THIOINOSINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N4O4S
Molecular Weight	284.292
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CNC3=S

InChI

InChIKey=NKGPJODWTZCHGF-KQYNXXCUSA-N

InChI=1S/C10H12N4O4S/c15-1-4-6(16)7(17)10(18-4)14-3-13-5-8(14)11-2-12-9(5)19/h2-4,6-7,10,15-17H,1H2,(H,11,12,19)/t4-,6-,7-,10-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3412035
Curator's Comment: Description was created based on several sources, including https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=39497

THIOINOSINE (Methylmercaptopurine riboside, NSC- 40774) is a purine derivative with antineoplastic and anti-angiogenic properties. THIOINOSINE is readily converted in cells to its active form, 6-methylmercaptopurine ribonucleoside 5'- monophosphate (MMPR-P), by the enzyme adenosine kinase. THIOINOSINE inhibits amidophosphoribosyltransferase, the first committed step in de novo purine synthesis, and inhibits fibroblast growth factor-2 (FGF2)-induced cell proliferation. It has been used similarly to Mercaptopurine in the treatment of Leukemia. It has being tested in clinical trials for advanced pancreatic cancer.

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacillus anthracis spore germination 1 Target ID: Bacillus anthracis spore germination Sources: https://www.ncbi.nlm.nih.gov/pubmed/20921305	Inhibitor 8297	40.0 µM [IC50]
Murine leukemia cells growth 1 Target ID: Murine leukemia cells growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/1906107	Inhibitor 8297	68.0 nM [IC50]
Free radical scavenging 5 Target ID: Free radical scavenging Sources: https://www.ncbi.nlm.nih.gov/pubmed/19692149	Activator 1430	3.9 µM [IC50]
Murine lymphoma cells growth 1 Target ID: Murine lymphoma cells growth Sources: https://www.ncbi.nlm.nih.gov/pubmed/221658	Inhibitor 8297	250.0 nM [EC50]
Serine/threonine-protein kinase N1 1 Target ID: Q63433 Gene ID: 29355.0 Gene Symbol: Pkn1 Target Organism: Rattus norvegicus (Rat) Sources: https://www.ncbi.nlm.nih.gov/pubmed/1309569	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Advanced pancreatic cancer 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7775133	Primary		Phase II 1132	Unknown Approved Use Unknown
Acute myelogenous leukemia 19 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1060503	Primary		Preclinical	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00E9X7	https://www.1pchem.com/search?query=1P00E9X7
AK Scientific	8273AJ	https://aksci.com/item_detail.php?cat=8273AJ
Alfa Chemistry	164151	http://www.alfa-chemistry.com/search.aspx?q=164151
Alfa Chemistry	183112	http://www.alfa-chemistry.com/search.aspx?q=183112
Alfa Chemistry	ACM4988641	http://www.alfa-chemistry.com/search.aspx?q=ACM4988641
Alfa Chemistry	ACM574254	http://www.alfa-chemistry.com/search.aspx?q=ACM574254
AstaTech	F12892	http://astatechinc.com/CPSResult.php?CRNO=F12892
BLD Pharm	BD109430	http://www.bldpharm.com/search/Search.html?keyword=BD109430
BOC Sciences	4988-64-1	http://www.bocsci.com/description.asp?cas=4988-64-1
BioSynth	W-202883	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-202883
BioSynth	W-203159	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/W-203159
Chem Scene	CS-0096560	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0096560
Combi-Blocks	QH-1051	http://www.combi-blocks.com/cgi-bin/find.cgi?QH-1051
Fluorochem	513018	http://www.fluorochem.co.uk/Products/Product?code=513018
KeyOrganics	AS-58433	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-58433
Lab Network	LN02126310	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN02126310
MedChem Express	HY-128671	https://www.medchemexpress.com/search.html?q=HY-128671&ft=&fa=&fp=
MolPort	MolPort-002-054-679	https://www.molport.com/shop/molecule-link/MolPort-002-054-679
MolPort	MolPort-046-788-428	https://www.molport.com/shop/molecule-link/MolPort-046-788-428
Tetrahedron	TS34728	http://www.thsci.com/search.do?q=TS34728
eMolecules	48853583	https://orderbb.emolecules.com/search/#?query=48853583
eMolecules	525862	https://orderbb.emolecules.com/search/#?query=525862
eMolecules	72976207	https://orderbb.emolecules.com/search/#?query=72976207
eNovation Chemicals	D752247	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D752247&searchbtn.x=0&searchbtn.y=0

PubMed

Title	Date	PubMed
Purine analogs as potential anticytomegalovirus agents.	1969 Sep	4309475
Synthesis and antiviral activity of certain carbamoylpyrrolopyrimidine and pyrazolopyrimidine nucleosides.	1982 Nov	7143371
Captopril and 6-mercaptopurine: whose SH possesses higher antioxidant ability?	2009 Dec	19692149

Patents

Sample Use Guides

In Vivo Use Guide

300 mg/m2/day by rapid i.v. injection

Route of Administration: Intravenous

In Vitro Use Guide

THIOINOSINE blocked PKN with apparent Ki values between 100 and 500uM in PC12 pheochromocytoma cells.

Name

Type

Language

THIOINOSINE

Systematic Name

English

THIOINOSINE [JAN]

Common Name

English

MERCAPTOPURINE RIBONUCLEOSIDE

Common Name

English

9H-PURINE-6(1H)-THIONE, 9-.BETA.-D-RIBOFURANOSYL-

Common Name

English

THIOINOSINE [MART.]

Common Name

English

NSC-4911

Code

English

6-THIOINOSINE

Systematic Name

English

9-.BETA.-D-RIBOFURANOSYL-6-MERCAPTOPURINE.

Common Name

English

9H-PURINE-6(1H)-THIONE, 9-.BETA.-D-RIBOFURANOSYL

Common Name

English

6H-PURINE-6-THIONE, 1,9-DIHYDRO-9-RIBOFURANOSYL-

Common Name

English

INOSINE, 6-THIO-

Systematic Name

English

6-MERCAPTOPURINE RIBONUCLEOSIDE

Common Name

English

Mercaptopurine ribonucleoside [WHO-DD]

Common Name

English

6-MERCAPTOPURINE RIBOSIDE [JAN]

Common Name

English

RIBOSYL-6-THIOPURINE

Common Name

English

6-MERCAPTOPURINE RIBOSIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C574