Acyclovir
- acyclovir
- Aciclovir
- 59277-89-3
- Acycloguanosine
- Zovirax
- Create:2019-01-10
- Modify:2025-01-18
Acyclovir is an antiviral prescription medicine approved by the U.S. Food and Drug Administration (FDA) to:
Treat and/or prevent the recurrence of certain types of herpes simplex virus (HSV) infections, including genital herpes
Treat varicella zoster virus (VZV) infections, including chicken pox (primary varicella infection) and shingles (herpes zoster)
Acyclovir is approved in different formulations and strengths for use in specific populations, including in people who are immunocompromised.
HSV and VZV infections can be opportunistic infections (OIs) of HIV.
- 9-((2-Hydroxyethoxy)methyl)guanine
- Aci Sanorania
- Aci-Sanorania
- Acic
- Aciclobeta
- Aciclostad
- Aciclovir
- Aciclovir Alonga
- Aciclovir Sanorania
- aciclovir von ct
- Aciclovir-Sanorania
- Acifur
- Acipen Solutab
- Acivir
- Activir
- Acyclo V
- Acyclo-V
- Acycloguanosine
- Acyclovir
- Acyclovir Sodium
- Alonga, Aciclovir
- Antiherpes Creme
- Avirax
- Cicloferon
- Clonorax
- Cusiviral
- Genvir
- Herpetad
- Herpofug
- Herpotern
- Herpoviric
- Isavir
- Laciken
- Mapox
- Maynar
- Milavir
- Opthavir
- Sodium, Acyclovir
- Solutab, Acipen
- Supraviran
- Viclovir
- Vipral
- Virax Puren
- Virax-Puren
- ViraxPuren
- Virherpes
- Virmen
- Virolex
- Virupos
- Virzin
- Wellcome 248U
- Wellcome-248U
- Wellcome248U
- Zoliparin
- Zovirax
- Zyclir
- acyclovir
- Aciclovir
- 59277-89-3
- Acycloguanosine
- Zovirax
- Virorax
- Vipral
- Wellcome-248U
- 9-[(2-Hydroxyethoxy)methyl]guanine
- Aciclovirum
- Zovir
- Sitavig
- 2-Amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one
- Gerpevir
- Hascovir
- Acyclovir-side chain-2-3H
- Aciclovirum [Latin]
- Acicloftal
- Cargosil
- Novirus
- 9-(2-Hydroxyethoxy)methylguanine
- 9-HYROXYETHOXYMETHYLGUANINE
- W-248-U
- 9-((2-Hydroxyethoxy)methyl)guanine
- Aciclovirum [INN-Latin]
- BW-248U
- DRG-0008
- MFCD00057880
- CCRIS 1953
- CHEBI:2453
- NSC 645011
- 141294-79-3
- HSDB 6511
- UNII-X4HES1O11F
- 2-Amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-6H-purin-6-one
- EINECS 261-685-1
- X4HES1O11F
- Aciclovir [INN]
- NSC-645011
- NSC-758477
- AVACLYR
- 2-amino-9-(2-hydroxyethoxymethyl)-3H-purin-6-one
- DTXSID1022556
- Acyclovir (Aciclovir)
- 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one
- 2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one
- 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-
- ACYCLOVIR-SIDECHAIN-2-3H
- Acyclovir [USAN:USP]
- Zovirax (TN)
- NSC645011
- 9-[(2-Hydroxyethoxy)-methyl]guanine
- 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one
- MLS000069633
- DTXCID102556
- Activir
- 9-(2-Hydroxyethoxymethyl)guanine
- 6H-Purin-6-one, 2-amino-1,9-dihydro-9-((2-hydroxyethoxy)methyl)-
- Aciclovirum (Latin)
- AC2
- Acyclovir [USAN]
- 2-amino-9-((2-hydroxyethoxy)methyl)-3H-purin-6(9H)-one
- NCGC00015061-02
- Aciclovier
- SMR000058225
- Genvir
- Maynar
- Zyclir
- Acyclovir (USAN:USP)
- ACICLOVIR (IARC)
- ACICLOVIR [IARC]
- 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one
- CAS-59277-89-3
- Aciclovirum (INN-Latin)
- 6H-Purin-6-one, 1,9-dihydro-2-amino-9-((2-hydroxyethoxy)methyl)-
- 2-amino-9-(2-hydroxyethoxymethyl)purin-6-ol
- ACICLOVIR (MART.)
- ACICLOVIR [MART.]
- ACYCLOVIR (USP-RS)
- ACYCLOVIR [USP-RS]
- ACICLOVIR (EP MONOGRAPH)
- ACICLOVIR [EP MONOGRAPH]
- ACYCLOVIR (USP MONOGRAPH)
- ACYCLOVIR [USP MONOGRAPH]
- Viropump
- AcycloFoam
- 2-amino-9-((2-hydroxyethoxy)methyl)-1,9-dihydro-6H-purin-6-one
- 2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-1H-purin-6-one
- Acic
- C8H11N5O3
- 2-amino-9-{[(2-hydroxyethyl)oxy]methyl}-1,9-dihydro-6H-purin-6-one
- Acyclo-V
- Acyclovir Lauriad
- Acyclovir (USP)
- 88713-38-6
- SR-01000075540
- ACV & Pluronic F-68
- B-LF& ACV
- VALACICLOVIR HYDROCHLORIDE IMPURITY B (EP IMPURITY)
- VALACICLOVIR HYDROCHLORIDE IMPURITY B [EP IMPURITY]
- Aclovir
- Acyclovir & Pluronic F-68
- Cyclovir
- Poviral
- Sitavir
- VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY B (EP IMPURITY)
- VALACICLOVIR HYDROCHLORIDE HYDRATE IMPURITY B [EP IMPURITY]
- Prestwick_6
- 1pwy
- BW-248-U
- Sitavig (TN)
- Acyclovir (Standard)
- Spectrum_001739
- ACICLOVIR [JAN]
- ACYCLOVIR [MI]
- ACYCLOVIR [HSDB]
- Opera_ID_1674
- Prestwick0_000086
- Prestwick1_000086
- Prestwick2_000086
- Prestwick3_000086
- Spectrum2_001563
- Spectrum3_001874
- Spectrum4_000225
- Spectrum5_001093
- ACYCLOVIR [VANDF]
- Lopac-A-4669
- Aciclovir (JP18/INN)
- CHEMBL184
- A 4669
- ACICLOVIR [WHO-DD]
- ACICLOVIR [WHO-IP]
- SCHEMBL3175
- Lopac0_000037
- ACICLOVIRUM [WHO-IP]
- BSPBio_000012
- BSPBio_003348
- KBioGR_000889
- KBioSS_002219
- BIDD:GT0646
- DivK1c_000185
- SPECTRUM1503603
- SPBio_001466
- SPBio_001951
- 2-amino-9-[(2-hydroxyethoxy)methyl]hydropurin-6-one
- BPBio1_000014
- GTPL4829
- SCHEMBL9828560
- 9(2-hydroxyethoxymethyl)guanine
- ACYCLOVIR [ORANGE BOOK]
- HMS500J07
- KBio1_000185
- KBio2_002219
- KBio2_004787
- KBio2_007355
- KBio3_002850
- D06BB03
- J05AB01
- S01AD03
- NINDS_000185
- GLXC-04946
- HMS1568A14
- HMS1922E08
- HMS2090G09
- HMS2095A14
- HMS2234K21
- HMS3259N10
- HMS3260G15
- HMS3269M15
- HMS3372K02
- HMS3413D21
- HMS3655C14
- HMS3677D21
- HMS3712A14
- Pharmakon1600-01503603
- 2-amino-9-[(2-hydroxyethoxy)methyl]-3,9-dihydro-6H-purin-6-one
- BCP11036
- 9-(2-hydroxyethoxy methyl) guanine
- Tox21_110075
- Tox21_500037
- 69657-51-8 (Na salt)
- BBL009642
- BDBM50021776
- BDBM50103518
- CCG-39909
- HY-17422R
- NSC335752
- NSC758477
- NSC780378
- s1807
- STK796771
- STL257059
- STL301862
- AKOS000656213
- AKOS015995680
- AKOS022135433
- Tox21_110075_1
- AC-8068
- CS-1353
- DB00787
- KS-1027
- LP00037
- NC00717
- NSC-780378
- SDCCGSBI-0050026.P003
- Bovine lactoferrin & 2-Amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-6H-purin-6-one
- IDI1_000185
- SMP1_000007
- NCGC00015061-01
- NCGC00015061-03
- NCGC00015061-04
- NCGC00015061-05
- NCGC00015061-06
- NCGC00015061-07
- NCGC00015061-08
- NCGC00015061-09
- NCGC00015061-10
- NCGC00015061-12
- NCGC00015061-13
- NCGC00015061-28
- NCGC00015061-29
- NCGC00022426-03
- NCGC00093555-01
- NCGC00093555-02
- NCGC00093555-03
- NCGC00093555-04
- NCGC00167756-01
- NCGC00167756-02
- NCGC00260722-01
- NCGC00381719-03
- HY-17422
- SY051130
- Acycloguanosine, >=99% (HPLC), powder
- Aciclovir 1.0 mg/ml in Dimethyl Sulfoxide
- A1915
- EU-0100037
- NS00009000
- SW196324-3
- C06810
- D00222
- EN300-123010
- A832236
- Q147101
- Q-200591
- SR-01000075540-1
- SR-01000075540-3
- SR-01000075540-5
- 2-amino-9-[(2-hydroxyethoxy)methyl]-9H-purin-6-ol
- 2-azanyl-9-(2-hydroxyethyloxymethyl)-3H-purin-6-one
- BRD-K32318651-001-17-9
- BRD-K32318651-001-21-1
- BRD-K32318651-001-22-9
- BRD-K32318651-001-23-7
- BRD-K32318651-001-24-5
- Aciclovir, British Pharmacopoeia (BP) Reference Standard
- F2173-0946
- Z1546610471
- Aciclovir, European Pharmacopoeia (EP) Reference Standard
- 2-Amino-9-(2-hydroxy-ethoxymethyl)-5,9-dihydro-purin-6-one
- Acyclovir, United States Pharmacopeia (USP) Reference Standard
- 2-Amino-9-(2-hydroxy-ethoxymethyl)-5,9-dihydro-purin-6-one (ACV)
- 2-Amino-9-[(2-hydroxyethoxy)methyl]-1,9-dihydro-6H-purin-6-one #
- ACV; Acycloguanosine; Acyclovir; NSC 645011; NSC-645011; NSC645011
- Acyclovir, Pharmaceutical Secondary Standard; Certified Reference Material
- Aciclovir for peak identification 1, European Pharmacopoeia (EP) Reference Standard
- Aciclovir for peak identification 2, European Pharmacopoeia (EP) Reference Standard
- Aciclovir for system suitability, European Pharmacopoeia (EP) Reference Standard
- InChI=1/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
155.82 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
145.91 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
155.98 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Antiherpes medicines
Ophthalmological preparations > Anti-infective agents
232.168594 65432
230.152679 53624
380.257111 44764
133.063354 42168
148.074387 33700
224.2 100
141.8 0.52
141.4 0.18
150.2 0.06
162.3 0.06
226.0935 999
227.0974 104
226.0971 999
165.0528 914
- Valacyclovir (is active moiety of)
- Valacyclovir Hydrochloride (active moiety of)
- Acyclovir Sodium (active moiety of)
- Acyclovir; hydrocortisone (component of)
Acyclovir is an antiviral prescription medicine approved by the U.S. Food and Drug Administration (FDA) to:
Treat and/or prevent the recurrence of certain types of herpes simplex virus (HSV) infections, including genital herpes
Treat varicella zoster virus (VZV) infections, including chicken pox (primary varicella infection) and shingles (herpes zoster)
Acyclovir is approved in different formulations and strengths for use in specific populations, including in people who are immunocompromised.
HSV and VZV infections can be opportunistic infections (OIs) of HIV.
D - Dermatologicals
D06 - Antibiotics and chemotherapeutics for dermatological use
D06B - Chemotherapeutics for topical use
D06BB - Antivirals
D06BB03 - Aciclovir
J - Antiinfectives for systemic use
J05 - Antivirals for systemic use
J05A - Direct acting antivirals
J05AB - Nucleosides and nucleotides excl. reverse transcriptase inhibitors
J05AB01 - Aciclovir
- Cytoplasm
- Membrane
Use (kg) in Switzerland (2009): >250
Use (kg; approx.) in Germany (2009): >10000
Use (kg; exact) in Germany (2009): 15729
Use (kg) in USA (2002): 21300
Consumption (g per capita) in Switzerland (2009): 0.032
Consumption (g per capita; approx.) in Germany (2009): 0.12
Consumption (g per capita; exact) in Germany (2009): 0.19
Consumption (g per capita) in the USA (2002): 0.076
Excretion rate: 0.9
Calculated removal (%): 22
H315 (77.9%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (77.9%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (71.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501
(The corresponding statement to each P-code can be found at the GHS Classification page.)
Aggregated GHS information provided per 95 reports by companies from 20 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Reported as not meeting GHS hazard criteria per 14 of 95 reports by companies. For more detailed information, please visit ECHA C&L website.
There are 18 notifications provided by 81 of 95 reports by companies with hazard statement code(s).
Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.
Skin Irrit. 2 (77.9%)
Eye Irrit. 2A (77.9%)
STOT SE 3 (71.6%)
Acute Tox. 4 (100%)
Acute Tox. 4 (100%)
Carc. 2 (100%)
IMAP assessments - 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-: Environment tier I assessment
IMAP assessments - 6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-: Human health tier I assessment
Despite widespread use, there is little evidence that acyclovir when given orally causes significant liver injury. Serum enzyme levels generally do not change during oral acyclovir therapy. High dose intravenous administration of acyclovir is associated with renal dysfunction and thrombocytopenia, and occasionally with transient mild-to-moderate elevations in serum ALT levels, which have been asymptomatic and self-limited. There have rare instances of acute, clinically apparent liver injury reported that were attributed to acyclovir or valacyclovir (a prodrug of acyclovir with better oral absorption), but these have not been particularly convincing. Some degree of liver injury and even jaundice can occur during the course of herpes simplex or varicella zoster infection, and these complications could be mistaken for drug induced liver injury. Furthermore, in the reported cases, patients were receiving other medications and had other unlying comorbidities that may have been responsible for the liver injury.
Likelihood score: D (possible rare cause of clinically apparent liver injury).
M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007
M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015
◉ Summary of Use during Lactation
Even with the highest maternal dosages, the dosage of acyclovir in milk is only about 1% of a typical infant dosage and would not be expected to cause any adverse effects in breastfed infants. Topical acyclovir applied to small areas of the mother's body away from the breast should pose no risk to the infant. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.
◉ Effects in Breastfed Infants
The mother of a 4-month-old infant noticed no adverse effects in her breastfed infant while she was taking an acyclovir dosage of 800 mg orally 5 times daily.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
Patents are available for this chemical structure:
https://patentscope.wipo.int/search/en/result.jsf?inchikey=MKUXAQIIEYXACX-UHFFFAOYSA-N
- Drink plenty of fluids. Dehydration with acyclovir predisposes patients to nephrotoxicity.
- Take with or without food. The absorption is unaffected by food.
- Australian Industrial Chemicals Introduction Scheme (AICIS)6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy)methyl]-https://services.industrialchemicals.gov.au/search-assessments/
- CAS Common ChemistryLICENSEThe data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.https://creativecommons.org/licenses/by-nc/4.0/
- ChemIDplusAcyclovir [USAN:USP]https://pubchem.ncbi.nlm.nih.gov/substance/?source=chemidplus&sourceid=0059277893ChemIDplus Chemical Information Classificationhttps://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
- DrugBankLICENSECreative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)https://www.drugbank.ca/legal/terms_of_use
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- CCSbaseCCSbase Classificationhttps://ccsbase.net/
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- Drug Induced Liver Injury Rank (DILIrank) DatasetLICENSEUnless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.https://www.fda.gov/about-fda/about-website/website-policies#linking
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- NIST Mass Spectrometry Data CenterLICENSEData covered by the Standard Reference Data Act of 1968 as amended.https://www.nist.gov/srd/public-lawAcyclovirhttp://www.nist.gov/srd/nist1a.cfm
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- Japan Chemical Substance Dictionary (Nikkaji)
- KEGGLICENSEAcademic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial licensehttps://www.kegg.jp/kegg/legal.htmlTherapeutic category of drugs in Japanhttp://www.genome.jp/kegg-bin/get_htext?br08301.kegUSP drug classificationhttp://www.genome.jp/kegg-bin/get_htext?br08302.kegAnatomical Therapeutic Chemical (ATC) classificationhttp://www.genome.jp/kegg-bin/get_htext?br08303.kegAntiinfectiveshttp://www.genome.jp/kegg-bin/get_htext?br08307.kegDrugs listed in the Japanese Pharmacopoeiahttp://www.genome.jp/kegg-bin/get_htext?br08311.kegRisk category of Japanese OTC drugshttp://www.genome.jp/kegg-bin/get_htext?br08312.kegClassification of Japanese OTC drugshttp://www.genome.jp/kegg-bin/get_htext?br08313.keg
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- NIPH Clinical Trials Search of Japan
- SpectraBase2-amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-onehttps://spectrabase.com/spectrum/4IEXY20hQyPAcycloguanosinehttps://spectrabase.com/spectrum/9BwhQHUAOkUAcycloguanosinehttps://spectrabase.com/spectrum/3vqVOVCbWEw9-[(2-HYDROXYETHOXY)-METHYL]-GUANINE;ACYCLOVIRhttps://spectrabase.com/spectrum/9i5uMToolCZMKUXAQIIEYXACX-UHFFFAOYSA-Nhttps://spectrabase.com/spectrum/CfmK5x2hMQr
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- Wikidata6H-Purin-6-one, 2-amino-1,9-dihydro-9-[(2-hydroxyethoxy-2-t)methyl]-https://www.wikidata.org/wiki/Q90542928
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- GHS Classification (UNECE)GHS Classification Treehttp://www.unece.org/trans/danger/publi/ghs/ghs_welcome_e.html
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