Saralasin

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
CAS Number	34273-10-4
ChEMBL	ChEMBL938 ChEMBL1200670
ChemSpider	4884380
Jmol interactive 3D	Image
PubChem	6324663
UNII	H2AFV2HE66
InChI 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 Key: PFGWGEPQIUAZME-NXSMLHPHSA-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
SMILES 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
Chemical formula	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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Infobox references

Saralasin is a partial agonist of angiotensin II receptors, though it is commonly mistaken as a competitive antagonist. Saralasin's distinction as a partial agonist is based on the fact that its therapeutic effect (i.e. reduced hypertension) is only observed in patients with high plasma angiotensin II levels, but in patients with low angiotensin II levels Saralasin causes hypertension. In other words, the effects of Saralasin on the angiotensin II receptor in the absence of angiotensin II is pharmacodynamically similar to angiotensin II itself thus it is a partial agonist, because if it was an antagonist it would not elicit an effect when bound to its receptor. Saralasin is an angiotensin II analogue, containing sarcosine-1 and alanine-8, hence the name (sarcosine, alanine, angiotensin).

External links

• Saralasin at the US 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.
• 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.
• 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.