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

Stem definitionDrug idCAS RN
374 514-65-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • biperiden
  • akineton
  • biperiden hydrochloride
  • biperiden lactate
  • biperiden HCl
A muscarinic antagonist that has effects in both the central and peripheral nervous systems. It has been used in the treatment of arteriosclerotic, idiopathic, and postencephalitic parkinsonism. It has also been used to alleviate extrapyramidal symptoms induced by phenothiazine derivatives and reserpine.
  • Molecular weight: 311.47
  • Formula: C21H29NO
  • CLOGP: 4.94
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 23.47
  • ALOGS: -4.86
  • ROTB: 5

  • Status: OFM

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

Drug dosage:

DoseUnitRoute
10 mg O
10 mg P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 1 mg/mL Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.64 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 30 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
fu (Fraction unbound in plasma) 0.10 % Lombardo F, Berellini G, Obach RS
Vd (Volume of distribution) 12 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 12 mL/min/kg Lombardo F, Berellini G, Obach RS
t_half (Half-life) 24 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Sept. 8, 1959 FDA ABBVIE

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
Suicide attempt 197.71 56.19 48 414 11234 2346389
Neuroleptic malignant syndrome 178.65 56.19 33 429 2047 2355576
Intentional overdose 166.99 56.19 42 420 11279 2346344
Sopor 145.64 56.19 31 431 3964 2353659
Intentional self-injury 127.70 56.19 28 434 4099 2353524
Somnolence 111.41 56.19 36 426 23449 2334174
Delirium 100.04 56.19 24 438 5199 2352424
Dyskinesia 96.86 56.19 23 439 4766 2352857
Confusional state 90.12 56.19 31 431 24313 2333310
Drug abuse 89.00 56.19 26 436 12000 2345623
Tremor 87.02 56.19 29 433 20632 2336991
Inappropriate affect 85.15 56.19 13 449 244 2357379
Coma 82.31 56.19 23 439 9033 2348590
Logorrhoea 76.79 56.19 13 449 476 2357147
Extrapyramidal disorder 67.30 56.19 15 447 2332 2355291
Urinary incontinence 63.45 56.19 16 446 4217 2353406
Disorganised speech 61.33 56.19 9 453 127 2357496
Agitation 56.43 56.19 18 444 11033 2346590

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
Neuroleptic malignant syndrome 247.84 57.00 51 454 3097 1743179
Intentional self-injury 208.30 57.00 43 462 2630 1743646
Delirium 151.31 57.00 39 466 6323 1739953
Disorientation 103.32 57.00 28 477 5441 1740835
Intentional overdose 93.95 57.00 28 477 7642 1738634
Sopor 86.93 57.00 20 485 1981 1744295
Confusional state 86.74 57.00 34 471 21244 1725032
Ileus paralytic 77.51 57.00 16 489 951 1745325
Suicide attempt 73.47 57.00 23 482 7358 1738918
Sedation 71.49 57.00 19 486 3398 1742878
Altered state of consciousness 71.06 57.00 19 486 3478 1742798
Coma 69.64 57.00 22 483 7240 1739036
Overdose 69.01 57.00 27 478 16674 1729602
Hyponatraemia 68.98 57.00 23 482 8977 1737299
Agitation 68.23 57.00 24 481 11002 1735274
Restlessness 67.07 57.00 19 486 4302 1741974
Intentional product misuse 65.22 57.00 21 484 7337 1738939
Dyskinesia 60.19 57.00 17 488 3802 1742474
Condition aggravated 59.54 57.00 26 479 21124 1725152
Blood creatine phosphokinase increased 57.50 57.00 20 485 8836 1737440

Pharmacologic Action:

SourceCodeDescription
ATC N04AA02 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
ANTICHOLINERGIC AGENTS
Tertiary amines
CHEBI has role CHEBI:136860 antidote to sarin poisoning
CHEBI has role CHEBI:66956 antidyskinesia agent
CHEBI has role CHEBI:48876 muscarinic antagonist
CHEBI has role CHEBI:50370 parasympatholytic
CHEBI has role CHEBI:48407 antiparkinson drug
MeSH PA D018726 Anti-Dyskinesia Agents
MeSH PA D000978 Antiparkinson Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D018678 Cholinergic Agents
MeSH PA D018680 Cholinergic Antagonists
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents
FDA EPC N0000175574 Anticholinergic

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Postencephalitic parkinsonism indication 19972008 DOID:14332
Parkinsonism indication 32798002
Parkinson's disease indication 49049000 DOID:14330
Extrapyramidal disease indication 76349003
Arteriosclerotic Parkinsonism indication
Urinary tract obstruction contraindication 7163005 DOID:5200
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Severe chronic ulcerative colitis contraindication 14311001
Disorder of autonomic nervous system contraindication 15241006
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Shigellosis contraindication 36188001
Hypertensive disorder contraindication 38341003 DOID:10763
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Dysuria contraindication 49650001
Paralytic ileus contraindication 55525008 DOID:8442
Ulcerative colitis contraindication 64766004 DOID:8577
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Myasthenia gravis contraindication 91637004 DOID:437
Tardive dyskinesia contraindication 102449007
Dysentery contraindication 111939009
Gastrointestinal obstruction contraindication 126765001
Bleeding contraindication 131148009
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Benign prostatic hyperplasia contraindication 266569009
Retention of urine contraindication 267064002
Fever contraindication 386661006
Angle-closure glaucoma contraindication 392291006 DOID:13550
Pseudomembranous enterocolitis contraindication 397683000
Gastric ulcer contraindication 397825006 DOID:10808
Disorder of coronary artery contraindication 414024009

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.2 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Muscarinic acetylcholine receptor M1 GPCR ANTAGONIST Kd 9.32 IUPHAR CHEMBL
Muscarinic acetylcholine receptor M5 GPCR Ki 8.20 PDSP
Neuronal acetylcholine receptor subunit alpha-2 Ion channel WOMBAT-PK
Muscarinic acetylcholine receptor M2 GPCR ANTAGONIST Kd 8.20 IUPHAR
Muscarinic acetylcholine receptor M3 GPCR ANTAGONIST Kd 8.41 IUPHAR
Muscarinic acetylcholine receptor M4 GPCR ANTAGONIST Kd 8.62 IUPHAR

External reference:

IDSource
D001712 MESH_DESCRIPTOR_UI
4019635 VUID
N0000147728 NUI
C0005578 UMLSCUI
D00779 KEGG_DRUG
09TD6C5147 UNII
7085-45-2 SECONDARY_CAS_RN
915 INN_ID
65041000 SNOMEDCT_US
4019635 VANDF
001644 NDDF
1589 RXNORM
387359004 SNOMEDCT_US
4285 MMSL
d00972 MMSL
CHEMBL1101 ChEMBL_ID
DB00810 DRUGBANK_ID
CHEBI:3112 CHEBI
7128 IUPHAR_LIGAND_ID
2381 PUBCHEM_CID
CHEMBL1201035 ChEMBL_ID
CHEMBL1201067 ChEMBL_ID
C036432 MESH_SUPPLEMENTAL_RECORD_UI

Pharmaceutical products:

None