oseltamivir Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 2 % Benet LZ, Broccatelli F, Oprea TI
BDDCS (Biopharmaceutical Drug Disposition Classification System) 3 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 99 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 2.71 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 75 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Oct. 27, 1999 FDA ROCHE

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
No adverse event 1612.59 36.66 370 2958 9158 2345599
Exposure during pregnancy 1376.10 36.66 397 2931 24822 2329935
Pregnancy 1068.63 36.66 257 3071 7692 2347065
Abnormal behaviour 953.10 36.66 213 3115 4547 2350210
Hallucination 433.65 36.66 127 3201 8021 2346736
Vomiting 314.49 36.66 186 3142 71416 2283341
Influenza 213.90 36.66 84 3244 12894 2341863
Seizure 210.61 36.66 100 3228 24366 2330391
Pathogen resistance 191.33 36.66 42 3286 801 2353956
Normal newborn 188.71 36.66 45 3283 1255 2353502
Delirium 186.23 36.66 60 3268 5163 2349594
Maternal exposure during pregnancy 163.07 36.66 72 3256 14791 2339966
Enterocolitis haemorrhagic 151.01 36.66 30 3298 342 2354415
Respiratory failure 133.87 36.66 61 3267 13467 2341290
Pneumonia 133.52 36.66 95 3233 49201 2305556
Loss of consciousness 132.19 36.66 67 3261 18700 2336057
Overdose 122.75 36.66 65 3263 19842 2334915
Acute respiratory distress syndrome 118.00 36.66 38 3290 3254 2351503
Rash 100.83 36.66 87 3241 59471 2295286
Acute kidney injury 99.38 36.66 64 3264 28058 2326699
International normalised ratio increased 98.33 36.66 41 3287 7295 2347462
Confusional state 92.46 36.66 58 3270 24286 2330471
Accidental overdose 88.07 36.66 32 3296 3940 2350817
Agitation 85.21 36.66 42 3286 11009 2343748
Nausea 84.40 36.66 106 3222 112083 2242674
Abortion spontaneous 74.66 36.66 41 3287 13404 2341353
Depressed level of consciousness 74.21 36.66 34 3294 7570 2347187
Drug ineffective 70.01 36.66 92 3236 101532 2253225
Hypothermia 69.67 36.66 23 3305 2125 2352632
Pyrexia 66.55 36.66 66 3262 53642 2301115
Urticaria 66.00 36.66 47 3281 24214 2330543
Hallucination, auditory 65.24 36.66 22 3306 2170 2352587
Hepatitis 63.92 36.66 29 3299 6308 2348449
Incorrect dose administered 60.61 36.66 32 3296 9663 2345094
Altered state of consciousness 59.97 36.66 24 3304 3836 2350921
Restlessness 59.42 36.66 25 3303 4538 2350219
Purpura senile 58.72 36.66 9 3319 16 2354741
Hallucination, visual 58.65 36.66 22 3306 2957 2351800
Delusion 58.61 36.66 20 3308 2045 2352712
Dyspnoea 58.38 36.66 74 3254 78659 2276098
Premature delivery 57.12 36.66 22 3306 3178 2351579
Diarrhoea 56.44 36.66 75 3253 83489 2271268
Respiratory syncytial virus infection 56.21 36.66 15 3313 661 2354096
Melaena 55.15 36.66 23 3305 4083 2350674
Hypoxia 55.02 36.66 26 3302 6201 2348556
Colitis ischaemic 54.98 36.66 18 3310 1619 2353138
Foetal growth restriction 52.71 36.66 16 3312 1124 2353633
Dehydration 51.17 36.66 39 3289 22256 2332501
Hepatic function abnormal 49.45 36.66 24 3304 6068 2348689
Cardiac failure acute 49.14 36.66 15 3313 1074 2353683
H1N1 influenza 48.65 36.66 11 3317 240 2354517
Abdominal pain 47.69 36.66 45 3283 34329 2320428
Nightmare 47.28 36.66 20 3308 3677 2351080
Tarsal tunnel syndrome 46.92 36.66 8 3320 35 2354722
Encephalopathy 46.39 36.66 21 3307 4540 2350217
Disseminated intravascular coagulation 45.78 36.66 19 3309 3331 2351426
Liver disorder 45.34 36.66 23 3305 6391 2348366
Multiple organ dysfunction syndrome 44.32 36.66 24 3304 7617 2347140
Cardio-respiratory arrest 42.92 36.66 25 3303 9121 2345636
Disorientation 42.58 36.66 22 3306 6350 2348407
Decreased appetite 42.33 36.66 39 3289 28852 2325905
Aggression 42.32 36.66 20 3308 4766 2349991
Pneumonia bacterial 42.21 36.66 13 3315 959 2353798
Abortion induced 41.99 36.66 18 3310 3418 2351339
Screaming 41.90 36.66 12 3316 688 2354069
Pneumonia influenzal 41.66 36.66 9 3319 158 2354599
Suicidal ideation 40.96 36.66 26 3302 11061 2343696
Atelectasis 40.46 36.66 15 3313 1950 2352807
White blood cell count decreased 39.89 36.66 31 3297 18177 2336580
Premature labour 39.44 36.66 15 3313 2091 2352666
Erythema multiforme 38.97 36.66 15 3313 2160 2352597
Vestibular disorder 38.79 36.66 9 3319 221 2354536
Tachypnoea 38.62 36.66 15 3313 2214 2352543
Stevens-Johnson syndrome 38.28 36.66 18 3310 4241 2350516
Drug interaction 38.19 36.66 37 3291 29126 2325631
Hepatitis fulminant 38.15 36.66 11 3317 646 2354111
Respiratory distress 38.03 36.66 19 3309 5110 2349647
Crying 37.74 36.66 18 3310 4378 2350379

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
Abnormal behaviour 1827.10 41.43 400 2303 5942 1738136
Hallucination 537.51 41.43 160 2543 8010 1736068
Delirium 384.86 41.43 117 2586 6245 1737833
Normal newborn 358.35 41.43 57 2646 94 1743984
No adverse event 299.00 41.43 92 2611 5090 1738988
Seizure 208.93 41.43 103 2600 20338 1723740
Vomiting 200.50 41.43 124 2579 38191 1705887
Exposure during pregnancy 183.54 41.43 55 2648 2762 1741316
Pathogen resistance 163.38 41.43 41 2662 1048 1743030
Pneumonia 142.49 41.43 108 2595 46074 1698004
Overdose 132.23 41.43 71 2632 16630 1727448
Depressed level of consciousness 130.81 41.43 53 2650 6539 1737539
Hallucination, visual 128.21 41.43 41 2662 2551 1741527
Influenza 119.30 41.43 50 2653 6717 1737361
Confusional state 113.63 41.43 70 2633 21208 1722870
Loss of consciousness 105.93 41.43 59 2644 14816 1729262
Respiratory failure 93.71 41.43 54 2649 14451 1729627
Agitation 93.12 41.43 49 2654 10977 1733101
Pyrexia 85.85 41.43 81 2622 46319 1697759
Hypothermia 79.66 41.43 26 2677 1722 1742356
Nightmare 78.72 41.43 29 2674 2758 1741320
Acute respiratory distress syndrome 71.89 41.43 29 2674 3522 1740556
Pneumonia influenzal 71.64 41.43 15 2688 164 1743914
Encephalopathy 68.81 41.43 30 2673 4422 1739656
Hallucination, auditory 67.14 41.43 24 2679 2093 1741985
Sleep terror 66.83 41.43 15 2688 232 1743846
Restlessness 59.96 41.43 27 2676 4294 1739784
Hepatic function abnormal 58.41 41.43 31 2672 7043 1737035
Rash 57.42 41.43 60 2643 38633 1705445
Nausea 56.49 41.43 68 2635 51128 1692950
Crying 55.51 41.43 19 2684 1456 1742622
Altered state of consciousness 55.45 41.43 24 2679 3473 1740605
Delusion 54.93 41.43 21 2682 2210 1741868
Rhabdomyolysis 52.80 41.43 34 2669 11056 1733022
Sudden death 52.65 41.43 22 2681 2918 1741160
Acute kidney injury 51.48 41.43 54 2649 34890 1709188
Urticaria 49.74 41.43 34 2669 12207 1731871
Drug ineffective 49.10 41.43 71 2632 63730 1680348
Accidental overdose 48.35 41.43 23 2680 4141 1739937
Liver disorder 47.37 41.43 25 2678 5611 1738467
Thrombocytopenia 46.76 41.43 41 2662 21208 1722870
Hepatitis fulminant 46.67 41.43 14 2689 700 1743378
Disorientation 45.23 41.43 24 2679 5445 1738633
Cholestasis 44.87 41.43 21 2682 3644 1740434
Diarrhoea 44.44 41.43 62 2641 53790 1690288
Mental disorder 43.39 41.43 19 2684 2824 1741254
Tremor 43.03 41.43 32 2671 13099 1730979
Product administration error 42.70 41.43 19 2684 2934 1741144
Shock 42.34 41.43 21 2682 4140 1739938

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