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

Details

Stereochemistry ABSOLUTE
Molecular Formula C10H15N5O3
Molecular Weight 253.2578
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OMACICLOVIR

SMILES

NC1=NC2=C(N=CN2C[C@H](CO)CCO)C(=O)N1

InChI

InChIKey=SCBFBAWJWLXVHS-ZCFIWIBFSA-N
InChI=1S/C10H15N5O3/c11-10-13-8-7(9(18)14-10)12-5-15(8)3-6(4-17)1-2-16/h5-6,16-17H,1-4H2,(H3,11,13,14,18)/t6-/m1/s1

HIDE SMILES / InChI

Molecular Formula C10H15N5O3
Molecular Weight 253.2578
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Omaciclovir (previously known as H2G), a cyclic guanosine analog that is structurally similar to acyclovir and was in clinical development for the treatment of herpesvirus infections. This drug acted against varicella-zoster virus (VZV), by the formation of high concentrations of relatively stable H2G-triphosphate, which is a potent inhibitor of the viral DNA polymerases. However, further development of this drug was discontinued.

Approval Year

PubMed

PubMed

TitleDatePubMed
The antiherpesvirus activity of H2G [(R)-9-[4-hydroxy-2-(hydroxymethyl)butyl]guanine] is markedly enhanced by the novel immunosuppressive agent mycophenolate mofetil.
1998 Dec
Activity of H2G on human herpesvirus-6B strains either sensitive or resistant to ganciclovir.
2010 Jun
Substance Class Chemical
Created
by admin
on Sat Dec 16 15:54:37 UTC 2023
Edited
by admin
on Sat Dec 16 15:54:37 UTC 2023
Record UNII
C9H909GLI3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OMACICLOVIR
INN   USAN  
INN   USAN  
Official Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-(4-HYDROXY-2-(HYDROXYMETHYL)BUTYL)- (R)-
Systematic Name English
A-1820910
Code English
ABT-091
Code English
A-182091.0
Code English
OMACICLOVIR [USAN]
Common Name English
9-[(R)-4-Hydroxy-2-(hydroxymethyl)butyl]guanine
Systematic Name English
2-HMHBG
Code English
H2G
Code English
omaciclovir [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29575
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
Code System Code Type Description
CAS
124265-89-0
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105375
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
USAN
LL-14
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
INN
7982
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
SMS_ID
300000034270
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
PUBCHEM
135433609
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
FDA UNII
C9H909GLI3
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
NCI_THESAURUS
C90785
Created by admin on Sat Dec 16 15:54:38 UTC 2023 , Edited by admin on Sat Dec 16 15:54:38 UTC 2023
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
Related Record Type Details
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY