Details of the Drug

General Information of Drug (ID: DMLOQ1V)

• Drug Name: Tasimelteon
• Synonyms: Tasimelteon; 609799-22-6; Hetlioz; VEC-162; BMS-214778; VEC 162; UNII-SHS4PU80D9; BMS 214778; SHS4PU80D9; CHEBI:79042; N-{[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl}propanamide; Tasimelteon [USAN:INN]; tasimelteonum; N-([(1r,2r)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl)propanamide; N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide; N-(((1R,2R)-2-(2,3-Dihydro-1-benzofuran-4-yl)cyclopropyl)methyl)propanamide; Hetlioz (TN); Tasimelteon (USAN/INN); SCHEMBL3505912; GTPL7393

Indication

Disease Entry	ICD 11	Status	REF
Insomnia	7A00-7A0Z	Approved	[1]

• Drug Type: Small molecular drug
• #Ro5 Violations (Lipinski): 0:
  Molecular Weight (mw); 245.32
  Logarithm of the Partition Coefficient (xlogp); 2.2
  Rotatable Bond Count (rotbonds); 4
  Hydrogen Bond Donor Count (hbonddonor); 1
  Hydrogen Bond Acceptor Count (hbondacc); 2
• ADMET Property:
  Clearance: The drug present in the plasma can be removed from the body at the rate of 9.04 mL/min/kg [2]
  Half-life: The concentration or amount of drug in body reduced by one-half in 1.3 +/- 0.4 hours [2]
  Metabolism: The drug is metabolized via the further oxidation to give a carboxylic acid []
  Vd: The volume of distribution (Vd) of drug is 56-126 L []
• Chemical Identifiers:
  Formula: C15H19NO2
  IUPAC Name: N-[[(1R,2R)-2-(2,3-dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide
  Canonical SMILES: CCC(=O)NC[C@@H]1C[C@H]1C2=C3CCOC3=CC=C2
  InChI: InChI=1S/C15H19NO2/c1-2-15(17)16-9-10-8-13(10)11-4-3-5-14-12(11)6-7-18-14/h3-5,10,13H,2,6-9H2,1H3,(H,16,17)/t10-,13+/m0/s1
  InChIKey: PTOIAAWZLUQTIO-GXFFZTMASA-N
• Cross-matching ID:
  PubChem CID: 10220503
  ChEBI ID: CHEBI:79042
  CAS Number: 609799-22-6
  DrugBank ID: DB09071
  TTD ID: D0Q5MQ
  INTEDE ID: DR1532
  ACDINA ID: D01461

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Melatonin receptor type 1A (MTNR1A)	TT0WAIE	MTR1A_HUMAN	Agonist	[1]
Melatonin receptor type 1B (MTNR1B)	TT32JK8	MTR1B_HUMAN	Agonist	[1]

Drug-Metabolizing Enzyme (DME)

DME Name	DME ID	UniProt ID	MOA	REF
Cytochrome P450 3A4 (CYP3A4) Main DME	DE4LYSA	CP3A4_HUMAN	Substrate	[3]
Cytochrome P450 1A2 (CYP1A2) Main DME	DEJGDUW	CP1A2_HUMAN	Substrate	[3]

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Tasimelteon (Comorbidity)

DDI Drug Name	DDI Drug ID	Severity	Mechanism	Comorbidity	REF
Ivosidenib	DM8S6T7	Moderate	Increased metabolism of Tasimelteon caused by Ivosidenib mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[4]
Arn-509	DMT81LZ	Major	Increased metabolism of Tasimelteon caused by Arn-509 mediated induction of CYP450 enzyme.	Acute myeloid leukaemia [2A60]	[4]
Oliceridine	DM6MDCF	Major	Additive CNS depression effects by the combination of Tasimelteon and Oliceridine.	Acute pain [MG31]	[5]
Pexidartinib	DMS2J0Z	Moderate	Increased metabolism of Tasimelteon caused by Pexidartinib mediated induction of CYP450 enzyme.	Bone/articular cartilage neoplasm [2F7B]	[4]
Tucatinib	DMBESUA	Moderate	Decreased metabolism of Tasimelteon caused by Tucatinib mediated inhibition of CYP450 enzyme.	Breast cancer [2C60-2C6Y]	[4]
Osilodrostat	DMIJC9X	Moderate	Decreased metabolism of Tasimelteon caused by Osilodrostat mediated inhibition of CYP450 enzyme.	Cushing syndrome [5A70]	[4]
Lumacaftor	DMCLWDJ	Major	Increased metabolism of Tasimelteon caused by Lumacaftor mediated induction of CYP450 enzyme.	Cystic fibrosis [CA25]	[6]
MK-8228	DMOB58Q	Moderate	Decreased metabolism of Tasimelteon caused by MK-8228 mediated inhibition of CYP450 enzyme.	Cytomegaloviral disease [1D82]	[4]
Esketamine	DMVU687	Moderate	Additive CNS depression effects by the combination of Tasimelteon and Esketamine.	Depression [6A70-6A7Z]	[7]
Stiripentol	DMMSDOY	Moderate	Decreased metabolism of Tasimelteon caused by Stiripentol mediated inhibition of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[4]
Eslicarbazepine	DMZREFQ	Moderate	Increased metabolism of Tasimelteon caused by Eslicarbazepine mediated induction of CYP450 enzyme.	Epilepsy/seizure [8A61-8A6Z]	[4]
Tazemetostat	DMWP1BH	Moderate	Increased metabolism of Tasimelteon caused by Tazemetostat mediated induction of CYP450 enzyme.	Follicular lymphoma [2A80]	[4]
Givosiran	DM5PFIJ	Moderate	Decreased metabolism of Tasimelteon caused by Givosiran mediated inhibition of CYP450 enzyme.	Inborn porphyrin/heme metabolism error [5C58]	[4]
Berotralstat	DMWA2DZ	Moderate	Decreased metabolism of Tasimelteon caused by Berotralstat mediated inhibition of CYP450 enzyme.	Innate/adaptive immunodeficiency [4A00]	[4]
PF-06463922	DMKM7EW	Moderate	Increased metabolism of Tasimelteon caused by PF-06463922 mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[4]
Osimertinib	DMRJLAT	Moderate	Increased metabolism of Tasimelteon caused by Osimertinib mediated induction of CYP450 enzyme.	Lung cancer [2C25]	[4]
Capmatinib	DMYCXKL	Moderate	Decreased metabolism of Tasimelteon caused by Capmatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[4]
Selpercatinib	DMZR15V	Moderate	Decreased metabolism of Tasimelteon caused by Selpercatinib mediated inhibition of CYP450 enzyme.	Lung cancer [2C25]	[4]
IPI-145	DMWA24P	Moderate	Decreased metabolism of Tasimelteon caused by IPI-145 mediated inhibition of CYP450 enzyme.	Mature B-cell leukaemia [2A82]	[4]
Allopregnanolone	DMNLHAC	Moderate	Additive CNS depression effects by the combination of Tasimelteon and Allopregnanolone.	Mental/behavioural/neurodevelopmental disorder [6E20-6E8Z]	[8]
Lasmiditan	DMXLVDT	Moderate	Additive CNS depression effects by the combination of Tasimelteon and Lasmiditan.	Migraine [8A80]	[9]
Fedratinib	DM4ZBK6	Moderate	Decreased metabolism of Tasimelteon caused by Fedratinib mediated inhibition of CYP450 enzyme.	Myeloproliferative neoplasm [2A20]	[4]
Rucaparib	DM9PVX8	Moderate	Decreased metabolism of Tasimelteon caused by Rucaparib mediated inhibition of CYP450 enzyme.	Ovarian cancer [2C73]	[4]
Abametapir	DM2RX0I	Moderate	Decreased metabolism of Tasimelteon caused by Abametapir mediated inhibition of CYP450 enzyme.	Pediculosis [1G00]	[10]
Lefamulin	DME6G97	Moderate	Decreased metabolism of Tasimelteon caused by Lefamulin mediated inhibition of CYP450 enzyme.	Pneumonia [CA40]	[11]
Voxelotor	DMCS6M5	Moderate	Decreased metabolism of Tasimelteon caused by Voxelotor mediated inhibition of CYP450 enzyme.	Sickle-cell disorder [3A51]	[4]
Telotristat ethyl	DMDIYFZ	Moderate	Increased metabolism of Tasimelteon caused by Telotristat ethyl mediated induction of CYP450 enzyme.	Small intestine developmental anomaly [DA90]	[12]
Larotrectinib	DM26CQR	Moderate	Decreased metabolism of Tasimelteon caused by Larotrectinib mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[7]
LEE011	DMMX75K	Moderate	Decreased metabolism of Tasimelteon caused by LEE011 mediated inhibition of CYP450 enzyme.	Solid tumour/cancer [2A00-2F9Z]	[4]
Fostamatinib	DM6AUHV	Moderate	Decreased metabolism of Tasimelteon caused by Fostamatinib mediated inhibition of CYP450 enzyme.	Thrombocytopenia [3B64]	[13]
Elagolix	DMB2C0E	Moderate	Increased metabolism of Tasimelteon caused by Elagolix mediated induction of CYP450 enzyme.	Uterine fibroid [2E86]	[4]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG

DIG Name	DIG ID	PubChem CID	Functional Classification
Erythrosine sodium anhydrous	E00324	27872	Colorant
FD&C blue no. 1	E00263	19700	Colorant
Mannitol	E00103	6251	Diluent; Flavoring agent; Lyophilization aid; Plasticizing agent; Tonicity agent
Sodium benzoate	E00432	517055	Antimicrobial preservative; lubricant
Sucralose	E00370	71485	Flavoring agent
Sunset yellow FCF	E00255	17730	Colorant
Ascorbic acid	E00579	54670067	Acidulant; Antioxidant
Beta-D-lactose	E00099	6134	Diluent; Dry powder inhaler carrier; Lyophilization aid
Carmellose sodium	E00625	Not Available	Disintegrant
Gelatin	E00630	Not Available	Other agent
Magnesium stearate	E00208	11177	lubricant
Polysorbate 80	E00665	Not Available	Dispersing agent; Emollient; Emulsifying agent; Plasticizing agent; Solubilizing agent; Surfactant; Suspending agent
Saccharose	E00091	5988	Binding agent; Coating agent; Cryoprotectant; Diluent; Flavoring agent; Suspending agent; Viscosity-controlling agent
Sodium chloride	E00077	5234	Diluent; Tonicity agent
Titanium dioxide	E00322	26042	Coating agent; Colorant; Opacifying agent
Water	E00035	962	Solvent
Hydrophobic colloidal silica	E00285	24261	Anticaking agent; Emulsion stabilizing agent; Glidant; Suspending agent; Viscosity-controlling agent
Cellulose microcrystalline	E00698	Not Available	Adsorbent; Suspending agent; Diluent

Pharmaceutical Formulation

Formulation Name	Drug Dosage	Dosage Form	Route
Tasimelteon 20mg capsule	20mg	Capsule	Oral
Tasimelteon 4mg/ml suspension	4mg/ml	Suspension	Oral

Jump to Detail Pharmaceutical Formulation Page of This Drug

References

• [1] URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7393).
• [2] Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
• [3] Clinical assessment of drug-drug interactions of tasimelteon, a novel dual melatonin receptor agonist. J Clin Pharmacol. 2015 Sep;55(9):1004-11.
• [4] Product Information. Hetlioz (tasimelteon). Vanda Pharmaceuticals Inc, Rockville, MD.
• [5] US Food and Drug Administration "FDA warns about serious risks and death when combining opioid pain or cough medicines with benzodiazepines requires its strongest warning.".
• [6] Patel S, Robinson R, Burk M "Hypertensive crisis associated with St. John's Wort." Am J Med 112 (2002): 507-8. [PMID: 11959071]
• [7] Cerner Multum, Inc. "Australian Product Information.".
• [8] Product Information. Zulresso (brexanolone). Sage Therapeutics, Inc., Cambridge, MA.
• [9] Product Information. Reyvow (lasmiditan). Lilly, Eli and Company, Indianapolis, IN.
• [10] Product Information. Xeglyze (abametapir topical). Dr. Reddy's Laboratories Inc, Upper Saddle River, NJ.
• [11] Product Information. Xenleta (lefamulin). Nabriva Therapeutics US, Inc., King of Prussia, PA.
• [12] Cerner Multum, Inc. "UK Summary of Product Characteristics.".
• [13] Product Information. Tavalisse (fostamatinib). Rigel Pharmaceuticals, South San Francisco, CA.