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Phentolamine Mesylate

Phentolamine Mesylate

Synopsis, Chemistry

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Also known as: 65-28-1, Phentolamine mesilate, Phentolamine methanesulfonate, Phentolamine (mesylate), Oraverse, Regitine mesylate

Molecular Formula

C₁₈H₂₃N₃O₄S

Molecular Weight

377.5 g/mol

InChI Key

OGIYDFVHFQEFKQ-UHFFFAOYSA-N

FDA UNII

Y7543E5K9T

A nonselective alpha-adrenergic antagonist. It is used in the treatment of hypertension and hypertensive emergencies, pheochromocytoma, vasospasm of RAYNAUD DISEASE and frostbite, clonidine withdrawal syndrome, impotence, and peripheral vascular disease.

1 2D Structure

Phentolamine Mesylate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

3-[N-(4,5-dihydro-1H-imidazol-2-ylmethyl)-4-methylanilino]phenol;methanesulfonic acid

2.1.2 InChI

InChI=1S/C17H19N3O.CH4O3S/c1-13-5-7-14(8-6-13)20(12-17-18-9-10-19-17)15-3-2-4-16(21)11-15;1-5(2,3)4/h2-8,11,21H,9-10,12H2,1H3,(H,18,19);1H3,(H,2,3,4)

2.1.3 InChI Key

OGIYDFVHFQEFKQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=CC=C(C=C1)N(CC2=NCCN2)C3=CC(=CC=C3)O.CS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

Y7543E5K9T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Fentolamin

2. Mesilate, Phentolamine

3. Mesylate, Phentolamine

4. Methanesulfonate, Phentolamine

5. Mono-hydrochloride, Phentolamine

6. Phentolamine

7. Phentolamine Mesilate

8. Phentolamine Methanesulfonate

9. Phentolamine Mono Hydrochloride

10. Phentolamine Mono-hydrochloride

11. Regitine

12. Regityn

13. Rogitine

14. Z-max

2.3.2 Depositor-Supplied Synonyms

1. 65-28-1

2. Phentolamine Mesilate

3. Phentolamine Methanesulfonate

4. Phentolamine (mesylate)

5. Oraverse

6. Regitine Mesylate

7. Phentolamine Methanesulfonate Salt

8. Phentolamine Mesylate [usp]

9. Mesylate Phentolamine

10. 3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(p-tolyl)amino)phenol Methanesulfonate

11. Nv-101

12. Mls000069487

13. Y7543e5k9t

14. M-(n-(2-imidazolin-2-ylmethyl)-p-toluidino)phenol Monomethanesulfonate (salt)

15. Phenol, 3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(4-methylphenyl)amino)-, Monomethanesulfonate (salt)

16. Phenol,3-[[(4,5-dihydro-1h-imidazol-2-yl)methyl](4-methylphenyl)amino]-,monomethanesulfonate (salt)

17. Smr000059054

18. 3-[n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-4-methylanilino]phenol;methanesulfonic Acid

19. Phentolamine Mesylate (usp)

20. Vasomax

21. Regitin Methanesulphonate

22. Regitine Methanesulfonate

23. Phenol, M-[n-(2-imidazolin-2-ylmethyl)-p-toluidino]-, Methanesulfonate (1:1)

24. Phentolamine Methanesulphonate

25. Ccris 9022

26. Phentolamine Mesilate [inn:ban]

27. Einecs 200-604-6

28. Vasofem

29. Unii-y7543e5k9t

30. Regitin Mesylate

31. Sr-01000000055

32. Regitine (tn)

33. Z-max

34. Mfcd00134201

35. Opera_id_1599

36. Lopac-p-7561

37. Phentolamine Meslate,(s)

38. Schembl40852

39. Mls001076484

40. Phentolamine, Methyl Sulfonate

41. Regid_for_cid_91430

42. Chembl1200873

43. Hy-b0362a

44. Dtxsid60215315

45. Phentolamine Mesilate (jan/inn)

46. Hms2233a24

47. Hms3263e05

48. Hms3373d03

49. Hms3655b13

50. Hms3884a22

51. Phentolamine Mesilate [jan]

52. Bcp09845

53. Tox21_500982

54. Phentolamine Mesylate [vandf]

55. S2038

56. 3-fluoropyridine-4-boronicacidhydrate

57. Phentolamine Mesilate [mart.]

58. Akos007930193

59. Phentolamine Mesilate [who-dd]

60. Phentolamine Mesylate [usp-rs]

61. Ac-7472

62. Ccg-222286

63. Lp00982

64. 3-[n-(4,5-dihydro-1h-imidazol-2-ylmethyl)-4-methylanilino]phenol; Methanesulfonic Acid

65. Phenol, M-(n-(2-imidazolin-2-ylmethyl)-p-toluidino)-, Monomethanesulfonate (salt)

66. Ncgc00016195-01

67. Ncgc00016195-02

68. Ncgc00094282-01

69. Ncgc00261667-01

70. As-13800

71. Phentolamine Methanesulfonate [mi]

72. Phentolamine Mesylate [orange Book]

73. Phentolamine Mesilate [ep Monograph]

74. Eu-0100982

75. Ft-0603267

76. P1985

77. Phentolamine Mesylate [usp Monograph]

78. Sw196637-3

79. D00509

80. P 7561

81. T72782

82. 134p201

83. A835046

84. Sr-01000000055-3

85. W-104799

86. Q27294332

87. Phentolamine Methanesulfonate Salt, >=98% (tlc), Powder

88. Phentolamine Mesilate, British Pharmacopoeia (bp) Reference Standard

89. 2-[n-(m-hydroxyphenyl)-p-toluidinomethyl]imidazoline Methanesulfonate

90. Phentolamine Mesilate, European Pharmacopoeia (ep) Reference Standard

91. Phentolamine Mesylate, United States Pharmacopeia (usp) Reference Standard

92. 3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(p-tolyl)amino)phenolmethanesulfonate

93. 3-[[(4,5-dihydro-1h-imidazol-2-yl)methyl](4-methylphenyl)amino]phenol Methanesulfonate

94. 3-[4,5-dihydro-1h-imidazol-2-ylmethyl-(4-methylphenyl)amino]phenol; Methanesulfonic Acid

95. 3-[n-(4,5-dihydro-1h-imidazol-1-ium-2-ylmethyl)-4-methylanilino]phenol;methanesulfonate

96. M-(n-(2-imidazolin-2-ylmethyl)-p-toluidino)phenol Monomethanesulphonate (salt)

97. Phentolamine Mesilate For System Suitability, European Pharmacopoeia (ep) Reference Standard

98. Phentolamine Mesylate, Pharmaceutical Secondary Standard; Certified Reference Material

99. Phenol, 3-(((4,5-dihydro-1h-imidazol-2-yl)methyl)(4-methylphenyl)amino)-, Monomethanesulphonate (salt)

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₃N₃O₄S
Molecular Weight	377.5 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	377.14092740 g/mol
Monoisotopic Mass	377.14092740 g/mol
Topological Polar Surface Area	111 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	456
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
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	Phentolamine mesylate
Drug Label	Phentolamine Mesylate for Injection USP, is an antihypertensive, available in vials for intravenous and intramuscular administration. Each vial contains phentolamine mesylate USP, 5 mg and mannitol USP, 25 mg in sterile, lyophilized form.Phentolamine...
Active Ingredient	Phentolamine mesylate
Dosage Form	Injectable
Route	Injection
Strength	5mg/vial
Market Status	Prescription
Company	Eurohlth Intl

2 of 4
Drug Name	Oraverse
PubMed Health	Phentolamine (Injection)
Drug Classes	Antihypertensive, Diagnostic Agent, Pheochromocytoma, Toxicology-Antidote Agent
Drug Label	Phentolamine mesylate is phenol,3-[[(4,5-dihydro-1 H-imidazol-2-yl)methyl](4-methyl-phenyl)amino]-, methanesulfonate (salt), a non-specific alpha adrenergic blocker.Phentolamine mesylate USP is a white to off-white, odorless crystalline powder with a...
Active Ingredient	Phentolamine mesylate
Dosage Form	Injectable
Route	Injection
Strength	0.4mg/1.7ml
Market Status	Prescription
Company	Septodont Holding

3 of 4
Drug Name	Phentolamine mesylate
Drug Label	Phentolamine Mesylate for Injection USP, is an antihypertensive, available in vials for intravenous and intramuscular administration. Each vial contains phentolamine mesylate USP, 5 mg and mannitol USP, 25 mg in sterile, lyophilized form.Phentolamine...
Active Ingredient	Phentolamine mesylate
Dosage Form	Injectable
Route	Injection
Strength	5mg/vial
Market Status	Prescription
Company	Eurohlth Intl

4 of 4
Drug Name	Oraverse
PubMed Health	Phentolamine (Injection)
Drug Classes	Antihypertensive, Diagnostic Agent, Pheochromocytoma, Toxicology-Antidote Agent
Drug Label	Phentolamine mesylate is phenol,3-[[(4,5-dihydro-1 H-imidazol-2-yl)methyl](4-methyl-phenyl)amino]-, methanesulfonate (salt), a non-specific alpha adrenergic blocker.Phentolamine mesylate USP is a white to off-white, odorless crystalline powder with a...
Active Ingredient	Phentolamine mesylate
Dosage Form	Injectable
Route	Injection
Strength	0.4mg/1.7ml
Market Status	Prescription
Company	Septodont Holding

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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