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Saralasin Acetate, Anhydrous

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1 FDF Dossiers
1 FDA Orange Book

Synopsis

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Chemistry

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Also known as: Saralasin acetate hydrate, Saralasin acetate [usan], 39698-78-7, Saralasin acetate (usan), Sarenin, Unii-fo21z580m4

Molecular Formula

C₄₄H₇₁N₁₃O₁₃

Molecular Weight

990.1 g/mol

InChI Key

YBZYNINTWCLDQA-UHKVWXOHSA-N

An octapeptide analog of angiotensin II (bovine) with amino acids 1 and 8 replaced with sarcosine and alanine, respectively. It is a highly specific competitive inhibitor of angiotensin II that is used in the diagnosis of HYPERTENSION.

1 2D Structure

Saralasin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

acetic acid;(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;hydrate

2.1.2 InChI

InChI=1S/C42H65N13O10.C2H4O2.H2O/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;1-2(3)4;/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);1H3,(H,3,4);1H2/t24-,28-,29-,30-,31-,33-,34-;;/m0../s1

2.1.3 InChI Key

YBZYNINTWCLDQA-UHKVWXOHSA-N

2.1.4 Canonical SMILES

CC(C)C(C(=O)NC(CC1=CC=C(C=C1)O)C(=O)NC(C(C)C)C(=O)NC(CC2=CN=CN2)C(=O)N3CCCC3C(=O)NC(C)C(=O)O)NC(=O)C(CCCN=C(N)N)NC(=O)CNC.CC(=O)O.O

2.1.5 Isomeric 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.CC(=O)O.O

2.2 Synonyms

2.2.1 MeSH Synonyms

1. (sar(1),ala(8))angii

2. (sar1,val5,ala8)angiotensin Ii

3. 1 Sar 8 Ala Angiotensin Ii

4. 1 Sarcosine 8 Alanine Angiotensin Ii

5. 1-sar-8-ala Angiotensin Ii

6. 1-sarcosine-8-alanine Angiotensin Ii

7. Angiotensin Ii, 1-sar-8-ala

8. Angiotensin Ii, 1-sarcosine-8-alanine

9. Angiotensin Ii, Sar(1)-ala(8)-

10. Angiotensin Ii, Sarcosyl(1)-alanine(8)-

11. Anhydrous Saralasin Acetate

12. Hydrated Saralasin Acetate

13. Sar-arg-val-tyr-val-his-pro-ala

14. Saralasin

15. Saralasin Acetate, Anhydrous

16. Saralasin Acetate, Hydrated

2.2.2 Depositor-Supplied Synonyms

1. Saralasin Acetate Hydrate

2. Saralasin Acetate [usan]

3. 39698-78-7

4. Saralasin Acetate (usan)

5. Sarenin

6. Unii-fo21z580m4

7. Sarenin (tn)

8. Saralasin Hydrated Acetate

9. Schembl2200145

10. Chembl1200670

11. Fo21z580m4

12. N-(1-(n-(n-(n-(n-(n2-(n-methylglycyl-l-arginyl)-l-l-valyl)-l-tyrosyl)-l-valyl)-l-histidyl)-l-prolyl)-l-alanine Acetate (salt) Hydrate

13. Saralasin Acetate(34273-10-4 Free Base)

14. D04126

15. Q27278095

16. [sar1, Val5, Ala8]-angiotensin Ii Acetate Salt Hydrate, >=97% (hplc), Powder

17. Angiotensin Ii, 1-(n-methylglycine)-5-l-valine-8-l-alanine-, Acetate (salt) Hydrate

18. N-(1-(n-(n-(n-(n-(n(sup 2)-(n-methylglycyl-l-arginyl)-l-valyl)-l-tyrosyl)-l-valyl)-l-histidyl)-l-prolyl)-l-alanine Acetate (salt) Hydrate

2.3 Create Date

2006-11-22

3 Chemical and Physical Properties

Molecular Formula	C₄₄H₇₁N₁₃O₁₃
Molecular Weight	990.1 g/mol
Hydrogen Bond Donor Count	14
Hydrogen Bond Acceptor Count	16
Rotatable Bond Count	25
Exact Mass	989.52942937 g/mol
Monoisotopic Mass	989.52942937 g/mol
Topological Polar Surface Area	396 Å²
Heavy Atom Count	70
Formal Charge	0
Complexity	1700
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Angiotensin II Type 1 Receptor Blockers

Agents that antagonize ANGIOTENSIN II TYPE 1 RECEPTOR. Included are ANGIOTENSIN II analogs such as SARALASIN and biphenylimidazoles such as LOSARTAN. Some are used as ANTIHYPERTENSIVE AGENTS. (See all compounds classified as Angiotensin II Type 1 Receptor Blockers.)

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