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Details

Stereochemistry ACHIRAL
Molecular Formula C9H13N5O3
Molecular Weight 239.2312
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TIVICICLOVIR

SMILES

NC1=NC2=C(N=CN2CC(CO)CO)C(=O)N1

InChI

InChIKey=ANFNNSIOGODJDN-UHFFFAOYSA-N
InChI=1S/C9H13N5O3/c10-9-12-7-6(8(17)13-9)11-4-14(7)1-5(2-15)3-16/h4-5,15-16H,1-3H2,(H3,10,12,13,17)

HIDE SMILES / InChI

Molecular Formula C9H13N5O3
Molecular Weight 239.2312
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
Renal excretion mechanisms of the antiviral nucleoside analogue AM 188 in the rat isolated perfused kidney.
2004 Jan-Feb
Renal secretion of the antiviral nucleoside analog AM188 is inhibited by probenecid, p-aminohippuric acid, and cimetidine in the isolated perfused rat kidney.
2004 Jun
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 15:30:41 GMT 2023
Edited
by admin
on Fri Dec 15 15:30:41 GMT 2023
Record UNII
JBP1N46HPN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TIVICICLOVIR
INN  
INN  
Official Name English
AM-188
Code English
tiviciclovir [INN]
Common Name English
AM188
Code English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
Code System Code Type Description
PUBCHEM
135436454
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
SMS_ID
300000037024
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
FDA UNII
JBP1N46HPN
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
ChEMBL
CHEMBL280531
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
INN
8159
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
CAS
103024-93-7
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID90869380
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
NCI_THESAURUS
C76500
Created by admin on Fri Dec 15 15:30:41 GMT 2023 , Edited by admin on Fri Dec 15 15:30:41 GMT 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY