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

Stem definitionDrug idCAS RN
4820 609799-22-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • tasimelteon
  • hetlioz
  • VEC-162
  • BMS-214778
an agonist at melatonin MT1 and MT2 receptors, these receptors are thought to be involved in the control of circadian rhythms
  • Molecular weight: 245.32
  • Formula: C15H19NO2
  • CLOGP: 1.89
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 38.33
  • ALOGS: -3.81
  • ROTB: 4

  • Status: ONP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
Vd (Volume of distribution) 0.33 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 9.04 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 0.75 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Jan. 31, 2014 FDA VANDA PHARMS INC

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
Insomnia 350.43 41.40 168 2209 186904 53159785
Drug ineffective 338.57 41.40 279 2098 816966 52529723
Middle insomnia 336.75 41.40 81 2296 10627 53336062
Product dose omission issue 241.27 41.40 132 2245 191488 53155201
Incorrect product administration duration 207.64 41.40 55 2322 10569 53336120
Nightmare 171.23 41.40 53 2324 17698 53328991
Abnormal dreams 170.14 41.40 47 2330 10554 53336135
Somnolence 135.37 41.40 87 2290 167647 53179042
Initial insomnia 131.39 41.40 33 2344 5122 53341567
Therapeutic product effect delayed 97.81 41.40 22 2355 2127 53344562
Therapeutic product effect decreased 90.94 41.40 61 2316 125594 53221095
Poor quality sleep 69.90 41.40 27 2350 17296 53329393
Sleep disorder 48.35 41.40 31 2346 58839 53287850
Therapeutic product effect variable 47.18 41.40 11 2366 1244 53345445
Hypersomnia 47.05 41.40 20 2357 16335 53330354
Headache 43.67 41.40 82 2295 536739 52809950

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
Drug ineffective 478.74 59.75 275 1467 383202 32128582
Middle insomnia 401.64 59.75 88 1654 6396 32505388
Insomnia 274.67 59.75 124 1618 100224 32411560
Incorrect product administration duration 235.32 59.75 53 1689 4325 32507459
Nightmare 203.86 59.75 59 1683 13107 32498677
Product dose omission issue 160.73 59.75 87 1655 102488 32409296
Abnormal dreams 144.13 59.75 41 1701 8523 32503261
Somnolence 135.08 59.75 78 1664 103719 32408065
Therapeutic product effect decreased 115.72 59.75 48 1694 30969 32480815
Initial insomnia 105.98 59.75 26 1716 3046 32508738
Feeling abnormal 61.67 59.75 39 1703 60384 32451400
Poor quality sleep 61.09 59.75 21 1721 8053 32503731

Pharmacologic Action:

SourceCodeDescription
ATC N05CH03 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Melatonin receptor agonists
FDA MoA N0000000250 Melatonin Receptor Agonists
FDA EPC N0000175743 Melatonin Receptor Agonist
CHEBI has role CHEBI:79046 melatonin receptor agonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Non-24 hour sleep-wake cycle indication 230496009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.05 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 5856529 Dec. 9, 2022 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 5856529 Dec. 9, 2022 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY ADMINISTERING TASIMELTEON
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 5856529 Dec. 9, 2022 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10149829 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH CYP1A2 STRONG INHIBITORS
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10149829 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH CYP1A2 STRONG INHIBITORS
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10449176 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY ADMINISTERING TASIMELTEON
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10610510 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON TO PATIENTS WITH A SMOKING HISTORY
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10610510 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY ADMINISTERING TASIMELTEON TO PATIENTS WITH A SMOKING HISTORY
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10945988 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY ADMINISTERING TASIMELTEON
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10980770 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENISSYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON TO SMOKERS OR TO PATIENTS BEING TREATED WITH A CYP1A2 INHIBITOR
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10980770 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE ADMINISTRATION OF TASIMELTEON TO SMOKERS OR TO PATIENTS BEING TREATED WITH A CYP1A2 INHIBITOR
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9060995 Jan. 25, 2033 TREATMENT OF NON-24-HOUR SLEEP-WAKE DISORDER BY AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH FLUVOXAMINE
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9539234 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH A STRONG CYP1A2 INHIBITOR
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9539234 Jan. 25, 2033 TREATMENT OF NON-24-HOUR SLEEP-WAKE DISORDER BY AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH A STRONG CYP1A2 INHIBITOR
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9549913 Jan. 25, 2033 TREATMENT OF NON-24-HOUR SLEEP-WAKE DISORDER
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9855241 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY ADMINISTERING TASIMELTEON
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL RE46604 Jan. 25, 2033 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY ORALLY ADMINISTERING 20MG OF TASIMELTEON ONCE DAILY BEFORE BEDTIME
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 10149829 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH CYP1A2 STRONG INHIBITORS
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 10610510 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON TO PATIENTS WITH A SMOKING HISTORY
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 10980770 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENISSYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON TO SMOKERS OR TO PATIENTS BEING TREATED WITH A CYP1A2 INHIBITOR
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 9539234 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH A STRONG CYP1A2 INHIBITOR
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9730910 May 17, 2034 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE USE OF TASIMELTEON WITH RIFAMPIN
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 9730910 May 17, 2034 TREATMENT OF NON-24-HOUR SLEEP-WAKE DISORDER BY AVOIDING THE USE OF TASIMELTEON IN COMBINATION WITH RIFAMPIN
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 9730910 May 17, 2034 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE USE OF TASIMELTEON WITH RIFAMPIN
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10610511 Oct. 10, 2034 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10610511 Oct. 10, 2034 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 11141400 Oct. 10, 2034 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 11141400 Oct. 10, 2034 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 10610511 Oct. 10, 2034 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 11141400 Oct. 10, 2034 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10376487 July 27, 2035 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10376487 July 27, 2035 TREATMENT OF NON-24 HOUR SLEEP-WAKE DISORDER BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 10376487 July 27, 2035 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH FOOD
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 10179119 Aug. 29, 2035 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 10179119 Aug. 29, 2035 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL Dec. 1, 2023 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME (SMS) IN PATIENTS 16 YEARS OF AGE AND OLDER
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL Dec. 1, 2023 NEW PRODUCT
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL Dec. 1, 2027 THE TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME (SMS) IN PATIENTS 16 YEARS OF AGE AND OLDER
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL Dec. 1, 2027 FOR THE TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME (SMS) IN PEDIATRIC PATIENTS 3 TO 15 YEARS OF AGE

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Melatonin receptor type 1A GPCR AGONIST Ki 9.45 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE
Melatonin receptor type 1B GPCR AGONIST Ki 9.80 SCIENTIFIC LITERATURE SCIENTIFIC LITERATURE

External reference:

IDSource
D09388 KEGG_DRUG
4033173 VUID
N0000190488 NUI
4033173 VANDF
CHEBI:79042 CHEBI
CHEMBL2103822 ChEMBL_ID
C478745 MESH_SUPPLEMENTAL_RECORD_UI
7393 IUPHAR_LIGAND_ID
8985 INN_ID
DB09071 DRUGBANK_ID
SHS4PU80D9 UNII
10220503 PUBCHEM_CID
1490468 RXNORM
211275 MMSL
30166 MMSL
d08240 MMSL
015295 NDDF
702394009 SNOMEDCT_US
704468000 SNOMEDCT_US
C1313052 UMLSCUI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Hetlioz HUMAN PRESCRIPTION DRUG LABEL 1 43068-220 CAPSULE 20 mg ORAL NDA 34 sections
HetliozLQ HUMAN PRESCRIPTION DRUG LABEL 1 43068-304 SUSPENSION 4 mg ORAL NDA 34 sections