asenapine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
psychoactive 4115 65576-45-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • Org-5222
  • Org 5222
  • asenapine
  • saphris
  • asenapine maleate
  • sycrest
  • Molecular weight: 285.77
  • Formula: C17H16ClNO
  • CLOGP: 4.58
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -3.96
  • ROTB: 0

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
20 mg O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.71 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 23 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 12.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.05 % Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Aug. 13, 2009 FDA FOREST LABS INC

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Inappropriate schedule of product administration 587.90 29.65 257 7032 64756 46614017
Anosognosia 494.77 29.65 97 7192 1308 46677465
Blood prolactin abnormal 490.74 29.65 95 7194 1194 46677579
Disturbance in social behaviour 468.68 29.65 96 7193 1635 46677138
Underdose 446.54 29.65 152 7137 19406 46659367
Sedation 445.75 29.65 158 7131 22752 46656021
Dystonia 445.36 29.65 133 7156 11124 46667649
Hypoaesthesia oral 440.58 29.65 130 7159 10429 46668344
Sexual dysfunction 431.75 29.65 95 7194 2308 46676465
Metabolic disorder 368.98 29.65 94 7195 4338 46674435
Personality change 343.55 29.65 92 7197 5166 46673607
Dyskinesia 322.56 29.65 133 7156 28792 46649981
Incorrect route of product administration 310.88 29.65 111 7178 16272 46662501
Akathisia 274.25 29.65 84 7205 7630 46671143
Suicide attempt 205.84 29.65 120 7169 54916 46623857
Schizophrenia 177.43 29.65 62 7227 8506 46670267
Blood glucose increased 173.81 29.65 119 7170 71894 46606879
Dysgeusia 137.44 29.65 83 7206 40408 46638365
Weight increased 120.61 29.65 138 7151 164335 46514438
Swollen tongue 117.83 29.65 67 7222 29165 46649608
Mania 91.46 29.65 41 7248 10805 46667968
Tardive dyskinesia 81.59 29.65 34 7255 7509 46671264
Tooth discolouration 81.38 29.65 20 7269 792 46677981
Insurance issue 78.91 29.65 23 7266 1755 46677018
Extrapyramidal disorder 71.50 29.65 35 7254 11233 46667540
Suicidal ideation 62.22 29.65 59 7230 56323 46622450
Glossodynia 61.92 29.65 53 7236 44320 46634453
Restless legs syndrome 60.29 29.65 35 7254 15808 46662965
Oropharyngeal blistering 51.66 29.65 14 7275 818 46677955
Oral discomfort 48.46 29.65 24 7265 7894 46670879
Tongue blistering 48.06 29.65 15 7274 1443 46677330
Diarrhoea 44.56 29.65 16 7273 559586 46119187
Somnolence 44.40 29.65 84 7205 156437 46522336
Psychotic disorder 37.76 29.65 30 7259 22591 46656182
Agitation 34.68 29.65 43 7246 55372 46623401
Drooling 33.14 29.65 14 7275 3195 46675578
Increased appetite 32.86 29.65 19 7270 8508 46670265
Product taste abnormal 32.33 29.65 12 7277 1951 46676822
Parkinsonism 31.40 29.65 18 7271 7930 46670843
Bipolar I disorder 31.26 29.65 11 7278 1535 46677238
Restlessness 30.62 29.65 28 7261 25496 46653277
Cataplexy 30.28 29.65 10 7279 1153 46677620

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Anosognosia 271.40 34.41 52 4451 642 29947333
Akathisia 268.19 34.41 77 4426 5827 29942148
Sedation 266.54 34.41 98 4405 16275 29931700
Blood prolactin abnormal 243.53 34.41 48 4455 693 29947282
Suicide attempt 222.92 34.41 109 4394 36588 29911387
Dystonia 222.38 34.41 75 4428 9652 29938323
Inappropriate schedule of product administration 211.79 34.41 108 4395 39620 29908355
Disturbance in social behaviour 210.72 34.41 48 4455 1423 29946552
Sexual dysfunction 172.29 34.41 55 4448 5946 29942029
Metabolic disorder 167.93 34.41 48 4455 3563 29944412
Dyskinesia 154.15 34.41 72 4431 21762 29926213
Antipsychotic drug level below therapeutic 145.03 34.41 35 4468 1337 29946638
Therapeutic product effect variable 144.60 34.41 35 4468 1354 29946621
Disinhibition 137.49 34.41 36 4467 1921 29946054
Obsessive-compulsive disorder 131.49 34.41 41 4462 4100 29943875
Schizophrenia 124.65 34.41 48 4455 9000 29938975
Increased appetite 123.12 34.41 42 4461 5575 29942400
Underdose 120.93 34.41 51 4452 12090 29935885
Hypoaesthesia oral 120.31 34.41 37 4466 3533 29944442
Personality change 119.12 34.41 39 4464 4561 29943414
Euphoric mood 109.58 34.41 36 4467 4254 29943721
Incorrect route of product administration 97.78 34.41 43 4460 11272 29936703
Emotional poverty 92.77 34.41 19 4484 335 29947640
Weight increased 78.92 34.41 75 4428 74838 29873137
Blood glucose increased 69.38 34.41 64 4439 61466 29886509
Dysgeusia 66.04 34.41 43 4460 24758 29923217
Drug ineffective 62.50 34.41 149 4354 340238 29607737
Swollen tongue 61.88 34.41 33 4470 13159 29934816
Extrapyramidal disorder 59.49 34.41 30 4473 10663 29937312
Therapeutic product effect incomplete 54.04 34.41 43 4460 33791 29914184
Dyslipidaemia 53.47 34.41 23 4480 5704 29942271
Suicidal ideation 51.57 34.41 43 4460 36071 29911904
Obesity 47.58 34.41 24 4479 8531 29939444
Mania 43.20 34.41 23 4480 9131 29938844
Prescribed overdose 38.97 34.41 21 4482 8540 29939435
Agitation 38.58 34.41 44 4459 54029 29893946
Oculogyric crisis 36.96 34.41 12 4491 1363 29946612
Parkinsonism 36.39 34.41 19 4484 7250 29940725

Pharmacologic Action:

SourceCodeDescription
ATC N05AH05 NERVOUS SYSTEM
PSYCHOLEPTICS
ANTIPSYCHOTICS
Diazepines, oxazepines, thiazepines and oxepines
FDA EPC N0000175430 Atypical Antipsychotic
MeSH PA D014150 Antipsychotic Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D011619 Psychotropic Drugs
MeSH PA D014149 Tranquilizing Agents
CHEBI has role CHEBI:35471 psychopharmaceuticals
CHEBI has role CHEBI:35530 beta-adrenoceptor antagonists
CHEBI has role CHEBI:37890 alpha-adrenoceptor antagonists
CHEBI has role CHEBI:48279 serotonin antagonists
CHEBI has role CHEBI:48561 dopamine blocker
CHEBI has role CHEBI:65191 atypical antipsychotics

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Mixed bipolar I disorder indication 16506000 DOID:3312
Schizophrenia indication 58214004 DOID:5419
Bipolar affective disorder, current episode manic indication 191618007
Depression Treatment Adjunct off-label use
Suicidal thoughts contraindication 6471006
Weight gain finding contraindication 8943002
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Agranulocytosis contraindication 17182001 DOID:12987
Lowered convulsive threshold contraindication 19260006
Myocardial infarction contraindication 22298006 DOID:5844
Alzheimer's disease contraindication 26929004 DOID:10652
Hypovolemia contraindication 28560003
Orthostatic hypotension contraindication 28651003
Torsades de pointes contraindication 31722008
Dehydration contraindication 34095006
Dysphagia contraindication 40739000
Hypokalemia contraindication 43339004
Bradycardia contraindication 48867003
Hepatic failure contraindication 59927004
Cerebrovascular disease contraindication 62914000 DOID:6713
Diabetes mellitus contraindication 73211009 DOID:9351
Hyperglycemia contraindication 80394007 DOID:4195
Leukopenia contraindication 84828003 DOID:615
Tardive dyskinesia contraindication 102449007
Prolonged QT interval contraindication 111975006
Seizure disorder contraindication 128613002
Hypomagnesemia contraindication 190855004
Cerebrovascular accident contraindication 230690007
Hyperprolactinemia contraindication 237662005 DOID:12700
Transient ischemic attack contraindication 266257000 DOID:224
Esophageal dysmotility contraindication 266434009 DOID:9192
Syncope contraindication 271594007
Neutropenic disorder contraindication 303011007 DOID:1227
Senile dementia with psychosis contraindication 371026009
At risk for aspiration contraindication 371736008
Impaired cognition contraindication 386806002
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Congenital long QT syndrome contraindication 442917000

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.13 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
EQ 10MG BASE ASENULLPINE MALEATE ALEMBIC PHARMS LTD A206098 Dec. 10, 2020 RX TABLET SUBLINGUAL June 8, 2021 PATENT CHALLENGE
3.8MG/24HR SECUADO HISAMITSU N212268 Oct. 11, 2019 RX SYSTEM TRANSDERMAL Oct. 11, 2022 NEW PRODUCT
5.7MG/24HR SECUADO HISAMITSU N212268 Oct. 11, 2019 RX SYSTEM TRANSDERMAL Oct. 11, 2022 NEW PRODUCT
7.6MG/24HR SECUADO HISAMITSU N212268 Oct. 11, 2019 RX SYSTEM TRANSDERMAL Oct. 11, 2022 NEW PRODUCT

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
5-hydroxytryptamine receptor 2A GPCR ANTAGONIST Ki 9.61 WOMBAT-PK CHEMBL
D(2) dopamine receptor GPCR ANTAGONIST Ki 8.75 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 5A GPCR Ki 8.60 WOMBAT-PK
D(4) dopamine receptor GPCR Ki 8.71 WOMBAT-PK
5-hydroxytryptamine receptor 1B GPCR Ki 8.40 WOMBAT-PK
Histamine H2 receptor GPCR IC50 8.21 WOMBAT-PK
Histamine H1 receptor GPCR Ki 9 WOMBAT-PK
D(3) dopamine receptor GPCR Ki 9.06 WOMBAT-PK
Alpha-2B adrenergic receptor GPCR Ki 8.73 WOMBAT-PK
Alpha-1A adrenergic receptor GPCR Ki 8.92 WOMBAT-PK
5-hydroxytryptamine receptor 7 GPCR Ki 9.47 WOMBAT-PK
5-hydroxytryptamine receptor 6 GPCR Ki 9.22 WOMBAT-PK
5-hydroxytryptamine receptor 2C GPCR Ki 9.93 WOMBAT-PK
5-hydroxytryptamine receptor 2B GPCR Ki 9.80 WOMBAT-PK
5-hydroxytryptamine receptor 1A GPCR Ki 7.97 WOMBAT-PK
D(1A) dopamine receptor GPCR Ki 8.70 WOMBAT-PK
D(1B) dopamine receptor GPCR Ki 7.64 PDSP
Alpha-2C adrenergic receptor GPCR Ki 7.89 PDSP
Muscarinic acetylcholine receptor M5 GPCR Ki 6.57 PDSP
5-hydroxytryptamine receptor 3A Ion channel Ki 6.35 PDSP
Muscarinic acetylcholine receptor M1 GPCR Ki 6.11 PDSP
Muscarinic acetylcholine receptor M2 GPCR Ki 6.04 PDSP
Sodium-dependent dopamine transporter Transporter Ki 5.50 PDSP
Muscarinic acetylcholine receptor M3 GPCR Ki 5.49 PDSP
Beta-2 adrenergic receptor GPCR Ki 5.30 PDSP
Beta-1 adrenergic receptor GPCR Ki 5.30 PDSP
5-hydroxytryptamine receptor 1E GPCR AGONIST Ki 8 IUPHAR
Alpha-1B adrenergic receptor GPCR Ki 8.41 PDSP
5-hydroxytryptamine receptor 1D GPCR AGONIST Ki 8.40 IUPHAR
Alpha-2A adrenergic receptor GPCR Ki 8.19 PDSP

External reference:

IDSource
JKZ19V908O UNII
4029058 VUID
N0000179817 NUI
D02995 KEGG_DRUG
85650-56-2 SECONDARY_CAS_RN
4029058 VANDF
C2000088 UMLSCUI
CHEBI:71253 CHEBI
CHEMBL3187365 ChEMBL_ID
CHEMBL3544974 ChEMBL_ID
DB06216 DRUGBANK_ID
163091 PUBCHEM_CID
8278 INN_ID
C522667 MESH_SUPPLEMENTAL_RECORD_UI
22 IUPHAR_LIGAND_ID
784649 RXNORM
167374 MMSL
26689 MMSL
341671 MMSL
d07473 MMSL
013233 NDDF
013234 NDDF
443374004 SNOMEDCT_US
443375003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0052-0118 TABLET 5 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0052-0119 TABLET 10 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0052-2139 TABLET 5 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0052-2142 TABLET 10 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0456-2402 TABLET 2.50 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0456-2405 TABLET 5 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 0456-2410 TABLET 10 mg SUBLINGUAL NDA 33 sections
SAPHRIS HUMAN PRESCRIPTION DRUG LABEL 1 16590-936 TABLET 10 mg SUBLINGUAL NDA 34 sections
ASENULLPINE HUMAN PRESCRIPTION DRUG LABEL 1 42794-016 TABLET 5 mg SUBLINGUAL ANDA 21 sections
ASENULLPINE HUMAN PRESCRIPTION DRUG LABEL 1 42794-017 TABLET 10 mg SUBLINGUAL ANDA 21 sections
Asenapine Human Prescription Drug Label 1 46708-198 TABLET 5 mg SUBLINGUAL ANDA 30 sections
Asenapine Human Prescription Drug Label 1 46708-199 TABLET 10 mg SUBLINGUAL ANDA 30 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 51991-358 TABLET 5 mg SUBLINGUAL ANDA 36 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 51991-359 TABLET 5 mg SUBLINGUAL ANDA 36 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 51991-360 TABLET 10 mg SUBLINGUAL ANDA 36 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 51991-361 TABLET 10 mg SUBLINGUAL ANDA 36 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 51991-928 TABLET 2.50 mg SUBLINGUAL ANDA 36 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 59762-1091 TABLET 2.50 mg SUBLINGUAL NDA AUTHORIZED GENERIC 33 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 59762-2012 TABLET 5 mg SUBLINGUAL NDA AUTHORIZED GENERIC 33 sections
Asenapine HUMAN PRESCRIPTION DRUG LABEL 1 59762-2888 TABLET 10 mg SUBLINGUAL NDA AUTHORIZED GENERIC 33 sections
Asenapine Human Prescription Drug Label 1 62332-198 TABLET 5 mg SUBLINGUAL ANDA 30 sections
Asenapine Human Prescription Drug Label 1 62332-199 TABLET 10 mg SUBLINGUAL ANDA 30 sections
Asenapine Maleate HUMAN PRESCRIPTION DRUG LABEL 1 64330-625 TABLET 2.50 1 SUBLINGUAL ANDA 1 sections
SECUADO HUMAN PRESCRIPTION DRUG LABEL 1 68968-0172 FILM, EXTENDED RELEASE 3.80 mg TRANSDERMAL NDA 32 sections
SECUADO HUMAN PRESCRIPTION DRUG LABEL 1 68968-0173 FILM, EXTENDED RELEASE 5.70 mg TRANSDERMAL NDA 32 sections
SECUADO HUMAN PRESCRIPTION DRUG LABEL 1 68968-0174 FILM, EXTENDED RELEASE 7.60 mg TRANSDERMAL NDA 32 sections
Asenapine Human Prescription Drug Label 1 69539-059 TABLET 10 mg SUBLINGUAL ANDA 20 sections