TASIMELTEON

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H19NO2
Molecular Weight	245.3169
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC(=O)NC[C@@H]1C[C@H]1C2=CC=CC3=C2CCO3

InChI

InChIKey=PTOIAAWZLUQTIO-GXFFZTMASA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H19NO2
Molecular Weight	245.3169
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205677s000lbledt.pdf
Curator's Comment: description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/?term=19579175

Tasimelteon, developed by Vanda Pharmaceuticals Inc under license from Bristol-Myers Squibb Co, is a melatonin receptor agonist. Tasimelteon differs structurally from melatonin and drugs with known melatonin agonist activity, in particular by its distinct aromatic group and linker. Tasimelteon bears also no structural relationship to any other approved active substance. Tasimelteon is presumably acts through activation of MT1 and MT2 G-protein coupled receptors, which are involved primarily in inhibition of neuronal firing and phase shift of circadian rhythms. Tasimelteon is approved for the treatment of Non24-Hour Sleep-Wake Disorder.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Melatonin receptor type 1B 4 Target ID: P49286 Gene ID: 4544.0 Gene Symbol: MTNR1B Target Organism: Homo sapiens (Human) Sources: http://www.pbm.va.gov/PBM/clinicalguidance/drugmonographs/Tasimelteon_Drug_Monograph.pdf	Agonist 2752		0.0692 nM [Ki]
Melatonin receptor type 1A 3 Target ID: P48039 Gene ID: 4543.0 Gene Symbol: MTNR1A Target Organism: Homo sapiens (Human) Sources: http://www.pbm.va.gov/PBM/clinicalguidance/drugmonographs/Tasimelteon_Drug_Monograph.pdf	Agonist 2752		0.304 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Sleep disorders, circadian rhythm 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/205677s000lbledt.pdf	Primary		Approved 8583	HETLIOZ Approved Use Indicated for the treatment of Non-24-Hour Sleep-Wake Disorder (Non-24). Launch Date 2014

C_max

Value	Dose	Analyte	Population
445 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
786 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
5 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
33 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
173 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
394 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
12 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
51 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
261 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
873 ng/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
2304 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
2269 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
59 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
426 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1823 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
17 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
96 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
611 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3797 ng × h/mL OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.06 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: HIGH-FAT
2.75 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
1.75 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	1 mg single, oral dose: 1 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.29 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.37 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.78 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.49 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	1 mg 1 times / day steady-state, oral dose: 1 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1.44 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	10 mg 1 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.57 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	50 mg 1 times / day steady-state, oral dose: 50 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.63 h OTHER GOV https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf	150 mg 1 times / day steady-state, oral dose: 150 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	TASIMELTEON plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Supraventricular extrasystoles, Vomiting... AEs leading to discontinuation/dose reduction: Supraventricular extrasystoles (0.7%) Vomiting (0.7%) Headache (0.7%) Syncope (0.7%) Insomnia (0.7%) Nightmare (1.3%) Anger (0.7%) Depression (0.7%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
20 mg 1 times / day multiple, oral Recommended Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Supraventricular extrasystoles, Tachycardia... AEs leading to discontinuation/dose reduction: Supraventricular extrasystoles (0.07%) Tachycardia (0.07%) Constipation (0.07%) Fatigue (0.07%) Oedema peripheral (0.07%) Cholestasis (0.07%) ALT increased (0.07%) AST increased (0.07%) GGT increased (0.07%) Blood creatine increased (0.07%) Hyperglycaemia (0.07%) Headache (0.07%) Loss of consciousness (0.07%) Syncope (0.07%) Transient ischaemic attack (0.07%) Insomnia (0.14%) Nightmare (0.14%) Renal pain (0.07%) Rash (0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
1 mg 1 times / day multiple, oral Studied dose Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Local swelling, Disorientation... AEs leading to discontinuation/dose reduction: Local swelling (0.07%) Disorientation (0.07%) Rash (0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
10 mg 1 times / day multiple, oral Studied dose Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Diarrhoea, Gastritis... AEs leading to discontinuation/dose reduction: Diarrhoea (0.07%) Gastritis (0.07%) Dizziness (0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
100 mg 1 times / day multiple, oral Studied dose Dose: 100 mg, 1 times / day Route: oral Route: multiple Dose: 100 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Vomiting... AEs leading to discontinuation/dose reduction: Vomiting (0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
150 mg 1 times / day multiple, oral Studied dose Dose: 150 mg, 1 times / day Route: oral Route: multiple Dose: 150 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
20 mg 1 times / day multiple, oral Studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Ventricular arrhythmia, Gastritis... AEs leading to discontinuation/dose reduction: Ventricular arrhythmia (0.9%) Gastritis (0.9%) Local swelling (0.9%) Electrocardiogram ST segment elevation (0.9%) Ataxia (0.9%) Dizziness (0.9%) Confusional state (0.9%) Disorientation (0.9%) Rash (0.9%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
25 mg 1 times / day multiple, oral Studied dose Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Supraventricular extrasystoles, Ventricular arrhythmia... AEs leading to discontinuation/dose reduction: Supraventricular extrasystoles (0.2%) Ventricular arrhythmia (0.2%) Diarrhoea (0.2%) Dyspepsia (0.2%) Gastritis (0.2%) Hypoaesthesia oral (0.2%) Vomiting (0.2%) Local swelling (0.2%) Somnolence (0.5%) Ataxia (0.2%) Dizziness (0.2%) Headache (0.2%) Syncope (0.2%) Insomnia (0.5%) Nightmare (0.5%) Anger (0.2%) Confusional state (0.2%) Depression (0.2%) Disorientation (0.2%) Rash (0.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Diarrhoea, Dyspepsia... AEs leading to discontinuation/dose reduction: Diarrhoea (0.6%) Dyspepsia (0.6%) Hypoaesthesia oral (0.6%) Blood creatine phosphokinase increased (0.6%) Somnolence (1.2%) Insomnia (0.6%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
50 mg 1 times / day multiple, oral Studied dose Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	unhealthy, 18 - 92 years Health Status: unhealthy Age Group: 18 - 92 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Disc. AE: Dyspepsia, Blood creatine increased... AEs leading to discontinuation/dose reduction: Dyspepsia (0.07%) Blood creatine increased (0.07%) Somnolence (0.07%) Insomnia (0.07%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf
300 mg 1 times / day multiple, oral Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	healthy, 18-44 years Health Status: healthy Age Group: 18-44 years Sex: M+F Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf	Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000MedR.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1946	substrate 1193 inhibitor 2438 inducer 440	substrate 1388 inhibitor 2507	inhibitor 2217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2B6 926 CYP2C8 1057 CYP2C19 2057 CYP3A4/5 296 OATP1B1 1079 OATP1B3 961 OAT1 725 BCRP 910 OCT2 779 OAT3 747 P-gp 1741	CYP1A2 1197 CYP1A1 389 CYP2C19 1119 OATP1B1 503 OATP1B3 435 P-gp 2052	CYP3A4/5 133 CYP2C8 198 CYP1A2 832 CYP2B6 669 CYP2C19 329

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
BCRP 985	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP1A2 2333	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP1A2 2333	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP2B6 1160	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP2B6 1160	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP2C19 2141	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP2C8 1117	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP2C9 2497	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
CYP3A4/5 357	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
OAT1 730	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
OAT3 749	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
OATP1B1 1095	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
OATP1B3 970	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M12 1
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M13 2
OCT2 782	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=7 Page: 7.0	no	M9 2
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M12 1
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M13 2
P-gp 1932	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M9 2
CYP2C8 1117	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes		yes (co-administration study) Comment: Rifampin, a strong CYP3A4 and moderate CYP2C8, CYP2C9/2C19 inducer, decreased the exposure of tasimelteon by approximately 90%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0
CYP3A4/5 357	inducer 1966 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes		yes (co-administration study) Comment: Rifampin, a strong CYP3A4 and moderate CYP2C8, CYP2C9/2C19 inducer, decreased the exposure of tasimelteon by approximately 90%. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
CYP1A2 1197	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	major		yes (co-administration study) Comment: Drug interaction studies with CY1A2 inhibitor, fluvoxamine and CYP3A4 inducer, rifampin resulted in 6.5 fold increase and 90% decrease in tasimelteon exposure respectively. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0
CYP3A4 1946	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	major		yes (co-administration study) Comment: Drug interaction studies with CY1A2 inhibitor, fluvoxamine and CYP3A4 inducer, rifampin resulted in 6.5 fold increase and 90% decrease in tasimelteon exposure respectively. Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0
CYP1A1 389	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	minor
CYP2C19 1119	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	minor
CYP2C9 1193	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	minor
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=5 Page: 5.0	minor
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M12 1
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M13 2
OATP1B1 503	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M9 2
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M12 1
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M13 2
OATP1B3 435	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M9 2
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M12 1
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M13 2
P-gp 2052	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no	M9 2

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	inhibitor 2237 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2014/205677Orig1s000PharmR.pdf#page=28 Page: 28.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:79042	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:79042
ChemicalBook	CB41518537	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB41518537
eMolecules	28326483	https://www.emolecules.com/cgi-bin/more?vid=28326483
MolPort	MolPort-028-600-027	https://www.molport.com/shop/molecule-link/MolPort-028-600-027
ZINC	ZINC000004392649	http://zinc15.docking.org/substances/ZINC000004392649

PubMed

Title	Date	PubMed
Analysis of low level radioactive metabolites in biological fluids using high-performance liquid chromatography with microplate scintillation counting: method validation and application.	2005 Sep 1	15899570
Melatonin and its agonists: an update.	2008 Oct	18827285
New approaches in the management of insomnia: weighing the advantages of prolonged-release melatonin and synthetic melatoninergic agonists.	2009	19557144
Melatonin agonist tasimelteon (VEC-162) for transient insomnia after sleep-time shift: two randomised controlled multicentre trials.	2009 Feb 7	19054552
Tasimelteon, a melatonin agonist for the treatment of insomnia and circadian rhythm sleep disorders.	2009 Jul	19579175
Sleep-promoting action of IIK7, a selective MT2 melatonin receptor agonist in the rat.	2009 Jun 26	19429170
Melatonin agonists and insomnia.	2010 Feb	20136385
Gateways to clinical trials.	2010 Jan-Feb	20383346
Investigational melatonin receptor agonists.	2010 Jun	20408738
Jet lag, circadian rhythm sleep disturbances, and depression: the role of melatonin and its analogs.	2010 Nov	20827520
A systematic, updated review on the antidepressant agomelatine focusing on its melatonergic modulation.	2010 Sep	21358978
[The newer sedative-hypnotics].	2010 Sep	20945020
Mechanism of action of tasimelteon in non-24 sleep-wake syndrome: treatment for a circadian rhythm disorder in blind patients.	2014 Dec	25422900
Tasimelteon: a selective and unique receptor binding profile.	2015 Apr	25534555
Tasimelteon for the treatment of non-24-hour sleep-wake disorder.	2015 Jan	25685859

Patents

Sample Use Guides

In Vivo Use Guide

The recommended dosage of HETLIOZ is 20 mg per day taken before bedtime, at the same time every night. Because of individual differences in circadian rhythms, drug effect may not occur for weeks or months. HETLIOZ should be taken without food.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:14:55 GMT 2025` Edited by `admin` on `Mon Mar 31 18:14:55 GMT 2025`
Record UNII	SHS4PU80D9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TASIMELTEON

Official Name

English

HETLIOZ

Preferred Name

English

TASIMELTEON [USAN]

Common Name

English

Tasimelteon [WHO-DD]

Common Name

English

PROPANAMIDE, N-(((1R,2R)-2-(2,3-DIHYDRO-4-BENZOFURANYL)CYCLOPROPYL)METHYL)-

Systematic Name

English

BMS-214778

Code

English

VEC-162

Code

English

BMS-214,778

Code

English

HETLIOZ LQ

Brand Name

English

N-[[(1R,2R)-2-(2,3-Dihydro-1-benzofuran-4-yl)cyclopropyl]methyl]propanamide

Systematic Name

English

TASIMELTEON [VANDF]

Common Name

English

TASIMELTEON [MI]

Common Name

English

TASIMELTEON [MART.]

Common Name

English

TASIMELTEON [ORANGE BOOK]

Common Name

English

tasimelteon [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

N05CH03