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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Acyclovir
- Accession Number
- DB00787 (APRD00567, EXPT00406, DB05347)
- Type
- Small Molecule
- Groups
- Approved
- Description
A guanosine analog antiviral drug that acts as an antimetabolite. Aciclovir is used for the treatment of herpes simplex virus infections, varicella zoster (chickenpox) and herpes zoster (shingles).
Aciclovir has also been investigated for the treatment of herpes labialis applied using an iontophoretic device. Currently approved drugs for the treatment of herpes labialis (cold sores) exhibit low levels of efficacy due to the limited ability of the drugs to penetrate the skin to the site where the herpes virus is replicating. Iontophoresis uses electric current to enhance the delivery of drugs through the skin.
- Structure
Structure for DB00787 (Acyclovir)
- Synonyms
- Aciclovir
- Aciclovirum
- Acycloguanosine
- External IDs
- NSC-645011
- Product Ingredients
Ingredient UNII CAS InChI Key Acyclovir sodium 927L42J563 69657-51-8 RMLUKZWYIKEASN-UHFFFAOYSA-M - Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Acyclovir Tablet 200 mg Oral Sanis Health Inc 2010-04-05 2014-08-01 Canada 
Acyclovir Tablet 400 mg Oral Sanis Health Inc 2010-04-05 Not applicable Canada Acyclovir Tablet 800 mg Oral Sanis Health Inc 2010-04-05 2014-08-01 Canada Acyclovir Sodium for Injection Powder, for solution 500 mg Intravenous Abbott 1998-02-11 2007-07-31 Canada Acyclovir Sodium for Injection Powder, for solution 500 mg Intravenous Novopharm Limited 1998-02-04 Not applicable Canada Acyclovir Sodium for Injection Powder, for solution 1 g Intravenous Novopharm Limited 1998-02-04 2005-08-10 Canada Acyclovir Sodium for Injection Powder, for solution 1 g Intravenous Abbott 1998-02-11 2007-07-31 Canada Acyclovir Sodium Injection Solution 25 mg Intravenous Pfizer 1998-03-18 Not applicable Canada Acyclovir Sodium Injection Solution 25 mg Intravenous Ivax Pharmaceuticals Incorporated Not applicable Not applicable Canada Acyclovir Sodium Injection Solution 50 mg Intravenous Fresenius Kabi 1998-05-08 Not applicable Canada - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Acyclovir Tablet 800 mg/1 Oral Amerincan Health Packaging 2014-01-29 Not applicable US 
Acyclovir Tablet 800 mg/1 Oral Ranbaxy Inc. 1999-02-08 Not applicable US Acyclovir Ointment 50 mg/g Topical North Star Rx Llc 2014-01-03 Not applicable US Acyclovir Tablet 800 mg/1 Oral Unit Dose Services 2009-10-22 Not applicable US Acyclovir Tablet 800 mg/1 Oral Av Kare, Inc. 1999-03-05 2018-03-08 US Acyclovir Capsule 200 mg/1 Oral Remedy Repack 2011-05-09 2016-10-13 US Acyclovir Tablet 400 mg/1 Oral Physicians Total Care, Inc. 1998-11-17 Not applicable US Acyclovir Tablet 400 mg/1 Oral DAVA Pharmaceuticals, Inc. 1997-11-19 2016-10-13 US Acyclovir Tablet 400 mg/1 Oral H.J. Harkins Company 2017-01-03 Not applicable US Acyclovir Capsule 200 mg/1 Oral Cadila Pharnmaceuticals 2016-05-03 Not applicable US - 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 Canada Xerese Acyclovir (50 mg/g) + Hydrocortisone (10 mg/g) Cream Topical Valeant Pharmaceuticals North America 2009-07-31 Not applicable US - International/Other Brands
- Zovir
- Categories
- Acyclovir-Valacyclovir
- Anti-Infective Agents
- Antiinfectives for Systemic Use
- Antiviral Agents
- Antivirals for Systemic Use
- Cytochrome P-450 CYP1A2 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Dermatologicals
- Direct Acting Antivirals
- Drugs for Obstructive Airway Diseases
- Guanine
- Herpes Simplex Virus Nucleoside Analog DNA Polymerase Inhibitor
- Herpes Zoster Virus Nucleoside Analog DNA Polymerase Inhibitor
- Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor
- MATE 1 Substrates
- MATE 2 Substrates
- MATE substrates
- Nucleosides and Nucleotides
- Nucleosides and Nucleotides Excl. Reverse Transcriptase Inhibitors
- OAT3 Inhibitors
- OAT3 Substrates
- Ophthalmologicals
- Purines
- Purinones
- Sensory Organs
- Xanthine derivatives
- 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
For the treatment and management of herpes zoster (shingles), genital herpes, and chickenpox.
- 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
- Severe Genital 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).
- Mechanism of action
Viral (HSV-1, HSV-2 and VZV) thymidine kinase converts aciclovir to the aciclovir monophosphate, which is then converted to the diphosphate by cellular guanylate kinase, and finally to the triphosphate by phosphoglycerate kinase, phosphoenolpyruvate carboxykinase, and pyruvate kinase. Aciclovir triphosphate competitively inhibits viral DNA polymerase and competes with the natural deoxyguanosine triphosphate, for incorporation into viral DNA. Once incorporated, aciclovir triphosphate inhibits DNA synthesis by acting as a chain terminator. One may consider aciclovir to be a prodrug as it is metabolized to more active compounds. Aciclovir is selective and low in cytotoxicity as the cellular thymidine kinase of normal, uninfected cells does not use aciclovir effectively as a substrate.
Target Actions Organism AThymidine kinase potentiatorHHV-1 ADNA polymerase catalytic subunit inhibitorHHV-1 ADNA polymerase catalytic subunit inhibitorHHV-3 - 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.
- Volume of distribution
- Not Available
- Protein binding
9%-33%
- 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.
- Route of elimination
Primarily excreted unchanged by the kidneys via active tubular secretion.
- Half life
2.5-3.3 hours
- Clearance
- Not Available
- Toxicity
Aciclovir 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.
- Affected organisms
- Human Herpes Virus
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Adalimumab The serum concentration of Acyclovir can be decreased when it is combined with Adalimumab. Approved Adenosine The therapeutic efficacy of Adenosine can be decreased when used in combination with Acyclovir. Approved, Investigational Benzphetamine The risk or severity of adverse effects can be increased when Benzphetamine is combined with Acyclovir. Approved, Illicit Carbamazepine The serum concentration of Acyclovir can be decreased when it is combined with Carbamazepine. Approved, Investigational Cimetidine The metabolism of Acyclovir can be decreased when combined with Cimetidine. Approved, Investigational Ciprofloxacin The serum concentration of Acyclovir can be increased when it is combined with Ciprofloxacin. Approved, Investigational Diethylpropion The risk or severity of adverse effects can be increased when Diethylpropion is combined with Acyclovir. Approved, Illicit Estradiol The excretion of Estradiol can be decreased when combined with Acyclovir. Approved, Investigational, Vet Approved Ethinyl Estradiol The serum concentration of Acyclovir can be increased when it is combined with Ethinyl Estradiol. Approved Ethosuximide Ethosuximide may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved Everolimus The metabolism of Acyclovir can be decreased when combined with Everolimus. Approved Flunarizine Flunarizine may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved Fluvoxamine The metabolism of Acyclovir can be decreased when combined with Fluvoxamine. Approved, Investigational Foscarnet Acyclovir may increase the nephrotoxic activities of Foscarnet. Approved Furosemide The excretion of Acyclovir can be decreased when combined with Furosemide. Approved, Vet Approved Gabapentin Gabapentin may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Investigational Interferon alfa-n3 The metabolism of Acyclovir can be decreased when combined with Interferon alfa-n3. Approved, Investigational Interferon beta-1a The metabolism of Acyclovir can be decreased when combined with Interferon beta-1a. Approved, Investigational Interferon gamma-1b The metabolism of Acyclovir can be decreased when combined with Interferon gamma-1b. Approved, Investigational Labetalol The risk or severity of adverse effects can be increased when Labetalol is combined with Acyclovir. Approved Lamotrigine Lamotrigine may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Investigational Levetiracetam Levetiracetam may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Investigational Magnesium sulfate Magnesium sulfate may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Investigational, Vet Approved Methimazole The serum concentration of Acyclovir can be increased when it is combined with Methimazole. Approved Methsuximide Methsuximide may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved Metoprolol The risk or severity of adverse effects can be increased when Metoprolol is combined with Acyclovir. Approved, Investigational Moxifloxacin The metabolism of Acyclovir can be decreased when combined with Moxifloxacin. Approved, Investigational Nylidrin The risk or severity of adverse effects can be increased when Nylidrin is combined with Acyclovir. Approved Nystatin The metabolism of Acyclovir can be decreased when combined with Nystatin. Approved, Vet Approved Oxymetazoline The risk or severity of adverse effects can be increased when Oxymetazoline is combined with Acyclovir. Approved, Investigational Peginterferon alfa-2a The metabolism of Acyclovir can be decreased when combined with Peginterferon alfa-2a. Approved, Investigational Peginterferon alfa-2b The metabolism of Acyclovir can be decreased when combined with Peginterferon alfa-2b. Approved Phenobarbital The serum concentration of Acyclovir can be decreased when it is combined with Phenobarbital. Approved, Investigational Phenylephrine The risk or severity of adverse effects can be increased when Phenylephrine is combined with Acyclovir. Approved Pregabalin Pregabalin may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Illicit, Investigational Propafenone The serum concentration of Acyclovir can be increased when it is combined with Propafenone. Approved Propranolol The risk or severity of adverse effects can be increased when Propranolol is combined with Acyclovir. Approved, Investigational Pseudoephedrine The risk or severity of adverse effects can be increased when Pseudoephedrine is combined with Acyclovir. Approved Tenofovir disoproxil Acyclovir may decrease the excretion rate of Tenofovir disoproxil which could result in a higher serum level. Approved, Investigational Teriflunomide The serum concentration of Acyclovir can be increased when it is combined with Teriflunomide. Approved Tetracycline The excretion of Acyclovir can be decreased when combined with Tetracycline. Approved, Vet Approved Tizanidine The serum concentration of Tizanidine can be increased when it is combined with Acyclovir. Approved, Investigational Topiramate Topiramate may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved Trimethadione Trimethadione may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved Valproic Acid Valproic Acid may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Investigational Varicella Zoster Vaccine (Live/Attenuated) The therapeutic efficacy of Varicella Zoster Vaccine (Live/Attenuated) can be decreased when used in combination with Acyclovir. Approved Vinpocetine Vinpocetine may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Investigational Zidovudine Acyclovir may increase the central nervous system depressant (CNS depressant) activities of Zidovudine. Approved Zonisamide Zonisamide may increase the excretion rate of Acyclovir which could result in a lower serum level and potentially a reduction in efficacy. Approved, Investigational - Food Interactions
- Increase liquid intake.
- Take without regard to meals.
References
- Synthesis Reference
- US4294831
- General References
- 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]
- 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]
- 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]
- 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
- S01AD03 — AciclovirD06BB03 — Aciclovir
- D06BB — Antivirals
- D06B — CHEMOTHERAPEUTICS FOR TOPICAL USE
- D06 — ANTIBIOTICS AND CHEMOTHERAPEUTICS FOR DERMATOLOGICAL USE
- D — DERMATOLOGICALS
- J05AB — Nucleosides and nucleotides excl. reverse transcriptase inhibitors
- J05A — DIRECT ACTING ANTIVIRALS
- J05 — ANTIVIRALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- 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
- Download (37 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Actavis elizabeth llc
- Apotex inc etobicoke site
- Belcher pharmaceuticals inc
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- Ivax pharmaceuticals inc sub teva pharmaceuticals usa
- Lek pharmaceutical and chemical co dd
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- Baxter healthcare corp anesthesia and critical care
- Apothecon inc div bristol myers squibb
- App pharmaceuticals llc
- Bedford laboratories div ben venue laboratories inc
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- Packagers
- Actavis Group
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- 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.
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- 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
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- 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/1 Injection, powder, lyophilized, for solution Intravenous 50 mg/mL Injection, powder, lyophilized, for solution Intravenous 500 mg/1 Injection, solution Intravenous 50 mg/mL Ointment Cutaneous 50 mg/g Ointment Topical 50 mg/g Tablet Oral 200 mg/1 Tablet Oral 400 mg/1 Injection, solution Intravenous 1000 mg/20mL Injection, solution Intravenous 500 mg/10mL Powder, for solution Intravenous 500 mg Solution Intravenous 25 mg Solution Intravenous 50 mg Tablet Oral 800 mg Tablet Oral 200 mg Tablet Oral 400 mg Tablet Buccal 50 mg Tablet, delayed release Buccal 50 mg/1 Cream Topical Cream Topical 5 % Cream Topical 50 mg/g Ointment Topical 5 % Powder, for solution Intravenous 1 g Suspension Oral 200 mg/5mL Suspension Oral 200 mg Tablet Oral 800 mg/1 Capsule Oral 200 mg - 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) CA2098108 No 2001-07-03 2012-01-29 Canada USRE39264 No 1996-08-02 2016-08-02 US US6514980 No 1999-01-24 2019-01-24 US US7223387 No 2001-07-24 2021-07-24 US US8747896 No 2007-06-03 2027-06-03 US US8791127 No 2007-03-23 2027-03-23 US US8592434 No 2010-06-16 2030-06-16 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 255 °C PhysProp water solubility 2.5 mg/mL at 37°C FDA label logP -1.56 KRISTL,A ET AL. (1993) Caco2 permeability -6.15 ADME Research, USCD pKa 2.27 and 9.25 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) 7.99 ChemAxon pKa (Strongest Basic) 2.63 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
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 compounds show 2 more
- Substituents
- 6-oxopurine / Hypoxanthine / Aminopyrimidine / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound / Vinylogous amide show 13 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- oxopurine, 2-aminopurines (CHEBI:2453)
Targets
- Kind
- Protein
- Organism
- HHV-1
- Pharmacological action
- Yes
- Actions
- Potentiator
- General Function
- Thymidine kinase activity
- Specific Function
- In latent infection, may allow the virus to be reactivated and to grow in cells lacking a high concentration of phosphorylated nucleic acid precursors, such as nerve cells that do not replicate the...
- Gene Name
- TK
- Uniprot ID
- P03176
- Uniprot Name
- Thymidine kinase
- Molecular Weight
- 40971.555 Da
References
- Bennett MS, Wien F, Champness JN, Batuwangala T, Rutherford T, Summers WC, Sun H, Wright G, Sanderson MR: Structure to 1.9 A resolution of a complex with herpes simplex virus type-1 thymidine kinase of a novel, non-substrate inhibitor: X-ray crystallographic comparison with binding of aciclovir. FEBS Lett. 1999 Jan 25;443(2):121-5. [PubMed:9989588]
- Kind
- Protein
- Organism
- HHV-1
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding pro...
- Gene Name
- Not Available
- Uniprot ID
- P04293
- Uniprot Name
- DNA polymerase catalytic subunit
- Molecular Weight
- 136419.66 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Sergerie Y, Boivin G: Hydroxyurea enhances the activity of acyclovir and cidofovir against herpes simplex virus type 1 resistant strains harboring mutations in the thymidine kinase and/or the DNA polymerase genes. Antiviral Res. 2008 Jan;77(1):77-80. Epub 2007 Sep 17. [PubMed:17913252]
- Suzuki M, Okuda T, Shiraki K: Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus. Antiviral Res. 2006 Nov;72(2):157-61. Epub 2006 May 30. [PubMed:16797734]
- Liu S, Knafels JD, Chang JS, Waszak GA, Baldwin ET, Deibel MR Jr, Thomsen DR, Homa FL, Wells PA, Tory MC, Poorman RA, Gao H, Qiu X, Seddon AP: Crystal structure of the herpes simplex virus 1 DNA polymerase. J Biol Chem. 2006 Jun 30;281(26):18193-200. Epub 2006 Apr 24. [PubMed:16638752]
- Kind
- Protein
- Organism
- HHV-3
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Rna-dna hybrid ribonuclease activity
- Specific Function
- Replicates viral genomic DNA. The replication complex is composed of six viral proteins: the DNA polymerase, processivity factor, primase, primase-associated factor, helicase, and ssDNA-binding pro...
- Gene Name
- Not Available
- Uniprot ID
- P09252
- Uniprot Name
- DNA polymerase catalytic subunit
- Molecular Weight
- 134046.615 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
- Sergerie Y, Boivin G: Hydroxyurea enhances the activity of acyclovir and cidofovir against herpes simplex virus type 1 resistant strains harboring mutations in the thymidine kinase and/or the DNA polymerase genes. Antiviral Res. 2008 Jan;77(1):77-80. Epub 2007 Sep 17. [PubMed:17913252]
- Suzuki M, Okuda T, Shiraki K: Synergistic antiviral activity of acyclovir and vidarabine against herpes simplex virus types 1 and 2 and varicella-zoster virus. Antiviral Res. 2006 Nov;72(2):157-61. Epub 2006 May 30. [PubMed:16797734]
- Liu S, Knafels JD, Chang JS, Waszak GA, Baldwin ET, Deibel MR Jr, Thomsen DR, Homa FL, Wells PA, Tory MC, Poorman RA, Gao H, Qiu X, Seddon AP: Crystal structure of the herpes simplex virus 1 DNA polymerase. J Biol Chem. 2006 Jun 30;281(26):18193-200. Epub 2006 Apr 24. [PubMed:16638752]
Enzymes
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
Transporters
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Secondary active organic cation transmembrane transporter activity
- Specific Function
- Translocates a broad array of organic cations with various structures and molecular weights including the model compounds 1-methyl-4-phenylpyridinium (MPP), tetraethylammonium (TEA), N-1-methylnico...
- Gene Name
- SLC22A1
- Uniprot ID
- O15245
- Uniprot Name
- Solute carrier family 22 member 1
- Molecular Weight
- 61153.345 Da
References
- Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
- Wada S, Tsuda M, Sekine T, Cha SH, Kimura M, Kanai Y, Endou H: Rat multispecific organic anion transporter 1 (rOAT1) transports zidovudine, acyclovir, and other antiviral nucleoside analogs. J Pharmacol Exp Ther. 2000 Sep;294(3):844-9. [PubMed:10945832]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
- Gene Name
- SLC22A8
- Uniprot ID
- Q8TCC7
- Uniprot Name
- Solute carrier family 22 member 8
- Molecular Weight
- 59855.585 Da
References
- Takeda M, Khamdang S, Narikawa S, Kimura H, Kobayashi Y, Yamamoto T, Cha SH, Sekine T, Endou H: Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24. [PubMed:11861798]
- Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [PubMed:12358729]
- Cha SH, Sekine T, Fukushima JI, Kanai Y, Kobayashi Y, Goya T, Endou H: Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. Mol Pharmacol. 2001 May;59(5):1277-86. [PubMed:11306713]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Bile acid:sodium symporter activity
- Specific Function
- Plays a critical role in the sodium-dependent reabsorption of bile acids from the lumen of the small intestine. Plays a key role in cholesterol metabolism.
- Gene Name
- SLC10A2
- Uniprot ID
- Q12908
- Uniprot Name
- Ileal sodium/bile acid cotransporter
- Molecular Weight
- 37713.405 Da
References
- Tolle-Sander S, Lentz KA, Maeda DY, Coop A, Polli JE: Increased acyclovir oral bioavailability via a bile acid conjugate. Mol Pharm. 2004 Jan 12;1(1):40-8. [PubMed:15832499]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Monovalent cation:proton antiporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide (NMN), metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfat...
- Gene Name
- SLC47A1
- Uniprot ID
- Q96FL8
- Uniprot Name
- Multidrug and toxin extrusion protein 1
- Molecular Weight
- 61921.585 Da
References
- Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [PubMed:22970772]
- Kind
- Protein
- Organism
- Human
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Drug transmembrane transporter activity
- Specific Function
- Solute transporter for tetraethylammonium (TEA), 1-methyl-4-phenylpyridinium (MPP), cimetidine, N-methylnicotinamide, metformin, creatinine, guanidine, procainamide, topotecan, estrone sulfate, acy...
- Gene Name
- SLC47A2
- Uniprot ID
- Q86VL8
- Uniprot Name
- Multidrug and toxin extrusion protein 2
- Molecular Weight
- 65083.915 Da
References
- Nies AT, Damme K, Schaeffeler E, Schwab M: Multidrug and toxin extrusion proteins as transporters of antimicrobial drugs. Expert Opin Drug Metab Toxicol. 2012 Dec;8(12):1565-77. doi: 10.1517/17425255.2012.722996. Epub 2012 Sep 13. [PubMed:22970772]
Drug created on June 13, 2005 07:24 / Updated on August 15, 2018 14:16