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2D Structure
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

2D Structure

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 Weight 585.6 g/mol
Molecular Formula C30H45NNaO7P
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count7
Rotatable Bond Count15
Exact Mass585.28313405 g/mol
Monoisotopic Mass585.28313405 g/mol
Topological Polar Surface Area113 Ų
Heavy Atom Count40
Formal Charge0
Complexity857
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count2
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameFosinopril sodium
Drug LabelFosinopril 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 IngredientFosinopril sodium
Dosage FormTablet
RouteOral
Strength10mg; 40mg; 20mg
Market StatusPrescription
CompanyActavis Labs Fl; Teva; Apotex; Aurobindo Pharma; Sandoz; Invagen Pharms

2 of 2  
Drug NameFosinopril sodium
Drug LabelFosinopril 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 IngredientFosinopril sodium
Dosage FormTablet
RouteOral
Strength10mg; 40mg; 20mg
Market StatusPrescription
CompanyActavis 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]