Cas no 85955-59-5 ((R) Lisinopril)

(R)-Lisinopril is the enantiomer of the widely used angiotensin-converting enzyme (ACE) inhibitor Lisinopril. As a stereospecific form, (R)-Lisinopril exhibits distinct pharmacological properties, potentially offering improved binding affinity and selectivity for the ACE active site. Its chiral purity enhances metabolic stability, reducing off-target effects compared to the racemic mixture. (R)-Lisinopril demonstrates potent antihypertensive and cardioprotective effects by inhibiting the conversion of angiotensin I to angiotensin II, thereby modulating vasoconstriction and aldosterone secretion. This enantiomer is of particular interest in research for optimizing therapeutic efficacy while minimizing adverse reactions. Its well-defined stereochemistry also facilitates precise pharmacokinetic and pharmacodynamic studies in cardiovascular applications.
(R) Lisinopril structure
(R) Lisinopril structure
Product Name:(R) Lisinopril
CAS No:85955-59-5
MF:C21H31N3O5
MW:405.487945795059
CID:991268
PubChem ID:55187
Update Time:2025-06-07

(R) Lisinopril Chemical and Physical Properties

Names and Identifiers

    • (R) Lisinopril
    • (R)-Lisinopril Sodium Salt
    • (2S)-1-[(2S)-6-amino-2-[[(1R)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
    • (R)-LISINOPRIL
    • (2S)-1-[(2S)-6-amino-2-[[(2R)-1-hydroxy-1-oxo-4-phenylbutan-2-yl]amino]hexanoyl]pyrrolidine-2-carboxylic acid
    • N2-((R)-1-carboxy-3-phenylpropyl)-L-lysyl-L-proline
    • L-Proline, 1-[N2-(1-carboxy-3-phenylpropyl)-L-lysyl]-, (R)- (ZCI)
    • N2-[(1R)-1-Carboxy-3-phenylpropyl]-L-lysyl-L-proline (ACI)
    • (2S)-1-[(2S)-6-Amino-2-[[(1R)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrole-2-carboxylic acid
    • LISINOPRIL EPIMER (USP IMPURITY)
    • L-Proline, 1-(N2-(1-carboxy-3-phenylpropyl)-L-lysyl)-, (R)-
    • LISINOPRIL EPIMER [USP IMPURITY]
    • Lisinopril R,S,S-isomer
    • DTXCID10157776
    • Lisinopril specified impurity E [EP]
    • (2S)-1-((2S)-6-Amino-2-(((1R)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic acid
    • LISINOPRIL IMPURITY E [EP IMPURITY]
    • 85955-59-5
    • 5W66M58H0T
    • UNII-5W66M58H0T
    • L-Proline, N2-((1R)-1-carboxy-3-phenylpropyl)-L-lysyl-
    • (S)-1-((S)-6-Amino-2-(((R)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylicacid
    • Lisinopril specified impurity E
    • Lisinopril Impurity E
    • PD128766
    • LISINOPRIL IMPURITY E (EP IMPURITY)
    • (S)-1-((S)-6-Amino-2-(((R)-1-carboxy-3-phenylpropyl)amino)hexanoyl)pyrrolidine-2-carboxylic acid
    • DTXSID10235285
    • Q27262951
    • Inchi： 1S/C21H31N3O5/c22-13-5-4-9-16(19(25)24-14-6-10-18(24)21(28)29)23-17(20(26)27)12-11-15-7-2-1-3-8-15/h1-3,7-8,16-18,23H,4-6,9-14,22H2,(H,26,27)(H,28,29)/t16-,17+,18-/m0/s1
    • InChI Key： RLAWWYSOJDYHDC-KSZLIROESA-N
    • SMILES： C(N1CCC[C@H]1C(=O)O)(=O)[C@H](CCCCN)N[C@@H](C(=O)O)CCC1C=CC=CC=1

Computed Properties

  • Exact Mass: 405.22600
  • Monoisotopic Mass: 405.22637110g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 29
  • Rotatable Bond Count: 12
  • Complexity: 550
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -2.9
  • Topological Polar Surface Area: 133?2

Experimental Properties

  • PSA: 132.96000
  • LogP: 2.26430

(R) Lisinopril Security Information

(R) Lisinopril Pricemore >>

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(R) Lisinopril Production Method

Production Method 1

Reaction Conditions
1.1 -
2.1 Reagents: Hydrogen Catalysts: Palladium
Reference
On the Michael type addition of dipeptides to 4-oxo-4-phenyl-2-butenoic acid derivatives
Fischer, Janos; et al, Monatshefte fuer Chemie, 1988, 119(5), 645-7

Production Method 2

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium
Reference
On the Michael type addition of dipeptides to 4-oxo-4-phenyl-2-butenoic acid derivatives
Fischer, Janos; et al, Monatshefte fuer Chemie, 1988, 119(5), 645-7

Production Method 3

Reaction Conditions
1.1 Reagents: Sodium hydroxide ,  Sodium cyanoborohydride Solvents: Water
1.2 Reagents: Dowex 50W
Reference
Synthesis of N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline (lisinopril)
Wu, M. T.; et al, Journal of Pharmaceutical Sciences, 1985, 74(3), 352-4

Production Method 4

Reaction Conditions
1.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Acetic acid
2.1 Reagents: Sodium hydroxide ,  Sodium cyanoborohydride Solvents: Water
2.2 Reagents: Dowex 50W
Reference
Synthesis of N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline (lisinopril)
Wu, M. T.; et al, Journal of Pharmaceutical Sciences, 1985, 74(3), 352-4

Production Method 5

Reaction Conditions
1.1 Reagents: Triethylamine ,  Dicyclohexylcarbodiimide Solvents: Dichloromethane
2.1 Reagents: Hydrogen Catalysts: Palladium Solvents: Ethanol ,  Acetic acid
3.1 Reagents: Sodium hydroxide ,  Sodium cyanoborohydride Solvents: Water
3.2 Reagents: Dowex 50W
Reference
Synthesis of N2-[(S)-1-carboxy-3-phenylpropyl]-L-lysyl-L-proline (lisinopril)
Wu, M. T.; et al, Journal of Pharmaceutical Sciences, 1985, 74(3), 352-4

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