(3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride

• ChemBase ID: 73276
• Molecular Formular: C25H31ClN2O5
• Molecular Mass: 474.97704
• Monoisotopic Mass: 474.19214978
• SMILES: c1cccc(c1)CC[C@H](N[C@H](C(=O)N1[C@@H](Cc2c(C1)cccc2)C(=O)O)C)C(=O)OCC.Cl
• Canonical SMILES: CCOC(=O)[C@@H](N[C@H](C(=O)N1Cc2ccccc2C[C@H]1C(=O)O)C)CCc1ccccc1.Cl
• InChI: InChI=1S/C25H30N2O5.ClH/c1-3-32-25(31)21(14-13-18-9-5-4-6-10-18)26-17(2)23(28)27-16-20-12-8-7-11-19(20)15-22(27)24(29)30;/h4-12,17,21-22,26H,3,13-16H2,1-2H3,(H,29,30);1H/t17-,21-,22-;/m0./s1
• InChIKey: IBBLRJGOOANPTQ-JKVLGAQCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S)-2-[(2S)-2-{[(2S)-1-ethoxy-1-oxo-4-phenylbutan-2-yl]amino}propanoyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid hydrochloride
• IUPAC Traditional name: quinapril hydrochloride hydrochloride; quinapril hydrochloride
• Synonyms: Accupril; Quinapril hydrochloride; (3S)-2-[(2S)-2-[[(1S)-1-(Ethoxycarbonyl)-3-phenylpropyl]amino]-1-oxopropyl]-1,2,3,4-tetrahydro-3-isoquinolinecarboxylic acid hydrochloride; Quinapril hydrochloride

Database IDs

• CAS Number: 82586-55-8
• MDL Number: MFCD00889215
• PubChem SID: 162038196
• PubChem CID: 54891

CALCULATED PROPERTIES

• Acid pKa: 3.7003553
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 1.6842206
• LogD (pH = 7.4): 0.31489024
• Log P: 1.9639356
• Molar Refractivity: 119.9558 cm^3
• Polarizability: 47.146 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: white solid

Safety Information

• Storage Condition: -20°C
• RTECS: NW7176000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: RAAS
• Gene Information: human ... ACE(1636)

Product Information

• Purity: ≥98% (HPLC)
• Salt Data: hydrochloride
• Empirical Formula (Hill Notation): C25H30N2O5 · HCl

DETAILS

Selleck Chemicals - S2581

Research Area: Neurological Disease
Biological Activity:
Quinapril hydrochloride (Accupril) is the hydrochloride salt of quinapril that is an angiotensin-converting enzyme inhibitor with a Ki of 20 μM. Quinapril hydrochloride (Accupril) used in the treatment of hypertension and congestive heart failure. Quinapril is a prodrug. Quinapril is converted to its active metabolite, quinaprilat, in the liver. Quinapril inhibits angiotensin converting enzyme, an enzyme which catalyses the formation of angiotensin II from its precursor, angiotensin I. Angiotensin II is a powerful vasoconstrictor and increases blood pressure through a variety of mechanisms. Due to reduced angiotensin production, plasma concentrations of aldosterone are also reduced, resulting in increased excretion of sodium in the urine and increased concentrations of potassium in the blood. [1][2]References on Quinapril HCl (Accupril)[1] J Pharmacokinet Biopharm., 1998 Jun, 26(3):269-87[2] http://en.wikipedia.org/wiki/Quinapril, ,

Sigma Aldrich - Q0632

Biochem/physiol Actions
Quinapril is a short-acting angiotensin converting enzyme (ACE) inhibitor.

REFERENCES

• Akarawut W et al. J Pharmacokinet Biopharm. 1998 Jun;26(3):269-87.