acyclovir (CHEBI:2453)

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CHEBI:2453 - acyclovir

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ChEBI Name	acyclovir

ChEBI ID	CHEBI:2453

Definition	An oxopurine that is guanine substituted by a (2-hydroxyethoxy)methyl substituent at position 9. Used in the treatment of viral infections.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:40459

Supplier Information	ChemicalBook:CB7126677, eMolecules:901331, eMolecules:29702921, eMolecules:768732, Selleckchem:Acyclovir(Aciclovir), ZINC000001530555

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Molfile

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The Resolver thinks Mol

Mrv0541 02271408473D

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Mrv0541 02271408473D

27 28 0 0 0 0 999 V2000

-0.1400 0.1090 0.4500 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.5010 0.1510 0.5370 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0210 0.1090 -0.6540 N 0 0 0 0 0 0 0 0 0 0 0 0

-1.0290 0.0370 -1.5740 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.9980 -0.0300 -2.9870 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0310 -0.0310 -3.6350 O 0 0 0 0 0 0 0 0 0 0 0 0

0.2040 -0.0870 -3.6000 N 0 0 0 0 0 0 0 0 0 0 0 0

1.3520 -0.0910 -2.8660 C 0 0 0 0 0 0 0 0 0 0 0 0

2.5590 -0.1560 -3.5160 N 0 0 0 0 0 0 0 0 0 0 0 0

1.3370 -0.0280 -1.5530 N 0 0 0 0 0 0 0 0 0 0 0 0

0.1840 0.0360 -0.8770 C 0 0 0 0 0 0 0 0 0 0 0 0

-2.0630 0.2110 1.4570 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2500 -0.1350 -4.5680 H 0 0 0 0 0 0 0 0 0 0 0 0

0.3290 0.3220 5.2010 C 0 0 2 0 0 0 0 0 0 0 0 0

-0.5210 -0.8140 5.3620 O 0 0 0 0 0 0 0 0 0 0 0 0

1.0430 0.2370 3.8510 C 0 0 2 0 0 0 0 0 0 0 0 0

0.0750 0.2140 2.8000 O 0 0 0 0 0 0 0 0 0 0 0 0

0.8010 0.1360 1.5720 C 0 0 1 0 0 0 0 0 0 0 0 0

1.0670 0.3390 6.0030 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.2690 1.2320 5.2390 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.9510 -0.7220 6.2230 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6420 -0.6720 3.8130 H 0 0 0 0 0 0 0 0 0 0 0 0

1.6920 1.1050 3.7280 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4030 -0.7720 1.5630 H 0 0 0 0 0 0 0 0 0 0 0 0

1.4520 1.0040 1.4780 H 0 0 0 0 0 0 0 0 0 0 0 0

3.3850 -0.1550 -3.0070 H 0 0 0 0 0 0 0 0 0 0 0 0

2.5860 -0.2070 -4.4840 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 4 0 0 0 0

1 11 4 0 0 0 0

2 3 4 0 0 0 0

2 12 1 0 0 0 0

3 4 4 0 0 0 0

4 5 1 0 0 0 0

4 11 4 0 0 0 0

5 6 2 0 0 0 0

5 7 1 0 0 0 0

7 8 1 0 0 0 0

7 13 1 0 0 0 0

8 9 1 0 0 0 0

8 10 2 0 0 0 0

9 26 1 0 0 0 0

9 27 1 0 0 0 0

10 11 1 0 0 0 0

14 15 1 0 0 0 0

14 16 1 0 0 0 0

14 19 1 0 0 0 0

14 20 1 0 0 0 0

15 21 1 0 0 0 0

16 17 1 0 0 0 0

16 22 1 0 0 0 0

16 23 1 0 0 0 0

17 18 1 0 0 0 0

18 1 1 0 0 0 0

18 24 1 0 0 0 0

18 25 1 0 0 0 0

M END): 17 ms

reading 27 atoms

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27 atoms created

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Molfile

Wikipedia	License
Aciclovir, also known as acyclovir, is an antiviral medication. It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles. Other uses include the prevention of cytomegalovirus infections following transplant, and severe complications of Epstein–Barr virus infection. It can be taken by mouth, applied as a cream, or injected. Common side effects include nausea and diarrhea. Potentially serious side effects include kidney problems and low platelets. Greater care is recommended in those with poor liver or kidney function. It is generally considered safe for use in pregnancy with no harm having been observed. It appears to be safe during breastfeeding. Aciclovir is a nucleoside analogue that mimics guanosine. It works by decreasing the production of the virus's DNA. Aciclovir was patented in 1974, by Burroughs Wellcome, and approved for medical use in 1981. It is on the World Health Organization's List of Essential Medicines. It is available as a generic medication and is marketed under many brand names worldwide. In 2022, it was the 134th most commonly prescribed medication in the United States, with more than 4 million prescriptions.
Read full article at Wikipedia

Formula

C8H11N5O3

Net Charge

Average Mass

225.20460

Monoisotopic Mass

225.08619

InChI

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)

InChIKey

MKUXAQIIEYXACX-UHFFFAOYSA-N

SMILES

Nc1nc2n(COCCO)cnc2c(=O)[nH]1

Roles Classification
Biological Role(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases. antimetabolite A substance which is structurally similar to a metabolite but which competes with it or replaces it, and so prevents or reduces its normal utilization.

Application(s):	antiviral drug A substance used in the prophylaxis or therapy of virus diseases.

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	acyclovir (CHEBI:2453) has functional parent guanine (CHEBI:16235) acyclovir (CHEBI:2453) has role antimetabolite (CHEBI:35221) acyclovir (CHEBI:2453) has role antiviral drug (CHEBI:36044) acyclovir (CHEBI:2453) is a 2-aminopurines (CHEBI:20702) acyclovir (CHEBI:2453) is a oxopurine (CHEBI:25810)

IUPAC Name

2-amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one

INNs	Sources
aciclovir	ChEBI
aciclovirum	ChemIDplus

Synonyms	Sources
acycloguanosine	ChEBI
acyclovir	UniProt

Brand Name	Source
Zovir	DrugBank

Manual Xrefs	Databases
85	DrugCentral
AC2	PDBeChem
Acyclovir	Wikipedia
C06810	KEGG COMPOUND
D00222	KEGG DRUG
DB00787	DrugBank
DE2539963	Patent
HMDB0014925	HMDB
LSM-5459	LINCS
US4199574	Patent
View more database links

Registry Numbers	Types	Sources
1219402	Reaxys Registry Number	Reaxys
59277-89-3	CAS Registry Number	KEGG COMPOUND
59277-89-3	CAS Registry Number	ChemIDplus

Citations

Keller AN, Eckle SB, Xu W, Liu L, Hughes VA, Mak JY, Meehan BS, Pediongco T, Birkinshaw RW, Chen Z, Wang H, D'Souza C, Kjer-Nielsen L, Gherardin NA, Godfrey DI, Kostenko L, Corbett AJ, Purcell AW, Fairlie DP, McCluskey J, Rossjohn J (2017)
Drugs and drug-like molecules can modulate the function of mucosal-associated invariant T cells.
Nature immunology 18, 402-411 [PubMed:28166217]
[show Abstract]

Metushi IG, Wriston A, Banerjee P, Gohlke BO, English AM, Lucas A, Lucas A, Moore C, Sidney J, Buus S, Ostrov DA, Mallal S, Phillips E, Shabanowitz J, Hunt DF, Preissner R, Peters B (2015)
Acyclovir Has Low but Detectable Influence on HLA-B*57:01 Specificity without Inducing Hypersensitivity.
PloS one 10, e0124878 [PubMed:26024233]
[show Abstract]

Sampson MR, Bloom BT, Lenfestey RW, Harper B, Kashuba AD, Anand R, Benjamin DK, Capparelli E, Cohen-Wolkowiez M, Smith PB, Best Pharmaceuticals for Children Act–Pediatric Trials Network (2014)
Population pharmacokinetics of intravenous acyclovir in preterm and term infants.
The Pediatric infectious disease journal 33, 42-49 [PubMed:24346595]
[show Abstract]

Stanberry LR, Rosenthal SL (2002)
Genital herpes simplex virus infection in the adolescent: special considerations for management.
Paediatric drugs 4, 291-297 [PubMed:11994034]
[show Abstract]

Sipe J, Dunn L (2001)
Aciclovir for Bell's palsy (idiopathic facial paralysis).
The Cochrane database of systematic reviewsCD001869 [PubMed:11687127]
[show Abstract]

Background

The most common disorder of the facial nerve is acute idiopathic facial paralysis or Bell's palsy and there may be significant morbidity or incomplete recovery associated with severe cases. Although the cause remains unknown, recent evidence suggests a possible association with Herpes simplex virus (HSV) infection. To test this hypothesis clinically four clinical trials have used aciclovir, an antiviral agent, either alone or in combination with corticosteroids to treat Bell's palsy.

Objectives

To assess the efficacy of aciclovir for treating Bell's palsy and to evaluate any adverse effects of the drug treatment.

Search strategy

Search of the Cochrane Neuromuscular Disease Group register, MEDLINE, EMBASE and LILACS databases for randomised trials. We also contacted authors of identified trials.

Selection criteria

Randomised or quasi-randomised trials of aciclovir therapy, alone or in combination with any other drug, in patients with Bell's palsy.

Data collection and analysis

We identified four randomised trials. One author extracted the data and the other checked them. We wrote to all the authors of the trials identified. No additional data were obtained.

Main results

Only two studies met our inclusion criteria and provided results from 200 patients. One study evaluated aciclovir with corticosteroid versus steroid alone and the other study evaluated aciclovir alone versus corticosteroid. PRIMARY OUTCOME Proportion of patients with incomplete recovery after one year: These data were not available. However an analysis was performed on data reported at the end of the study period, three or four months after the start of treatment. The results from the Adour study significantly favoured the treatment group whilst the De Diego study significantly favoured the control group. Adverse events: This analysis was not performed as the data were not reported. Complete facial paralysis six months after start of treatment: Only one patient had complete paralysis upon entering only one of the studies. This patient was assigned to the control group and the level of recovery attained was not reported. Motor synkinesis/Crocodile tears one year after start of treatment: Data were available up to a maximum of four months after onset of paralysis. One study reported a significant difference between the treatment groups in favour of the aciclovir group and the other demonstrated an inconclusive result.

Reviewer's conclusions

More data are needed from a large multicentre randomised controlled and blinded study with at least 12 months' follow up before a definitive recommendation can be made regarding the routine use of aciclovir in Bell's palsy.

Spangler JG, Kirk JK, Knudson MP (1994)
Uses and safety of acyclovir in pregnancy.
The Journal of family practice 38, 186-191 [PubMed:8308511]
[show Abstract]

Last Modified

05 February 2025

ChEBI

CHEBI:2453 - acyclovir

Background

Methods

Results

Conclusions

Background

Objectives

Search strategy

Selection criteria

Data collection and analysis

Main results

Reviewer's conclusions

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