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Saralasin

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Saralasin
Names
IUPAC name
(2S)-2-[[(2S)-1-[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-5-(diaminomethylideneamino)-2-[[2-(methylamino)acetyl]amino]pentanoyl]amino]-3-methylbutanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-3-methylbutanoyl]amino]-3-(1H-imidazol-5-yl)propanoyl]pyrrolidine-2-carbonyl]amino]propanoic acid
Other names
Sar-Arg-Val-Tyr-Val-His-Pro-Ala
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
UNII
  • InChI=1S/C42H65N13O10/c1-22(2)33(53-35(58)28(50-32(57)20-45-6)9-7-15-47-42(43)44)38(61)51-29(17-25-11-13-27(56)14-12-25)36(59)54-34(23(3)4)39(62)52-30(18-26-19-46-21-48-26)40(63)55-16-8-10-31(55)37(60)49-24(5)41(64)65/h11-14,19,21-24,28-31,33-34,45,56H,7-10,15-18,20H2,1-6H3,(H,46,48)(H,49,60)(H,50,57)(H,51,61)(H,52,62)(H,53,58)(H,54,59)(H,64,65)(H4,43,44,47)/t24-,28-,29-,30-,31-,33-,34-/m0/s1 ☒N
    Key: PFGWGEPQIUAZME-NXSMLHPHSA-N ☒N
  • InChI=1/C42H65N13O10/c1-22(2)33(53-35(58)28(50-32(57)20-45-6)9-7-15-47-42(43)44)38(61)51-29(17-25-11-13-27(56)14-12-25)36(59)54-34(23(3)4)39(62)52-30(18-26-19-46-21-48-26)40(63)55-16-8-10-31(55)37(60)49-24(5)41(64)65/h11-14,19,21-24,28-31,33-34,45,56H,7-10,15-18,20H2,1-6H3,(H,46,48)(H,49,60)(H,50,57)(H,51,61)(H,52,62)(H,53,58)(H,54,59)(H,64,65)(H4,43,44,47)/t24-,28-,29-,30-,31-,33-,34-/m0/s1
    Key: PFGWGEPQIUAZME-NXSMLHPHBA
  • C[C@@H](C(=O)O)NC(=O)[C@@H]1CCCN1C(=O)[C@H](CC2=CN=CN2)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CC3=CC=C(C=C3)O)NC(=O)[C@H](C(C)C)NC(=O)[C@H](CCCN=C(N)N)NC(=O)CNC
Properties
C42H65N13O10
Molar mass 912.05 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Saralasin is a competitive angiotensin II receptor antagonist with partial agonistic activity. The aminopeptide sequence for saralasin differs from angiotensin II at three sites:

References

[edit]
  1. ^ Pals et al (1979)
  2. ^ Hutchison and Shahan (2004)
[edit]
  • Saralasin at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  • Olsson M, Annerbrink K, Hedner J, Eriksson E (2004). "Intracerebroventricular administration of the angiotensin II receptor antagonist saralasin reduces respiratory rate and tidal volume variability in freely moving Wistar rats". Psychoneuroendocrinology. 29 (1): 107–12. doi:10.1016/S0306-4530(02)00147-6. PMID 14575733. S2CID 44451942.
  • Ip S, Tsang S, Wong T, Che C, Leung P (2003). "Saralasin, a nonspecific angiotensin II receptor antagonist, attenuates oxidative stress and tissue injury in cerulein-induced acute pancreatitis". Pancreas. 26 (3): 224–9. doi:10.1097/00006676-200304000-00003. PMID 12657946. S2CID 28646144.
  • Tsang S, Ip S, Wong T, Che C, Leung P (2003). "Differential effects of saralasin and ramiprilat, the inhibitors of renin-angiotensin system, on cerulein-induced acute pancreatitis". Regul Pept. 111 (1–3): 47–53. doi:10.1016/S0167-0115(02)00226-4. PMID 12609748. S2CID 2150707.