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E9658 Sigma-Aldrich

Enalaprilat dihydrate

≥98% (HPLC)

Synonym: (2S)-1-[(2S)-2-[[(1S)-1-Carboxy-3-phenyl-propyl]amino]propanoyl]pyrrolidine-2-carboxylic acid, Vasotec



Related Categories Angiotensin Metabolism, Angiotensins, Approved Therapeutics/Drug Candidates, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
Quality Level   100
assay   ≥98% (HPLC)
solubility   H2O: 14 mg/mL at 60 °C (warming for 5 minutes)
  DMSO: 64 mg/mL
originator   Merck & Co., Inc., Kenilworth, NJ, U.S.
storage temp.   room temp
SMILES string   O.O.C[C@H](N[C@@H](CCc1ccccc1)C(O)=O)C(=O)N2CCC[C@H]2C(O)=O
InChI   1S/C18H24N2O5.2H2O/c1-12(16(21)20-11-5-8-15(20)18(24)25)19-14(17(22)23)10-9-13-6-3-2-4-7-13;;/h2-4,6-7,12,14-15,19H,5,8-11H2,1H3,(H,22,23)(H,24,25);2*1H2/t12-,14-,15-;;/m0../s1
Gene Information   human ... ACE(1636)



5, 25 mg in glass bottle

Biochem/physiol Actions

Enalapril, the ethyl ester of enalaprilat exhibits slight pharmacological activity until it is hydrolyzed in the liver to enalaprilat. Enalaprilat, a IV form of an angiotensin-converting-enzyme inhibitor (ACE) prevents the transformation of angiotensin I to angiotensin II, a potent vasoconstrictor.

Enalaprilat is an inhibitor of angiotensin converting enzyme (ACE), antihypertensive, and a Bradykinin B1 receptor activator. Enalaprilat has nM potency versus ACE and also activates B1 receptors to release NO.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

This compound is featured on the Angiotensin Receptors and Bradykinin Receptors pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

This compound was developed by Merck & Co., Inc., Kenilworth, NJ, U.S.. To browse the list of other pharma-developed compounds and Approved Drugs/Drug Candidates, click here.

Legal Information

LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

Safety & Documentation

Safety Information

Personal Protective Equipment 
NONH for all modes of transport
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable


Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles


Angiotensin Receptors

Different receptors/binding sites have been identified for the biologically active angiotensin (Ang) peptides, i.e. Ang II (1-8), Ang III (2-8), Ang IV (3-8) and Ang (1-7), based on the availability ...
Keywords: Atomic absorption spectroscopy, Cardiovascular, Catalysis, Cell proliferation, Gene expression, Ligands, Metabolites, Transduction

Antihypertensive Agents

Agents that inhibit angiontensin-converting enzymes (ACE) and angiotensin II formation are essential to cardiovascular medicine.1 These inhibitors are used not only to treat essential hypertension an...
Sami Barghshoon
BioFiles v7 n5, 2012, 5–20
Keywords: AGE, Antihypertensives, Cardiovascular, Clinical, Diuretics, PAGE, Reductions

Bradykinin Receptors

The nonapeptide bradykinin (BK) and Lys-BK (kallidin) are naturally occurring substances produced in most species by the proteolytic digestion of high or low molecular weight kininogen by plasma and ...
Keywords: Angiogenesis, Atomic absorption spectroscopy, Cloning, Diabetes, Digestions, Gene expression, Growth factors, Inflammation, Ligands, Pharmacological actions, Transduction

Peer-Reviewed Papers


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