tasimelteon 🐶 Veterinary Use | 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: OFP
    • 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
fu (Fraction unbound in plasma) 0.12 % Kawashima H, Watanabe R, Esaki T, Kuroda M, Nagao C, Natsume-Kitatani Y, Ohashi R, Komura H, Mizuguchi K

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 355.67 43.91 169 2255 215083 63271515
Middle insomnia 335.78 43.91 81 2343 12562 63474036
Drug ineffective 330.44 43.91 286 2138 1044479 62442119
Product dose omission issue 246.47 43.91 136 2288 234177 63252421
Incorrect product administration duration 211.51 43.91 55 2369 11491 63475107
Abnormal dreams 177.70 43.91 47 2377 10469 63476129
Nightmare 175.20 43.91 53 2371 19141 63467457
Somnolence 147.83 43.91 89 2335 178596 63308002
Initial insomnia 130.62 43.91 33 2391 6124 63480474
Therapeutic product effect delayed 98.86 43.91 22 2402 2369 63484229
Therapeutic product effect decreased 77.99 43.91 62 2362 193125 63293473
Poor quality sleep 73.86 43.91 28 2396 19907 63466691
Therapeutic product effect variable 49.15 43.91 11 2413 1212 63485386
Sleep disorder 48.20 43.91 33 2391 81533 63405065
Hypersomnia 48.12 43.91 20 2404 18035 63468563

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 456.77 58.94 278 1487 456473 34498693
Middle insomnia 402.61 58.94 88 1677 6714 34948452
Insomnia 267.87 58.94 121 1644 103786 34851380
Incorrect product administration duration 233.46 58.94 53 1712 4758 34950408
Nightmare 202.12 58.94 59 1706 14332 34940834
Product dose omission issue 161.14 58.94 90 1675 119621 34835545
Abnormal dreams 151.50 58.94 41 1724 7537 34947629
Somnolence 134.42 58.94 78 1687 111038 34844128
Therapeutic product effect decreased 116.55 58.94 49 1716 34694 34920472
Initial insomnia 107.08 58.94 26 1739 3098 34952068
Feeling abnormal 62.16 58.94 39 1726 63196 34891970
Poor quality sleep 61.85 58.94 21 1744 8235 34946931

FDA Adverse Event Reporting System (Geriatric)

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 448.22 48.31 321 2210 1080592 78661265
Middle insomnia 409.15 48.31 96 2435 15973 79725884
Incorrect product administration duration 370.90 48.31 84 2447 11938 79729919
Insomnia 333.14 48.31 159 2372 245011 79496846
Nightmare 265.54 48.31 75 2456 25786 79716071
Product dose omission issue 245.67 48.31 130 2401 247407 79494450
Abnormal dreams 217.18 48.31 54 2477 11358 79730499
Somnolence 159.40 48.31 97 2434 238884 79502973
Initial insomnia 122.77 48.31 31 2500 6907 79734950
Therapeutic product effect decreased 97.50 48.31 62 2469 163801 79578056
Therapeutic product effect delayed 76.24 48.31 18 2513 3028 79738829
Poor quality sleep 71.67 48.31 27 2504 22695 79719162
Headache 62.28 48.31 89 2442 653683 79088174

FDA Adverse Event Reporting System (Pediatric)

None

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 | Suggest Off label Use Form| |View source of the data|

DiseaseRelationSNOMED_IDDOID
Non-24 hour sleep-wake cycle indication 230496009




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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 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-MAGENIS SYNDROME 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 11285129 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH BETA-ADRENERGIC RECEPTOR ANTAGONISTS
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 11285129 Jan. 25, 2033 TREATMENT OF NON-24-HOUR SLEEP-WAKE DISORDER BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH BETA-ADRENERGIC RECEPTOR ANTAGONISTS
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 11633377 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY ADMINISTERING TASIMELTEON
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 11633377 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 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-MAGENIS SYNDROME 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 11285129 Jan. 25, 2033 TREATMENT OF NIGHTTIME SLEEP DISTURBANCES IN SMITH-MAGENIS SYNDROME BY AVOIDING THE ADMINISTRATION OF TASIMELTEON WITH BETA-ADRENERGIC RECEPTOR ANTAGONISTS
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 11633377 Jan. 25, 2033 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 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
20MG HETLIOZ VANDA PHARMS INC N205677 Jan. 31, 2014 RX CAPSULE ORAL 11266622 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
4MG/ML HETLIOZ LQ VANDA PHARMS INC N214517 Dec. 1, 2020 RX SUSPENSION ORAL 11266622 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 TASIMELTEON APOTEX A211607 Dec. 20, 2022 RX CAPSULE ORAL June 27, 2023 PATENT CHALLENGE
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
DB09071 DRUGBANK_ID
1490468 RXNORM
211275 MMSL
30166 MMSL
364462 MMSL
d08240 MMSL
015295 NDDF
702394009 SNOMEDCT_US
704468000 SNOMEDCT_US
C1313052 UMLSCUI
8985 INN_ID
10220503 PUBCHEM_CID
SHS4PU80D9 UNII

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Tasimelteon HUMAN PRESCRIPTION DRUG LABEL 1 0480-4490 CAPSULE, GELATIN COATED 20 mg ORAL ANDA 27 sections
Hetlioz HUMAN PRESCRIPTION DRUG LABEL 1 43068-220 CAPSULE 20 mg ORAL NDA 34 sections
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
HetliozLQ HUMAN PRESCRIPTION DRUG LABEL 1 43068-304 SUSPENSION 4 mg ORAL NDA 34 sections
Tasimelteon HUMAN PRESCRIPTION DRUG LABEL 1 69238-2548 CAPSULE 20 mg ORAL ANDA 31 sections