Lisinopril Dihydrate - ≥98% , Angiotensin-converting enzyme inhibitor, CAS No.83915-83-7, Angiotensin-converting enzyme inhibitor

CAS: 83915-83-7 Cat. No.: L129324 Molecular Weight: 405.49(as Anhydrous) EC Number: 627-033-9

GRADE & PURITY ≥98%

Synonyms

MK-521 | LISINOPRIL COMPONENT OF PRINZIDE | LISINOPRIL [USAN] | Prestwick_613 | (S)-Lisinopril | AC-6226 | UNII-E7199S1YWR | DTXSID7041253 | Lisinopril, United States Pharmacopeia (USP) Reference Standard | (S)-1-(N(2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-

Storage

Store at 2-8°C

Shipped In

Wet ice

Overview

Lisinopril is an angiotensin-converting enzyme inhibitor, used in treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing renal and retinal complications of diabetes.

Specifications

Synonyms

MK-521 | LISINOPRIL COMPONENT OF PRINZIDE | LISINOPRIL [USAN] | Prestwick_613 | (S)-Lisinopril | AC-6226 | UNII-E7199S1YWR | DTXSID7041253 | Lisinopril, United States Pharmacopeia (USP) Reference Standard | (S)-1-(N(2)-(1-carboxy-3-phenylpropyl)-L-lysyl)-

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Angiotensin converting enzyme (ACE) inhibitor.Potent, competitive angiotensin converting enzyme inhibitor (IC 50 = 4 nM). Cardiotonic and antihypertensive effects. Orally active. Poor blood-brain barrier permeability. Active in vitro and in vivo .

Storage

Store at 2-8°C

Shipped In

Wet ice

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Mechanism of action

Angiotensin-converting enzyme inhibitor

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504763708
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504763708
• Canonical Smiles: C1CC(N(C1)C(=O)C(CCCCN)NC(CCC2=CC=CC=C2)C(=O)O)C(=O)O.O.O
• IUPAC Name: (2S)-1-[(2S)-6-amino-2-[[(1S)-1-carboxy-3-phenylpropyl]amino]hexanoyl]pyrrolidine-2-carboxylic acid;dihydrate
• InChIKey: CZRQXSDBMCMPNJ-ZUIPZQNBSA-N
• INCHI: 1S/C21H31N3O5.2H2O/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);2*1H2/t16-,17-,18-;;/m0../s1
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)[C@H](CCCCN)N[C@@H](CCC2=CC=CC=C2)C(=O)O)C(=O)O.O.O
• WGK Germany: 3
• RTECS: TW3589990
• Molecular Weight: 405.49(as Anhydrous)
• Reaxy-Rn: 49510439
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=49510439&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Class Carboxylic acids and derivatives
      • Subclass Amino acids, peptides, and analogues
        • Level5 Peptides
          • Level6 Dipeptides

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Class: Carboxylic acids and derivatives
• Subclass: Amino acids, peptides, and analogues
• Intermediate Tree Nodes: Peptides
• Direct Parent: Dipeptides
• Alternative Parents: Proline and derivatives N-acyl-L-alpha-amino acids Alpha amino acid amides L-alpha-amino acids Pyrrolidine carboxylic acids N-acylpyrrolidines Aralkylamines Benzene and substituted derivatives Dicarboxylic acids and derivatives Tertiary carboxylic acid amides Amino acids Dialkylamines Carboxylic acids Azacyclic compounds Hydrocarbon derivatives Carbonyl compounds Organopnictogen compounds Organic oxides Monoalkylamines
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: Alpha-dipeptide - N-acyl-alpha-amino acid - Proline or derivatives - N-acyl-alpha amino acid or derivatives - N-acyl-l-alpha-amino acid - Alpha-amino acid amide - Alpha-amino acid - Alpha-amino acid or derivatives - L-alpha-amino acid - N-acylpyrrolidine - Pyrrolidine carboxylic acid - Pyrrolidine carboxylic acid or derivatives - Aralkylamine - Benzenoid - Monocyclic benzene moiety - Dicarboxylic acid or derivatives - Tertiary carboxylic acid amide - Pyrrolidine - Amino acid or derivatives - Carboxamide group - Amino acid - Organoheterocyclic compound - Secondary amine - Azacycle - Carboxylic acid - Secondary aliphatic amine - Hydrocarbon derivative - Primary aliphatic amine - Organic oxide - Organic nitrogen compound - Organonitrogen compound - Carbonyl group - Organooxygen compound - Primary amine - Amine - Organic oxygen compound - Organopnictogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
• External Descriptors: hydrate

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

ACE Tclin Angiotensin-converting enzyme (0 Activities)

Discover Target: ACE

Activity Type	Activity Value -log(M)	Mechanism of Action	Activity Reference	Publications (PubMed IDs)

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2D6 Tclin Cytochrome P450 2D6 (33882 Activities)

Discover Target: CYP2D6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP1A2 Tchem Cytochrome P450 1A2 (26471 Activities)

Discover Target: CYP1A2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C9 Tchem Cytochrome P450 2C9 (32119 Activities)

Discover Target: CYP2C9

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP2C19 Tchem Cytochrome P450 2C19 (29246 Activities)

Discover Target: CYP2C19

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

LMNA Tbio Prelamin-A/C (36751 Activities)

Discover Target: LMNA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

USP1 Tchem Ubiquitin carboxyl-terminal hydrolase 1 (22556 Activities)

Discover Target: USP1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

GCN5 Histone acetyltransferase GCN5 (89 Activities)

Discover Target: GCN5

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO Water 20 mg/mL Ethanol
• Sensitivity: Heat sensitive
• Specific Rotation[α]: -45° (C=1,0.25mol/L ZnAcetate Buff. sol.)
• Melt Point(°C): 148°C
• Molecular Weight: 441.500 g/mol
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 9
• Rotatable Bond Count: 12
• Exact Mass: 441.248 Da
• Monoisotopic Mass: 441.248 Da
• Topological Polar Surface Area: 135.000 Ų
• Heavy Atom Count: 31
• Formal Charge: 0
• Complexity: 550.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 3
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 3

XLogP3

References

1. Hui Luo, Yin Qian, Jin Qi, Xinyu Liu.  (2022)  A novel strategy for screening angiotensin-converting enzyme inhibitors from natural products based on enzyme-immobilized ligand fishing combined with active-site blocking and directional enrichment.  JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES,      [PMID:35248900] [10.1016/j.jchromb.2022.123203]