Details of the Drug

General Information of Drug (ID: DMHKS94)

Drug Name

Valaciclovir

Synonyms

Talavir; VACV; ValACV; Valacyclovir; Virval; Zelitrex; Valaciclovir Hcl; Valacyclover Hydrochloric; Valacyclover Hydrochloride; BW256U87; TBB067866; Acyclovir-valine; BW-256U; Valaciclovir (INN); Valaciclovir [INN:BAN]; Valaciclovir, Valtrex; Valtrex (TN); Zelitrex (TN); Valacyclovir, (L)-isomer; L-Valine ester with 9-((2-hydroxyethoxy)methyl)guanine; L-Valine, 2-((2-amino-1,6-dihydro-6-oxo-9H-purin-9-yl)methoxy)ethyl ester; L-valine, 2-[(2-amino-1,6-dihydro-6-oxo-9 H-purin-9-yl)methoxy]ethyl ester, monohydrochloride; 2-[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methoxy]ethyl L-valinate; 2-[(2-amino-6-oxo-3H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate; 2-{[(2-amino-6-oxo-1,6-dihydro-9H-purin-9-yl)methyl]oxy}ethyl L-valinate

Indication

Disease Entry	ICD 11	Status	REF
Genital herpes	1A94	Approved	[1]
Herpes simplex labialis	1F00.01	Approved	[2]
Varicella	1E90	Approved	[3]
Virus infection	1A24-1D9Z	Approved	[4]
------------------------------------------------------------------------------------

Therapeutic Class

Antiviral Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

324.34

Logarithm of the Partition Coefficient (xlogp)

-0.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption Cmax: The maximum plasma concentration (Cmax) of drug is 47 mcg/L [5]
Absorption Tmax: The time to maximum plasma concentration (Tmax) is 1.5 h [5]
BDDCS Class: Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability [6]
Bioavailability: The bioavailability of drug is 91% [5]
Clearance: The renal clearance of drug is 255 +/- 86 mL/min []
Elimination: After oral administration of a single 1 gram dose of radiolabeled valacyclovir to 4 healthy subjects, 46% and 47% of administered radioactivity was measured in urine and feces, respectively, over 96 hours []
Half-life: The concentration or amount of drug in body reduced by one-half in 2.5 - 3.3 hours []
Metabolism: The drug is metabolized via the first-pass intestinal and/or hepatic metabolism []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 154.15819 micromolar/kg/day [7]
Vd: The volume of distribution (Vd) of drug is 1.34 +/- 0.65 L/kg []
Water Solubility: The ability of drug to dissolve in water is measured as 174 mg/mL [6]

Chemical Identifiers

Formula: C13H20N6O4
IUPAC Name: 2-[(2-amino-6-oxo-1H-purin-9-yl)methoxy]ethyl (2S)-2-amino-3-methylbutanoate
Canonical SMILES: CC(C)[C@@H](C(=O)OCCOCN1C=NC2=C1N=C(NC2=O)N)N
InChI: InChI=1S/C13H20N6O4/c1-7(2)8(14)12(21)23-4-3-22-6-19-5-16-9-10(19)17-13(15)18-11(9)20/h5,7-8H,3-4,6,14H2,1-2H3,(H3,15,17,18,20)/t8-/m0/s1
InChIKey: HDOVUKNUBWVHOX-QMMMGPOBSA-N

Cross-matching ID

PubChem CID: 135398742
ChEBI ID: CHEBI:35854
CAS Number: 124832-26-4
DrugBank ID: DB00577
TTD ID: D04QJD
VARIDT ID: DR00078
ACDINA ID: D00714

Combinatorial Drugs (CBD)

Click to Jump to the Detailed CBD Information of This Drug

Repurposed Drugs (RPD)

Click to Jump to the Detailed RPD Information of This Drug

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	Inhibitor	[8]

------------------------------------------------------------------------------------

Drug Transporter (DTP)

DTP Name	DTP ID	UniProt ID	MOA	REF
Alanine/serine/cysteine/threonine transporter 2 (SLC1A5)	DTW7AE3	AAAT_HUMAN	Substrate	[9]
Peptide transporter 2 (SLC15A2)	DT8QKNP	S15A2_HUMAN	Substrate	[10]
Peptide transporter 1 (SLC15A1)	DT9G7XN	S15A1_HUMAN	Substrate	[10]
Organic anion transporter 3 (SLC22A8)	DTVP67E	S22A8_HUMAN	Substrate	[11]

------------------------------------------------------------------------------------

Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cytochrome P450 1A1 (CYP1A1)	OTE4EFH8	CP1A1_HUMAN	Gene/Protein Processing	[12]
Cytochrome P450 1B1 (CYP1B1)	OTYXFLSD	CP1B1_HUMAN	Gene/Protein Processing	[12]

------------------------------------------------------------------------------------

Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

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

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Remdesivir	DMBFZ6L	Moderate	Decreased renal excretion of Valaciclovir caused by Remdesivir mediated nephrotoxicity.	1D6YCoronavirus Disease 2019 [1D6YCoronavirus Disease 2019]	[13]
Framycetin	DMF8DNE	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Framycetin.	Alcoholic liver disease [DB94]	[13]
Paromomycin	DM1AGXN	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Paromomycin.	Amoebiasis [1A36]	[13]
Inotersen	DMJ93CT	Major	Increased risk of nephrotoxicity by the combination of Valaciclovir and Inotersen.	Amyloidosis [5D00]	[13]
Streptomycin	DME1LQN	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Streptomycin.	Bacterial infection [1A00-1C4Z]	[13]
Gentamicin	DMKINJO	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Gentamicin.	Bacterial infection [1A00-1C4Z]	[13]
Netilmicin	DMRD1QK	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Netilmicin.	Bacterial infection [1A00-1C4Z]	[13]
Tobramycin	DMUI0CH	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Tobramycin.	Bacterial infection [1A00-1C4Z]	[13]
Iodipamide	DMXIQYS	Major	Increased risk of nephrotoxicity by the combination of Valaciclovir and Iodipamide.	Cholelithiasis [DC11]	[14]
Pentamidine	DMHZJCG	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Pentamidine.	Fungal infection [1F29-1F2F]	[13]
Givosiran	DM5PFIJ	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Givosiran.	Inborn porphyrin/heme metabolism error [5C58]	[13]
Probenecid	DMMFWOJ	Minor	Decreased elimination of Valaciclovir caused by Probenecid mediated competitive inhibition of renal tubular secretion.	Inborn purine/pyrimidine/nucleotide metabolism error [5C55]	[15]
Balsalazide	DM7I1T9	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Balsalazide.	Indeterminate colitis [DD72]	[16]
Clofarabine	DMCVJ86	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Clofarabine.	Mature B-cell lymphoma [2A85]	[17]
Carboplatin	DMG281S	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Carboplatin.	Ovarian cancer [2C73]	[13]
Everolimus	DM8X2EH	Major	Increased risk of nephrotoxicity by the combination of Valaciclovir and Everolimus.	Renal cell carcinoma [2C90]	[18]
Temsirolimus	DMS104F	Major	Increased risk of nephrotoxicity by the combination of Valaciclovir and Temsirolimus.	Renal cell carcinoma [2C90]	[18]
Sulfasalazine	DMICA9H	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Sulfasalazine.	Rheumatoid arthritis [FA20]	[16]
Sirolimus	DMGW1ID	Major	Increased risk of nephrotoxicity by the combination of Valaciclovir and Sirolimus.	Transplant rejection [NE84]	[18]
Tacrolimus	DMZ7XNQ	Major	Increased risk of nephrotoxicity by the combination of Valaciclovir and Tacrolimus.	Transplant rejection [NE84]	[18]
Olsalazine	DMZW9HA	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Olsalazine.	Ulcerative colitis [DD71]	[16]
Plazomicin	DMKMBES	Moderate	Increased risk of nephrotoxicity by the combination of Valaciclovir and Plazomicin.	Urinary tract infection [GC08]	[13]
-----------


⏷ Show the Full List of 22 DDI Information of This Drug

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
FD&C blue no. 2	E00446	2723854	Colorant
Sodium stearyl fumarate	E00545	23665634	lubricant
Ammonia	E00007	222	Alkalizing agent
Carmellose sodium	E00625	Not Available	Disintegrant
Crospovidone	E00626	Not Available	Disintegrant
Ferrosoferric oxide	E00231	14789	Colorant
Lactose monohydrate	E00393	104938	Binding agent; Diluent; Dry powder inhaler carrier; Lyophilization aid
Magnesium stearate	E00208	11177	lubricant
Polyethylene glycol 400	E00653	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polyethylene glycol 6000	E00655	Not Available	Coating agent; Diluent; Ointment base; Plasticizing agent; Solvent; Suppository base; lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending 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
--------------------


⏷ Show the Full List of 16 Pharmaceutical Excipients of This Drug

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Valacyclovir 1000 mg tablet	1000 mg	Oral Tablet	Oral
Valacyclovir 500 mg tablet	500 mg	Oral Tablet	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1	Interventions for men and women with their first episode of genital herpes. Cochrane Database Syst Rev. 2016 Aug 30;2016(8):CD010684.
2	Interventions for prevention of herpes simplex labialis (cold sores on the lips). Cochrane Database Syst Rev. 2015 Aug 7;2015(8):CD010095.
3	Chickenpox. BMJ Clin Evid. 2011 Apr 11;2011:0912.
4	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: 4824).
5	Bayer Inc: VISANNE (2mg dienogest tablets) Product Monograph
6	BDDCS applied to over 900 drugs
7	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
8	Extensive oral shedding of human herpesvirus 8 in a renal allograft recipient. Oral Microbiol Immunol. 2009 Apr;24(2):109-15.
9	Transport of amino acid-based prodrugs by the Na+- and Cl(-) -coupled amino acid transporter ATB0,+ and expression of the transporter in tissues amenable for drug delivery. J Pharmacol Exp Ther. 2004 Mar;308(3):1138-47.
10	Valacyclovir: a substrate for the intestinal and renal peptide transporters PEPT1 and PEPT2. Biochem Biophys Res Commun. 1998 May 19;246(2):470-5.
11	Human organic anion transporters and human organic cation transporters mediate renal antiviral transport. J Pharmacol Exp Ther. 2002 Mar;300(3):918-24.
12	Association of CYP1A1 and CYP1B1 inhibition in in vitro assays with drug-induced liver injury. J Toxicol Sci. 2021;46(4):167-176. doi: 10.2131/jts.46.167.
13	Cerner Multum, Inc. "UK Summary of Product Characteristics.".
14	Bentley ML, Corwin HL, Dasta J "Drug-induced acute kidney injury in the critically ill adult: recognition and prevention strategies." Crit Care Med 38(6 Suppl) (2010): S169-74. [PMID: 20502171]
15	Laskin OL, de Miranda P, King DH, et al "Effects of probenecid on the pharmacokinetics and elimination of acyclovir in humans." Antimicrob Agents Chemother 21 (1982): 804-7. [PMID: 7103460]
16	Product Information. Canasa (mesalamine (5-aminosalicylic acid)). Axcan Scandipharm Inc, Birmingham, AL.
17	Product Information. Clolar (clofarabine). sanofi-aventis, Bridgewater, NJ.
18	Product Information. Prograf (tacrolimus). Fujisawa, Deerfield, IL.