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Chemistry

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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

Orphenadrine
A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm.
1 2D Structure

Orphenadrine

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)


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04-Jan-2021
31-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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