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

Stem definitionDrug idCAS RN
1999 83-98-7

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • disipal
  • orphenadrine
  • orphenadine
  • orphenadrin
  • orphenadrine citrate
  • orphenadrine hydrochloride
  • orphenadrine (chloride)
  • orphenadrine HCl
A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.
  • Molecular weight: 269.39
  • Formula: C18H23NO
  • CLOGP: 3.90
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 12.47
  • ALOGS: -3.95
  • ROTB: 6

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.20 g O
0.20 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 10 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 8 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 21.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 90 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
May 10, 1957 FDA

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
Completed suicide 128.90 48.99 30 108 21004 2336943
Toxicity to various agents 125.72 48.99 32 106 32722 2325225
Intentional self-injury 65.24 48.99 13 125 4114 2353833
Drug abuse 56.43 48.99 14 124 12012 2345935

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

Pharmacologic Action:

SourceCodeDescription
ATC M03BC51 MUSCULO-SKELETAL SYSTEM
MUSCLE RELAXANTS
MUSCLE RELAXANTS, CENTRALLY ACTING AGENTS
Ethers, chemically close to antihistamines
ATC N04AB02 NERVOUS SYSTEM
ANTI-PARKINSON DRUGS
ANTICHOLINERGIC AGENTS
Ethers chemically close to antihistamines
FDA PE N0000175730 Centrally-mediated Muscle Relaxation
CHEBI has role CHEBI:66956 antidyskinesia agent
CHEBI has role CHEBI:37955 H1-receptor antagonist
CHEBI has role CHEBI:48407 antiparkinson drug
CHEBI has role CHEBI:50370 parasympatholytic
CHEBI has role CHEBI:51371 muscle relaxant
CHEBI has role CHEBI:48876 muscarinic antagonist
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 D065686 Cytochrome P-450 CYP2B6 Inhibitors
MeSH PA D065607 Cytochrome P-450 Enzyme Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D065606 Metabolic Side Effects of Drugs and Substances
MeSH PA D018727 Muscarinic Antagonists
MeSH PA D009125 Muscle Relaxants, Central
MeSH PA D009465 Neuromuscular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010276 Parasympatholytics
MeSH PA D018373 Peripheral Nervous System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Parkinsonism indication 32798002
Spasticity indication 221360009
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Tachyarrhythmia contraindication 6285003
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Glaucoma contraindication 23986001 DOID:1686
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Conduction disorder of the heart contraindication 44808001
Achalasia of esophagus contraindication 45564002 DOID:9164
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Hemophilia contraindication 90935002
Myasthenia gravis contraindication 91637004 DOID:437
Obstruction of duodenum contraindication 95532008 DOID:3558
Anemia due to enzyme deficiency contraindication 111577008
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Decompensated cardiac failure contraindication 195111005
Impaired renal function disorder contraindication 197663003
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Anemia contraindication 271737000 DOID:2355
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Panic disorder contraindication 371631005 DOID:594
Breastfeeding (mother) contraindication 413712001
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Acute erosive gastritis contraindication 444926003

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.52 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
Sodium channel protein type 1 subunit alpha Ion channel BLOCKER IC50 4.89 WOMBAT-PK CHEMBL
Histamine H1 receptor GPCR ANTAGONIST Ki 7.96 WOMBAT-PK CHEMBL
Sodium channel protein type 5 subunit alpha Ion channel BLOCKER IC50 4.89 WOMBAT-PK CHEMBL
Sodium channel protein type 9 subunit alpha Ion channel BLOCKER IC50 4.76 WOMBAT-PK CHEMBL
Sodium channel protein type 4 subunit alpha Ion channel BLOCKER Ki 5.66 WOMBAT-PK CHEMBL
Sodium channel protein type 10 subunit alpha Ion channel BLOCKER IC50 5.20 WOMBAT-PK CHEMBL
5-hydroxytryptamine receptor 2C GPCR Ki 6.55 DRUG MATRIX
5-hydroxytryptamine receptor 6 GPCR Ki 6.28 DRUG MATRIX
Alpha-2B adrenergic receptor GPCR Ki 6.06 DRUG MATRIX
Histamine H2 receptor GPCR Ki 5.16 DRUG MATRIX
Muscarinic acetylcholine receptor M2 GPCR Ki 6.87 DRUG MATRIX
Muscarinic acetylcholine receptor M3 GPCR Ki 7.43 DRUG MATRIX
Muscarinic acetylcholine receptor M4 GPCR Ki 7.77 DRUG MATRIX
Muscarinic acetylcholine receptor M5 GPCR Ki 7.70 DRUG MATRIX
Cytochrome P450 2D6 Enzyme IC50 6.40 DRUG MATRIX
Solute carrier family 22 member 1 Transporter IC50 4.90 CHEMBL
Muscarinic acetylcholine receptor M1 GPCR Ki 7.39 WOMBAT-PK
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.17 WOMBAT-PK
Glutamate [NMDA] receptor Ion channel Ki 5.22 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 6.09 DRUG MATRIX
Sodium-dependent serotonin transporter Transporter Ki 6.61 DRUG MATRIX
Sodium-dependent noradrenaline transporter Transporter INHIBITOR Ki 5.58 DRUG MATRIX
5-hydroxytryptamine receptor 2A GPCR Ki 6.90 DRUG MATRIX
5-hydroxytryptamine receptor 2B GPCR Ki 5.67 DRUG MATRIX
Histamine H1 receptor GPCR IC50 6.79 CHEMBL

External reference:

IDSource
4019866 VUID
N0000147952 NUI
C0029309 UMLSCUI
D00774 KEGG_DRUG
35035001 SNOMEDCT_US
4019866 VANDF
7715 RXNORM
372714007 SNOMEDCT_US
d00966 MMSL
001648 NDDF
AL805O9OG9 UNII
658 INN_ID
CHEBI:7789 CHEBI
CHEMBL900 ChEMBL_ID
CHEMBL1200395 ChEMBL_ID
341-69-5 SECONDARY_CAS_RN
DB01173 DRUGBANK_ID
4601 PUBCHEM_CID
CHEMBL1201023 ChEMBL_ID
D009966 MESH_DESCRIPTOR_UI
7251 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0115-2011 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 11 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0185-0022 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 14 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 0591-3222 INJECTION 30 mg INTRAMUSCULAR ANDA 10 sections
Orphenadrine citrate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6182 INJECTION 60 mg INTRAMUSCULAR ANDA 13 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 10544-283 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
ORPHENADRINE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 16590-177 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 10 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 17478-538 INJECTION 30 mg INTRAMUSCULAR ANDA 13 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 21695-099 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate, Aspirin and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 21695-726 TABLET, MULTILAYER 50 mg ORAL ANDA 11 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 33261-088 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 33358-274 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
ORPHENADRINE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 42549-559 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
ORPHENADRINE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 43063-407 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
ORPHENADRINE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 43386-480 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 45865-363 TABLET 100 mg ORAL ANDA 14 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 49999-046 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 11 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 50090-0169 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 50090-3150 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 14 sections
Norgesic Forte HUMAN PRESCRIPTION DRUG LABEL 3 50991-999 TABLET, MULTILAYER 50 mg ORAL ANDA 11 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 52959-527 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 13 sections
ORPHENADRINE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 54868-4102 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 60760-810 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphengesic Forte HUMAN PRESCRIPTION DRUG LABEL 3 61825-999 TABLET 50 mg ORAL ANDA 10 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 61919-177 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 11 sections
ORPHENADRINE CITRATE HUMAN PRESCRIPTION DRUG LABEL 1 61919-507 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 11 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 63187-122 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 63187-632 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 14 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 63629-1564 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 66267-158 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections
Orphenadrine Citrate HUMAN PRESCRIPTION DRUG LABEL 1 66336-554 TABLET, EXTENDED RELEASE 100 mg ORAL ANDA 12 sections