THIOGUANOSINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/28264514 | https://www.ncbi.nlm.nih.gov/pubmed/4232285

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

Condition	Modality	Targets	Highest Phase	Product
Cancer 609 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4359880	Primary		Not Provided 511	Unknown Approved Use Unknown
Idiopathic myocardial hypertrophy 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/4232285	Primary		Not Provided 511	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Excited-State Dynamics of the Thiopurine Prodrug 6-Thioguanine: Can N9-Glycosylation Affect Its Phototoxic Activity?	2017-02-28	28264514
IMP dehydrogenase basal activity in MOLT-4 human leukaemia cells is altered by mycophenolic acid and 6-thioguanosine.	2008	18609073
Inhibition of sandfly fever Sicilian virus (Phlebovirus) replication in vitro by antiviral compounds.	1997-12-24	9403935
Purine analogs as potential anticytomegalovirus agents.	1969-09	4309475
Clinical evaluation of thioguanosine.	1961-09	13753894

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:47 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:47 GMT 2025`
Record UNII	C558LI0K8P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

THIOGUANOSINE

Systematic Name

English

NSC-29422

Preferred 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

Code System Code Type Description

FDA UNII

C558LI0K8P