oseltamivir Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
antivirals neuraminidase inhibitors 2001 196618-13-0

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ebilfumin
  • oseltamivir
  • tamvir
  • tamiflu
  • oseltamivir phosphate
Oseltamivir phosphate is an ethyl ester prodrug requiring ester hydrolysis for conversion to the active form, oseltamivir carboxylate. Oseltamivir carboxylate is an inhibitor of influenza virus neuraminidase affecting release of viral particles. The median IC50 values of oseltamivir against influenza A/H1N1, influenza A/H3N2, and influenza B clinical isolates were 2.5 nM (range 0.93-4.16 nM, N=74), 0.96 nM (range 0.13 - 7.95 nM, N=774), and 60 nM (20-285 nM, N=256), respectively, in a neuraminidase assay with a fluorescently labeled MUNANA substrate.
  • Molecular weight: 312.41
  • Formula: C16H28N2O4
  • CLOGP: 2.13
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 90.65
  • ALOGS: -2.66
  • ROTB: 8

Drug dosage:

DoseUnitRoute
0.15 g O

Approvals:

DateAgencyCompanyOrphan
Oct. 27, 1999 FDA ROCHE

FDA Adverse Event Reporting System

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
Abnormal behaviour 2912.25 41.42 650 6371 11406 4620565
No adverse event 2741.57 41.42 695 6326 21468 4610503
Exposure during pregnancy 2132.48 41.42 621 6400 32350 4599621
Normal newborn 1836.72 41.42 324 6697 1458 4630513
Hallucination 1040.16 41.42 311 6710 17357 4614614
Pregnancy 1024.99 41.42 265 6756 8579 4623392
Delirium 598.45 41.42 189 6832 12563 4619408
Vomiting 570.92 41.42 352 6669 119347 4512624
Seizure 436.99 41.42 220 6801 50017 4581954
Overdose 433.12 41.42 209 6812 43350 4588621
Pathogen resistance 402.48 41.42 100 6921 2716 4629255
Influenza 390.27 41.42 156 6865 20567 4611404
Pneumonia 289.28 41.42 219 6802 102596 4529375
Respiratory failure 231.77 41.42 122 6899 30204 4601767
Loss of consciousness 223.99 41.42 126 6895 35556 4596415
Foetal exposure during pregnancy 214.16 41.42 106 6915 23063 4608908
Accidental overdose 203.28 41.42 78 6943 9177 4622794
Confusional state 197.20 41.42 130 6891 48704 4583267
Acute respiratory distress syndrome 196.62 41.42 72 6949 7441 4624530
Depressed level of consciousness 194.51 41.42 87 6934 15067 4616904
Hallucination, visual 186.30 41.42 65 6956 5837 4626134
Agitation 178.13 41.42 95 6926 24105 4607866
Maternal exposure during pregnancy 172.26 41.42 83 6938 17010 4614961
Caesarean section 168.06 41.42 58 6963 5040 4626931
Rash 158.01 41.42 159 6862 108229 4523742
Pyrexia 157.70 41.42 158 6863 106986 4524985
Hypothermia 157.30 41.42 53 6968 4281 4627690
Enterocolitis haemorrhagic 156.78 41.42 36 6985 688 4631283
Incorrect dose administered 156.57 41.42 81 6940 19304 4612667
Acute kidney injury 142.34 41.42 124 6897 70307 4561664
Nausea 138.95 41.42 189 6832 177144 4454827
International normalised ratio increased 134.33 41.42 70 6951 16918 4615053
Drug ineffective 133.38 41.42 190 6831 185871 4446100
Nightmare 131.86 41.42 53 6968 7037 4624934
Hallucination, auditory 131.60 41.42 47 6974 4514 4627457
Medication error 124.37 41.42 63 6958 14353 4617618
Encephalopathy 123.82 41.42 56 6965 9931 4622040
Altered state of consciousness 119.22 41.42 51 6970 7920 4624051
Restlessness 113.93 41.42 52 6969 9417 4622554
Diarrhoea 112.84 41.42 157 6864 150028 4481943
Delusion 112.54 41.42 42 6979 4568 4627403
Pneumonia influenzal 110.53 41.42 24 6997 351 4631620
Maternal exposure timing unspecified 110.40 41.42 27 6994 682 4631289
Urticaria 107.85 41.42 83 6938 39490 4592481
Hepatic function abnormal 101.44 41.42 55 6966 14381 4617590
H1N1 influenza 96.69 41.42 23 6998 515 4631456
Multiple organ dysfunction syndrome 90.59 41.42 56 6965 18700 4613271
Crying 90.12 41.42 39 6982 6224 4625747
Liver disorder 89.52 41.42 49 6972 13049 4618922
Product administration error 88.79 41.42 42 6979 8242 4623729
Hepatitis fulminant 86.30 41.42 26 6995 1459 4630512
Disorientation 86.23 41.42 47 6974 12412 4619559
Aggression 84.10 41.42 48 6973 13851 4618120
Hypoxia 83.95 41.42 47 6974 13074 4618897
Rhabdomyolysis 83.47 41.42 54 6967 19504 4612467
Mental disorder 80.13 41.42 38 6983 7496 4624475
Sudden death 79.19 41.42 34 6987 5321 4626650
Cardio-respiratory arrest 77.94 41.42 52 6969 19770 4612201
Sleep terror 75.60 41.42 19 7002 538 4631433
Live birth 73.28 41.42 23 6998 1480 4630491
Stevens-Johnson syndrome 72.28 41.42 37 6984 8602 4623369
Respiratory distress 71.60 41.42 40 6981 11076 4620895
Shock 71.17 41.42 37 6984 8879 4623092
Tremor 69.40 41.42 62 6959 36197 4595774
Anxiety 68.89 41.42 70 6951 47941 4584030
Dehydration 68.73 41.42 66 6955 42224 4589747
Hepatitis 68.12 41.42 40 6981 12165 4619806
Dyspnoea 67.45 41.42 119 6902 138866 4493105
Abdominal pain 65.94 41.42 76 6945 59948 4572023
Abortion spontaneous 65.05 41.42 41 6980 14151 4617820
Premature labour 63.38 41.42 23 6998 2309 4629662
Cardiac failure acute 61.83 41.42 23 6998 2476 4629495
Screaming 60.94 41.42 19 7002 1196 4630775
Cholestasis 60.74 41.42 32 6989 7888 4624083
Psychiatric symptom 60.72 41.42 21 7000 1832 4630139
Thrombocytopenia 60.32 41.42 65 6956 47608 4584363
Blood creatine phosphokinase increased 60.29 41.42 40 6981 15059 4616912
Erythema multiforme 59.77 41.42 26 6995 4197 4627774
Disseminated intravascular coagulation 59.61 41.42 31 6990 7442 4624529
Platelet count decreased 59.47 41.42 56 6965 34946 4597025
Insomnia 59.44 41.42 63 6958 45282 4586689
White blood cell count decreased 58.29 41.42 54 6967 33011 4598960
Melaena 56.52 41.42 33 6988 9925 4622046
Premature baby 56.24 41.42 33 6988 10018 4621953
Influenza A virus test positive 55.15 41.42 11 7010 103 4631868
Foetal death 54.16 41.42 21 7000 2531 4629440
Purpura senile 53.93 41.42 9 7012 26 4631945
Suicidal ideation 53.82 41.42 43 6978 21540 4610431
Fear 53.72 41.42 24 6997 4128 4627843
Premature delivery 53.54 41.42 24 6997 4160 4627811
Colitis ischaemic 52.75 41.42 21 7000 2714 4629257
Delirium febrile 52.51 41.42 9 7012 32 4631939
Lymphocyte stimulation test positive 52.05 41.42 14 7007 520 4631451
Pneumonia bacterial 51.74 41.42 20 7001 2390 4629581
Drug resistance 51.63 41.42 29 6992 8107 4623864
Amnesia 51.02 41.42 34 6987 12887 4619084
Foetal growth restriction 50.53 41.42 20 7001 2546 4629425
Speech disorder 49.49 41.42 32 6989 11530 4620441
Toxic epidermal necrolysis 47.43 41.42 25 6996 6167 4625804
Encephalitis 46.78 41.42 19 7002 2586 4629385
Decreased appetite 46.74 41.42 62 6959 56335 4575636
Pyloric stenosis 46.27 41.42 12 7009 386 4631585
Ventricular septal defect 44.98 41.42 18 7003 2357 4629614
Malaise 44.68 41.42 78 6943 90079 4541892
Stillbirth 44.26 41.42 17 7004 1997 4629974
Erythema 44.17 41.42 52 6969 41888 4590083
Headache 43.59 41.42 92 6929 122281 4509690
Tarsal tunnel syndrome 43.39 41.42 8 7013 47 4631924
Leukopenia 43.21 41.42 38 6983 21698 4610273
Aspartate aminotransferase increased 42.53 41.42 40 6981 24898 4607073
Alanine aminotransferase increased 41.81 41.42 42 6979 28331 4603640
Atelectasis 41.63 41.42 20 7001 4055 4627916
Renal failure 41.44 41.42 50 6971 41319 4590652

Pharmacologic Action:

SourceCodeDescription
ATC J05AH02 ANTIINFECTIVES FOR SYSTEMIC USE
ANTIVIRALS FOR SYSTEMIC USE
DIRECT ACTING ANTIVIRALS
Neuraminidase inhibitors
FDA EPC N0000175524 Neuraminidase Inhibitor
FDA MoA N0000175436 Neuraminidase Inhibitors
CHEBI has role CHEBI:50266 prodrug
CHEBI has role CHEBI:52425 EC 3.2.1.18 (exo-alpha-sialidase) inhibitor
CHEBI has role CHEBI:36044 antiviral drug
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000998 Antiviral Agents
MeSH PA D004791 Enzyme Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Influenza indication 6142004 DOID:8469
Coronavirus infection off-label use 186747009
Delirium contraindication 2776000
Suicidal thoughts contraindication 6471006
Acute nephropathy contraindication 58574008
Impaired cognition contraindication 386806002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.54 acidic
pKa2 7.67 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 30MG BASE TAMIFLU ROCHE N021087 July 2, 2007 RX CAPSULE ORAL Aug. 2, 2022 INFORMATION ADDED TO THE CLINICAL PHARMACOLOGY SECTION REGARDING INFLUENZA VIRUS RESISTANCE TO OSELTAMIVIR IN IMMUNOCOMPROMISED PATIENTS
EQ 45MG BASE TAMIFLU ROCHE N021087 July 2, 2007 RX CAPSULE ORAL Aug. 2, 2022 INFORMATION ADDED TO THE CLINICAL PHARMACOLOGY SECTION REGARDING INFLUENZA VIRUS RESISTANCE TO OSELTAMIVIR IN IMMUNOCOMPROMISED PATIENTS
EQ 75MG BASE TAMIFLU ROCHE N021087 Oct. 27, 1999 RX CAPSULE ORAL Aug. 2, 2022 INFORMATION ADDED TO THE CLINICAL PHARMACOLOGY SECTION REGARDING INFLUENZA VIRUS RESISTANCE TO OSELTAMIVIR IN IMMUNOCOMPROMISED PATIENTS
EQ 12MG BASE/ML TAMIFLU ROCHE N021246 Dec. 14, 2000 DISCN FOR SUSPENSION ORAL Aug. 2, 2022 INFORMATION ADDED TO THE CLINICAL PHARMACOLOGY SECTION REGARDING INFLUENZA VIRUS RESISTANCE TO OSELTAMIVIR IN IMMUNOCOMPROMISED PATIENTS
EQ 6MG BASE/ML TAMIFLU ROCHE N021246 March 21, 2011 RX FOR SUSPENSION ORAL Aug. 2, 2022 INFORMATION ADDED TO THE CLINICAL PHARMACOLOGY SECTION REGARDING INFLUENZA VIRUS RESISTANCE TO OSELTAMIVIR IN IMMUNOCOMPROMISED PATIENTS

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Neuraminidase Enzyme INHIBITOR IC50 8.15 CHEMBL CHEMBL
Neuraminidase Enzyme INHIBITOR Ki 8.96 CHEMBL CHEMBL
Neuraminidase Enzyme Ki 8.96 CHEMBL
Neuraminidase Enzyme Ki 8.31 CHEMBL
Neuraminidase Enzyme Ki 8.10 CHEMBL
Neuraminidase Enzyme Ki 10 CHEMBL
Neuraminidase Enzyme IC50 8.81 CHEMBL
Neuraminidase Enzyme IC50 6.10 CHEMBL
Neuraminidase Enzyme IC50 9.83 WOMBAT-PK
Neuraminidase Enzyme IC50 8.10 WOMBAT-PK
Neuraminidase Unclassified IC50 8.86 CHEMBL
Neuraminidase Enzyme IC50 6.32 CHEMBL
Neuraminidase Enzyme IC50 8.54 CHEMBL
Neuraminidase Enzyme IC50 10.22 CHEMBL

External reference:

IDSource
4021189 VUID
N0000175097 NUI
C0874161 UMLSCUI
D00900 KEGG_DRUG
20O93L6F9H UNII
7793 INN_ID
204255-11-8 SECONDARY_CAS_RN
386142008 SNOMEDCT_US
260101 RXNORM
412261005 SNOMEDCT_US
4021189 VANDF
d04462 MMSL
007918 NDDF
CHEMBL674 ChEMBL_ID
CHEMBL1229 ChEMBL_ID
C403132 MESH_SUPPLEMENTAL_RECORD_UI
DB00198 DRUGBANK_ID
CHEMBL1200340 ChEMBL_ID
CHEBI:7798 CHEBI
65028 PUBCHEM_CID
D053139 MESH_DESCRIPTOR_UI
C535162 MESH_SUPPLEMENTAL_RECORD_UI
DB02600 DRUGBANK_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tamiflu HUMAN PRESCRIPTION DRUG LABEL 1 0004-0800 CAPSULE 75 mg ORAL NDA 19 sections
Tamiflu HUMAN PRESCRIPTION DRUG LABEL 1 0004-0801 CAPSULE 45 mg ORAL NDA 19 sections
Tamiflu HUMAN PRESCRIPTION DRUG LABEL 1 0004-0802 CAPSULE 30 mg ORAL NDA 19 sections
Tamiflu HUMAN PRESCRIPTION DRUG LABEL 1 0004-0822 POWDER, FOR SUSPENSION 6 mg ORAL NDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 0093-8180 POWDER, FOR SUSPENSION 6 mg ORAL ANDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 16714-817 CAPSULE 30 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 16714-818 CAPSULE 45 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 16714-819 CAPSULE 75 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 31722-630 CAPSULE 30 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 31722-631 CAPSULE 45 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 31722-632 CAPSULE 75 mg ORAL ANDA 18 sections
oseltamavir phosphate HUMAN PRESCRIPTION DRUG LABEL 1 33342-256 CAPSULE 30 mg ORAL ANDA 17 sections
oseltamavir phosphate HUMAN PRESCRIPTION DRUG LABEL 1 33342-257 CAPSULE 45 mg ORAL ANDA 17 sections
oseltamavir phosphate HUMAN PRESCRIPTION DRUG LABEL 1 33342-258 CAPSULE 75 mg ORAL ANDA 17 sections
Tamiflu HUMAN PRESCRIPTION DRUG LABEL 1 42254-092 POWDER, FOR SUSPENSION 6 mg ORAL NDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 42291-567 FOR SUSPENSION 6 mg ORAL ANDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 42291-664 CAPSULE 75 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 42291-666 CAPSULE 30 mg ORAL ANDA 18 sections
OSELTAMIVIR HUMAN PRESCRIPTION DRUG LABEL 1 46708-413 CAPSULE 30 mg ORAL ANDA 18 sections
OSELTAMIVIR HUMAN PRESCRIPTION DRUG LABEL 1 46708-414 CAPSULE 45 mg ORAL ANDA 18 sections
OSELTAMIVIR HUMAN PRESCRIPTION DRUG LABEL 1 46708-415 CAPSULE 75 mg ORAL ANDA 18 sections
Oseltamivir Phosphate for Oral Suspension HUMAN PRESCRIPTION DRUG LABEL 1 47781-384 POWDER, FOR SUSPENSION 6 mg ORAL ANDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 47781-468 CAPSULE 30 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 47781-469 CAPSULE 45 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 47781-470 CAPSULE 75 mg ORAL ANDA 18 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 48792-7899 CAPSULE 30 mg ORAL ANDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 48792-7900 CAPSULE 45 mg ORAL ANDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 48792-7901 CAPSULE 75 mg ORAL ANDA 19 sections
Tamiflu HUMAN PRESCRIPTION DRUG LABEL 1 50090-0662 CAPSULE 75 mg ORAL NDA 19 sections
Oseltamivir Phosphate HUMAN PRESCRIPTION DRUG LABEL 1 50090-2726 CAPSULE 75 mg ORAL ANDA 17 sections