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Also known as: 4474-91-3, Angiotensin ii human, Hypertensin, Human angiotensin ii, Angiotensin ii (human), Ang ii

Molecular Formula

C₅₀H₇₁N₁₃O₁₂

Molecular Weight

1046.2 g/mol

InChI Key

CZGUSIXMZVURDU-JZXHSEFVSA-N

An octapeptide that is a potent but labile vasoconstrictor. It is produced from angiotensin I after the removal of two amino acids at the C-terminal by ANGIOTENSIN CONVERTING ENZYME. The amino acid in position 5 varies in different species. To block VASOCONSTRICTION and HYPERTENSION effect of angiotensin II, patients are often treated with ACE INHIBITORS or with ANGIOTENSIN II TYPE 1 RECEPTOR BLOCKERS.

1 2D Structure

Angiotensin II

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3S)-3-amino-4-[[(2S)-1-[[(2S)-1-[[(2S)-1-[[(2S,3S)-1-[[(2S)-1-[(2S)-2-[[(1S)-1-carboxy-2-phenylethyl]carbamoyl]pyrrolidin-1-yl]-3-(1H-imidazol-5-yl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxopentan-2-yl]amino]-3-(4-hydroxyphenyl)-1-oxopropan-2-yl]amino]-3-methyl-1-oxobutan-2-yl]amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]amino]-4-oxobutanoic acid

2.1.2 InChI

InChI=1S/C50H71N13O12/c1-5-28(4)41(47(72)59-36(23-31-25-54-26-56-31)48(73)63-20-10-14-38(63)45(70)60-37(49(74)75)22-29-11-7-6-8-12-29)62-44(69)35(21-30-15-17-32(64)18-16-30)58-46(71)40(27(2)3)61-43(68)34(13-9-19-55-50(52)53)57-42(67)33(51)24-39(65)66/h6-8,11-12,15-18,25-28,33-38,40-41,64H,5,9-10,13-14,19-24,51H2,1-4H3,(H,54,56)(H,57,67)(H,58,71)(H,59,72)(H,60,70)(H,61,68)(H,62,69)(H,65,66)(H,74,75)(H4,52,53,55)/t28-,33-,34-,35-,36-,37-,38-,40-,41-/m0/s1

2.1.3 InChI Key

CZGUSIXMZVURDU-JZXHSEFVSA-N

2.1.4 Canonical SMILES

CCC(C)C(C(=O)NC(CC1=CN=CN1)C(=O)N2CCCC2C(=O)NC(CC3=CC=CC=C3)C(=O)O)NC(=O)C(CC4=CC=C(C=C4)O)NC(=O)C(C(C)C)NC(=O)C(CCCN=C(N)N)NC(=O)C(CC(=O)O)N

2.1.5 Isomeric SMILES

CC[C@H](C)[C@@H](C(=O)N[C@@H](CC1=CN=CN1)C(=O)N2CCC[C@H]2C(=O)N[C@@H](CC3=CC=CC=C3)C(=O)O)NC(=O)[C@H](CC4=CC=C(C=C4)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)[C@H](CC(=O)O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. 5 L Isoleucine Angiotensin Ii

2. 5-l-isoleucine Angiotensin Ii

3. Ang-(1-8)octapeptide

4. Angiotensin Ii, 5-l-isoleucine

5. Angiotensin Ii, Ile(5)-

6. Angiotensin Ii, Isoleucine(5)-

7. Angiotensin Ii, Val(5)-

8. Angiotensin Ii, Valine(5)-

9. Angiotensin-(1-8) Octapeptide

10. Isoleucine(5)-angiotensin

11. Isoleucyl(5)-angiotensin Ii

12. Valyl(5)-angiotensin Ii

2.2.2 Depositor-Supplied Synonyms

1. 4474-91-3

2. Angiotensin Ii Human

3. Hypertensin

4. Human Angiotensin Ii

5. Angiotensin Ii (human)

6. Ang Ii

7. Giapreza

8. 5-l-isoleucineangiotensin Ii

9. Angiotensin Ii (mouse)

10. 5-isoleucine-angiotensin Ii

11. Asp-arg-val-tyr-ile-his-pro-phe

12. Drvyihpf

13. 1-8-angiotensin I

14. Angiotensin Ii, Human

15. Ile(5)-angiotensin Ii

16. Isoleucine5-angiotensin Ii

17. Chebi:2719

18. Ang-(1-8)octapeptide

19. Isoleucine(5)-angiotensin Ii

20. Chembl408403

21. 1-l-aspasaginyl-5-l-valyl Angiotensin Octapeptide

22. 11128-99-7

23. Delivert

24. Angiotensin Ii (usan)

25. L-alpha-aspartyl-l-arginyl-l-valyl-l-tyrosyl-l-isoleucyl-l-histidyl-l-prolyl-l-phenylalanine

26. (2s,5s,8s,11s,14s,17s)-2-((1h-imidazol-5-yl)methyl)-17-amino-5-((s)-sec-butyl)-1-((s)-2-(((s)-1-carboxy-2-phenylethyl)carbamoyl)pyrrolidin-1-yl)-14-(3-((diaminomethylene)amino)propyl)-8-(4-hydroxybenzyl)-11-isopropyl-1,4,7,10,13,16-hexaoxo-3,6,9,12,15-pentaazanonadecan-19-oic Acid

27. N-(1-(n-(n-(n-(n-(n(2)-l-alpha-aspartyl-l-arginyl)-l-valyl)-l-tyrosyl)-l-isoleucyl)-l-histidyl)-l-prolyl)-l-phenylalanine

28. Angiotensinii,human

29. Ile5-angiotensin Ii

30. Angiotensin Ii, Ile(5)-

31. Angiotensin Ii [inn:jan]

32. Unii-m089efu921

33. Hypertensin Ii

34. Angiotensin 2

35. Angiotensin Ii, 5-l-isoleucine-

36. Delivert (tn)

37. C50h71n13o12

38. Angiotensin Ii Heavy

39. Angiotensin Ii (rat)

40. Angiotensin Ii (9ci)

41. Angiotensin Ii-human

42. Angiotensin Ii Acetate Salt

43. Schembl1189

44. Angiotensin Ii (human Type)

45. Gtpl2504

46. Ljpc-501

47. Schembl9013957

48. Schembl20502357

49. Dtxsid30196288

50. Chebi:131170

51. Ty-10721

52. M089efu921

53. Angiotensin Ii (human Type) (jan)

54. Bdbm50228195

55. Bdbm50236697

56. Akos016010178

57. Zinc169676920

58. Db11842

59. H-asp-arg-val-tyr-ile-his-pro-phe-oh

60. Ncgc00167130-01

61. Hy-13948

62. L-phenylalanine, N-(1-(n-(n-(n-(n-(n2-l-alpha-aspartyl-l-arginyl)-l-valyl)-l-tyrosyl)-l-isoleucyl)-l-histidyl)-l-prolyl)-

63. Asp1-arg2-val3-tyr4-ile5-his6-pro7-phe8

64. C02135

65. C75211

66. D02014

67. Drvy-i*-hpf [i*= I(13c6,15n)]

68. A872469

69. Q412999

70. Ang-(1-8)octapeptide, Hypertensin, 4474-91-3, Giapreza

71. Conalbumin (328-332), 1226776-54-0, Rvpsl Peptide

72. Proteomass(tm) Angiotensin Ii Maldi-ms Standard, Vial Of 10 Nmol

73. (3s)-3-amino-3-{[(1s)-1-{[(1s)-1-{[(1s)-1-{[(1s,2s)-1-{[(2s)-1-[(2s)-2-{[(1s)-1-carboxy-2-phenylethyl]carbamoyl}pyrrolidin-1-yl]-3-(1h-imidazol-5-yl)-1-oxopropan-2-yl]carbamoyl}-2-methylbutyl]carbamoyl}-2-(4-hydroxyphenyl)ethyl]carbamoyl}-2-methylpropyl]carbamoyl}-4-[(diaminomethylidene)amino]butyl]carbamoyl}propanoic Acid

74. Alanine, N-(1-(n-(n-(n-(n-(n2-l-alpha-aspartyl-l-arginyl)-l-valyl)-l-tyrosyl)-l-isoleucyl)-l-histidyl)-l-prolyl)-3-phenyl-, L-

75. L-phenylalanine, L-alpha-aspartyl-l-arginyl-l-valyl-l-tyrosyl-l-isoleucyl-l-histidyl-l-prolyl-

2.3 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₅₀H₇₁N₁₃O₁₂
Molecular Weight	1046.2 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	13
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	29
Exact Mass	1045.53451475 g/mol
Monoisotopic Mass	1045.53451475 g/mol
Topological Polar Surface Area	409 Å²
Heavy Atom Count	75
Formal Charge	0
Complexity	1980
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Angiotensin II is a vasoconstrictor indicated for increasing blood pressure in adults with septic or other distributive shock.

FDA Label

Giapreza is indicated for the treatment of refractory hypotension in adults with septic or other distributive shock who remain hypotensive despite adequate volume restitution and application of catecholamines and other available vasopressor therapies.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Angiotensin II is a naturally occurring peptide hormone of the renin-angiotensin-aldosterone-system (RAAS) that has the capacity to cause vasoconstriction and an increase in blood pressure in the human body. In the RAAS, juxtaglomerular cells of the renal afferent arteriole synthesize the proteolytic enzyme renin. Although stored in an inactive form called pro-renin, decreases in arterial blood pressure or extracellular fluid volume depletion can cause various enzymatic reactions to release active renin into the systemic circulation and surrounding tissues. Such renin release allows for the production of the alpha-2-globulin angiotensinogen predominantly in the liver and to some extent, the kidneys and other organs. Angiotensin I, itself a decapeptide with weak biological activity, is produced from angiotensinogen and then quickly converted to angiotensin II by angiotensin converting enzymes (ACE). Consequently, angiotensin II demonstrates its strong vasopressor activity when it is rapidly degraded by aminopeptidases A and M into further entities like angiotensin III and angiotensin IV, respectively. Such species like angiotensin III can then bind and interact with specific G protein coupled receptors like angiotensin receptor 1, or AT-1 where strong vasoconstricson can occur. Furthermore, in the ATHOS-3 clinical trial, for the 114 (70%) patient subjects in the angiotensin II arm who reached the target mean arterial pressure (MAP) at Hour 3, the median time to reach the target MAP endpoint was approximately 5 minutes. The angiotensin II was titrated to effect for each individual patient..

5.2 MeSH Pharmacological Classification

Vasoconstrictor Agents

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

5.3 FDA Pharmacological Classification

5.3.1 Pharmacological Classes

Vasoconstrictor [EPC]; Vasoconstriction [PE]

5.4 ATC Code

C09

C - Cardiovascular system

C01 - Cardiac therapy

C01C - Cardiac stimulants excl. cardiac glycosides

C01CX - Other cardiac stimulants

C01CX09 - Angiotensin II

5.5 Absorption, Distribution and Excretion

Absorption

Following the intravenous infusion of angiotensin II in adult patients with septic or other distributive shock, the serum levels of angiotensin II observed were similar at baseline and hour 3 after the intravenous infusion. After 3 hours of treatment, the serum level of angiotensin I (the angiotensin II precursos peptide) is however, reduced by about 40%.

Route of Elimination

The official prescribing information notes that no specific studies have been conducted that examine the elimination of angiotensin II.

Volume of Distribution

The official prescribing information for angiotensin II notes that no specific studies have yet been conducted that examine the distribution of angiotensin II.

Clearance

The official prescribing information notes that the clearnace of angiotensin II is not dependent on hepatic function or renal function.

5.6 Metabolism/Metabolites

It is metabolized by aminopeptidase A and angiotensin converting enzyme 2 to angiotensin-(2-8) [angiotensin III] and angiotensin-(1-7), respectively in plasma, erythrocytes and many of the major organs (i.e. intestine, kidney, liver and lung). Angiotensin II type 1 receptor (AT1) mediated activity of angiotensin III is approximately 40% of angiotensin II; however, aldosterone synthesis activity is similar to angiotensin II. Angiotensin-(1-7) exerts the opposite effects of angiotensin II on AT1 receptors and causes vasodilation. Nevertheless, the official prescribing information also notes that no formal studies have been conducted that examine the metabolism of angiotensin II.

5.7 Biological Half-Life

The plasma half-life of intravenously administered angiotensin II is less than one minute.

5.8 Mechanism of Action

As part of the renin-angiotensin-aldosterone-system (RAAS), angiotensin II raises blood pressure by vasoconstriction, increased aldosterone release by the adrenal zona glomerulosa, sodium and water reabsorption in the proximal tubular cells, and vasopressin secretion The direct action of angiotensin II on surrounding vessel walls is facilitated by binding to the G-protein-coupled angiotensin II receptor type 1 (AT-1) on vascular smooth muscle cells, which stimulates Ca2+/calmodulin-dependent phosphorylation of myosin and causes smooth muscle contraction that results in vasoconstriction. The RAAS is ultimately regulated by a negative feedback effect of angiotensin II on renin production by the juxtaglomerular cells of the renal afferent arteriole. Unresuscitated septic shock associated with marked hypovolemia, extracellular fluid volume depletion, decreased cardiac output, low arterial blood pressure and decreased systemic vascular resistance causes an increase in renin secretion by the juxtaglomerular cells, resulting in elevated angiotensin II plasma levels and an increased secretion of aldosterone from the adrenal cortex. Angiotensin II binding to AT-1 receptors causes dose-dependent vasoconstriction of both afferent and efferent glomerular arterioles. The most pronounced effect of angiotensin II results on efferent arterioles, resulting in reduced renal blood flow and increased glomerular filtration pressure.

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