Details of the Drug

General Information of Drug (ID: DMYLOVR)

Drug Name

Aciclovir

Synonyms

acyclovir; Acycloguanosine; 59277-89-3; Zovirax; Vipral; Virorax; Wellcome-248U; 9-[(2-Hydroxyethoxy)methyl]guanine; Aciclovirum; Zovir; Aciclovirum [Latin]; Sitavig; Aciclovier; Zyclir; 9-HYROXYETHOXYMETHYLGUANINE; Aciclovirum [INN-Latin]; 2-Amino-9-((2-hydroxyethoxy)methyl)-1H-purin-6(9H)-one; W-248-U; 9-(2-Hydroxyethoxy)methylguanine; Acyclovir-side chain-2-3H; ACYCLOVIR SODIUM; 9-((2-Hydroxyethoxy)methyl)guanine; Acicloftal; Cargosil; BW-248U; UNII-X4HES1O11F; DRG-0008; NSC 645011; CHEBI:2453; CCRIS 1953; Iontophoretic acyclovir

Indication

Disease Entry	ICD 11	Status	REF
Genital herpes	1A94	Approved	[1]
Herpes simplex encephalitis	N.A.	Approved	[2]
Herpes simplex infection	1F00	Approved	[3]
Herpes simplex labialis	1F00.01	Approved	[4]
Varicella	1E90	Approved	[5]
Virus infection	1A24-1D9Z	Approved	[6]
Herpes simplex virus infection	1F00	Phase 3	[7]
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Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

225.2

Logarithm of the Partition Coefficient (xlogp)

-1.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1-2 h [8]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 4: low solubility and low permeability [9]
Bioavailability: The bioavailability of drug is 100% [8]
Clearance: The drug present in the plasma can be removed from the body at the rate of 4.7 mL/min/kg [10]
Elimination: 90-92% of the drug can be excreted unchanged through glomerular filtration and tubular secretion [11]
Half-life: The concentration or amount of drug in body reduced by one-half in 2.5 - 3 hours [11]
Metabolism: The drug is metabolized via the alcohol dehydrogenase and aldehyde dehydrogenase [12]
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 59.05637 micromolar/kg/day [13]
Unbound Fraction: The unbound fraction of drug in plasma is 0.85% [10]
Vd: The volume of distribution (Vd) of drug is 0.6 L/kg [14]
Water Solubility: The ability of drug to dissolve in water is measured as 2.5 mg/mL [9]

Adverse Drug Reaction (ADR)

ADR Term	Variation	Related DOT	DOT ID	REF
Neurological symptom	Not Available	MBP	OTFZCEDB	[15]
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Chemical Identifiers

Formula: C8H11N5O3
IUPAC Name: 2-amino-9-(2-hydroxyethoxymethyl)-1H-purin-6-one
Canonical SMILES: C1=NC2=C(N1COCCO)N=C(NC2=O)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)
InChIKey: MKUXAQIIEYXACX-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 135398513
ChEBI ID: CHEBI:2453
CAS Number: 59277-89-3
TTD ID: D0B5MP
VARIDT ID: DR00325
ACDINA ID: D00013

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Herpes simplex virus DNA polymerase UL30 (HSV UL30)	TTIU7X1	DPOL_HHV11	Modulator	[16]
Varicella-zoster virus DNA polymerase (VZV ORF28)	TTHPJTK	DPOL_VZVD	Modulator	[17]

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Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Alanine/serine/cysteine/threonine transporter 2 (SLC1A5)	DTW7AE3	AAAT_HUMAN	Substrate	[18]
Organic anion transporter 2 (SLC22A7)	DT0OC1Q	S22A7_HUMAN	Substrate	[19]
Multidrug resistance-associated protein 2 (ABCC2)	DTFI42L	MRP2_HUMAN	Substrate	[20]
Organic cation transporter 1 (SLC22A1)	DTT79CX	S22A1_HUMAN	Substrate	[21]
Multidrug and toxin extrusion protein 2 (SLC47A2)	DT3TX4H	S47A2_HUMAN	Substrate	[22]
Multidrug and toxin extrusion protein 1 (SLC47A1)	DTZGT0P	S47A1_HUMAN	Substrate	[22]
Breast cancer resistance protein (ABCG2)	DTI7UX6	ABCG2_HUMAN	Substrate	[23]
Organic anion transporter 1 (SLC22A6)	DTQ23VB	S22A6_HUMAN	Substrate	[21]
Organic anion transporter 3 (SLC22A8)	DTVP67E	S22A8_HUMAN	Substrate	[24]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
3-hydroxyanthranilate 3,4-dioxygenase (HAAO)	OTK9Y6SG	3HAO_HUMAN	Gene/Protein Processing	[25]
Antileukoproteinase (SLPI)	OTUNFUU8	SLPI_HUMAN	Gene/Protein Processing	[26]
Broad substrate specificity ATP-binding cassette transporter ABCG2 (ABCG2)	OTW8V2V1	ABCG2_HUMAN	Regulation of Drug Effects	[27]
Cystine/glutamate transporter (SLC7A11)	OTKJ6PXW	XCT_HUMAN	Gene/Protein Processing	[26]
Indoleamine 2,3-dioxygenase 1 (IDO1)	OT91DBN7	I23O1_HUMAN	Gene/Protein Processing	[25]
Interleukin-1 alpha (IL1A)	OTPSGILV	IL1A_HUMAN	Gene/Protein Processing	[26]
Interleukin-1 beta (IL1B)	OT0DWXXB	IL1B_HUMAN	Gene/Protein Processing	[26]
Interleukin-24 (IL24)	OT4VUWH1	IL24_HUMAN	Gene/Protein Processing	[26]
Interleukin-8 (CXCL8)	OTS7T5VH	IL8_HUMAN	Gene/Protein Processing	[26]
Major histocompatibility complex class I-related gene protein (MR1)	OTZU3XX7	HMR1_HUMAN	Gene/Protein Processing	[28]

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Molecular Interaction Atlas (MIA)

MIA Detail

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Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Aciclovir (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Decreased renal excretion of Aciclovir caused by Remdesivir mediated nephrotoxicity.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[29]
Inotersen	DMJ93CT	Major	Increased risk of nephrotoxicity by the combination of Aciclovir and Inotersen.	Amyloidosis [5D00]	[30]
Iodipamide	DMXIQYS	Major	Increased risk of nephrotoxicity by the combination of Aciclovir and Iodipamide.	Cholelithiasis [DC11]	[31]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Aciclovir and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[29]
Balsalazide	DM7I1T9	Moderate	Increased risk of nephrotoxicity by the combination of Aciclovir and Balsalazide.	Indeterminate colitis [DD72]	[32]
Ramelteon	DM7IW9J	Moderate	Decreased metabolism of Aciclovir caused by Ramelteon mediated inhibition of CYP450 enzyme.	Insomnia [7A00-7A0Z]	[33]
Everolimus	DM8X2EH	Major	Increased risk of nephrotoxicity by the combination of Aciclovir and Everolimus.	Renal cell carcinoma [2C90]	[34]
Temsirolimus	DMS104F	Major	Increased risk of nephrotoxicity by the combination of Aciclovir and Temsirolimus.	Renal cell carcinoma [2C90]	[34]
Sulfasalazine	DMICA9H	Moderate	Increased risk of nephrotoxicity by the combination of Aciclovir and Sulfasalazine.	Rheumatoid arthritis [FA20]	[32]
Ifosfamide	DMCT3I8	Moderate	Increased risk of nephrotoxicity by the combination of Aciclovir and Ifosfamide.	Solid tumour/cancer [2A00-2F9Z]	[29]
Sirolimus	DMGW1ID	Major	Increased risk of nephrotoxicity by the combination of Aciclovir and Sirolimus.	Transplant rejection [NE84]	[34]
Tacrolimus	DMZ7XNQ	Major	Increased risk of nephrotoxicity by the combination of Aciclovir and Tacrolimus.	Transplant rejection [NE84]	[34]
Olsalazine	DMZW9HA	Moderate	Increased risk of nephrotoxicity by the combination of Aciclovir and Olsalazine.	Ulcerative colitis [DD71]	[32]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Aciclovir and Plazomicin.	Urinary tract infection [GC08]	[29]
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Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Allura red AC dye	E00338	33258	Colorant
D&C red no. 28	E00491	6097185	Colorant
D&C red no. 33	E00261	19116	Colorant
FD&C blue no. 1	E00263	19700	Colorant
FD&C blue no. 2	E00446	2723854	Colorant
Isopropyl alcohol	E00070	3776	Antimicrobial preservative; Solvent
Quinoline yellow WS	E00309	24671	Colorant
Sodium lauryl sulfate	E00464	3423265	Emulsifying agent; Modified-release agent; Penetration agent; Solubilizing agent; Surfactant; lubricant
Ammonia	E00007	222	Alkalizing agent
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Butyl alcohol	E00011	263	Flavoring agent; Solvent
Carmellose sodium	E00625	Not Available	Disintegrant
Eisenoxyd	E00585	56841934	Colorant
FD&C red no. 3	E00629	Not Available	Colorant
Ferrosoferric oxide	E00231	14789	Colorant
Ferrous oxide	E00241	14945	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Potassium hydroxide	E00233	14797	Alkalizing agent
Povidone	E00667	Not Available	Binding agent; Coating agent; Disintegrant; Film/membrane-forming agent; Solubilizing agent; Suspending agent
Propylene glycol	E00040	1030	Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Silicon dioxide	E00670	Not Available	Anticaking agent; Opacifying agent; Viscosity-controlling agent
Talc	E00520	16211421	Anticaking agent; Diluent; Glidant; lubricant
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
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Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Acyclovir 200 mg capsule	200 mg	Oral Capsule	Oral
Acyclovir 50 mg tablet	50 mg	Buccal Tablet	Oral
Acyclovir 200 mg tablet	200 mg	Oral Tablet	Oral
Acyclovir 400 mg tablet	400 mg	Oral Tablet	Oral
Acyclovir 800 mg tablet	800 mg	Oral Tablet	Oral

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References

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2	Management of suspected viral encephalitis in adults--Association of British Neurologists and British Infection Association National Guidelines. J Infect. 2012 Apr;64(4):347-73.
3	Prevention and management of genital herpes simplex infection during pregnancy and delivery: Guidelines from the French College of Gynaecologists and Obstetricians (CNGOF). Eur J Obstet Gynecol Reprod Biol. 2018 May;224:93-101.
4	Interventions for prevention of herpes simplex labialis (cold sores on the lips). Cochrane Database Syst Rev. 2015 Aug 7;2015(8):CD010095.
5	Neonatal varicella. Arch Dis Child. 2023 Oct 31:archdischild-2022-324820.
6	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 4829).
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8	FDA Approved Drug Products: Zyvox (linezolid) for intravenous or oral administration
9	BDDCS applied to over 900 drugs
10	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
11	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.
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13	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
14	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.
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21	Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24.
22	Substrate specificity of MATE1 and MATE2-K, human multidrug and toxin extrusions/H(+)-organic cation antiporters. Biochem Pharmacol. 2007 Jul 15;74(2):359-71.
23	Acyclovir is a substrate for the human breast cancer resistance protein (BCRP/ABCG2): implications for renal tubular transport and acyclovir-induced nephrotoxicity. Can J Physiol Pharmacol. 2011 Sep;89(9):675-80.
24	Expression of organic anion transporter 2 in the human kidney and its potential role in the tubular secretion of guanine-containing antiviral drugs. Drug Metab Dispos. 2012 Mar;40(3):617-24.
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26	An in vitro coculture system of human peripheral blood mononuclear cells with hepatocellular carcinoma-derived cells for predicting drug-induced liver injury. Arch Toxicol. 2021 Jan;95(1):149-168. doi: 10.1007/s00204-020-02882-4. Epub 2020 Aug 20.
27	Acyclovir is a substrate for the human breast cancer resistance protein (BCRP/ABCG2): implications for renal tubular transport and acyclovir-induced nephrotoxicity. Can J Physiol Pharmacol. 2011 Sep;89(9):675-80. doi: 10.1139/y11-045. Epub 2011 Aug 22.
28	Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis. Chem Res Toxicol. 2015 May 18;28(5):927-34. doi: 10.1021/tx5005248. Epub 2015 Apr 3.
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30	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
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33	Product Information. Rozerem (ramelteon). Takeda Pharmaceuticals America, Lincolnshire, IL.
34	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.