APRATASTAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H22N2O6S2
Molecular Weight	414.496
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1(C)SCCN([C@H]1C(=O)NO)S(=O)(=O)C2=CC=C(OCC#CCO)C=C2

InChI

InChIKey=MAVDNGWEBZTACC-HNNXBMFYSA-N

InChI=1S/C17H22N2O6S2/c1-17(2)15(16(21)18-22)19(9-12-26-17)27(23,24)14-7-5-13(6-8-14)25-11-4-3-10-20/h5-8,15,20,22H,9-12H2,1-2H3,(H,18,21)/t15-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C17H22N2O6S2
Molecular Weight	414.496
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17117591 | https://clinicaltrials.gov/ct2/show/NCT00095342

Apratastat (Tmi 005) was developed by Wyeth Research as a dual TNF-alpha-converting enzyme and matrix metalloprotease-13 inhibitor for the treatment of rheumatoid arthritis. Apratastat was in phase II clinical trials, but because of the lack of efficacy, this trial was terminated.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Disintegrin and metalloproteinase domain-containing protein 17 1 Target ID: P78536 Gene ID: 6868.0 Gene Symbol: ADAM17 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14718605	Inhibitor 8297
Collagenase 3 1 Target ID: P45452 Gene ID: 4322.0 Gene Symbol: MMP13 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/14718605	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://clinicaltrials.gov/ct2/show/NCT00095342	Primary		Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Axon MedChem	1507	https://www.axonmedchem.com/product/1507
Chem Scene	CS-0066985	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0066985
Compound Cloud	11452716
MedChem Express	HY-119307	https://www.medchemexpress.com/search.html?q=HY-119307&ft=&fa=&fp=
MolPort	MolPort-021-805-014	https://www.molport.com/shop/molecule-link/MolPort-021-805-014
MuseChem	I002604	https://www.musechem.com/product/I002604.html
eMolecules	275129619	https://orderbb.emolecules.com/search/#?query=275129619
eMolecules	300547540	https://orderbb.emolecules.com/search/#?query=300547540
eMolecules	36367122	https://orderbb.emolecules.com/search/#?query=36367122
mcule	MCULE-4565931715	https://mcule.com/MCULE-4565931715/

PubMed

Title	Date	PubMed
Identification and characterization of 4-[[4-(2-butynyloxy)phenyl]sulfonyl]-N-hydroxy-2,2-dimethyl-(3S)thiomorpholinecarboxamide (TMI-1), a novel dual tumor necrosis factor-alpha-converting enzyme/matrix metalloprotease inhibitor for the treatment of rheumatoid arthritis.	2004 Apr	14718605
Drug evaluation: apratastat, a novel TACE/MMP inhibitor for rheumatoid arthritis.	2006 Nov	17117591
A disintegrin and metalloproteinase 17 (ADAM17) mediates inflammation-induced shedding of syndecan-1 and -4 by lung epithelial cells.	2010 Jan 1	19875451
Pharmacokinetic-pharmacodynamic modeling of apratastat: a population-based approach.	2011 Apr	21059888

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

Apratastat inhibited TNF-α release with a population mean IC(50) of 144 ng/mL in vitro

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:11:18 UTC 2023` Edited by `admin` on `Fri Dec 15 16:11:18 UTC 2023`
Record UNII	C6BZ5263BJ
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

APRATASTAT

Official Name

English

TMI-005

Code

English

3-THIOMORPHOLINECARBOXAMIDE, N-HYDROXY-4-((4-((4-HYDROXY-2-BUTYNYL)OXY)PHENYL)SULFONYL)-2,2-DIMETHYL, (3S)-

Common Name

English

apratastat [INN]

Common Name

English

(3S)-N-Hydroxy-4-[[4-[(4-hydroxybut-2-ynyl)oxy]phenyl]sulfonyl]-2,2-dimethylthiomorpholine-3-carboxamide

Systematic Name

English

TMI-05

Code

English

APRATASTAT [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1970