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^Y
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL938^N ChEMBL1200670^N
ChemSpider	4884380^N
PubChem CID	6324663
UNII	H2AFV2HE66^N
CompTox Dashboard (EPA)	DTXSID2046549
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^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
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). N verify (what is ^YN ?) Infobox references

Saralasin is a competitive angiotensin II receptor antagonist with partial agonistic activity. The aminopeptide sequence for saralasin differs from angiotensin II at three sites:

• At position 1, sarcosine replaces aspartic acid, thereby increasing the affinity for vascular smooth muscle AT II receptors and making sara resistant to degradation by aminopeptidases.^[1]
• At position 5, isoleucine is replaced by valine
• At position 8, phenylalanine is replaced by alanine which leads to a smaller stimulatory effect. Saralasin was used to distinguish renovascular hypertension from essential hypertension before its discontinuation in January 1984 because of many false-positive and false-negative reports.^[2]

References

1. Pals et al (1979)
2. Hutchison and Shahan (2004)

External links

• 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.