TANOMASTAT

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H19ClO3S
Molecular Weight	410.913
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC(=O)[C@@H](CSC1=CC=CC=C1)CC(=O)C2=CC=C(C=C2)C3=CC=C(Cl)C=C3

InChI

InChIKey=JXAGDPXECXQWBC-LJQANCHMSA-N

InChI=1S/C23H19ClO3S/c24-20-12-10-17(11-13-20)16-6-8-18(9-7-16)22(25)14-19(23(26)27)15-28-21-4-2-1-3-5-21/h1-13,19H,14-15H2,(H,26,27)/t19-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C23H19ClO3S
Molecular Weight	410.913
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/10589777 | https://www.ncbi.nlm.nih.gov/pubmed/16442153 | Airley Rachel, Cancer Chemotherapy: Basic Science to the Clinic, p. 207, retrieved from: https://books.google.ru/books?id=wjjYyYpfiQ8C&pg=PA206&lpg=PA206&dq=TANOMASTAT+discontinued&source=bl&ots=x4wobF4wf7&sig=ACfU3U34pe4xdzK33TDmx9FSaEU-dADcbA&hl=ru&sa=X&ved=2ahUKEwiY55SZpZvjAhWIxcQBHTt6B5MQ6AEwAXoECAkQAQ#v=onepage&q=TANOMASTAT%20discontinued&f=false

Tanomastat (previously known as BAY 12-9566) is an inhibitor of angiogenesis and a biphenyl matrix metalloprotease (MMP). The drug was selective towards MMPs 2,3, and 9 and no activity against MMP1. Tanomastat was developed for the treatment of cancer and arthritis. Tanomastat participated in phase III clinical trials as maintenance therapy in patients with advanced ovarian cancer, and in patients with pancreatic, lung cancers. However, all studied were discontinued after the recommendation of the independent data safety monitoring board.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Matrix metalloproteinase-2 13 Target ID: CHEMBL333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11754593	Inhibitor 8297	11.0 nM [IC50]
Matrix metalloproteinase 3 13 Target ID: CHEMBL283 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11754593	Inhibitor 8297	134.0 nM [IC50]
Matrix metalloproteinase-9 3 Target ID: P14780 Gene ID: 4318.0 Gene Symbol: MMP9 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/11754593	Inhibitor 8297	301.0 nM [IC50]

PubMed

Title	Date	PubMed
BAY12-9566. BAY 12 9566, BAY12 9566.	1999 Feb	10566009
A phase III randomized trial of BAY 12-9566 (tanomastat) as maintenance therapy in patients with advanced ovarian cancer responsive to primary surgery and paclitaxel/platinum containing chemotherapy: a National Cancer Institute of Canada Clinical Trials Group Study.	2006 Aug	16442153
Recent advances in MMP inhibitor design.	2006 Mar	16680577

Patents

Sample Use Guides

In Vivo Use Guide

BAY 12-9566 (TANOMASTAT) 800 mg p.o. b.i.d.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:54:31 UTC 2023` Edited by `admin` on `Fri Dec 15 18:54:31 UTC 2023`
Record UNII	AM1ZX94EXH
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

TANOMASTAT

Official Name

English

BAY-129566

Code

English

TANOMASTAT [USAN]

Common Name

English

tanomastat [INN]

Common Name

English

BAY-12-9566

Code

English

BAY 12-9566

Code

English

Tanomastat [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1970