U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H13N5O2
Molecular Weight 223.2318
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DETIVICICLOVIR

SMILES

NC1=NC=C2N=CN(CC(CO)CO)C2=N1

InChI

InChIKey=PIWJGZWZNOWIGH-UHFFFAOYSA-N
InChI=1S/C9H13N5O2/c10-9-11-1-7-8(13-9)14(5-12-7)2-6(3-15)4-16/h1,5-6,15-16H,2-4H2,(H2,10,11,13)

HIDE SMILES / InChI

Molecular Formula C9H13N5O2
Molecular Weight 223.2318
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tiviciclovir (A188) is a nucleoside analog used in the synthesis of antiviral drugs. This acyclic guanosine analog has a potential for the treatment of hepatitis B virus. However, as with penciclovir and the related compounds acyclovir and ganciclovir, the intestinal absorption of Tiviciclovir is limited. One approach to overcome this is through synthesis of the 6-deoxy prodrug version of AM188, i.e. AM365, which has improved intestinal absorption. Following absorption, the 6-deoxyguanosine analog AM365 is converted to the corresponding anti-virally active guanosine analog, AM188, probably by the liver molybdenum hydroxylases, aldehyde oxidase and xanthine oxidase. Renal tubular secretion of AM188 involves organic anion and cation transport systems.

Approval Year

PubMed

PubMed

TitleDatePubMed
Synthesis and anti-herpes-virus activity of acyclic 2'-deoxyguanosine analogues related to 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine.
1986 Aug
Metabolism and disposition of the antiviral nucleoside analogue AM365 in the isolated perfused rat liver.
2005 Oct
Determination of antiviral nucleoside analogues AM365 and AM188 in perfusate and bile of the isolated perfused rat liver using HPLC.
2006 Mar
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 16:22:24 GMT 2023
Edited
by admin
on Fri Dec 15 16:22:24 GMT 2023
Record UNII
088W05943X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DETIVICICLOVIR
INN  
INN  
Official Name English
detiviciclovir [INN]
Common Name English
AM365
Code English
2-((2-AMINO-9H-PURIN-9-YL)METHYL)PROPANE-1,3-DIOL
Systematic Name English
AM-365
Code English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
Code System Code Type Description
SMS_ID
300000037022
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
NCI_THESAURUS
C77926
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
FDA UNII
088W05943X
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
CAS
220984-26-9
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL2105503
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
INN
8160
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID70176605
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
PUBCHEM
3025970
Created by admin on Fri Dec 15 16:22:24 GMT 2023 , Edited by admin on Fri Dec 15 16:22:24 GMT 2023
PRIMARY
Related Record Type Details
METABOLITE ACTIVE -> PRODRUG
Related Record Type Details
ACTIVE MOIETY