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Chemistry

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Also known as: Arginine vasopressin, 113-79-1, Argipressine, Pitressin, Beta-hypophamine, 8-arginine-vasopressin

Molecular Formula

C₄₆H₆₅N₁₅O₁₂S₂

Molecular Weight

1084.2 g/mol

InChI Key

KBZOIRJILGZLEJ-LGYYRGKSSA-N

The predominant form of mammalian antidiuretic hormone. It is a nonapeptide containing an ARGININE at residue 8 and two disulfide-linked cysteines at residues of 1 and 6. Arg-vasopressin is used to treat DIABETES INSIPIDUS or to improve vasomotor tone and BLOOD PRESSURE.

1 2D Structure

Arginine Vasopressin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-1-[(4R,7S,10S,13S,16S,19R)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-N-[(2S)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

2.1.2 InChI

InChI=1S/C46H65N15O12S2/c47-27-22-74-75-23-33(45(73)61-17-5-9-34(61)44(72)56-28(8-4-16-53-46(51)52)39(67)54-21-37(50)65)60-43(71)32(20-36(49)64)59-40(68)29(14-15-35(48)63)55-41(69)31(18-24-6-2-1-3-7-24)58-42(70)30(57-38(27)66)19-25-10-12-26(62)13-11-25/h1-3,6-7,10-13,27-34,62H,4-5,8-9,14-23,47H2,(H2,48,63)(H2,49,64)(H2,50,65)(H,54,67)(H,55,69)(H,56,72)(H,57,66)(H,58,70)(H,59,68)(H,60,71)(H4,51,52,53)/t27-,28-,29-,30-,31-,32-,33-,34-/m0/s1

2.1.3 InChI Key

KBZOIRJILGZLEJ-LGYYRGKSSA-N

2.1.4 Canonical SMILES

C1CC(N(C1)C(=O)C2CSSCC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)NC(C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)NC(CCCN=C(N)N)C(=O)NCC(=O)N

2.1.5 Isomeric SMILES

C1C[C@H](N(C1)C(=O)[C@@H]2CSSC[C@@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N[C@H](C(=O)N2)CC(=O)N)CCC(=O)N)CC3=CC=CC=C3)CC4=CC=C(C=C4)O)N)C(=O)N[C@@H](CCCN=C(N)N)C(=O)NCC(=O)N

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Arg Vasopressin

2. Arg-vasopressin

3. Arginine Vasopressin

4. Argipressin Tannate

5. Vasopressin, Arginine

2.2.2 Depositor-Supplied Synonyms

1. Arginine Vasopressin

2. 113-79-1

3. Argipressine

4. Pitressin

5. Beta-hypophamine

6. 8-arginine-vasopressin

7. Argipressin Tannate

8. Vasopressin (arginine Form)

9. Arginine-vasopressin

10. Chebi:34543

11. Vasophysin

12. Arg-vasopressin

13. Chembl373742

14. (arg8)-vasopressin

15. [arg8]-vasopressin

16. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

17. 8-l-arginine Vasopressin

18. Argipresina

19. Argipressina

20. Argipressinum

21. Avp

22. Arg8-vasopressin

23. Argipressin [inn]

24. Argipressina [dcit]

25. Ncgc00166306-01

26. Argipressin [inn:ban]

27. 8-l-arginine-vasopressin

28. Argipresina [inn-spanish]

29. Argipressine [inn-french]

30. Argipressinum [inn-latin]

31. Unii-y4907o6mfd

32. Rindervasopressin

33. [3h]vasopressin

34. Einecs 204-035-4

35. 3-(phenylalanine)-8-arginineoxytocin

36. Arg8-vasopressin;avp

37. Arginine-8-vasopressin

38. Argipressin Or Lypressin

39. [8-arginine]vasopressin

40. [3h]argipressin Tannate

41. Antidiuretic Hormone (adh)

42. Arginine Vasopressin (avp)

43. Argipressin Tannate [usan]

44. Arginine Antidiuretic Hormone

45. Dsstox_cid_28324

46. Dsstox_rid_82752

47. Dsstox_gsid_48349

48. Schembl43139

49. Vasopressin, 8-l-arginine-

50. [cyclo S-s]cyfqncprg-nh2

51. Gtpl2168

52. Y4907o6mfd

53. Dtxsid0048349

54. Schembl17874853

55. Bdbm35667

56. Tox21_113037

57. Bdbm50044777

58. Mfcd00076738

59. Ncgc00166306-02

60. Ncgc00188439-01

61. Cas-113-79-1

62. H-cys-tyr-phe-gln-asn-cys-pro-arg-gly-nh2

63. Oxytocin, 3-(l-phenylalanine)-8-l-arginine-

64. Vasopressin, 8-l-arginine- (7ci,8ci,9ci)

65. Roxybenzyl-6,9,12,15,18-pentaoxo- (6ci)

66. 113a791

67. Q183011

68. Cys-tyr-phe-gln-asn-cys-pro-arg-gly-nh2[disulfide Bridge: 1-6]

69. (2s)-1-[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-16-[(4-hydroxyphenyl)methyl]-6,9,12,15,18-pentaoxo-13-(phenylmethyl)1,2-dithia-5,8,11,14,17-pentazacycloicosane-4-carbonyl]-n-[(2s)-1-[(2-amino-2-oxoethyl)amino]-5-(diaminomethylideneamino)-1-oxopentan-2-yl]pyrrolidine-2-carboxamide

70. 1,2-dithia-5,8,11,14,17-pentaazacycloeicosane-10-propionamide, 19-amino-13-benzyl-7-(carbamoylmethyl)-4-[2-[[1-[(carbamoylmethyl)carbamoyl]-4-guanidinobutyl]carbamoyl]-1-pyrrolidinylcarbonyl]-16-p-hyd

71. 1-{[(4r,7s,10s,13s,16s,19r)-19-amino-7-(2-amino-2-oxoethyl)-10-(3-amino-3-oxopropyl)-13-benzyl-16-(4-hydroxybenzyl)-6,9,12,15,18-pentaoxo-1,2-dithia-5,8,11,14,17-pentaazacycloicosan-4-yl]carbonyl}-l-prolyl-l-arginylglycinamide

72. Glycinamide, L-cysteinyl-l-tyrosyl-l-phenylalanyl-l-glutaminyl-l-asparaginyl-l-cysteinyl-l-prolyl-l-arginyl-, Cyclic (1>6)-disulfide

2.3 Create Date

2005-06-01

3 Chemical and Physical Properties

Molecular Formula	C₄₆H₆₅N₁₅O₁₂S₂
Molecular Weight	1084.2 g/mol
XLogP3	-4.8
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	19
Exact Mass	1083.43785492 g/mol
Monoisotopic Mass	1083.43785492 g/mol
Topological Polar Surface Area	515 Å²
Heavy Atom Count	75
Formal Charge	0
Complexity	2070
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Vasoconstrictor Agents

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

Antidiuretic Agents

Agents that reduce the excretion of URINE, most notably the octapeptide VASOPRESSINS. (See all compounds classified as Antidiuretic Agents.)

Hemostatics

Agents acting to arrest the flow of blood. Absorbable hemostatics arrest bleeding either by the formation of an artificial clot or by providing a mechanical matrix that facilitates clotting when applied directly to the bleeding surface. These agents function more at the capillary level and are not effective at stemming arterial or venous bleeding under any significant intravascular pressure. (See all compounds classified as Hemostatics.)

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