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    Orphenadrine

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    2D Structure
    Also known as: 4682-36-4, Norflex, Banflex, Orphenadrine dihydrogen citrate, Flexon, Orphenadrine (citrate)
    Molecular Formula
    C24H31NO8
    Molecular Weight
    461.5  g/mol
    InChI Key
    MMMNTDFSPSQXJP-UHFFFAOYSA-N
    FDA UNII
    X0A40N8I4S
    A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    N,N-dimethyl-2-[(2-methylphenyl)-phenylmethoxy]ethanamine;2-hydroxypropane-1,2,3-tricarboxylic acid
    2.1.2 InChI
    InChI=1S/C18H23NO.C6H8O7/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16;7-3(8)1-6(13,5(11)12)2-4(9)10/h4-12,18H,13-14H2,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
    2.1.3 InChI Key
    MMMNTDFSPSQXJP-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=CC=CC=C1C(C2=CC=CC=C2)OCCN(C)C.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    X0A40N8I4S
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Citrate, Norflex Orphenadrine

    2. Citrate, Orphenadrine

    3. Disipal

    4. Hydrochloride, Orphenadrine

    5. Lysantin

    6. Mefenamine

    7. Mefenamine, Sodium

    8. Mephenamine

    9. Methyldiphenylhydramine

    10. Norflex

    11. Norflex Orphenadrine Citrate

    12. Orphenadrine

    13. Orphenadrine Citrate, Norflex

    14. Orphenadrine Hydrochloride

    15. Sodium Mefenamine

    2.3.2 Depositor-Supplied Synonyms

    1. 4682-36-4

    2. Norflex

    3. Banflex

    4. Orphenadrine Dihydrogen Citrate

    5. Flexon

    6. Orphenadrine (citrate)

    7. Flexoject

    8. X-otag

    9. Orphenadrine Citrate Salt

    10. 2-hydroxypropane-1,2,3-tricarboxylic Acid; Dimethyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine

    11. 4596-23-0

    12. Nsc-757238

    13. Orphenadrine Citrate [usp]

    14. N,n-dimethyl-2-[(2-methylphenyl)-phenylmethoxy]ethanamine;2-hydroxypropane-1,2,3-tricarboxylic Acid

    15. Orphenadrine Citrate (norflex)

    16. Chebi:7790

    17. X0a40n8i4s

    18. N,n-dimethyl-2-(phenyl(o-tolyl)methoxy)ethanamine 2-hydroxypropane-1,2,3-tricarboxylate

    19. Ncgc00094745-01

    20. Plenactol

    21. Euflex

    22. Flexor

    23. Tega-flex

    24. Orphenadrine Citrate (usp)

    25. Dsstox_cid_24678

    26. Dsstox_rid_80390

    27. Dsstox_gsid_44678

    28. Norflex (pharmaceutical)

    29. Orphenadrinecitrate

    30. N,n-dimethyl-2-(phenyl(o-tolyl)methoxy)ethan-1-amine 2-hydroxypropane-1,2,3-tricarboxylate

    31. Cas-4682-36-4

    32. Einecs 225-137-5

    33. Unii-x0a40n8i4s

    34. Norflex (tn)

    35. Orphenadine Citrate

    36. N,n-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)ethylamine Citrate (1:1)

    37. Ethanamine, N,n-dimethyl-2-((2-methylphenyl)phenylmethoxy)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    38. Mls000069549

    39. Schembl119470

    40. Spectrum1500447

    41. Chembl1200395

    42. Dtxsid8044678

    43. Hms502k15

    44. Hy-b0369a

    45. Orphenadrine Citrate [mi]

    46. Hms1920d10

    47. Hms2091l10

    48. Hms2231j06

    49. Hms3259m21

    50. Hms3370m12

    51. Hms3651a10

    52. Hms3884m22

    53. Pharmakon1600-01500447

    54. Citric Acid; N,n-dimethyl-2-[o-tolyl(phenyl)methoxy]ethanamine

    55. O-methyldiphenhydramine Citrate Salt

    56. Orphenadrine Citrate [vandf]

    57. Tox21_111323

    58. Tox21_113543

    59. Tox21_301079

    60. Ccg-40242

    61. Nsc757238

    62. Orphenadrine Citrate [mart.]

    63. Orphenadrine Citrate [who-dd]

    64. Akos008132385

    65. Tox21_111323_1

    66. Nc00525

    67. Nsc 757238

    68. (+-)-n,n-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)ethylamine Citrate (1:1)

    69. Ethylamine, N,n-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)-, Citrate (1:1)

    70. Ncgc00015771-13

    71. Ncgc00094745-02

    72. Ncgc00094745-03

    73. Ncgc00254980-01

    74. As-74807

    75. Ethanamine, N,n-dimethyl-2-((2-methylphenyl)phenylmethoxy)-, (+-)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    76. Orphenadrine Citrate [ep Impurity]

    77. Orphenadrine Citrate [orange Book]

    78. Smr000058817

    79. Orphenadrine Citrate [ep Monograph]

    80. Orphenadrine Citrate [usp Monograph]

    81. Ft-0655842

    82. Ft-0673305

    83. S2054

    84. Sw102176-4

    85. En300-53019

    86. Norgesic Component Orphenadrine Citrate

    87. C75247

    88. D00774

    89. Invagesic Component Orphenadrine Citrate

    90. Orphenadrine Citrate Component Of Norgesic

    91. Orphengesic Component Orphenadrine Citrate

    92. A826945

    93. Orphenadrine Citrate Component Of Invagesic

    94. Orphenadrine Citrate Component Of Orphengesic

    95. Sr-01000002975-5

    96. Invagesic Forte Component Orphenadrine Citrate

    97. Orphengesic Forte Component Orphenadrine Citrate

    98. Q27107584

    99. Orphenadrine Citrate Component Of Invagesic Forte

    100. Orphenadrine Citrate Component Of Orphengesic Forte

    101. Beta-dimethylaminoethyl 2-methylbenzhydryl Ether Citrate Salt

    102. N,n-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)ethylamine Citrate

    103. (+-)-n,n-dimethyl-2-((o-methyl-alpha-phenylbenzyl)oxy)ethylamine Citrate

    104. (+/-)-n,n-dimethyl-2-((o-methyl-.alpha.-phenylbenzyl)oxy)ethylamine Citrate (1:1)

    105. Ethanamine, N,n-dimethyl-2-((2-methylphenyl)phenylmethoxy)-, (+/-)-, 2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    106. Ethanamine, N,n-dimethyl-2-[(2-methylphenyl)phenylmethoxy]-,2-hydroxy-1,2,3-propanetricarboxylate (1:1)

    107. N,n-dimethyl-2-[(2-methylphenyl)(phenyl)methoxy]ethanamine 2-hydroxypropane-1,2,3-tricarboxylate

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 461.5 g/mol
    Molecular Formula C24H31NO8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count11
    Exact Mass461.20496695 g/mol
    Monoisotopic Mass461.20496695 g/mol
    Topological Polar Surface Area145 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity488
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameNorflex
    PubMed HealthOrphenadrine
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelOrphenadrine citrate is the citrate salt of orphenadrine (2-dimethylaminoethyl 2- methylbenzhydryl ether citrate). It occurs as a white, crystalline powder having a bitter taste. It is practically odorless; sparingly soluble in water, slightly solubl...
    Active IngredientOrphenadrine citrate
    Dosage FormInjectable
    RouteInjection
    Strength30mg/ml
    Market StatusPrescription
    CompanyMedicis

    2 of 4  
    Drug NameOrphenadrine citrate
    PubMed HealthOrphenadrine Citrate/Aspirin/Caffeine (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting/Salicylate, Aspirin Combination
    Drug LabelOrphenadrine citrate is the citrate salt of orphenadrine. It occurs as a white, crystalline powder having a bitter taste. It is practically odorless; sparingly soluble in water, slightly soluble in alcohol. The chemical name of orphenadrine citrate i...
    Active IngredientOrphenadrine citrate
    Dosage FormTablet, extended release; Injectable
    RouteInjection; Oral
    Strength30mg/ml; 100mg
    Market StatusPrescription
    CompanyImpax Pharms; Tedor Pharma; Sandoz; Invagen Pharms; Watson Labs; Gavis Pharms; Sagent Pharms; Eurohlth Intl; Akorn

    3 of 4  
    Drug NameNorflex
    PubMed HealthOrphenadrine
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelOrphenadrine citrate is the citrate salt of orphenadrine (2-dimethylaminoethyl 2- methylbenzhydryl ether citrate). It occurs as a white, crystalline powder having a bitter taste. It is practically odorless; sparingly soluble in water, slightly solubl...
    Active IngredientOrphenadrine citrate
    Dosage FormInjectable
    RouteInjection
    Strength30mg/ml
    Market StatusPrescription
    CompanyMedicis

    4 of 4  
    Drug NameOrphenadrine citrate
    PubMed HealthOrphenadrine Citrate/Aspirin/Caffeine (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting/Salicylate, Aspirin Combination
    Drug LabelOrphenadrine citrate is the citrate salt of orphenadrine. It occurs as a white, crystalline powder having a bitter taste. It is practically odorless; sparingly soluble in water, slightly soluble in alcohol. The chemical name of orphenadrine citrate i...
    Active IngredientOrphenadrine citrate
    Dosage FormTablet, extended release; Injectable
    RouteInjection; Oral
    Strength30mg/ml; 100mg
    Market StatusPrescription
    CompanyImpax Pharms; Tedor Pharma; Sandoz; Invagen Pharms; Watson Labs; Gavis Pharms; Sagent Pharms; Eurohlth Intl; Akorn

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Cytochrome P-450 CYP2B6 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2B6. (See all compounds classified as Cytochrome P-450 CYP2B6 Inhibitors.)

    Antiparkinson Agents

    Agents used in the treatment of Parkinson's disease. The most commonly used drugs act on the dopaminergic system in the striatum and basal ganglia or are centrally acting muscarinic antagonists. (See all compounds classified as Antiparkinson Agents.)

    Muscarinic Antagonists

    Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system. (See all compounds classified as Muscarinic Antagonists.)

    Muscle Relaxants, Central

    A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)

    Parasympatholytics

    Agents that inhibit the actions of the parasympathetic nervous system. The major group of drugs used therapeutically for this purpose is the MUSCARINIC ANTAGONISTS. (See all compounds classified as Parasympatholytics.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Muscle Relaxant [EPC]; Centrally-mediated Muscle Relaxation [PE]
    5.3 ATC Code

    M - Musculo-skeletal system

    M03 - Muscle relaxants

    M03B - Muscle relaxants, centrally acting agents

    M03BC - Ethers, chemically close to antihistamines

    M03BC01 - Orphenadrine (citrate)