valaciclovir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
antivirals bicyclic heterocycle compounds 2798 124832-27-5

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • valacyclovir
  • valaciclovir
  • valcivir
  • valacyclovir hydrochloride
  • valacyclovir HCl
A prodrug of acyclovir that is used in the treatment of HERPES ZOSTER and HERPES SIMPLEX VIRUS INFECTION of the skin and mucous membranes, including GENITAL HERPES.
  • Molecular weight: 324.34
  • Formula: C13H20N6O4
  • CLOGP: -1.22
  • LIPINSKI: 0
  • HAC: 10
  • HDO: 3
  • TPSA: 146.85
  • ALOGS: -1.97
  • ROTB: 8

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
3 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 174 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0.50 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 154.16 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
June 23, 1995 FDA GLAXOSMITHKLINE

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Acute kidney injury 1460.27 41.81 399 2121 27723 2327842
Altered state of consciousness 1040.92 41.81 210 2310 3650 2351915
Blood creatinine increased 786.28 41.81 201 2319 10332 2345233
Dysarthria 706.60 41.81 167 2353 6135 2349430
Blood urea increased 695.84 41.81 149 2371 3456 2352109
Depressed level of consciousness 630.03 41.81 158 2362 7446 2348119
Encephalopathy 622.87 41.81 142 2378 4419 2351146
Nervous system disorder 408.46 41.81 94 2426 3022 2352543
Decreased appetite 403.77 41.81 153 2367 28738 2326827
Dizziness 384.23 41.81 181 2339 58484 2297081
Nausea 382.52 41.81 223 2297 111966 2243599
Toxic encephalopathy 363.85 41.81 68 2452 750 2354815
Vomiting 349.94 41.81 181 2339 71421 2284144
Renal impairment 328.53 41.81 101 2419 9991 2345574
Neurotoxicity 309.80 41.81 70 2450 2060 2353505
Delirium 307.63 41.81 83 2437 5140 2350425
Hallucination 296.97 41.81 89 2431 8059 2347506
Dyslalia 282.19 41.81 43 2477 110 2355455
Disorientation 277.80 41.81 80 2440 6292 2349273
Malaise 269.13 41.81 140 2380 55445 2300120
Confusional state 265.50 41.81 108 2412 24236 2331329
Renal disorder 239.33 41.81 66 2454 4422 2351143
Restlessness 238.24 41.81 66 2454 4497 2351068
Pyrexia 233.46 41.81 126 2394 53582 2301983
Speech disorder 228.39 41.81 69 2451 6395 2349170
Somnolence 228.19 41.81 96 2424 23389 2332176
Overdose 219.14 41.81 89 2431 19818 2335747
Gait disturbance 205.12 41.81 88 2432 22457 2333108
Urine output decreased 167.97 41.81 40 2480 1479 2354086
Renal failure 161.83 41.81 69 2451 17280 2338285
Headache 146.92 41.81 109 2411 80070 2275495
Hallucination, visual 145.78 41.81 41 2479 2938 2352627
Drug reaction with eosinophilia and systemic symptoms 132.80 41.81 44 2476 5474 2350091
Abnormal behaviour 130.92 41.81 42 2478 4718 2350847
Toxic skin eruption 128.50 41.81 35 2485 2225 2353340
Dehydration 121.16 41.81 61 2459 22234 2333331
Feeling abnormal 120.82 41.81 62 2458 23519 2332046
Asthenia 118.93 41.81 78 2442 46848 2308717
Toxicity to various agents 117.52 41.81 68 2452 32686 2322879
Herpes zoster 115.40 41.81 46 2474 9679 2345886
Psychiatric symptom 111.91 41.81 26 2494 860 2354705
Pancytopenia 111.46 41.81 47 2473 11405 2344160
C-reactive protein increased 104.52 41.81 38 2482 6217 2349348
Drug ineffective 104.39 41.81 99 2421 101525 2254040
Toxic epidermal necrolysis 99.96 41.81 31 2489 3113 2352452
Agranulocytosis 96.84 41.81 31 2489 3451 2352114
Dyskinesia 94.80 41.81 33 2487 4756 2350809
Neutropenia 94.23 41.81 51 2469 21497 2334068
Muscular weakness 93.48 41.81 45 2475 14852 2340713
Rash 93.40 41.81 74 2446 59484 2296081
Condition aggravated 92.88 41.81 58 2462 31921 2323644
Blood uric acid increased 92.03 41.81 21 2499 640 2354925
Hyponatraemia 92.02 41.81 43 2477 13282 2342283
Pruritus 85.93 41.81 62 2458 43278 2312287
Interstitial lung disease 85.89 41.81 35 2485 7777 2347788
Agitation 83.59 41.81 38 2482 11013 2344552
Oliguria 81.71 41.81 22 2498 1335 2354230
Loss of consciousness 80.85 41.81 44 2476 18723 2336842
Coordination abnormal 77.75 41.81 23 2497 1965 2353600
Lymphopenia 77.16 41.81 24 2496 2430 2353135
Hypophagia 76.99 41.81 27 2493 3973 2351592
Herpes virus infection 76.04 41.81 19 2501 857 2354708
Blood potassium increased 75.49 41.81 23 2497 2173 2353392
Diarrhoea 75.45 41.81 76 2444 83488 2272077
Urinary retention 75.39 41.81 26 2494 3641 2351924
Anuria 75.27 41.81 22 2498 1802 2353763
Exposure during pregnancy 68.79 41.81 44 2476 25175 2330390
Ataxia 68.50 41.81 22 2498 2470 2353095
Delusion 68.31 41.81 21 2499 2044 2353521
Herpes simplex 67.55 41.81 18 2502 1049 2354516
Product substitution issue 67.17 41.81 26 2494 5043 2350522
Dysstasia 64.94 41.81 22 2498 2917 2352648
Hepatic function abnormal 62.54 41.81 26 2494 6066 2349499
Abdominal pain 60.89 41.81 46 2474 34328 2321237
Incoherent 60.61 41.81 16 2504 899 2354666
Myoclonus 60.47 41.81 20 2500 2463 2353102
Cotard's syndrome 59.89 41.81 9 2511 20 2355545
Drug level increased 58.20 41.81 20 2500 2767 2352798
Eating disorder 58.07 41.81 19 2501 2262 2353303
Alanine aminotransferase increased 57.91 41.81 32 2488 14000 2341565
Seizure 57.72 41.81 39 2481 24427 2331138
Stevens-Johnson syndrome 56.97 41.81 22 2498 4237 2351328
Tremor 56.19 41.81 36 2484 20625 2334940
Aspartate aminotransferase increased 55.46 41.81 30 2490 12582 2342983
Hepatocellular injury 54.43 41.81 21 2499 4034 2351531
Thrombocytopenia 53.67 41.81 34 2486 19097 2336468
Cerebral thrombosis 52.18 41.81 12 2508 378 2355187
Hypoaesthesia 51.96 41.81 34 2486 20181 2335384
Dysuria 51.44 41.81 20 2500 3921 2351644
Drug eruption 51.43 41.81 19 2501 3240 2352325
Face oedema 51.41 41.81 20 2500 3928 2351637
Genital herpes 49.05 41.81 11 2509 309 2355256
Meningitis 48.85 41.81 14 2506 1068 2354497
Hepatitis 48.53 41.81 22 2498 6315 2349250
Liver disorder 48.28 41.81 22 2498 6392 2349173
Cerebral ventricle dilatation 48.27 41.81 10 2510 191 2355374
Skull malformation 47.67 41.81 9 2511 104 2355461
Erythema multiforme 46.94 41.81 16 2504 2159 2353406
Coma 46.79 41.81 24 2496 9032 2346533
Completed suicide 45.97 41.81 32 2488 21002 2334563
Spina bifida 45.81 41.81 9 2511 130 2355435
Dyspnoea 45.76 41.81 57 2463 78676 2276889
Abortion spontaneous 45.63 41.81 27 2493 13418 2342147
Hypoglycaemic seizure 45.49 41.81 9 2511 135 2355430
Haemodialysis 43.79 41.81 15 2505 2054 2353511
Hyperkalaemia 43.68 41.81 20 2500 5873 2349692
Erythema 43.02 41.81 33 2487 25126 2330439

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Dysarthria 580.68 53.61 140 1540 5119 1739982
Acute kidney injury 578.23 53.61 213 1467 34731 1710370
Encephalopathy 561.32 53.61 132 1548 4320 1740781
Altered state of consciousness 489.53 53.61 113 1567 3384 1741717
Depressed level of consciousness 353.14 53.61 99 1581 6493 1738608
Hallucination 349.71 53.61 103 1577 8067 1737034
Nervous system disorder 346.47 53.61 80 1600 2374 1742727
Overdose 288.51 53.61 106 1574 16595 1728506
Delirium 266.47 53.61 79 1601 6283 1738818
Gait disturbance 265.99 53.61 93 1587 12577 1732524
Blood creatinine increased 249.74 53.61 91 1589 13855 1731246
Neurotoxicity 248.58 53.61 59 1621 1965 1743136
Dyslalia 228.78 53.61 37 1643 138 1744963
Dizziness 223.79 53.61 109 1571 34252 1710849
Confusional state 215.75 53.61 92 1588 21186 1723915
Toxic encephalopathy 210.39 53.61 43 1637 699 1744402
Disorientation 190.47 53.61 59 1621 5410 1739691
Speech disorder 188.04 53.61 56 1624 4492 1740609
Renal impairment 178.68 53.61 69 1611 12245 1732856
Restlessness 177.72 53.61 53 1627 4268 1740833
Blood urea increased 177.48 53.61 54 1626 4657 1740444
Decreased appetite 134.81 53.61 69 1611 23802 1721299
Hallucination, visual 129.44 53.61 37 1643 2555 1742546
Vomiting 124.44 53.61 77 1603 38238 1706863
Psychiatric symptom 122.60 53.61 28 1652 778 1744323
Nausea 117.97 53.61 83 1597 51113 1693988
Pyrexia 115.71 53.61 79 1601 46321 1698780
Renal failure 104.62 53.61 55 1625 19962 1725139
Drug resistance 100.37 53.61 32 1648 3198 1741903
Thrombocytopenia 90.48 53.61 51 1629 21198 1723903
Somnolence 90.26 53.61 47 1633 16692 1728409
Renal disorder 89.10 53.61 31 1649 4055 1741046
Agranulocytosis 85.23 53.61 29 1651 3547 1741554
Dermatitis exfoliative generalised 84.60 53.61 18 1662 356 1744745
Abnormal behaviour 82.74 53.61 33 1647 6309 1738792
Herpes zoster 81.96 53.61 30 1650 4543 1740558
Drug reaction with eosinophilia and systemic symptoms 78.94 53.61 30 1650 5040 1740061
Pathogen resistance 74.86 53.61 20 1660 1069 1744032
Logorrhoea 74.22 53.61 17 1663 477 1744624
Alanine aminotransferase increased 70.50 53.61 36 1644 12242 1732859
Malaise 70.21 53.61 49 1631 29516 1715585
Demodicidosis 69.40 53.61 10 1670 12 1745089
Cholestasis 69.21 53.61 25 1655 3640 1741461
Urine output decreased 69.05 53.61 20 1660 1440 1743661
Anuria 68.19 53.61 21 1659 1867 1743234
Seizure 65.80 53.61 41 1639 20400 1724701
Agitation 65.24 53.61 33 1647 10993 1734108
C-reactive protein increased 64.37 53.61 27 1653 5858 1739243
Jaundice 63.59 53.61 27 1653 6035 1739066
Muscular weakness 61.58 53.61 31 1649 10218 1734883
Photosensitivity reaction 61.23 53.61 19 1661 1731 1743370
Polyneuropathy 61.18 53.61 19 1661 1736 1743365
Dyskinesia 60.87 53.61 23 1657 3796 1741305
Condition aggravated 59.57 53.61 39 1641 21111 1723990
Insomnia 58.37 53.61 35 1645 16241 1728860
Myoclonus 56.17 53.61 19 1661 2276 1742825
Aspartate aminotransferase increased 54.44 53.61 29 1651 10727 1734374
Status epilepticus 54.28 53.61 18 1662 2028 1743073

Pharmacologic Action:

SourceCodeDescription
ATC J05AB11 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Nucleosides and nucleotides excl. reverse transcriptase inhibitors
FDA MoA N0000020060 DNA Polymerase Inhibitors
FDA EPC N0000180187 Herpes Simplex Virus Nucleoside Analog DNA Polymerase Inhibitor
FDA EPC N0000180188 Herpes Zoster Virus Nucleoside Analog DNA Polymerase Inhibitor
FDA EPC N0000175468 Herpesvirus Nucleoside Analog DNA Polymerase Inhibitor
FDA EXT N0000175459 Nucleoside Analog
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000998 Antiviral Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Herpes labialis indication 1475003
Herpes zoster indication 4740000 DOID:8536
Genital herpes simplex indication 33839006 DOID:8704
Varicella indication 38907003 DOID:8659
Recurrent genital herpes simplex indication 402894005
Suppression of Recurrent Herpes Simplex Infection in HIV indication
Suppression of Recurrent Herpes Simplex Infection indication
Prevention of Cytomegalovirus Disease off-label use
Prevention of Herpes Zoster in Immunocompromised Patient off-label use
Dehydration contraindication 34095006
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Hemolytic uremic syndrome contraindication 111407006 DOID:12554
Impaired renal function disorder contraindication 197663003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.97 acidic
pKa2 7.83 Basic
pKa3 3.83 Basic
pKa4 2.12 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
DNA polymerase catalytic subunit Enzyme INHIBITOR WOMBAT-PK CHEMBL

External reference:

IDSource
D000077483 MESH_DESCRIPTOR_UI
4024006 VUID
N0000022011 NUI
C0249458 UMLSCUI
D08664 KEGG_DRUG
324820003 SNOMEDCT_US
4024006 VANDF
005049 NDDF
73645 RXNORM
d03838 MMSL
96098007 SNOMEDCT_US
CHEMBL1349 ChEMBL_ID
DB00577 DRUGBANK_ID
G447S0T1VC UNII
7106 INN_ID
124832-26-4 SECONDARY_CAS_RN
TXC PDB_CHEM_ID
135398742 PUBCHEM_CID
CHEMBL1201110 ChEMBL_ID
4824 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Valacyclovir Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-832 TABLET, FILM COATED 500 mg ORAL ANDA 18 sections
Valacyclovir Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 21695-965 TABLET, FILM COATED 1 g ORAL ANDA 18 sections
Valacyclovir Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 52959-303 TABLET, FILM COATED 1 g ORAL ANDA 18 sections
Valacyclovir Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-6089 TABLET, FILM COATED 1 g ORAL ANDA 18 sections
Valacyclovir Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 54868-6090 TABLET, FILM COATED 500 mg ORAL ANDA 18 sections
Valacyclovir Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 66116-482 TABLET, FILM COATED 1 g ORAL ANDA 18 sections
VALACYCLOVIR HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 75921-208 TABLET, COATED 500 mg ORAL ANDA 17 sections