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Phenoxybenzamine

Phenoxybenzamine

Synopsis, Chemistry

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Also known as: 63-92-3, Phenoxybenzamine hcl, Dibenzyline, N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine hydrochloride, Dibenzyline hydrochloride, Dibenzyran

Molecular Formula

C₁₈H₂₃Cl₂NO

Molecular Weight

340.3 g/mol

InChI Key

VBCPVIWPDJVHAN-UHFFFAOYSA-N

FDA UNII

X1IEG24OHL

An alpha-adrenergic antagonist with long duration of action. It has been used to treat hypertension and as a peripheral vasodilator.

1 2D Structure

Phenoxybenzamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

N-benzyl-N-(2-chloroethyl)-1-phenoxypropan-2-amine;hydrochloride

2.1.2 InChI

InChI=1S/C18H22ClNO.ClH/c1-16(15-21-18-10-6-3-7-11-18)20(13-12-19)14-17-8-4-2-5-9-17;/h2-11,16H,12-15H2,1H3;1H

2.1.3 InChI Key

VBCPVIWPDJVHAN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC(COC1=CC=CC=C1)N(CCCl)CC2=CC=CC=C2.Cl

2.2 Other Identifiers

2.2.1 UNII

X1IEG24OHL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Dibenylene

2. Dibenyline

3. Dibenziran

4. Dibenzylin

5. Dibenzyline

6. Dibenzyran

7. Hydrochloride, Phenoxybenzamine

8. Phenoxybenzamine

2.3.2 Depositor-Supplied Synonyms

1. 63-92-3

2. Phenoxybenzamine Hcl

3. Dibenzyline

4. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine Hydrochloride

5. Dibenzyline Hydrochloride

6. Dibenzyran

7. Dibenzyline Chloride

8. Phenoxybenzamine Chloride

9. Phenoxybenzamine (hydrochloride)

10. Bensylyt Nen

11. Dibenzylin

12. Phenoxybenzamine.hcl

13. Nci-c01661

14. Nsc-37448

15. 2-(n-benzyl-2-chloroethylamino)-1-phenoxypropane Hydrochloride

16. N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)benzylamine Hydrochloride

17. Mls000069374

18. Chebi:8078

19. Nsc 37448

20. 63-92-3 (hcl)

21. Smr000058422

22. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine;hydrochloride

23. Dsstox_cid_1127

24. N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)benzenemethanamine Hydrochloride

25. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-,hydrochloride

26. Dsstox_rid_75958

27. Dsstox_gsid_21127

28. N-2-phenoxyisopropyl-n-benzyl-chloroethylamine Hydrochloride

29. Benzyl(2-chloroethyl)(1-methyl-2-phenoxyethyl)amine Hydrochloride

30. X1ieg24ohl

31. Benzylamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-, Hydrochloride

32. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-, Hydrochloride

33. Phenoxybenzamine Hydrochloride (usp)

34. Sr-01000000017

35. Dibenzylene

36. Dibenzyline (tn)

37. Mfcd00055152

38. Pob Hcl

39. Cpd000058422

40. Opera_id_300

41. Cas-63-92-3

42. Phenoxybenzaminehydrochloride

43. Schembl50729

44. Bensylyte Hydrochloride

45. Mls002222313

46. Spectrum2300176

47. Chembl1200787

48. Dtxsid0021127

49. Hy-b0431a

50. Hms1570n10

51. Pharmakon1600-02300176

52. Phenoxybenzamine Hydrochloride,(s)

53. Bcp28467

54. Nsc37448

55. Tox21_201588

56. Tox21_302978

57. Wln: G2n1r&y1&1or &gh

58. Ccg-39614

59. Nsc759572

60. Akos015966790

61. Ac-8077

62. Lp00235

63. Nc00598

64. Nsc-759572

65. Ncgc00089748-02

66. Ncgc00089748-06

67. Ncgc00093699-01

68. Ncgc00093699-02

69. Ncgc00093699-03

70. Ncgc00093699-04

71. Ncgc00256370-01

72. Ncgc00259137-01

73. As-16927

74. Phenoxybenzamine Hydrochloride [mi]

75. Db-054579

76. B-019

77. D0158

78. Eu-0100235

79. Ft-0603264

80. Ft-0673569

81. Ft-0673570

82. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan

83. Phenoxybenzamine Hydrochloride [iarc]

84. Phenoxybenzamine Hydrochloride [vandf]

85. S2499

86. Sw197327-3

87. En300-52514

88. Phenoxybenzamine Hydrochloride [mart.]

89. C07436

90. D00507

91. Phenoxybenzamine Hydrochloride [usp-rs]

92. Phenoxybenzamine Hydrochloride [who-dd]

93. Phenoxybenzamine Hydrochloride, >=97%, Powder

94. 055p152

95. J-009731

96. Phenoxybenzamine Hydrochloride [orange Book]

97. Sr-01000000017-2

98. Sr-01000000017-6

99. Phenoxybenzamine Hydrochloride [usp Monograph]

100. Q27107723

101. N-benzyl-n-(2-chloroethyl)-1-phenoxypropan-2-amine;hydron;chloride

102. N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)benzylamine, Hydrochloride

103. N-2-phenoxyisopropyl-n-benzyl-.beta.-chloroethylamine Hydrochloride

104. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-, Hydrochloride (1:1)

105. Benzenemethanamine, N-(2-chloroethyl)-n-(1-methyl-2-phenoxyethyl)-,hcl

106. Phenoxybenzamine Hydrochloride, United States Pharmacopeia (usp) Reference Standard

107. 34238-85-2

108. Phenoxybenzamine Hcl Pound>>nci-c01661 Pound>> Nci C01661 Pound>> Ncic01661 Pound>>nsc 37448 Pound>>nsc37448 Pound>>nsc-37448

109. Phenoxybenzamine Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date

2005-11-20

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₃Cl₂NO
Molecular Weight	340.3 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	8
Exact Mass	339.1156697 g/mol
Monoisotopic Mass	339.1156697 g/mol
Topological Polar Surface Area	12.5 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	262
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Dibenzyline
Drug Label	Each Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
Active Ingredient	Phenoxybenzamine hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Wellspring Pharm

2 of 4
Drug Name	Phenoxybenzamine hydrochloride
PubMed Health	Phenoxybenzamine (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Each Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
Active Ingredient	Phenoxybenzamine hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Roxane

3 of 4
Drug Name	Phenoxybenzamine hydrochloride
PubMed Health	Phenoxybenzamine (By mouth)
Drug Classes	Cardiovascular Agent
Drug Label	Each Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
Active Ingredient	Phenoxybenzamine hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Roxane

4 of 4
Drug Name	Dibenzyline
Drug Label	Each Dibenzyline capsule, with red cap and body, is imprinted WPC 001 and 10 mg, and contains 10 mg of Phenoxybenzamine Hydrochloride USP. Inactive ingredients consist of D&C Red No. 33, FD&C Red No. 3, FD&C Yellow No. 6, Gelatin NF, Lactose N
Active Ingredient	Phenoxybenzamine hydrochloride
Dosage Form	Capsule
Route	Oral
Strength	10mg
Market Status	Prescription
Company	Wellspring Pharm

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Adrenergic alpha-Antagonists

Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma. (See all compounds classified as Adrenergic alpha-Antagonists.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)

Vasodilator Agents

Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

alpha-Adrenergic Blocker [EPC]; Adrenergic alpha-Antagonists [MoA]