Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C17H16ClNO |
| Molecular Weight | 285.768 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12CN(C)C[C@]1([H])C3=C(OC4=CC=C(Cl)C=C24)C=CC=C3
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
DescriptionCurator'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
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P14416 Gene ID: 1813.0 Gene Symbol: DRD2 Target Organism: Homo sapiens (Human) |
1.3 nM [Ki] | ||
Target ID: P28223 Gene ID: 3356.0 Gene Symbol: HTR2A Target Organism: Homo sapiens (Human) |
0.06 nM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | SAPHRIS Approved UseSAPHRIS 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 Date2009 |
|||
| Primary | SAPHRIS Approved UseSAPHRIS 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 Date2009 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
4.73 ng/mL |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
32.1 ng × h/mL |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
30 h |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5% |
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
| Dose | Population | Adverse 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: Page: p.16 |
unhealthy, pediatric patients n = 99 Health Status: unhealthy Condition: Bipolar Mania Age Group: pediatric patients Population Size: 99 Sources: Page: p.16 |
Disc. AE: Somnolence, Abdominal pain... AEs leading to discontinuation/dose reduction: Somnolence (2%) Sources: Page: p.16Abdominal pain (2%) Nausea (2%) |
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: Page: p.12 |
unhealthy n = 1953 Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Population Size: 1953 Sources: Page: p.12 |
Disc. AE: Somnolence... AEs leading to discontinuation/dose reduction: Somnolence (0.6%) Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: Page: p.1 |
Disc. AE: Cerebrovascular disorder (NOS), Neuroleptic malignant syndrome... AEs leading to discontinuation/dose reduction: Cerebrovascular disorder (NOS) Sources: Page: p.1Neuroleptic malignant syndrome Tardive dyskinesia Orthostatic hypotension Leukopenia Neutropenia Agranulocytosis QT interval prolonged Seizures Cognitive impairment Hyperglycemia Diabetes mellitus Dyslipidemia Weight gain |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: Page: p.16 |
unhealthy, pediatric patients n = 99 Health Status: unhealthy Condition: Bipolar Mania Age Group: pediatric patients Population Size: 99 Sources: 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: Page: p.16 |
unhealthy, pediatric patients n = 99 Health Status: unhealthy Condition: Bipolar Mania Age Group: pediatric patients Population Size: 99 Sources: 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: Page: p.16 |
unhealthy, pediatric patients n = 99 Health Status: unhealthy Condition: Bipolar Mania Age Group: pediatric patients Population Size: 99 Sources: 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: Page: p.12 |
unhealthy n = 1953 Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Population Size: 1953 Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Schizophrenia|Bipolar I disorder Sources: Page: p.1 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| minor [Ki 105 uM] | ||||
| minor [Ki 360 uM] | ||||
| no | ||||
| no | ||||
| no | ||||
| 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 |
|||
| yes [Ki 1.5 uM] | ||||
| yes [Ki 2 uM] | ||||
| yes [Ki 91.4 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | no (co-administration study) Comment: valproate has no effect on asenapine Page: 23.0 |
|||
| major | weak (co-administration study) Comment: fluvoxamine increased cmax of asenapine 13%, auc 29% Page: 23.0 |
|||
| no | ||||
| yes | no (co-administration study) Comment: paroxetine has no effect on asenapine Page: 30.0 |
|||
| yes | weak (co-administration study) Comment: cimetidine has no effect on asenapine; carbamazepine has weak effect on asenapine Page: 30.0 |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Asenapine in the treatment of negative symptoms of schizophrenia: clinical trial design and rationale. | 2007 |
|
| Efficacy and tolerability of asenapine in acute schizophrenia: a placebo- and risperidone-controlled trial. | 2007 Oct |
|
| Bipolar depression: trial-based insights to guide patient care. | 2008 |
|
| Acute and long-term treatment of mania. | 2008 |
|
| Asenapine, a novel psychopharmacologic agent: preclinical evidence for clinical effects in schizophrenia. | 2008 Feb |
|
| Actions of novel agonists, antagonists and antipsychotic agents at recombinant rat 5-HT6 receptors: a comparative study of coupling to G alpha s. | 2008 Jul 7 |
|
| 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 monotherapy in the acute treatment of both schizophrenia and bipolar I disorder. | 2009 |
|
| 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 exerts distinctive regional effects on ionotropic glutamate receptor subtypes in rat brain. | 2009 May |
|
| Asenapine. | 2009 Nov |
|
| Exposure-response analysis in patients with schizophrenia to assess the effect of asenapine on QTc prolongation. | 2009 Nov |
|
| A 3-week, randomized, placebo-controlled trial of asenapine in the treatment of acute mania in bipolar mania and mixed states. | 2009 Nov |
|
| Asenapine effects in animal models of psychosis and cognitive function. | 2009 Nov |
|
| Asenapine. | 2009 Sep |
|
| 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 |
|
| Repeated effects of asenapine on adrenergic and cholinergic muscarinic receptors. | 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 |
|
| Asenapine induces differential regional effects on serotonin receptor subtypes. | 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
Sample Use Guides
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
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| Classification Tree | Code System | Code | ||
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NDF-RT |
N0000175430
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WHO-ATC |
N05AH05
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NCI_THESAURUS |
C29710
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LIVERTOX |
NBK548092
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WHO-VATC |
QN05AH05
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DTXSID8049048
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JKZ19V908O
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71253
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m2091
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DB06216
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100000115346
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CHEMBL3187365
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163091
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SUB30497
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8061
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C522667
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JKZ19V908O
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784649
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4115
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65576-45-6
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C72705
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Asenapine
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22
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8278
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265-829-4
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
SALT/SOLVATE (PARENT)
