General
Preferred name
ACYCLOVIR
Synonyms
aciclovir ()
Acycloguanosine ()
Aciclovir (Acyclovir) ()
2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one ()
ACYCLOVIR SODIUM ()
Aciclovir (BW 248U) ()
Acyclovir, Acycloguanosine, Zovirax, ACV, NSC 645011,BW 248U ()
Lypsyl ()
NSC-645011 ()
Virovir 800 ()
Soraway ()
Virovir 400 ()
Cyclovir ()
Ranovir ()
Aciclovirum ()
Sitavig ()
Zovirax ()
Aviral ()
Duvimex ()
NSC-758477 ()
Viralief ()
Aciclovir ()
Virasorb ()
Soothelip ()
Virovir 200 ()
Clearsore ()
Avert ()
Gerpevir ()
Avaclyr ()
Lipsore ()
Herpetad ()
Novirus ()
Cymex Ultra ()
Acyclovir ()
BW-248U-SODIUM ()
Acyclovir sodium salt ()
Aciclovir sodium ()
BW 248U SODIUM ()
BW-248U Sodium ()
BW 248U ()
Sodium acyclovir ()
Acyclovir-d4 ()
P&D ID
PD000980
CAS
59277-89-3
69657-51-8
1185179-33-2
Tags
prodrug
natural product
drug
available
Approved by
FDA
First approval
1982
Drug Status
approved
Drug indication
Virus infection
Herpes simplex virus infection
Antiviral
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
DESCPRITION A GUANOSINE analog that acts as an antimetabolite. Viruses are especially susceptible. Used especially against herpes.
PHARMACODYNAMICS Aciclovir (INN) or acyclovir (USAN, former BAN) is a synthetic deoxyguanosine analog and it is the prototype antiviral agent that is activated by viral thymidine kinase. The selective activity of aciclovir is due to its affinity for the thymidine kinase enzyme encoded by HSV and VZV. EC50 value of acyclovir against clinical herpes virus isolates was 1.3 μM (range: < 0.56 to 3.3 μM).
TOXICITY Acyclovir may cause nephrotoxicity (crystallization of aciclovir within renal tubules, elevation of serum creatinine, transient), and neurotoxicity (coma, hallucinations, lethargy, seizures, tremors). Nephrotoxicity and neurotoxicity usually resolve after cessation of aciclovir therapy. However, there is no well-defined relationship between aciclovir concentrations in the blood and these adverse effects.
METABOLISM Hepatic, Acyclovir is metabolized to 9-[(carboxymethoxy)methyl]guanine (CMMG) and 8­ hydroxy-acyclovir (8-OH-ACV) by oxidation and hydroxylation. It is suggested in studies that acyclovir is first metabolized to acyclovir aldehyde by alcohol dehydrogenase and then converted to CMMG. The build up of acyclovir aldehyde may be the cause of acyclovir-induced nephrotoxicity in the absence of crystalluria.
ABSORPTION The oral bioavailability is 10% to 20%, and decreases with increasing dose. Food does not affect the absorption of acyclovir. The following are the pharmacokinetic parameters for 50 mg buccal tablet, Sitavig, in the saliva: AUC 0 - 24 hours = 2900±2400 mcg.h/mL; Cmax = 440±241 mcg/mL; Tmax = 7.95 ± 4.08 hours.
ABSORPTION The oral bioavailability is 10% to 20%, and decreases with increasing dose. Food does not affect the absorption of acyclovir. The following are the pharmacokinetic parameters for 50 mg buccal tablet, Sitavig, in the saliva:; AUC 0 - 24 hours = 2900±2400 mcg.h/mL;; Cmax = 440±241 mcg/mL;; Tmax = 7.95 ± 4.08 hours.
DESCRIPTION Aciclovir is a nucleoside analogue antiviral drug.
Aciclovir is on the World Health Organisation's List of Essential Medicines. Click here to access the pdf version of the WHO's 21st Essential Medicines list (2019). (GtoPdb)
DESCRIPTION Broad spectrum MMP inhibitor (Tocris Bioactive Compound Library)
DESCRIPTION Inhibits viral DNA polymerase; antiherpetic agent (Tocriscreen Plus)
DESCRIPTION Antiviral agent (LOPAC library)
DESCRIPTION Inhibits viral DNA polymerase; antiherpetic agent (Tocriscreen Total)
Cell lines
7
Organisms
18
Compound Sets
33
AdooQ Bioactive Compound Library
A10037
Axon Medchem Screening Library
3384
Cayman Chemical Bioactives
14160
26272
ChEMBL Approved Drugs
CHEMBL184
CHEMBL1200380
ChEMBL Drugs
CHEMBL184
CHEMBL1200380
Concise Guide to Pharmacology 2017/18
4829
Concise Guide to Pharmacology 2019/20
4829
Concise Guide to Pharmacology 2021/22
4829
Concise Guide to Pharmacology 2023/24
4829
Drug Repurposing Hub
DrugBank
DB00787
DrugBank Approved Drugs
DB00787
DrugCentral
85
DrugCentral Approved Drugs
85
DrugMAP
DMYLOVR
DrugMAP Approved Drugs
DMYLOVR
DrugMatrix
Enamine BioReference Compounds
Guide to Pharmacology
4829
LOPAC library
MedChem Express Bioactive Compound Library
HY-17422
NCATS Inxight Approved Drugs
X4HES1O11F
NIH Clinical Collections (NCC)
NPC Screening Collection
Pandemic Response Box
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
Acyclovir(Aciclovir)
TargetMol Bioactive Compound Library
T1454
The Spectrum Collection
Tocris Bioactive Compound Library
2513
Tocriscreen Plus
2513
Tocriscreen Total
External IDs
82
Properties
(calculated by RDKit )
Molecular Weight
225.09
Hydrogen Bond Acceptors
7
Hydrogen Bond Donors
3
Rotatable Bonds
4
Ring Count
2
Aromatic Ring Count
2
cLogP
-1.33
TPSA
119.05
Fraction CSP3
0.38
Chiral centers
0.0
Largest ring
6.0
QED
0.55
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Target Type
Enzymes
Selectivity
Viral DNA synthesis
Pathway
DNA Damage/DNA Repair
Anti-infection
Apoptosis
Target
DNA synthesis
PNP
Polymerase inhibitor
antibiotic
Bacterial
HSV
Antiviral,Apoptosis related,DNA/RNA Synthesis,Nucleoside Analog/Antimetabolite
Primary Target
RNA/DNA Polymerase
MOA
Inhibitor
DNA polymerase inhibitor
Indication
genitial herpes, shingles, chicken pox
Therapeutic Class
Antiviral Agents
Source data