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Fosinopril

Synopsis, Chemistry

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Also known as: Fosinopril sodium, 88889-14-9, Chebi:5164, 1217528-56-7, Dynacil, Eliten

Molecular Formula

C₃₀H₄₅NNaO₇P

Molecular Weight

585.6 g/mol

InChI Key

TVTJZMHAIQQZTL-HREVRLCXSA-M

A phosphinic acid-containing angiotensin-converting enzyme inhibitor that is effective in the treatment of hypertension. It is a prodrug that is converted to its active metabolite fosinoprilat.

1 2D Structure

Fosinopril

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

sodium;(2S,4S)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate

2.1.2 InChI

InChI=1S/C30H46NO7P.Na/c1-4-28(33)37-30(22(2)3)38-39(36,18-12-11-15-23-13-7-5-8-14-23)21-27(32)31-20-25(19-26(31)29(34)35)24-16-9-6-10-17-24;/h5,7-8,13-14,22,24-26,30H,4,6,9-12,15-21H2,1-3H3,(H,34,35);/q;+1/p-1/t25-,26+,30?,39?;/m1./s1

2.1.3 InChI Key

TVTJZMHAIQQZTL-HREVRLCXSA-M

2.1.4 Canonical SMILES

CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2CC(CC2C(=O)[O-])C3CCCCC3.[Na+]

2.1.5 Isomeric SMILES

CCC(=O)OC(C(C)C)OP(=O)(CCCCC1=CC=CC=C1)CC(=O)N2C[C@@H](C[C@H]2C(=O)[O-])C3CCCCC3.[Na+]

2.2 Synonyms

2.2.1 MeSH Synonyms

1. Dynacil

2. Fosenopril

3. Fosinil

4. Fosinopril

5. Fosinopril Sodium

6. Fosinopril, (1(s*(r*)),2 Alpha,4 Alpha)-(d-pro)-isomer

7. Fosinopril, (1(s*(r*)),2 Alpha,4 Beta)-isomer

8. Fosinopril, (1(s*(s*)),2 Alpha,4 Beta)-isomer

9. Fosinorm

10. Fositens

11. Fozitec

12. Hiperlex

13. Monopril

14. Newace

15. Sodium, Fosinopril

16. Sq 28,555

17. Sq 28555

18. Sq-28,555

19. Sq-28555

20. Sq28,555

21. Sq28555

22. Staril

23. Tenso Stop

24. Tensocardil

2.2.2 Depositor-Supplied Synonyms

1. Fosinopril Sodium

2. 88889-14-9

3. Chebi:5164

4. 1217528-56-7

5. Dynacil

6. Eliten

7. Sodium;(2s,4s)-4-cyclohexyl-1-[2-[(2-methyl-1-propanoyloxypropoxy)-(4-phenylbutyl)phosphoryl]acetyl]pyrrolidine-2-carboxylate

8. Sodium (2s,4s)-4-cyclohexyl-1-(2-((2-methyl-1-(propionyloxy)propoxy)(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylate

9. Fosinopril Sodium- Bio-x

10. Ncgc00167432-01

11. Dsstox_cid_26621

12. Dsstox_rid_81772

13. Dsstox_gsid_46621

14. Schembl40690

15. Chembl3188382

16. Dtxsid7046621

17. Tox21_112436

18. Mfcd00897699

19. Akos015888700

20. Ac-6227

21. Bcp9000703

22. Bs-1003

23. Sq28555

24. Bf164489

25. Cas-88889-14-9

26. A842989

27. Sodium (2s,4s)-4-cyclohexyl-1-({[2-methyl-1-(propanoyloxy)propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylate

28. Sodium (2s,4s)-4-cyclohexyl-1-(2-((2-methyl-1-(propionyloxy)propoxy)(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-

29. Sodium (2s,4s)-4-cyclohexyl-1-(2-((2-methyl-1-(propionyloxy)propoxy)-(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylate

30. Sodium (2s,4s)-4-cyclohexyl-1-(2-{[2-methyl-1-(propionyloxy) Propoxy](4-phenylbutyl)phosphoryl}acetyl)pyrrolidine-2-carboxylate

31. Sodium(2s,4s)-4-cyclohexyl-1-(2-((2-methyl-1-(propionyloxy)propoxy)(4-phenylbutyl)phosphoryl)acetyl)pyrrolidine-2-carboxylate

2.3 Create Date

2008-02-05

3 Chemical and Physical Properties

Molecular Formula	C₃₀H₄₅NNaO₇P
Molecular Weight	585.6 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	15
Exact Mass	585.28313405 g/mol
Monoisotopic Mass	585.28313405 g/mol
Topological Polar Surface Area	113 Å²
Heavy Atom Count	40
Formal Charge	0
Complexity	857
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Fosinopril sodium
Drug Label	Fosinopril sodium tablet, USP is the sodium salt of fosinopril USP, the ester prodrug of an angiotensin converting enzyme (ACE) inhibitor, fosinoprilat. It contains a phosphinate group capable of specific binding to the active site of angiotensin con...
Active Ingredient	Fosinopril sodium
Dosage Form	Tablet
Route	Oral
Strength	10mg; 40mg; 20mg
Market Status	Prescription
Company	Actavis Labs Fl; Teva; Apotex; Aurobindo Pharma; Sandoz; Invagen Pharms

2 of 2
Drug Name	Fosinopril sodium
Drug Label	Fosinopril sodium tablet, USP is the sodium salt of fosinopril USP, the ester prodrug of an angiotensin converting enzyme (ACE) inhibitor, fosinoprilat. It contains a phosphinate group capable of specific binding to the active site of angiotensin con...
Active Ingredient	Fosinopril sodium
Dosage Form	Tablet
Route	Oral
Strength	10mg; 40mg; 20mg
Market Status	Prescription
Company	Actavis Labs Fl; Teva; Apotex; Aurobindo Pharma; Sandoz; Invagen Pharms

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Angiotensin-converting Enzyme Inhibitors [MoA]; Angiotensin Converting Enzyme Inhibitor [EPC]