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
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)
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
Title | Date | PubMed |
---|---|---|
Synthesis and anti-herpes-virus activity of acyclic 2'-deoxyguanosine analogues related to 9-[(1,3-dihydroxy-2-propoxy)methyl]guanine. | 1986 Aug |
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Renal excretion mechanisms of the antiviral nucleoside analogue AM 188 in the rat isolated perfused kidney. | 2004 Jan-Feb |
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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 |
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Metabolism and disposition of the antiviral nucleoside analogue AM365 in the isolated perfused rat liver. | 2005 Oct |
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Determination of antiviral nucleoside analogues AM365 and AM188 in perfusate and bile of the isolated perfused rat liver using HPLC. | 2006 Mar |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:30:41 GMT 2023
by
admin
on
Fri Dec 15 15:30:41 GMT 2023
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Record UNII |
JBP1N46HPN
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C281
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135436454
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300000037024
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JBP1N46HPN
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CHEMBL280531
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8159
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103024-93-7
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DTXSID90869380
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C76500
Created by
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Related Record | Type | Details | ||
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TARGET ORGANISM->INHIBITOR |
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Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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