteroaryl carboxamide / Alpha-amino acid amide / Aromatic heteropolycyclic compound / Azacycle / Azepane / Benzenoid / Benzofuran / Carbonyl group / Carboxamide group / Cyclic ketone
show 25 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
BL51M8CB8R
CAS number
362505-84-8
InChI Key
BWYBBMQLUKXECQ-GIVPXCGWSA-N
InChI
InChI=1S/C27H32N4O6S/c1-17(2)14-21(30-27(34)24-15-19-8-4-5-9-23(19)37-24)26(33)29-20-12-11-18(3)31(16-22(20)32)38(35,36)25-10-6-7-13-28-25/h4-10,13,15,17-18,20-21H,11-12,14,16H2,1-3H3,(H,29,33)(H,30,34)/t18-,20+,21+/m1/s1
IUPAC Name
(2S)-2-[(1-benzofuran-2-yl)formamido]-4-methyl-N-[(4S,7R)-7-methyl-3-oxo-1-(pyridine-2-sulfonyl)azepan-4-yl]pentanamide
SMILES
CC(C)C[C@H](NC(=O)C1=CC2=CC=CC=C2O1)C(=O)N[C@H]1CC[C@@H](C)N(CC1=O)S(=O)(=O)C1=CC=CC=N1

References

General References
  1. Kumar S, Dare L, Vasko-Moser JA, James IE, Blake SM, Rickard DJ, Hwang SM, Tomaszek T, Yamashita DS, Marquis RW, Oh H, Jeong JU, Veber DF, Gowen M, Lark MW, Stroup G: A highly potent inhibitor of cathepsin K (relacatib) reduces biomarkers of bone resorption both in vitro and in an acute model of elevated bone turnover in vivo in monkeys. Bone. 2007 Jan;40(1):122-31. Epub 2006 Sep 7. [Article]
ChemSpider
5293798
BindingDB
19778
ChEMBL
CHEMBL203665
ZINC
ZINC000003955058

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedDiagnosticOsteoarthritis (OA)1

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 Solubility0.0302 mg/mLALOGPS
logP2.37ALOGPS
logP2.79Chemaxon
logS-4.2ALOGPS
pKa (Strongest Acidic)12.07Chemaxon
pKa (Strongest Basic)-2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area138.68 Å2Chemaxon
Rotatable Bond Count7Chemaxon
Refractivity140.67 m3·mol-1Chemaxon
Polarizability54.77 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
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/MSsplash10-0006-0072090000-5a39bfd3a894efa57ca6
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0019-0190070000-de017af5fc567f584082
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-001r-4791010000-3c33ba96aa2c28fc8338
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-0691230000-d1624782e7eb08edc6bc
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00s7-6910020000-a58132f8f16dca8bc3ec
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0900000000-cee2671066f0ee1a0c6d
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-213.18275
predicted
DeepCCS 1.0 (2019)
[M+H]+215.00764
predicted
DeepCCS 1.0 (2019)
[M+Na]+220.7
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Cathepsin K
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Proteoglycan binding
Specific Function
Closely involved in osteoclastic bone resorption and may participate partially in the disorder of bone remodeling. Displays potent endoprotease activity against fibrinogen at acid pH. May play an i...
Gene Name
CTSK
Uniprot ID
P43235
Uniprot Name
Cathepsin K
Molecular Weight
36965.82 Da
References
  1. Gauthier JY, Chauret N, Cromlish W, Desmarais S, Duong LT, Falgueyret JP, Kimmel DB, Lamontagne S, Leger S, LeRiche T, Li CS, Masse F, McKay DJ, Nicoll-Griffith DA, Oballa RM, Palmer JT, Percival MD, Riendeau D, Robichaud J, Rodan GA, Rodan SB, Seto C, Therien M, Truong VL, Venuti MC, Wesolowski G, Young RN, Zamboni R, Black WC: The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K. Bioorg Med Chem Lett. 2008 Feb 1;18(3):923-8. doi: 10.1016/j.bmcl.2007.12.047. Epub 2008 Jan 15. [Article]

Drug created at March 19, 2008 16:27 / Updated at February 21, 2021 18:52