RELACATIB

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H32N4O6S
Molecular Weight	540.631
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)C[C@H](NC(=O)C1=CC2=C(O1)C=CC=C2)C(=O)N[C@H]3CC[C@@H](C)N(CC3=O)S(=O)(=O)C4=NC=CC=C4

InChI

InChIKey=BWYBBMQLUKXECQ-GIVPXCGWSA-N

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

HIDE SMILES / InChI

Molecular Formula	C27H32N4O6S
Molecular Weight	540.631
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16962401 | https://www.drugbank.ca/drugs/DB06367 | https://clinicaltrials.gov/ct2/show/NCT00411190

Relacatib (SB-462795) is a potent and orally bioavailable small molecule inhibitor of cathepsin K that inhibits bone resorption. This has been shown in vitro in human tissue and in vivo in cynomolgus monkeys. The drug was developed for treatment in (postmenopausal) osteoporosis, osteoarthritis and potentially other bone disorders. Interactions with other drugs have been reported, and were subject of investigation of a phase I clinical trial (evaluating interactions of relacatib with ibuprofen, acetaminophen, and atorvastatin).

Approval Year

PubMed

Title	Date	PubMed
Structure activity relationships of 5-, 6-, and 7-methyl-substituted azepan-3-one cathepsin K inhibitors.	2006 Mar 9	16509577
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.	2007 Jan	16962401
[Bony lesion with prostate cancer].	2008 Apr	18379023
The discovery of odanacatib (MK-0822), a selective inhibitor of cathepsin K.	2008 Feb 1	18226527
Cathepsin K inhibitors as treatment of bone metastasis.	2008 Sep	18685424
[Prevention of joint destruction by osteoclast-targeting therapy in search of new tools, such as OPG or cathepsin K inhibitor].	2009 Mar	19252249
Treatment with a potent cathepsin K inhibitor preserves cortical and trabecular bone mass in ovariectomized monkeys.	2009 Oct	19763376
Emerging targets in osteoporosis disease modification.	2010 Jun 10	20218623
Odanacatib, a new drug for the treatment of osteoporosis: review of the results in postmenopausal women.	2010 Jun 14	20948576
Bisphosphonate use and hip fracture epidemiology: ecologic proof from the contrary.	2010 Nov 19	21228901

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:28:51 GMT 2023` Edited by `admin` on `Fri Dec 15 16:28:51 GMT 2023`
Record UNII	BL51M8CB8R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RELACATIB

Official Name

English

RELACATIB [USAN]

Common Name

English

relacatib [INN]

Common Name

English

SB-462795

Code

English

N-[(1S)-3-Methyl-1-{[(4S,7R)-7-methyl-3-oxo-1-(pyridin-2-ylsulfonyl)hexahydro-1H-azepin-4-yl]carbamoyl}butyl]benzofuran-2-carboxamide

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C783