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Guanethidine

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ACTIVE PHARMA INGREDIENTS

2 API Suppliers, 2 USDMF

2 API Suppliers
2 USDMF

FINISHED DOSAGE FORMULATIONS

5 FDF Dossiers, 5 FDA Orange Book

5 FDF Dossiers
5 FDA Orange Book

REF. STANDARDS & IMPURITIES

1 USP , 1 Others

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1 USP
1 Others

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

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FDF

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Europe

Canada

Australia

South Africa

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0 DRUGS IN DEVELOPMENT

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REF. STANDARDS OR IMPURITIES

EDQM

USP

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Chemistry

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Also known as: 645-43-2, Guanethidine monosulfate, Ismelin, Ismelin sulfate, Guanethidine (sulfate), Guanethidine sulphae

Molecular Formula

C₁₀H₂₄N₄O₄S

Molecular Weight

296.39 g/mol

InChI Key

YUFWAVFNITUSHI-UHFFFAOYSA-N

FDA UNII

5UBY8Y002G

An antihypertensive agent that acts by inhibiting selectively transmission in post-ganglionic adrenergic nerves. It is believed to act mainly by preventing the release of norepinephrine at nerve endings and causes depletion of norepinephrine in peripheral sympathetic nerve terminals as well as in tissues.

1 2D Structure

Guanethidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-[2-(azocan-1-yl)ethyl]guanidine;sulfuric acid

2.1.2 InChI

InChI=1S/C10H22N4.H2O4S/c11-10(12)13-6-9-14-7-4-2-1-3-5-8-14;1-5(2,3)4/h1-9H2,(H4,11,12,13);(H2,1,2,3,4)

2.1.3 InChI Key

YUFWAVFNITUSHI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1CCCN(CCC1)CCN=C(N)N.OS(=O)(=O)O

2.2 Other Identifiers

2.2.1 UNII

5UBY8Y002G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. ((2-hexahydro-1(2h)-azocinyl)ethyl)guanidine

2. Guanethidine

3. Guanethidine Monosulfate

4. Guanethidine Sulfate (1:1)

5. Guanethidine Sulfate (1:2)

6. Guanethidine Sulfate (2:1)

7. Guanethidine Sulfate (2:1), 14c-labeled

8. Ismelin

9. Isobarin

10. Monosulfate, Guanethidine

11. Octadine

12. Oktadin

13. Sulfate, Guanethidine

2.3.2 Depositor-Supplied Synonyms

1. 645-43-2

2. Guanethidine Monosulfate

3. Ismelin

4. Ismelin Sulfate

5. Guanethidine (sulfate)

6. Guanethidine Sulphae

7. 1-(2-(azocan-1-yl)ethyl)guanidine Sulfate

8. Guanethidine Monosulphate

9. 645-43-2 (sulfate)

10. 5uby8y002g

11. 2-[2-(azocan-1-yl)ethyl]guanidine;sulfuric Acid

12. Guanidine, (2-(hexahydro-1(2h)-azocinyl)ethyl)-, Sulfate (1:1)

13. Guanidine, [2-(hexahydro-1(2h)-azocinyl)ethyl]-, Sulfate (1:1)

14. Isobarin

15. Octadin

16. Octadine

17. Iporal

18. Guanetidin Sulfate

19. Guanethidinesulfate

20. 2-(octahydro-1-azocinyl)ethyl Guanidine Sulphate

21. Guanethidine Bisulfate

22. (2-(hexahydro-1(2h)-azocinyl)ethyl) Guanidine Hydrogen Sulfate

23. (2-(hexahydro-1(2h)-azocinyl)ethyl)guanidine Sulfate (1:1)

24. Ismelin Sulfate (2:1)

25. Su 5864 Sulfate (1:1)

26. Chebi:51016

27. Nsc29863

28. Guanethidine Monosulfate [usan]

29. Einecs 211-442-0

30. Unii-5uby8y002g

31. Isomelin

32. Guanethidine Sulfate (1:1)

33. N-(2-guanidino Ethyl)heptamethylenimine Sulfate

34. Prestwick_249

35. Ismelin (tn)

36. [2-(hexahydro-1(2h)-azocinyl)ethyl]guanidine Sulfate (2:1)

37. Guanethidine Monosulfate [usan:usp]

38. Azocine, Sulfate (2:1)

39. Chembl1345

40. Schembl51039

41. Guanethidine Monosulphate Usp

42. Guanethidine Sulfate (jp17)

43. Spectrum1500323

44. Guanethidine Monosulfate (usp)

45. Schembl11658850

46. Hms501k21

47. (2-(hexahydro-(2h)-azocin-1-yl)ethyl)guanidinium Sulphate

48. Dtxsid20110019

49. Hms1568p16

50. Hms1920b19

51. Hms2091j05

52. Hms3749o19

53. Pharmakon1600-01500323

54. Methyltriallylammoniumbromide

55. Hy-b0800

56. Ac-479

57. Ccg-39688

58. Guanethidine Monosulfate [mi]

59. Mfcd00035403

60. Nsc757045

61. S5496

62. Akos015856688

63. Akos026750543

64. Wln: T8ntj A2myzum & 2wsqq

65. Cs-3931

66. Nsc-757045

67. Guanethidine Monosulfate [mart.]

68. Guanethidine Monosulfate [vandf]

69. Guanethidine Monosulfate [usp-rs]

70. Guanethidine Monosulfate [who-dd]

71. Ncgc00094691-01

72. Ncgc00094691-02

73. As-57397

74. .beta.-1-azacyclooctylethylguanidine Sulfate

75. Ft-0603504

76. Guanethidine Monosulfate [ep Impurity]

77. D04382

78. Esimil Component Guanethidine Monosulfate

79. Guanethidine Monosulfate [ep Monograph]

80. Guanethidine Monosulfate [usp Monograph]

81. [2-(octahydro-1-azocinyl)ethyl]guanidine Sulfate

82. Guanethidine Monosulfate Component Of Esimil

83. N-[2-(azocan-1-yl)ethyl]guanidine; Sulfuric Acid

84. Sr-05000001637

85. 1-[2-(azocan-1-yl)ethyl]guanidine (1/2h2so4)

86. Sr-05000001637-1

87. [2-(hexahydro-1(2h)-azocinyl)ethyl]guanidine Sulfate

88. N''-[2-(azocan-1-yl)ethyl]guanidine; Sulfuric Acid

89. Q27122277

90. N-[2-(hexahydro-1(2h)-azocinyl)ethyl]guanidine Sulfate

91. (2-(hexahydro-1(2h)-azocinyl)ethyl)guanidine Sulfate (1:1).

92. (2-(hexahydro-1(2h)-azocinyl)ethyl)guanidine Sulphate (1:1).

93. Guanidine, (2-(hexahydro-1(2h)-azocinyl)ethyl)-, Sulphate (1:1)

94. Guanethidine Monosulfate, United States Pharmacopeia (usp) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₂₄N₄O₄S
Molecular Weight	296.39 g/mol
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	3
Exact Mass	296.15182643 g/mol
Monoisotopic Mass	296.15182643 g/mol
Topological Polar Surface Area	151 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	248
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

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.)

Sympatholytics

Drugs that inhibit the actions of the sympathetic nervous system by any mechanism. The most common of these are the ADRENERGIC ANTAGONISTS and drugs that deplete norepinephrine or reduce the release of transmitters from adrenergic postganglionic terminals (see ADRENERGIC AGENTS). Drugs that act in the central nervous system to reduce sympathetic activity (e.g., centrally acting alpha-2 adrenergic agonists, see ADRENERGIC ALPHA-AGONISTS) are included here. (See all compounds classified as Sympatholytics.)

Adrenergic Agents

Drugs that act on adrenergic receptors or affect the life cycle of adrenergic transmitters. Included here are adrenergic agonists and antagonists and agents that affect the synthesis, storage, uptake, metabolism, or release of adrenergic transmitters. (See all compounds classified as Adrenergic Agents.)

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