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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 of THIOINOSINE

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

Molecular Formula C10H12N4O4S
Molecular Weight 284.292
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Bacillus anthracis spore germination
40.0 µM [IC50]
Target ID: Murine leukemia cells growth
68.0 nM [IC50]
3.9 µM [IC50]
Target ID: Murine lymphoma cells growth
250.0 nM [EC50]
Target ID: Q63433
Gene ID: 29355.0
Gene Symbol: Pkn1
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Synthesis and antiviral activity of certain carbamoylpyrrolopyrimidine and pyrazolopyrimidine nucleosides.
1982 Nov
Patents

Patents

Sample Use Guides

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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:16:36 GMT 2023
Edited
by admin
on Fri Dec 15 16:16:36 GMT 2023
Record UNII
46S541971T
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOINOSINE
JAN   MART.  
Systematic Name English
THIOINOSINE [JAN]
Common Name English
MERCAPTOPURINE RIBONUCLEOSIDE
WHO-DD  
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
JAN  
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C574
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
Code System Code Type Description
MESH
D013868
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID5046019
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
209-371-5
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
FDA UNII
46S541971T
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
CAS
4988-64-1
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
NON-SPECIFIC STEREOCHEMISTRY
SMS_ID
100000127651
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
PUBCHEM
676166
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
NCI_THESAURUS
C877
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
CAS
574-25-4
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
NSC
4911
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
ChEMBL
CHEMBL448290
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY
EVMPD
SUB33710
Created by admin on Fri Dec 15 16:16:36 GMT 2023 , Edited by admin on Fri Dec 15 16:16:36 GMT 2023
PRIMARY