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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H13N5O4S
Molecular Weight 299.306
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIOGUANOSINE

SMILES

NC1=NC2=C(N=CN2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=S)N1

InChI

InChIKey=OTDJAMXESTUWLO-UUOKFMHZSA-N
InChI=1S/C10H13N5O4S/c11-10-13-7-4(8(20)14-10)12-2-15(7)9-6(18)5(17)3(1-16)19-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,20)/t3-,5-,6-,9-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H13N5O4S
Molecular Weight 299.306
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

6-Thioguanosine (or thioguanosine) is a metabolite of 6-thioguanine, an immunosuppressant and anticancer prodrug, and plays a major role in the prodrug's overall photoreactivity. 6-Thioguanosine has been shown to induce DNA damage and cell death upon exposure to UVA radiation, which is correlated to the significant increase in skin cancers following prolonged treatment with thiopurine prodrug. Also existed experiments where 6-thioguanosine was used to treat idiopathic myocardial hypertrophy and where it showed clinical value in cancer chemotherapy.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Clinical evaluation of thioguanosine.
1961 Sep
Purine analogs as potential anticytomegalovirus agents.
1969 Sep
Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.
1997 Sep-Oct

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Curator's Comment: inosine 5'-monophosphate dehydrogenase basal activity in MOLT-4 human leukaemia cells is reduced by 6-thioguanosine
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:22 UTC 2023
Edited
by admin
on Fri Dec 15 15:15:22 UTC 2023
Record UNII
C558LI0K8P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
THIOGUANOSINE
MI  
Systematic Name English
6-THIOGUANOSINE
Systematic Name English
6-THIOGUANINE RIBONUCLEOSIDE
Common Name English
9-.BETA.-D-RIBOFURANOSYLTHIOGUANINE
Common Name English
THIOGUANOSINE [MI]
Common Name English
NSC-29422
Code English
Code System Code Type Description
FDA UNII
C558LI0K8P
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
201-597-2
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
MERCK INDEX
m10761
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY Merck Index
EVMPD
SUB195657
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
SMS_ID
100000181870
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
CAS
85-31-4
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
EPA CompTox
DTXSID201018977
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
MESH
C005783
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
NSC
29422
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY
PUBCHEM
2724387
Created by admin on Fri Dec 15 15:15:22 UTC 2023 , Edited by admin on Fri Dec 15 15:15:22 UTC 2023
PRIMARY