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

Details

Stereochemistry ACHIRAL
Molecular Formula C8H11N5O3
Molecular Weight 225.2046
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACYCLOVIR

SMILES

NC1=NC2=C(N=CN2COCCO)C(=O)N1

InChI

InChIKey=MKUXAQIIEYXACX-UHFFFAOYSA-N
InChI=1S/C8H11N5O3/c9-8-11-6-5(7(15)12-8)10-3-13(6)4-16-2-1-14/h3,14H,1-2,4H2,(H3,9,11,12,15)

HIDE SMILES / InChI
Molecular Formula C8H11N5O3
Molecular Weight 225.2046
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Approval Year

Unknown
86413
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:23:38 UTC 2023
Edited
by admin
on Fri Dec 15 15:23:38 UTC 2023
Record UNII
X4HES1O11F
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACYCLOVIR
HSDB   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF  
USAN  
Official Name English
SITAVIG
Brand Name English
ZOVIRAX
Brand Name English
aciclovir [INN]
Common Name English
ACYCLOVIR [VANDF]
Common Name English
NSC-758477
Code English
Aciclovir [WHO-DD]
Common Name English
ACICLOVIR [JAN]
Common Name English
ACICLOVIR
EP   INN   JAN   MART.   WHO-DD   WHO-IP  
INN  
Official Name English
ACYCLOVIR [USP-RS]
Common Name English
ACICLOVIR [WHO-IP]
Common Name English
ACICLOVIR [MART.]
Common Name English
VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY B [EP IMPURITY]
Common Name English
ACYCLOVIR [HSDB]
Common Name English
VALACICLOVIR HYDROCHLORIDE IMPURITY B [EP IMPURITY]
Common Name English
GERPEVIR
Common Name English
NOVIRUS
Common Name English
9-[(2-Hydroxyethoxy)methyl]guanine
Systematic Name English
6H-PURIN-6-ONE, 2-AMINO-1,9-DIHYDRO-9-((2-HYDROXYETHOXY)METHYL)-
Systematic Name English
ACYCLOVIR [MI]
Common Name English
ACICLOVIR [IARC]
Common Name English
ACYCLOVIR [ORANGE BOOK]
Common Name English
NSC-645011
Code English
AVACLYR
Brand Name English
ACYCLOVIR [USAN]
Common Name English
ACICLOVIRUM [WHO-IP]
Common Name English
ACICLOVIR [EP MONOGRAPH]
Common Name English
ACYCLOVIR [USP MONOGRAPH]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000175468
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000175459
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-VATC QS01AD03
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
FDA ORPHAN DRUG 313210
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 21.1
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
FDA ORPHAN DRUG 513615
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.4.1
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-VATC QD06BB53
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000175459
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000180187
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-ATC D06BB03
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-ATC D06BB53
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NCI_THESAURUS C1556
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-ATC J05AB01
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
FDA ORPHAN DRUG 325010
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-VATC QD06BB03
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-VATC QJ05AB01
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
WHO-ATC S01AD03
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000020060
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
LIVERTOX NBK548548
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000180188
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NCI_THESAURUS C29575
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
FDA ORPHAN DRUG 37589
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
NDF-RT N0000175459
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
Code System Code Type Description
RS_ITEM_NUM
1012065
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
IUPHAR
4829
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
EPA CompTox
DTXSID1022556
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
CAS
59277-89-3
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
NSC
758477
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
DRUG CENTRAL
85
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
DRUG BANK
DB00787
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
NSC
645011
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
HSDB
6511
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
SMS_ID
100000092808
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
FDA UNII
X4HES1O11F
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
WIKIPEDIA
ACICLOVIR
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
CHEBI
2453
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
ChEMBL
CHEMBL184
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
LACTMED
Acyclovir
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
MESH
D000212
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
NCI_THESAURUS
C205
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
DAILYMED
X4HES1O11F
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
INN
4435
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
ECHA (EC/EINECS)
261-685-1
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
MERCK INDEX
m1404
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY Merck Index
WHO INTERNATIONAL PHARMACOPEIA
ACYCLOVIR
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY Description: White or almost white, crystalline powder. Solubility: Slightly soluble in water; freely soluble in dimethyl sulfoxide; very slightly soluble in ethanol (96%). It dissolves in dilute solutions of mineral acids and alkali hydroxides. Category: Antiviral (Purine nucleoside analogue). Storage: Preserve in well-closed containers. Protect from light and moisture. Additional information: Aciclovir may exhibit polymorphism. Definition: Aciclovir contains not less than 98.5% and not more than 101.0% of C8H11N5O3, calculated with reference to the dried substance.
RXCUI
281
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY RxNorm
PUBCHEM
135398513
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
EVMPD
SUB05235MIG
Created by admin on Fri Dec 15 15:23:38 UTC 2023 , Edited by admin on Fri Dec 15 15:23:38 UTC 2023
PRIMARY
Related Record Type Details
MATE-2
TRANSPORTER -> SUBSTRATE
Km
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
acyclovir crosses the placenta
BINDING
OAT-1
TRANSPORTER -> SUBSTRATE
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> SUBSTRATE
Km
Structure of ACYCLOVIR
EXCRETED UNCHANGED
URINE
HUMAN HERPESVIRUS 3
TARGET ORGANISM->INHIBITOR
IC50
HUMAN HERPESVIRUS 2
TARGET ORGANISM->INHIBITOR
IC50
OCT-1
TRANSPORTER -> SUBSTRATE
ATP-BINDING CASSETTE SUB-FAMILY G MEMBER 2
TRANSPORTER -> SUBSTRATE
HUMAN HERPESVIRUS 1
TARGET ORGANISM->INHIBITOR
IC50
Structure of ACYCLOVIR SODIUM
SALT/SOLVATE -> PARENT
Structure of ACYCLOVIR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
MATE-2
TRANSPORTER -> SUBSTRATE
Vmax
MULTIDRUG AND TOXIN EXTRUSION PROTEIN 1
TRANSPORTER -> SUBSTRATE
Vmax
Structure of 2-((2-ACETAMIDO-6-OXO-1H-PURIN-7(6H)-YL)METHOXY)ETHYL ACETATE
ACTIVE CONSTITUENT ALWAYS PRESENT -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of Acyclovir Sodium Dihydrate
SALT/SOLVATE -> PARENT
OAT-2
TRANSPORTER -> SUBSTRATE
Related Record Type Details
Structure of DESCICLOVIR
PRODRUG -> METABOLITE ACTIVE
Structure of 9-CARBOXYMETHOXYMETHYLGUANINE
METABOLITE -> PARENT
MAJOR
URINE
Structure of Acyclovir triphosphate
METABOLITE ACTIVE -> PARENT
Structure of 8-HYDROXYACYCLOVIR
METABOLITE -> PARENT
MINOR
URINE
Structure of VALACYCLOVIR
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N7-((2-HYDROXYETHOXY)METHYL)GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of 7,9'-(ETHYLENEBIS(OXYMETHYLENE))DIGUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of N2,N2'-METHYLENEDIACICLOVIR
IMPURITY -> PARENT
sum of impurities K and R: not more than 1.5 times the area of the principal peak in the chromatogram obtained with reference solution (b) (0.15 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of VALACYCLOVIR HYDROCHLORIDE MONOHYDRATE
PARENT -> IMPURITY
sum of impurities A and B: maximum 2.0 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DIACETYLACYCLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2,9-DIACETYLGUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2-((2-ACETAMIDO-6-OXO-1H-PURIN-7(6H)-YL)METHOXY)ETHYL ACETATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of 7,9'-(ETHYLENEBIS(OXYMETHYLENE))DIGUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N2-ACETYLACICLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of VALACYCLOVIR HYDROCHLORIDE
PARENT -> IMPURITY
sum of impurities A and B: maximum 2.0 per cent
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of O-((GUANIN-9-YL)METHYL) ACYCLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of N7-((2-HYDROXYETHOXY)METHYL)GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9-(2-HYDROXYETHYL)GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9-(2-ACETOXYETHOXYMETHYL)GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of N2,N2'-METHYLENEDIACICLOVIR
IMPURITY -> PARENT
IDENTIFIED AS IMPURITY K The following peaks are eluted at the following relative retention with reference to the peak of aciclovir (retention time about 13 min): impurity K about 2.5.
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of N2-ACETYLACICLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9-(2-HYDROXYETHYL)GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 2,9-DIACETYLGUANINE
IMPURITY -> PARENT
ACYCLOVIR IMPURITY L AMOUNT NOT SPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9-(2-ACETOXYETHOXYMETHYL)GUANINE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of 2-((2-ACETAMIDO-6-OXO-1H-PURIN-7(6H)-YL)METHOXY)ETHYL ACETATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of 9,9'-(2,5,7,10-TETRAOXAUNDECANE-1,11-DIYL)BIS(2-AMINO-1,9-DIHYDRO-6H-PURIN-6-ONE)
IMPURITY -> PARENT
sum of impurities K and R: not more than 1.5 times the area of the principal peak in the chromatogram obtained with reference solution (b) (0.15 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of DIACETYLACYCLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
INTERNATIONAL PHARMACOPEIA
Structure of O-((GUANIN-9-YL)METHYL) ACYCLOVIR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of ACYCLOVIR
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Cmax PHARMACOKINETIC ROUTE OF ADMINSTRATION
PHARMACOKINETIC
DOSE
PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC
ORAL BIOAVAILABILITY PHARMACOKINETIC
CSF/PLASMA RATIO PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966