Acyclovir

Identification

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Name

Acyclovir

Accession Number

DB00787  (APRD00567, EXPT00406, DB05347)

Type

Small Molecule

Groups

Approved

Description

Acyclovir is a nucleotide analog antiviral used to treat herpes simplex, Varicella zoster, herpes zoster, herpes labialis, and acute herpetic keratitis^{10,11,12,13,14,15}. Acyclovir is generally used first line in the treatment of these viruses and some products are indicated for patients as young as 6 years old.¹³

Acyclovir was granted FDA approval on 29 March 1982.¹²

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Acyclovir (DB00787)

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Synonyms

• Aciclovir
• Aciclovirum
• Acycloguanosine
• Acyclovir

External IDs

NSC-645011

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Acyclovir sodium	927L42J563	69657-51-8	RMLUKZWYIKEASN-UHFFFAOYSA-M

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Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Acyclovir	Tablet	800 mg	Oral	Sanis Health Inc	2010-04-05	2014-08-01
Acyclovir	Capsule	200 mg/1	Oral	Boscogen, Inc.	2004-08-01	2010-12-10
Acyclovir	Tablet	200 mg	Oral	Sanis Health Inc	2010-04-05	2014-08-01
Acyclovir	Tablet	400 mg	Oral	Sanis Health Inc	2010-04-05	2017-07-31
Acyclovir Sodium for Injection	Powder, for solution		Intravenous	Novopharm Limited	1998-02-04	2005-08-10
Acyclovir Sodium for Injection	Powder, for solution		Intravenous	Novopharm Limited	1998-02-04	2018-05-08
Acyclovir Sodium for Injection	Powder, for solution		Intravenous	Abbott	1998-02-11	2007-07-31
Acyclovir Sodium for Injection	Powder, for solution		Intravenous	Abbott	1998-02-11	2007-07-31
Acyclovir Sodium Injection	Solution		Intravenous	Fresenius Kabi	1998-05-08	Not applicable
Acyclovir Sodium Injection	Solution		Intravenous	Sterimax Inc	2018-09-24	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Acyclovir	Tablet	800 mg/1	Oral	Mc Kesson Packaging Services A Buisness Unit Of Mc Kesson Corporation	2007-09-05	2011-08-31
Acyclovir	Ointment	50 mg/1g	Topical	Zydus Pharmaceuticals (USA) Inc.	2019-03-21	Not applicable
Acyclovir	Tablet	400 mg/1	Oral	Denton Pharma, Inc. Dba Northwind Pharmaceuticals	2018-06-06	Not applicable
Acyclovir	Tablet	800 mg/1	Oral	Heritage	2013-08-08	Not applicable
Acyclovir	Capsule	200 mg/1	Oral	Blenheim Pharmacal, Inc.	2013-11-13	2016-11-30
Acyclovir	Capsule	200 mg/1	Oral	Preferreed Pharmaceuticals Inc.	2013-03-26	Not applicable
Acyclovir	Tablet	800 mg/1	Oral	Blenheim Pharmacal, Inc.	2010-11-08	2017-08-31
Acyclovir	Tablet	400 mg/1	Oral	Nucare Pharmaceuticals,inc.	2018-05-04	Not applicable
Acyclovir	Cream	50 mg/1g	Topical	Teva Pharmaceuticals, Inc.	2019-08-29	Not applicable
Acyclovir	Tablet	400 mg/1	Oral	A-S Medication Solutions	2013-11-29	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Acyclovir	Ointment	50 mg/1g	Topical	OASIS TRADING	2018-11-15	Not applicable

Additional Data Available

Application Number
Application Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
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Product Code
Product Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Xerese	Acyclovir (5 %) + Hydrocortisone (1 %)	Cream	Topical	Valeant Canada Lp Valeant Canada S.E.C.	2013-07-26	Not applicable
Xerese	Acyclovir (50 mg/1g) + Hydrocortisone (10 mg/1g)	Cream	Topical	Bausch Health US, LLC	2009-07-31	Not applicable
Xerese	Acyclovir (50 mg/1g) + Hydrocortisone (10 mg/1g)	Cream	Topical	Meda Pharmaceuticals Ltd	2010-07-15	2013-02-28

Unapproved/Other Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Acyclovir	Acyclovir (50 mg/1g)	Ointment	Topical	OASIS TRADING	2018-11-15	Not applicable

International/Other Brands

Zovir

Categories

• Acyclovir and prodrug
• Anti-Infective Agents
• Antiinfectives for Systemic Use
• Antiviral Agents
• Antivirals for Systemic Use
• Cytochrome P-450 CYP1A2 Substrates
• Dermatologicals
• Direct Acting Antivirals
• Drugs that are Mainly Renally Excreted
• Herpes Simplex Virus Nucleoside Analog DNA Polymerase Inhibitor
• Herpes Zoster Virus Nucleoside Analog DNA Polymerase Inhibitor
• Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor
• Heterocyclic Compounds, Fused-Ring
• MATE 1 Substrates
• MATE 2 Substrates
• MATE substrates
• Nephrotoxic agents
• Nucleic Acid Synthesis Inhibitors
• Nucleosides and Nucleotides
• Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors
• OAT1/SLC22A6 inhibitors
• OAT1/SLC22A6 Substrates
• OAT3/SLC22A8 Inhibitors
• OAT3/SLC22A8 Substrates
• OCT1 inhibitors
• OCT1 substrates
• Ophthalmologicals
• Purines
• Purinones
• Sensory Organs

UNII

X4HES1O11F

CAS number

59277-89-3

Weight

Average: 225.2046
Monoisotopic: 225.086189243

Chemical Formula

C₈H₁₁N₅O₃

InChI Key

MKUXAQIIEYXACX-UHFFFAOYSA-N

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)

IUPAC Name

2-amino-9-[(2-hydroxyethoxy)methyl]-6,9-dihydro-3H-purin-6-one

SMILES

NC1=NC(=O)C2=C(N1)N(COCCO)C=N2

Pharmacology

Indication

An acyclovir topical cream is indicated to treat recurrent herpes labialis in immunocompetent patients 12 years and older.¹⁰ Acyclovir oral tablets, capsules, and suspensions are indicated to treat herpes zoster, genital herpes, and chickenpox.¹¹ An acyclovir topical ointment is indicated to treat initial genital herpes and limited non-life-threatening mucocutaneous herpes simplex in immunocompromised patients.¹² An acyclovir cream with hydrocortisone is indicated to treat recurrent herpes labialis, and shortening lesion healing time in patients 6 years and older.¹³ An acyclovir buccal tablet is indicated for the treatment of recurrent herpes labialis.¹⁴ An acyclovir ophthalmic ointment is indicated to treat acute herpetic keratitis.¹⁵

Associated Conditions

• Bell's Palsy
• Chickenpox
• Encephalitis, Herpes Simplex
• Herpes Simplex Infection
• Herpes Zoster
• Herpes simplex of the oral-labial
• Herpes simplex type I reactivation
• Infections, Cytomegalovirus
• Recurrent Genital Herpes (RGH)
• Recurrent Herpes Labialis
• VZV re-activation
• Acute Genital herpes
• Acute Herpes labialis
• Acute Herpetic keratitis
• Severe Genital herpes

Pharmacodynamics

Acyclovir is a nucleoside analog that inhibits the action of viral DNA polymerase and DNA replication of different herpesvirus.^{10,11,12,13,14,15} Acyclovir has a wide therapeutic window as overdose is rare in otherwise healthy patients.¹¹

Mechanism of action

Acyclovir is becomes acyclovir monophosphate due to the action of viral thymidine kinase.⁵ Acyclovir monophosphate is converted to the diphosphate form by guanylate kinase.¹ Acyclovir diphosphate is converted to acyclovir triphosphate by nucleoside diphosphate kinase, pyruvate kinase, creatine kinase, phosphoglycerate kinase, succinyl-CoA synthetase, phosphoenolpyruvate carboxykinase and adenylosuccinate synthetase.^1,7 Acyclovir triphosphate has higher affinity for viral DNA polymerase than cellular DNA polymerase and incorporates into the DNA where the missing 2' and 3' carbons causes DNA chain termination.⁵ In other cases acyclovir triphosphate competes so strongly for viral DNA polymerase that other bases cannot associate with the enzyme, inactivating it.⁵

Target	Actions	Organism
AThymidine kinase	potentiator
ADNA polymerase catalytic subunit	inhibitor	HHV-1
ADNA polymerase catalytic subunit	inhibitor	HHV-3

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

The oral bioavailability of acyclovir is 10-20% but decreases with increasing doses.¹¹ Acyclovir ointment is <0.02-9.4% absorbed.¹² Acyclovir buccal tablets and ophthalmic ointment are minimally absorbed.^14,15 The bioavailability of acyclovir is not affected by food.¹¹

Acyclovir has a mean T_max of 1.1±0.4 hours, mean C_max of 593.7-656.5ng/mL, and mean AUC of 2956.6-3102.5h*ng/mL.⁹

Volume of distribution

The volume of distribution of acyclovir is 0.6L/kg.⁶

Protein binding

Acyclovir is 9-33% protein bound in plasma.^6,11

Metabolism

Acyclovir is <15% oxidized to 9-carboxymethoxymethylguanine by alcohol dehydrogenase and aldehyde dehydrogenase and 1% 8-hydroxylated to 8-hydroxy-acyclovir by aldehyde oxidase.⁴

Acyclovir is becomes acyclovir monophosphate due to the action of viral thymidine kinase.⁵ Acyclovir monophosphate is converted to the diphosphate form by guanylate kinase.¹ Acyclovir diphosphate is converted to acyclovir triphosphate by nucleoside diphosphate kinase, pyruvate kinase, creatine kinase, phosphoglycerate kinase, succinyl-CoA synthetase, phosphoenolpyruvate carboxykinase and adenylosuccinate synthetase.^1,7

• Acyclovir
  9-carboxymethoxymethylguanine
• Acyclovir
  8-hydroxy-acyclovir

Route of elimination

The majority of acyclovir is excreted in the urine as unchanged drug.^4,14 90-92% of the drug can be excreted unchanged through glomerular filtration and tubular secretion.⁵ <2% of the drug is recovered in feces and <0.1% is expired as CO₂.⁸

Half life

The clearance of acyclovir varies from 2.5-3 hours depending on the creatinine clearance of the patient.⁵ The plasma half life of acyclovir during hemodialysis is approximately 5 hours.¹¹ The mean half life in patients from 7 months to 7 years old is 2.6 hours.¹¹

Clearance

The renal clearance of acyclovir is 248mL/min/1.73m².⁸ The total clearance in neonates if 105-122mL/min/1.73m².⁸

Toxicity

Symptoms of overdose include agitation, coma, seizures, lethargy, and precipitation in renal tubules.¹¹ These symptoms are more common in patients given high doses without monitoring of fluid and electrolyte balance or reduced kidney function.^11,4,6 In the case of an overdose, treat with symptomatic and supportive care.¹³

Affected organisms

• Human Herpes Virus

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

• All Drugs
• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be decreased when combined with Acyclovir.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be decreased when combined with Acyclovir.
8-azaguanine	The metabolism of 8-azaguanine can be decreased when combined with Acyclovir.
8-chlorotheophylline	The metabolism of 8-chlorotheophylline can be decreased when combined with Acyclovir.
9-Deazaguanine	The metabolism of 9-Deazaguanine can be decreased when combined with Acyclovir.
9-Methylguanine	The metabolism of 9-Methylguanine can be decreased when combined with Acyclovir.
Abacavir	Acyclovir may decrease the excretion rate of Abacavir which could result in a higher serum level.
Abatacept	The metabolism of Acyclovir can be increased when combined with Abatacept.
Abemaciclib	The excretion of Abemaciclib can be decreased when combined with Acyclovir.
Abiraterone	The serum concentration of Acyclovir can be increased when it is combined with Abiraterone.

Additional Data Available

Extended Description
Extended Description
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Severity
Severity
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Evidence Level
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Food Interactions

• Increase liquid intake.
• Take without regard to meals.

References

Synthesis Reference

US4294831

General References

1. O'Brien JJ, Campoli-Richards DM: Acyclovir. An updated review of its antiviral activity, pharmacokinetic properties and therapeutic efficacy. Drugs. 1989 Mar;37(3):233-309. [PubMed:2653790]
2. Gunness P, Aleksa K, Bend J, Koren G: Acyclovir-induced nephrotoxicity: the role of the acyclovir aldehyde metabolite. Transl Res. 2011 Nov;158(5):290-301. doi: 10.1016/j.trsl.2011.07.002. Epub 2011 Aug 3. [PubMed:22005269]
3. Morrel EM, Spruance SL, Goldberg DI: Topical iontophoretic administration of acyclovir for the episodic treatment of herpes labialis: a randomized, double-blind, placebo-controlled, clinic-initiated trial. Clin Infect Dis. 2006 Aug 15;43(4):460-7. Epub 2006 Jul 3. [PubMed:16838235]
4. Smith JP, Weller S, Johnson B, Nicotera J, Luther JM, Haas DW: Pharmacokinetics of acyclovir and its metabolites in cerebrospinal fluid and systemic circulation after administration of high-dose valacyclovir in subjects with normal and impaired renal function. Antimicrob Agents Chemother. 2010 Mar;54(3):1146-51. doi: 10.1128/AAC.00729-09. Epub 2009 Dec 28. [PubMed:20038622]
5. King DH: History, pharmacokinetics, and pharmacology of acyclovir. J Am Acad Dermatol. 1988 Jan;18(1 Pt 2):176-9. doi: 10.1016/s0190-9622(88)70022-5. [PubMed:2828440]
6. Sadjadi SA, Regmi S, Chau T: Acyclovir Neurotoxicity in a Peritoneal Dialysis Patient: Report of a Case and Review of the Pharmacokinetics of Acyclovir. Am J Case Rep. 2018 Dec 9;19:1459-1462. doi: 10.12659/AJCR.911520. [PubMed:30531673]
7. Miller WH, Miller RL: Phosphorylation of acyclovir diphosphate by cellular enzymes. Biochem Pharmacol. 1982 Dec 1;31(23):3879-84. doi: 10.1016/0006-2952(82)90305-7. [PubMed:7159465]
8. Laskin OL: Clinical pharmacokinetics of acyclovir. Clin Pharmacokinet. 1983 May-Jun;8(3):187-201. doi: 10.2165/00003088-198308030-00001. [PubMed:6342900]
9. Yuen KH, Peh KK, Billa N, Chan KL, Toh WT: Bioavailability and pharmacokinetics of acyclovir tablet preparation. Drug Dev Ind Pharm. 1998 Feb;24(2):193-6. doi: 10.3109/03639049809085607. [PubMed:15605452]
10. FDA Approved Drug Products: Zovirax Topical Cream [Link]
11. FDA Drug Approval Package: Zovirax Oral Capsules, Oral Tablets, Oral Suspension [Link]
12. FDA Approved Drug Products: Zovirax Topical Ointment [Link]
13. FDA Approved Drug Products: Xerese Topical Cream With Hydrocortisone [Link]
14. FDA Approved Drug Products: Sitavig Buccal Tablets [Link]
15. FDA Approved Drug Products: Avaclyr Ophthalmic Ointment [Link]

External Links

Human Metabolome Database

HMDB0014925

KEGG Drug

D00222

KEGG Compound

C06810

PubChem Compound

2022

PubChem Substance

46506002

ChemSpider

1945

BindingDB

50021776

ChEBI

2453

ChEMBL

CHEMBL184

Therapeutic Targets Database

DNC000157

PharmGKB

PA448045

HET

AC2

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Aciclovir

ATC Codes

J05AB01 — Aciclovir

• J05AB — Nucleosides and nucleotides excl. reverse transcriptase inhibitors
• J05A — DIRECT ACTING ANTIVIRALS
• J05 — ANTIVIRALS FOR SYSTEMIC USE
• J — ANTIINFECTIVES FOR SYSTEMIC USE

D06BB03 — Aciclovir

• D06BB — Antivirals
• D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
• D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

S01AD03 — Aciclovir

• S01AD — Antivirals
• S01A — ANTIINFECTIVES
• S01 — OPHTHALMOLOGICALS
• S — SENSORY ORGANS

D06BB53 — Aciclovir, combinations

• D06BB — Antivirals
• D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
• D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
• D — DERMATOLOGICALS

AHFS Codes

• 84:04.06 — Antivirals
• 08:18.32 — Nucleosides and Nucleotides

PDB Entries

1pwy / 2ki5 / 3mjr / 4da7 / 5i3c

MSDS

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Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1	Active Not Recruiting	Treatment	Progressive Multiple Sclerosis	1
1	Completed	Not Available	Infection NOS	1
1	Completed	Basic Science	Healthy Volunteers	1
1	Completed	Treatment	Acute and Chronic Inflammation / Autoimmune Diseases / Disorder of Pleura and Pleural Cavity / Disorder of Synovium / Felty's Syndrome / Rheumatoid Arthritis / Rheumatoid Nodules / Sjögren's Syndrome	1
1	Completed	Treatment	Herpes Simplex Virus / Neonatal Sepsis	1
1	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
1	Completed	Treatment	Progressive Multiple Sclerosis	2
1, 2	Completed	Treatment	Acute Undifferentiated Leukemia (AUL) / B-cell Adult Acute Lymphoblastic Leukemia / B-cell Childhood Acute Lymphoblastic Leukemia / L1 Adult Acute Lymphoblastic Leukemia / L1 Childhood Acute Lymphoblastic Leukemia / L2 Adult Acute Lymphoblastic Leukemia / L2 Childhood Acute Lymphoblastic Leukemia / Philadelphia Chromosome Negative Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Adult Precursor Acute Lymphoblastic Leukemia / Philadelphia Chromosome Positive Childhood Precursor Acute Lymphoblastic Leukemia / T-cell Adult Acute Lymphoblastic Leukemia / T-cell Childhood Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia	1
1, 2	Completed	Treatment	Herpes Simplex	1
1, 2	Completed	Treatment	Kidney Diseases / Transplantation, Kidney	1
2	Completed	Prevention	Critical Illness	1
2	Completed	Prevention	Herpes simplex of the genitals / Ulcers	1
2	Completed	Treatment	Chickenpox / Human Immunodeficiency Virus (HIV) Infections	1
2	Completed	Treatment	Herpes Labialis	3
2	Completed	Treatment	Herpes simplex of the genitals / Human Immunodeficiency Virus (HIV) Infections	1
2	Completed	Treatment	Herpesvirus 2, Human / Human Immunodeficiency Virus (HIV) Infections	1
2	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
2	Completed	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
2	Completed	Treatment	Metastatic Castration Resistant Prostate Cancer	1
2	Suspended	Supportive Care	Stem Cell Transplant Complications	1
2, 3	Completed	Prevention	HIV-1 and HSV-2 Coinfection / Human Immunodeficiency Virus (HIV) Infections	1
2, 3	Completed	Treatment	Herpes Simplex / Human Immunodeficiency Virus (HIV) Infections / Ulcers	1
2, 3	Unknown Status	Treatment	Menière's Disease	1
2, 3	Withdrawn	Treatment	Herpes Simplex	1
3	Active Not Recruiting	Treatment	Drug Use for Unapproved Schedule	1
3	Completed	Not Available	VZV Infection After Bone Marrow Transplantation	1
3	Completed	Prevention	Cytomegalovirus / Transplantation, Bone Marrow	1
3	Completed	Prevention	Herpes simplex of the genitals / HIV Seronegativity / Human Immunodeficiency Virus (HIV) Infections	1
3	Completed	Prevention	Herpes Labialis	1
3	Completed	Prevention	Herpes Simplex, Genital / Human Immunodeficiency Virus (HIV) Infections / Sexually Transmitted Disease (STD)	1
3	Completed	Supportive Care	Herpes Simplex	1
3	Completed	Supportive Care	Malignancies	1
3	Completed	Treatment	Chickenpox / Human Immunodeficiency Virus (HIV) Infections	1
3	Completed	Treatment	Genital Herpes	1
3	Completed	Treatment	Herpes Labialis	5
3	Completed	Treatment	Herpes Simplex	4
3	Completed	Treatment	Herpes Simplex / Human Immunodeficiency Virus (HIV) Infections	1
3	Completed	Treatment	Herpes Simplex / Keratitis, Herpetic / Ocular Herpes Simplex	1
3	Completed	Treatment	Herpes Zoster	1
3	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Infections, Cytomegalovirus	1
3	Recruiting	Prevention	CMV Disease	1
3	Recruiting	Treatment	Disseminated Sclerosis	1
3	Unknown Status	Treatment	Herpes Simplex	1
3	Unknown Status	Treatment	Keratitis, Herpetic / Ocular Herpes Simplex	1
4	Active Not Recruiting	Not Available	Genital Herpes	1
4	Active Not Recruiting	Treatment	Viral Pneumonia	1
4	Completed	Prevention	Herpes / Human Immunodeficiency Virus (HIV)	1
4	Completed	Treatment	Genital Herpes	2
4	Completed	Treatment	Genital Herpes / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Healthy Volunteers	1
4	Completed	Treatment	Herpes Simplex Infection / Human Immunodeficiency Virus (HIV) Infections	1
4	Completed	Treatment	Relapsing Remitting Multiple Sclerosis (RRMS)	1
4	Not Yet Recruiting	Prevention	Herpes Simplex Virus Keratitis	1
4	Recruiting	Treatment	Genital Herpes	1
4	Unknown Status	Treatment	Herpes Zoster	1
4	Unknown Status	Treatment	Reccurent Herpes Labialis	1
Not Available	Completed	Not Available	Genital Herpes	1
Not Available	Completed	Basic Science	Dermatologic Disorders	1
Not Available	Completed	Treatment	Cytomegalovirus Retinitis / Human Immunodeficiency Virus (HIV) Infections	1
Not Available	Completed	Treatment	Facial Paralysis	1
Not Available	Completed	Treatment	Genital Herpes	1
Not Available	Completed	Treatment	Herpes Simplex / Human Immunodeficiency Virus (HIV) Infections	4
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections	1
Not Available	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Oral hairy leukoplakia	1
Not Available	Completed	Treatment	Ulcers of Female Genital Organs	1
Not Available	Recruiting	Not Available	Children; Infection / Newborn; Infection	1
Not Available	Recruiting	Not Available	Meningitis, Aseptic	1
Not Available	Recruiting	Treatment	Uveitis	1

Pharmacoeconomics

Manufacturers

• Actavis elizabeth llc
• Apotex inc etobicoke site
• Belcher pharmaceuticals inc
• Dava pharmaceuticals inc
• Genpharm inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Lek pharmaceutical and chemical co dd
• Mylan pharmaceuticals inc
• Ranbaxy laboratories ltd
• Roxane laboratories inc
• Stason industrial corp
• Teva pharmaceuticals usa inc
• Teva pharmaceuticals usa
• Watson laboratories inc
• Glaxosmithkline
• Actavis mid atlantic llc
• Hi tech pharmacal co inc
• Carlsbad technology inc
• Mylan laboratories inc
• Abbott laboratories
• Baxter healthcare corp anesthesia and critical care
• Apothecon inc div bristol myers squibb
• App pharmaceuticals llc
• Bedford laboratories div ben venue laboratories inc
• Hospira inc
• Teva parenteral medicines inc

Packagers

• Actavis Group
• Advanced Pharmaceutical Services Inc.
• Amerisource Health Services Corp.
• Amneal Pharmaceuticals
• Apotex Inc.
• Apotheca Inc.
• Apothecary Shop Wholesale
• APP Pharmaceuticals
• AQ Pharmaceuticals Inc.
• A-S Medication Solutions LLC
• Atlantic Biologicals Corporation
• Bedford Labs
• Ben Venue Laboratories Inc.
• Bryant Ranch Prepack
• BTA Pharmaceuticals
• Cardinal Health
• Carlsbad Technology Inc.
• Comprehensive Consultant Services Inc.
• Corepharma LLC
• DAVA Pharmaceuticals
• Direct Dispensing Inc.
• Dispensing Solutions
• Diversified Healthcare Services Inc.
• DSM Corp.
• East Coast Medical Network Inc.
• Eczacibasi Health Products Co.
• GlaxoSmithKline Inc.
• Goldline Laboratories Inc.
• H.J. Harkins Co. Inc.
• Heritage Pharmaceuticals
• Hi Tech Pharmacal Co. Inc.
• Hospira Inc.
• Ivax Pharmaceuticals
• Kaiser Foundation Hospital
• Lake Erie Medical and Surgical Supply
• Liberty Pharmaceuticals
• Major Pharmaceuticals
• Mckesson Corp.
• Medvantx Inc.
• Meridian Medical Technologies Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• Mylan
• Neuman Distributors Inc.
• Novopharm Ltd.
• Nucare Pharmaceuticals Inc.
• Palmetto Pharmaceuticals Inc.
• Patheon Inc.
• PCA LLC
• PD-Rx Pharmaceuticals Inc.
• Pharmaceutical Utilization Management Program VA Inc.
• Pharmedix
• Pharmpak Inc.
• Physicians Total Care Inc.
• Preferred Pharmaceuticals Inc.
• Prepackage Specialists
• Prepak Systems Inc.
• Ranbaxy Laboratories
• Rebel Distributors Corp.
• Redpharm Drug
• Remedy Repack
• Resource Optimization and Innovation LLC
• Roxane Labs
• Southwood Pharmaceuticals
• St Mary's Medical Park Pharmacy
• Stason Pharmaceuticals Inc.
• Teva Pharmaceutical Industries Ltd.
• UDL Laboratories
• Watson Pharmaceuticals
• Xactdose Inc.
• Yung Shin Pharmaceutical Industry Ltd.

Dosage forms

Form	Route	Strength
Capsule	Oral	200 mg/1
Capsule	Oral	400 mg/1
Injection, powder, lyophilized, for solution	Intravenous	1 g/1
Injection, powder, lyophilized, for solution	Intravenous	1000 mg/20mL
Injection, powder, lyophilized, for solution	Intravenous	1000 mg/1
Injection, powder, lyophilized, for solution	Intravenous	500 mg/10mL
Injection, powder, lyophilized, for solution	Intravenous	500 mg/1
Injection, solution	Intravenous	25 mg/1mL
Injection, solution	Intravenous	50 mg/1mL
Ointment	Cutaneous	50 mg/1g
Suspension	Oral	200 mg/5mL
Tablet	Oral	200 mg
Tablet	Oral	200 mg/1
Tablet	Oral	400 mg/1
Tablet	Oral	400 mg
Tablet	Oral	400.00 mg/1
Tablet	Oral	800 mg/1
Tablet	Oral	800 mg
Tablet	Oral	800.00 mg/1
Injection, solution	Intravenous	1000 mg/20mL
Injection, solution	Intravenous	500 mg/10mL
Powder, for solution	Intravenous
Solution	Intravenous
Ointment	Topical
Kit	Not applicable
Tablet	Oral
Tablet	Buccal	50 mg
Tablet, delayed release	Buccal	50 mg/1
Cream	Topical
Cream	Topical	5 %
Cream	Topical	50 mg/1g
Injection, powder, lyophilized, for solution	Intravenous	50 mg/1mL
Ointment	Topical	5 %
Ointment	Topical	50 mg/1g
Powder, for solution	Intravenous	1 g
Powder, for solution	Intravenous	500 mg
Suspension	Oral	200 mg
Capsule	Oral

Prices

Unit description	Cost	Unit
Zovirax 200 mg/5ml Suspension 473ml Bottle	264.95USD	bottle
Zovirax 5% Ointment 15 gm Tube	191.56USD	tube
Zovirax 5% Cream 5 gm Tube	165.07USD	tube
Zovirax 5% Cream 2 gm Tube	69.44USD	tube
Zovirax 5% cream	30.22USD	g
Zovirax 800 mg tablet	11.83USD	tablet
Zovirax 400 mg tablet	6.09USD	tablet
Zovirax 800 mg Tablet	5.71USD	tablet
Acyclovir 800 mg tablet	3.81USD	tablet
Zovirax 200 mg capsule	3.08USD	capsule
Acyclovir 800 mg Tablet	2.99USD	tablet
Apo-Acyclovir 800 mg Tablet	2.99USD	tablet
Mylan-Acyclovir 800 mg Tablet	2.99USD	tablet
Novo-Acyclovir 800 mg Tablet	2.99USD	tablet
Nu-Acyclovir 800 mg Tablet	2.99USD	tablet
Ratio-Acyclovir 800 mg Tablet	2.99USD	tablet
Zovirax 400 mg Tablet	2.9USD	tablet
Acyclovir 400 mg tablet	2.26USD	tablet
Acyclovir 400 mg Tablet	1.63USD	tablet
Apo-Acyclovir 400 mg Tablet	1.63USD	tablet
Mylan-Acyclovir 400 mg Tablet	1.63USD	tablet
Novo-Acyclovir 400 mg Tablet	1.63USD	tablet
Nu-Acyclovir 400 mg Tablet	1.63USD	tablet
Ratio-Acyclovir 400 mg Tablet	1.63USD	tablet
Zovirax 200 mg Tablet	1.44USD	tablet
Acyclovir 200 mg capsule	1.01USD	capsule
Acyclovir 200 mg Tablet	0.81USD	tablet
Apo-Acyclovir 200 mg Tablet	0.81USD	tablet
Mylan-Acyclovir 200 mg Tablet	0.81USD	tablet
Novo-Acyclovir 200 mg Tablet	0.81USD	tablet
Ratio-Acyclovir 200 mg Tablet	0.81USD	tablet
Acyclovir 200 mg/5ml Suspension	0.3USD	ml
Zovirax 40 mg/ml Suspension	0.28USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
Unlock Additional Data
CA2098108	No	2001-07-03	2012-01-29
USRE39264	No	2006-09-05	2016-08-02
US6514980	No	2003-02-04	2019-01-24
US7223387	No	2007-05-29	2021-07-24
US8747896	No	2014-06-10	2027-06-03
US8791127	No	2014-07-29	2027-03-23
US8592434	No	2013-11-26	2030-06-16

Additional Data Available

Filed On
Filed On
The date on which a patent was filed with the relevant government.
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Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	255 °C	http://www.chemspider.com/Chemical-Structure.1945.html
boiling point (°C)	595	http://www.chemspider.com/Chemical-Structure.1945.html
water solubility	1.41mg/mL at 25°C	Avaclyr Ophthalmic Ointment FDA label
logP	-1.76	http://www.chemspider.com/Chemical-Structure.1945.html
Caco2 permeability	-6.15	ADME Research, USCD
pKa	2.52 and 9.35	Avaclyr Ophthalmic Ointment FDA label

Predicted Properties

Property	Value	Source
Water Solubility	9.08 mg/mL	ALOGPS
logP	-0.95	ALOGPS
logP	-1	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Acidic)	11.98	ChemAxon
pKa (Strongest Basic)	3.02	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.76 Å2	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.63 m3·mol-1	ChemAxon
Polarizability	21.51 Å3	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-00di-0090000000-59599385810ae2952ce5
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-00di-0290000000-9410504409e66bcd08f9
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-0uyi-1900000000-0930eb38cecf2a197001
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-05nf-4900000000-10d8c1e33c5d46d6ff80
LC-MS/MS Spectrum - LC-ESI-QQ , negative	LC-MS/MS	splash10-05mo-9600000000-e25ed55283d7d66d80c5
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-004i-0390000000-079dc309c9ffbbde3375
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0udi-0900000000-201a17a51960fdc3bcef
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0udi-0900000000-6c63ec4268a52381191c
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-0f79-1900000000-20fdfa17569c6b2f479f
LC-MS/MS Spectrum - LC-ESI-QQ , positive	LC-MS/MS	splash10-000i-2900000000-4f7a822e6652ec471aee
LC-MS/MS Spectrum - LC-ESI-IT , positive	LC-MS/MS	splash10-0udi-0900000000-69b23ed6f334f4571ecc
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0udr-2910100000-2b1624536b0084ca299c

Taxonomy

Description

This compound belongs to the class of organic compounds known as hypoxanthines. These are compounds containing the purine derivative 1H-purin-6(9H)-one. Purine is a bicyclic aromatic compound made up of a pyrimidine ring fused to an imidazole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Imidazopyrimidines

Sub Class

Purines and purine derivatives

Direct Parent

Hypoxanthines

Alternative Parents

6-oxopurines / Pyrimidones / Aminopyrimidines and derivatives / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Azacyclic compounds / Primary amines / Primary alcohols / Organopnictogen compoundsOrganic oxides / Hydrocarbon derivatives

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Substituents

6-oxopurine / Hypoxanthine / Aminopyrimidine / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amideAzacycle / Primary alcohol / Organooxygen compound / Organonitrogen compound / Organic nitrogen compound / Hydrocarbon derivative / Organic oxide / Organopnictogen compound / Organic oxygen compound / Amine / Alcohol / Primary amine / Aromatic heteropolycyclic compound

show 13 more

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

oxopurine, 2-aminopurines (CHEBI:2453)

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Drug created on June 13, 2005 07:24 / Updated on September 17, 2019 03:42