ISATORIBINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H12N4O6S.H2O
Molecular Weight	334.306
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.NC1=NC2=C(SC(=O)N2[C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C(=O)N1

InChI

InChIKey=BZWQQOVSUSJJJO-QAGDRQIHSA-N

InChI=1S/C10H12N4O6S.H2O/c11-9-12-6-5(7(18)13-9)21-10(19)14(6)8-4(17)3(16)2(1-15)20-8;/h2-4,8,15-17H,1H2,(H3,11,12,13,18);1H2/t2-,3-,4-,8-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C10H12N4O6S
Molecular Weight	316.29
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/2817849 | https://www.ncbi.nlm.nih.gov/pubmed/12738885

ISATORIBINE, a guanosine analog, is an immunopotentiating agent. It is a selective agonist of toll‐like receptor 7, a pattern-recognition receptor that activates the innate immune response.

Originator

Approval Year

PubMed

Title	Date	PubMed
Masked oral prodrugs of toll-like receptor 7 agonists: a new approach for the treatment of infectious disease.	2006-08	16955681
Isatoribine, an agonist of TLR7, reduces plasma virus concentration in chronic hepatitis C infection.	2005-09	16116638
Broad-spectrum activity of 8-chloro-7-deazaguanosine against RNA virus infections in mice and rats.	1995-03	7605116
Antiviral and immunomodulating inhibitors of experimentally-induced Punta Toro virus infections.	1994-10	7847873
Alkylpurines as immunopotentiating agents. Synthesis and antiviral activity of certain alkylguanines.	1993-10-29	8230133
Synthesis and antiviral activity of certain guanosine analogues in the thiazolo[4,5-d]pyrimidine ring system.	1991-10	1656042
Guanosine analogues. Synthesis of nucleosides of certain 3-substituted 6-aminopyrazolo[3,4-d]pyrimidin-4(5H)-ones as potential immunotherapeutic agents.	1990-08	2165164
Antiviral activity of the novel immune modulator 7-thia-8-oxoguanosine.	1990-02	2156954
Roles of interferon and natural killer cells in the antiviral activity of 7-thia-8-oxoguanosine against Semliki Forest virus infections in mice.	1990-02	1693058
Thiazolo[4,5-d]pyrimidine nucleosides. The synthesis of certain 3-beta-D-ribofuranosylthiazolo[4,5-d]pyrimidines as potential immunotherapeutic agents.	1990-01	2153211
Broad-spectrum in vivo antiviral activity of 7-thia-8-oxoguanosine, a novel immunopotentiating agent.	1989-09	2817849

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:44 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:44 GMT 2025`
Record UNII	85141ONN7O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISATORIBINE

Official Name

English

IMMUSINE

Preferred Name

English

5-AMINO-3-.BETA.-D-RIBOFURANOSYLTHIAZOLO(4,5-D)PYRIMIDINE-2,7(3H,6H)-DIONE MONOHYDRATE

Common Name

English

ICN-10146

Code

English

ISATORIBINE [USAN]

Common Name

English

NARI-10146

Code

English

ISATORIBINE MONOHYDRATE

Common Name

English

N10146

Code

English

N-10146

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C308