U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C17H16ClNO
Molecular Weight 285.7686
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ASENAPINE

SMILES

CN1C[C@]2([H])c3ccccc3Oc4ccc(cc4[C@@]2([H])C1)Cl

InChI

InChIKey=VSWBSWWIRNCQIJ-HUUCEWRRSA-N
InChI=1S/C17H16ClNO/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19/h2-8,14-15H,9-10H2,1H3/t14-,15-/m1/s1

HIDE SMILES / InChI
Molecular Formula C17H16ClNO
Molecular Weight 285.7686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/19876039 | https://www.ncbi.nlm.nih.gov/pubmed/18308814

Asenapine is an antipsychotic drug. The mechanism of action of asenapine, as with other drugs having efficacy in schizophrenia and bipolar disorder, is unknown. Asenapine exhibits high affinity for serotonin 5-HT1A, 5-HT1B, 5-HT2A, 5-HT2B, 5-HT2C, 5-HT5, 5-HT6, and 5-HT7 receptors, dopamine D2, D3, D4, and D1 receptors, α1 and α2-adrenergic receptors, and histamine H1 receptors, and moderate affinity for H2 receptors. In in vitro assays asenapine acts as an antagonist at these receptors. It has been suggested that the efficacy of asenapine in schizophrenia is mediated through a combination of antagonist activity at D2 and 5-HT2A receptors. Asenapine is approved by the FDA for the acute treatment of schizophrenia in adults and for the acute treatment of manic or mixed episodes associated with bipolar I disorder, with or without psychotic features, in adults.

CNS Activity

Originator

Approval Year

2009
323
Targets

Targets

Primary TargetPharmacologyConditionPotency
D(2) dopamine receptor
57
Target ID: P14416
Gene ID: 1813.0
Gene Symbol: DRD2
Target Organism: Homo sapiens (Human)
Antagonist
2575
 1.3 nM [Ki]
Antagonist
2575
 0.06 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8043
SAPHRIS

Approved Use

SAPHRIS is indicated for the treatment of schizophrenia. SAPHRIS is indicated for the acute treatment of manic or mixed episodes associated with bipolar I disorder. SAPHRIS is indicated as adjunctive therapy with either lithium or valproate for the acute treatment of manic or mixed episodes associated with bipolar I disorder.

Launch Date

1.25012161E12
Primary
Approved
8043
SAPHRIS

Approved Use

SAPHRIS is indicated for the treatment of schizophrenia. SAPHRIS is indicated for the acute treatment of manic or mixed episodes associated with bipolar I disorder. SAPHRIS is indicated as adjunctive therapy with either lithium or valproate for the acute treatment of manic or mixed episodes associated with bipolar I disorder.

Launch Date

1.25012161E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
4.73 ng/mL
EXPERIMENT
https://onlinelibrary.wiley.com/doi/epdf/10.1002/gps.2737
5 mg 2 times / day multiple, sublingual
dose: 5 mg
route of administration: Sublingual
experiment type: MULTIPLE
co-administered:
ASENAPINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
32.1 ng × h/mL
EXPERIMENT
https://onlinelibrary.wiley.com/doi/epdf/10.1002/gps.2737
5 mg 2 times / day multiple, sublingual
dose: 5 mg
route of administration: Sublingual
experiment type: MULTIPLE
co-administered:
ASENAPINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
30 h
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212268s000lbl.pdf
3.8 mg single, transdermal
dose: 3.8 mg
route of administration: Transdermal
experiment type: SINGLE
co-administered:
ASENAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2019/212268s000lbl.pdf
3.8 mg single, transdermal
dose: 3.8 mg
route of administration: Transdermal
experiment type: SINGLE
co-administered:
ASENAPINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
unhealthy, pediatric patients
n = 99
Health Status: unhealthy
Condition: Bipolar Mania
Age Group: pediatric patients
Population Size: 99
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
Disc. AE: Somnolence, Abdominal pain...
AEs leading to
discontinuation/dose reduction:
Somnolence (2%)
Abdominal pain (2%)
Nausea (2%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.12
unhealthy
n = 1953
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Population Size: 1953
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.12
Disc. AE: Somnolence...
AEs leading to
discontinuation/dose reduction:
Somnolence (0.6%)
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.12
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Disc. AE: Cerebrovascular disorder (NOS), Neuroleptic malignant syndrome...
AEs leading to
discontinuation/dose reduction:
Cerebrovascular disorder (NOS)
Neuroleptic malignant syndrome
Tardive dyskinesia
Orthostatic hypotension
Leukopenia
Neutropenia
Agranulocytosis
QT interval prolonged
Seizures
Cognitive impairment
Hyperglycemia
Diabetes mellitus
Dyslipidemia
Weight gain
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
AEs

AEs

AESignificanceDosePopulation
Abdominal pain 2%
Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
unhealthy, pediatric patients
n = 99
Health Status: unhealthy
Condition: Bipolar Mania
Age Group: pediatric patients
Population Size: 99
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
Nausea 2%
Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
unhealthy, pediatric patients
n = 99
Health Status: unhealthy
Condition: Bipolar Mania
Age Group: pediatric patients
Population Size: 99
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
Somnolence 2%
Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
unhealthy, pediatric patients
n = 99
Health Status: unhealthy
Condition: Bipolar Mania
Age Group: pediatric patients
Population Size: 99
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.16
Somnolence 0.6%
Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.12
unhealthy
n = 1953
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Population Size: 1953
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.12
Agranulocytosis Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Cerebrovascular disorder (NOS) Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Cognitive impairment Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Diabetes mellitus Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Dyslipidemia Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Hyperglycemia Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Leukopenia Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Neuroleptic malignant syndrome Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Neutropenia Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Orthostatic hypotension Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
QT interval prolonged Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Seizures Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Tardive dyskinesia Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Weight gain Disc. AE
10 mg 2 times / day multiple, sublingual
Recommended
Dose: 10 mg, 2 times / day
Route: sublingual
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
unhealthy
Health Status: unhealthy
Condition: Schizophrenia|Bipolar I disorder
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/022117s020s021lbl.pdf
Page: p.1
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
substrate
1601

inducer
707

inhibitor
1467
inhibitor
1604
inhibitor
1702

substrate
1118
inhibitor
1475

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2C19
1325

CYP1A2
1383

CYP2C8
818

CYP2A6
627
UGT1A4
330

CYP1A2
972

P-gp
1400
CYP1A2
637
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2C9
1648
 minor [Ki 105 uM]
CYP2C8
865
 minor [Ki 360 uM]
CYP1A2
1532
 no
CYP2A6
659
 no
CYP3A4
1772
 no
CYP2D6
1738
 weak [Ki 0.016 uM]
weak (co-administration study)
Comment: asenapine increased exposure of paroxetine by 2x; asenapine had no effect on imipramine in separate study, so paroxetine may be an outlier
Page: 24.0
CYP1A2
1532
 yes [Ki 1.5 uM]
CYP2C19
1392
 yes [Ki 2 uM]
CYP3A4
1772
 yes [Ki 91.4 uM]
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
UGT1A4
330
 major
no (co-administration study)
Comment: valproate has no effect on asenapine
Page: 23.0
CYP1A2
972
 major
weak (co-administration study)
Comment: fluvoxamine increased cmax of asenapine 13%, auc 29%
Page: 23.0
P-gp
1400
 no
CYP2D6
1118
 yes
no (co-administration study)
Comment: paroxetine has no effect on asenapine
Page: 30.0
CYP3A4
1601
 yes
weak (co-administration study)
Comment: cimetidine has no effect on asenapine; carbamazepine has weak effect on asenapine
Page: 30.0
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
hERG
1507
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0036UH
1PlusChem LLC
1P009CPQ
1PlusChem LLC
1P00E9LQ
A2B Chem
AB48041
AChemBlock
10451
AK Scientific
X2936
AbovChem LLC
HY-11100
AbovChem LLC
HY-16567
ApexBio Technology
A3192
ApexBio Technology
A5010
AstaTech
43030
Axon MedChem
1503
BLD Pharm
BD154848
BLD Pharm
BD630244
BOC Sciences
85650-56-2
Chem Scene
CS-0009346
Chem Scene
CS-0859
Chem Scene
CS-1053
Compound Cloud
163091
Compound Cloud
6917875
Enamine
EN300-123441
Hairui
HR104226
Hairui
HR116489
Hangzhou APIChem Technology
AC-24116
Lab Network
LN01342767
Lab Seeker
SC-82643
MedChem Express
HY-10121
MedChem Express
HY-11100
MedChem Express
HY-16567
MolPort
MolPort-006-133-817
MolPort
MolPort-006-142-524
MolPort
MolPort-023-276-919
MolPort
MolPort-046-417-148
MolPort
MolPort-046-702-063
Molnova
M15492
Molnova
M16209
MuseChem
I000516
MuseChem
I002919
MuseChem
R027114
MuseChem
R027986
MuseChem
R037024
PI Chemicals
PI-37740
ShangHai Biochempartner
BCP05157
Sigma Aldrich
A-101
Sigma Aldrich
A7861
Sigma Aldrich
A7861|SIGMA
TargetMol
T1951
Tocris
3737
Toronto Research Chemicals
A788000
Toronto Research Chemicals
A788025
Toronto Research Chemicals
M225790
ZINC
ZINC000000002299
http://zinc15.docking.org/substances/ZINC000000002299
eMolecules
106929509
eMolecules
300929760
eMolecules
303168224
eMolecules
31217067
eMolecules
43473206
eNovation Chemicals
D389071
mcule
MCULE-3469383831
mcule
MCULE-4789699486
mcule
MCULE-5342667273
mcule
MCULE-7804068322
mcule
MCULE-8379278884
PubMed

PubMed

TitleDatePubMed
Asenapine in the treatment of negative symptoms of schizophrenia: clinical trial design and rationale.
2007
Drug-drug interactions associated with second-generation antipsychotics: considerations for clinicians and patients.
2007
Efficacy and tolerability of asenapine in acute schizophrenia: a placebo- and risperidone-controlled trial.
2007 Oct
Asenapine, a novel psychopharmacologic agent: preclinical evidence for clinical effects in schizophrenia.
2008 Feb
American psychiatric association.
2008 Jun
Differential regional and dose-related effects of asenapine on dopamine receptor subtypes.
2008 May
Asenapine increases dopamine, norepinephrine, and acetylcholine efflux in the rat medial prefrontal cortex and hippocampus.
2008 Nov
Asenapine maleate: a new drug for the treatment of schizophrenia and bipolar mania.
2009 Dec
Asenapine for schizophrenia and bipolar disorder: a review of the efficacy and safety profile for this newly approved sublingually absorbed second-generation antipsychotic.
2009 Dec
Asenapine versus olanzapine in acute mania: a double-blind extension study.
2009 Dec
Asenapine restores cognitive flexibility in rats with medial prefrontal cortex lesions.
2009 Jan
Asenapine: a novel psychopharmacologic agent with a unique human receptor signature.
2009 Jan
Modeling and simulation of the time course of asenapine exposure response and dropout patterns in acute schizophrenia.
2009 Jul
Asenapine elevates cortical dopamine, noradrenaline and serotonin release. Evidence for activation of cortical and subcortical dopamine systems by different mechanisms.
2009 Jun
Electrophysiological characterization of the effects of asenapine at 5-HT(1A), 5-HT(2A), alpha(2)-adrenergic and D(2) receptors in the rat brain.
2009 Mar
Asenapine.
2009 Nov
Exposure-response analysis in patients with schizophrenia to assess the effect of asenapine on QTc prolongation.
2009 Nov
Asenapine approved for treatment of schizophrenia, bipolar disorder.
2009 Sep 15
Neuroleptic malignant syndrome after exposure to asenapine: a case report.
2010
Efficacy and safety of asenapine in a placebo- and haloperidol-controlled trial in patients with acute exacerbation of schizophrenia.
2010 Apr
Asenapine in the treatment of acute mania in bipolar I disorder: a randomized, double-blind, placebo-controlled trial.
2010 Apr
Evaluation of the clinical efficacy of asenapine in schizophrenia.
2010 Aug
A review of new atypical antipsychotic launches in the United States.
2010 Dec
Effects of asenapine, olanzapine, and risperidone on psychotomimetic-induced reversal-learning deficits in the rat.
2010 Dec 25
Asenapine (Saphris) sublingual tablets for schizophrenia and bipolar disorder.
2010 Feb 8
Asenapine, a new sublingual atypical antipsychotic.
2010 Jan
New drugs: asenapine, iloperidone, and bepotastine besilate.
2010 Jan-Feb
Effect of absorption site on the pharmacokinetics of sublingual asenapine in healthy male subjects.
2010 Jul
Long-term assessment of Asenapine vs. Olanzapine in patients with schizophrenia or schizoaffective disorder.
2010 Jun
New drug information. Saphris.
2010 Mar
Pharmacology and efficacy of asenapine for manic and mixed states in adults with bipolar disorder.
2010 May
Effects of asenapine on prefrontal N-methyl-D-aspartate receptor-mediated transmission: involvement of dopamine D1 receptors.
2010 Nov
Asenapine for long-term treatment of bipolar disorder: a double-blind 40-week extension study.
2010 Nov
A genetic network model of cellular responses to lithium treatment and cocaine abuse in bipolar disorder.
2010 Nov 19
New antipsychotic drugs: how do their receptor-binding profiles compare?
2010 Sep
Adjunctive use of atypical antipsychotics for treatment-resistant generalized anxiety disorder.
2010 Sep
[The quest for the pharmacological treatment of schizophrenia: from conventional neuroleptics to atypical antipsychotics and beyond].
2010 Sep-Oct
Patents

Patents

WO2014090386A1
2
WO2014207664A2
2

Sample Use Guides

In Vivo Use Guide
SAPHRIS is a sublingual tablet. To ensure optimal absorption, patients should be instructed to place the tablet under the tongue and allow it to dissolve completely. The tablet will dissolve in saliva within seconds. SAPHRIS sublingual tablets should not be crushed, chewed, or swallowed. Patients should be instructed to not eat or drink for 10 minutes after administration. Schizophrenia Usual Dose for Acute Treatment in Adults: The recommended starting and target dose of SAPHRIS is 5 mg given twice daily. In short term controlled trials, there was no suggestion of added benefit with a 10 mg twice daily dose, but there was a clear increase in certain adverse reactions. The safety of doses above 10 mg twice daily has not been evaluated in clinical studies. Maintenance Treatment: Efficacy was demonstrated with SAPHRIS in a maintenance trial in patients with schizophrenia. The starting dose in this study was 5 mg twice daily with an increase up to 10 mg twice daily after 1 week based on tolerability. While there is no body of evidence available to answer the question of how long the schizophrenic patient should remain on SAPHRIS, patients should be periodically reassessed to determine the need for maintenance treatment. Bipolar Disorder Usual Dose for Acute Treatment of Manic or Mixed Episodes Associated with Bipolar I Disorder in Adults: Monotherapy: The recommended starting dose of SAPHRIS, and the dose maintained by 90% of the patients studied, is 10 mg twice daily. The dose can be decreased to 5 mg twice daily if warranted by adverse effects or based on individual tolerability. In controlled monotherapy trials, the starting dose for SAPHRIS was 10 mg twice daily. On the second and subsequent days of the trials, the dose could be lowered to 5 mg twice daily, based on tolerability, but less than 10% of patients had their dose reduced. The safety of doses above 10 mg twice daily has not been evaluated in clinical trials. Adjunctive Therapy: The recommended starting dose of SAPHRIS is 5 mg twice daily when administered as adjunctive therapy with either lithium or valproate. Depending on the clinical response and tolerability in the individual patient, the dose can be increased to 10 mg twice daily. The safety of doses above 10 mg twice daily as adjunctive therapy with lithium or valproate has not been evaluated in clinical trials. Maintenance Treatment: While there is no body of evidence available to answer the question of how long the bipolar patient should remain on SAPHRIS, whether used as monotherapy or as adjunctive therapy with lithium or valproate, it is generally recommended that responding patients be continued beyond the acute response. If SAPHRIS is used for extended periods in bipolar disorder, the physician should periodically re-evaluate the long-term risks and benefits of the drug for the individual patient.
Route of Administration: Oral
In Vitro Use Guide
like clozapine (100 nM), but at a considerably lower concentration (5 nM), asenapine significantly potentiated the NMDA-induced responses in the rat medial prefrontal cortex pyramidal neurons
Substance Class Chemical
Created
by admin
on Sat Jun 26 01:21:43 UTC 2021
Edited
by admin
on Sat Jun 26 01:21:43 UTC 2021
Record UNII
JKZ19V908O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ASENAPINE
DASH   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
ASENAPINE [INN]
Common Name English
1H-DIBENZ(2,3:6,7)OXEPINO(4,5-C)PYRROLE, 5-CHLORO-2,3,3A,12B-TETRAHYDRO-2-METHYL-, (3AR,12BR)-REL-
Common Name English
ASENAPINE [WHO-DD]
Common Name English
ASENAPINE [MI]
Common Name English
ASENAPINE [ORANGE BOOK]
Common Name English
(3ARS,12BRS)-5-CHLORO-2-METHYL-2,3,3A,12B-TETRAHYDRO-1H-DIBENZO(2,3:6,7)OXEPINO(4,5-C)PYRROLE
Common Name English
ASENAPINE [VANDF]
Common Name English
SECUADO
Brand Name English
Classification Tree Code System Code
NDF-RT N0000175430
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
WHO-ATC N05AH05
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
NCI_THESAURUS C29710
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
LIVERTOX 66
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
WHO-VATC QN05AH05
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
Code System Code Type Description
EPA CompTox
65576-45-6
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
MERCK INDEX
M2091
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY Merck Index
DRUG BANK
DB06216
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL3187365
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
PUBCHEM
163091
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
EVMPD
SUB30497
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
HSDB
8061
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
MESH
C522667
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
FDA UNII
JKZ19V908O
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
RXCUI
784649
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
4115
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
CAS
65576-45-6
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
NCI_THESAURUS
C72705
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
LACTMED
Asenapine
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
IUPHAR
22
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
INN
8278
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
ECHA (EC/EINECS)
265-829-4
Created by admin on Sat Jun 26 01:21:43 UTC 2021 , Edited by admin on Sat Jun 26 01:21:43 UTC 2021
PRIMARY
Related Record Type Details
CYTOCHROME P450 2D6
METABOLIC ENZYME -> SUBSTRATE
MINOR
5-HYDROXYTRYPTAMINE RECEPTOR 2A
TARGET -> INHIBITOR
Ki
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
Structure of ASENAPINE
EXCRETED UNCHANGED
AMOUNT EXCRETED
FECAL; URINE
Structure of ASENAPINE MALEATE
SALT/SOLVATE -> PARENT
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MINOR
D(2) DOPAMINE RECEPTOR
TARGET -> INHIBITOR
Ki
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
MAJOR
URIDINE DIPHOSPHATE GLUCURONOSYLTRANSFERASE 1A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of (2S,3S,4S,5R,6S)-6-(((3ARS,12BRS)-11-CHLORO-2,3,3A,12B-TETRAHYDRO-1H-DIBENZO(2,3:6,7)OXEPINO(4,5-C)PYRROL-5-YL)OXY)-3,4,5-TRIHYDROXYTETRAHYDRO-2H-PYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
URINE
Structure of (3AS,12BS)-11-CHLORO-2,3,3A,12B-TETRAHYDRO-1H-DIBENZO(2,3:6,7)OXEPINO(4,5-C)PYRROLE-5,6-DIOL
METABOLITE -> PARENT
FECAL
Structure of 10,11-DIHYDROXYASENAPINE
METABOLITE -> PARENT
MINOR
FECAL
Structure of (2S,3S,4S,5R,6S)-6-(((3A-RS,12B-RS)-11-CHLORO-2-METHYL-2,3,3A,12B-TETRAHYDRO-1H-DIBENZO(2,3:6,7)OXEPINO(4,5-C)PYRROL-5-YL)OXY)-3,4,5-TRIHYDROXYTETRAHYDRO-2H-PYRAN-2-CARBOXYLIC ACID
METABOLITE -> PARENT
PLASMA; URINE
Structure of 1H-DIBENZ(2,3:6,7)OXEPINO(4,5-C)PYRROLE, 5-CHLORO-2,3,3A,12B-TETRAHYDRO-2-METHYL-, 2-OXIDE, (3AR,12BR)-REL-
METABOLITE -> PARENT
MINOR
PLASMA
Structure of 1H-DIBENZ(2,3:6,7)OXEPINO(4,5-C)PYRROL-5-OL, 11-CHLORO-2,3,3A,12B-TETRAHYDRO-2-METHYL-, 5-(HYDROGEN SULFATE), (3AR,12BR)-REL-
METABOLITE -> PARENT
PLASMA; URINE
Structure of 1H-DIBENZ(2,3:6,7)OXEPINO(4,5-C)PYRROLE, 5-CHLORO-2,3,3A,12B-TETRAHYDRO-, (3AR,12BR)-REL-
METABOLITE -> PARENT
FECAL; PLASMA
Related Record Type Details
Structure of ASENAPINE
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC FOLLOWING AN INITIAL MORE RAPID DISTRIBUTION PHASE

Tmax PHARMACOKINETIC SINGLE DOSE ADMINISTRATION

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