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CAS 80830-42-8

CAS 80830-42-8

Chemistry

Chemistry

Also known as: Fentiapril, 80830-42-8, Rentiapril [inn], Sa 466, D0tam1017b, (2r,4r)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic acid

Molecular Formula

C₁₃H₁₅NO₄S₂

Molecular Weight

313.4 g/mol

InChI Key

BSHDUMDXSRLRBI-JOYOIKCWSA-N

FDA UNII

D0TAM1017B

Rentiapril is a potent angiotensin-converting enzyme (ACE) inhibitor with antihypertensive activity. Rentiapril competitively binds to and inhibits ACE, thereby blocking the conversion of angiotensin I to angiotensin II. This prevents the potent vasoconstrictive actions of angiotensin II and results in vasodilation. Rentiapril also decreases angiotensin II-induced aldosterone secretion by the adrenal cortex, which leads to an increase in sodium excretion and subsequently increases water outflow.

1 2D Structure

CAS 80830-42-8

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2R,4R)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic acid

2.1.2 InChI

InChI=1S/C13H15NO4S2/c15-10-4-2-1-3-8(10)12-14(11(16)5-6-19)9(7-20-12)13(17)18/h1-4,9,12,15,19H,5-7H2,(H,17,18)/t9-,12+/m0/s1

2.1.3 InChI Key

BSHDUMDXSRLRBI-JOYOIKCWSA-N

2.1.4 Canonical SMILES

C1C(N(C(S1)C2=CC=CC=C2O)C(=O)CCS)C(=O)O

2.1.5 Isomeric SMILES

C1[C@H](N([C@H](S1)C2=CC=CC=C2O)C(=O)CCS)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

D0TAM1017B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-(2'-hydroxyphenyl)-3-(3-mercaptopropanoyl)-4-thiazolidine Carboxylic Acid

2. Rentiapril, (2r-cis)-isomer

3. Sa 446

4. Sa-446

2.3.2 Depositor-Supplied Synonyms

1. Fentiapril

2. 80830-42-8

3. Rentiapril [inn]

4. Sa 466

5. D0tam1017b

6. (2r,4r)-2-(2-hydroxyphenyl)-3-(3-sulfanylpropanoyl)-1,3-thiazolidine-4-carboxylic Acid

7. Prescrin

8. Sa 446

9. 4-thiazolidinecarboxylicacid, 2-(2-hydroxyphenyl)-3-(3-mercapto-1-oxopropyl)-, (2r,4r)-

10. Rentiaprilum [latin]

11. Rentiaprilum

12. Sa-446

13. Ccris 2341

14. Brn 5762860

15. Unii-d0tam1017b

16. Rentiapril [jan]

17. (2r,4r)-2-(o-hydroxyphenyl)-3-(3-mercaptopropionyl)-4-thiazolidinecarboxylic Acid

18. Schembl294980

19. Chembl309962

20. Dtxsid80230646

21. Zinc3814177

22. Bdbm50406931

23. De-040

24. 4-thiazolidinecarboxylic Acid, 2-(2-hydroxyphenyl)-3-(3-mercapto-1-oxopropyl)-, (2r-cis)-

25. Hy-106446

26. Cs-0025839

27. Q7313544

28. (2r,4r)-2-(2-hydroxyphenyl)-3-(3-mercaptopropanoyl)thiazolidine-4-carboxylic Acid

29. (2r,4r)--2--(2--hydroxyphenyl) --3--(3--mercaptopropionyl)--4--thiazolidinecarboxylic Acid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₅NO₄S₂
Molecular Weight	313.4 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	313.04425031 g/mol
Monoisotopic Mass	313.04425031 g/mol
Topological Polar Surface Area	104 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	379
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Angiotensin-Converting Enzyme Inhibitors

A class of drugs whose main indications are the treatment of hypertension and heart failure. They exert their hemodynamic effect mainly by inhibiting the renin-angiotensin system. They also modulate sympathetic nervous system activity and increase prostaglandin synthesis. They cause mainly vasodilation and mild natriuresis without affecting heart rate and contractility. (See all compounds classified as Angiotensin-Converting Enzyme Inhibitors.)

Antihypertensive Agents

Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)