(2S)-2-[(2R)-2-benzyl-3-(2-methylpropane-2-sulfonyl)propanamido]-N-[(2R,3S,4R)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-3-(1H-imidazol-5-yl)propanamide

• ChemBase ID: 97
• Molecular Formular: C33H50N4O6S
• Molecular Mass: 630.8383
• Monoisotopic Mass: 630.34510634
• SMILES: S(=O)(=O)(C[C@@H](C(=O)N[C@H](C(=O)N[C@@H]([C@H](O)[C@H](O)C1CC1)CC1CCCCC1)Cc1[nH]cnc1)Cc1ccccc1)C(C)(C)C
• Canonical SMILES: O=C([C@H](Cc1cnc[nH]1)NC(=O)[C@H](CS(=O)(=O)C(C)(C)C)Cc1ccccc1)N[C@@H]([C@@H]([C@@H](C1CC1)O)O)CC1CCCCC1
• InChI: InChI=1S/C33H50N4O6S/c1-33(2,3)44(42,43)20-25(16-22-10-6-4-7-11-22)31(40)37-28(18-26-19-34-21-35-26)32(41)36-27(17-23-12-8-5-9-13-23)30(39)29(38)24-14-15-24/h4,6-7,10-11,19,21,23-25,27-30,38-39H,5,8-9,12-18,20H2,1-3H3,(H,34,35)(H,36,41)(H,37,40)/t25-,27+,28-,29+,30-/m0/s1
• InChIKey: UXIGZRQVLGFTOU-PUNKFERVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(2R)-2-benzyl-3-(2-methylpropane-2-sulfonyl)propanamido]-N-[(2R,3S,4R)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-3-(1H-imidazol-5-yl)propanamide
• IUPAC Traditional name: (2S)-2-[(2R)-2-benzyl-3-(2-methylpropane-2-sulfonyl)propanamido]-N-[(2R,3S,4R)-1-cyclohexyl-4-cyclopropyl-3,4-dihydroxybutan-2-yl]-3-(3H-imidazol-4-yl)propanamide
• Synonyms: Ro 42-5892; Remikiren

Database IDs

• CAS Number: 126222-34-2
• PubChem SID: 160963560; 46507286
• PubChem CID: 5462340

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.323535
• H Acceptors: 7
• H Donor: 5
• LogD (pH = 5.5): 1.840877
• LogD (pH = 7.4): 2.3054776
• Log P: 2.368043
• Molar Refractivity: 169.5993 cm^3
• Polarizability: 67.33697 Å^3
• Polar Surface Area: 161.48 Å^2
• Rotatable Bonds: 16
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.42
• LOG S: -4.47
• Solubility (Water): 2.13e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.9

DETAILS

DrugBank - DB00212

• Drug Groups: approved
• Description: Remikiren is an orally active, high specificity renin inhibitor.
• Indication: For the treatment of hypertension and heart failure
• Pharmacology: Remikiren is an orally available renin inhibitor with an established blood pressure-lowering effect in patients with essential hypertension. No data are available on the renal effects of remikiren in humans. In patients with essential hypertension, a single oral dose of remikiren can induce a renal vasodilation, without affecting the GFR and despite a significant decrease in blood pressure. This systemic and renal hemodynamic response is more pronounced in case of a more activated renin-angiotensin system.
• Affected Organisms: Humans and other mammals
• Absorption: Absorbed following oral administration.
• Protein Binding: 83%
• References: Clozel JP, Fischli W: Discovery of remikiren as the first orally active renin inhibitor. Arzneimittelforschung. 1993 Feb;43(2A):260-2. [Pubmed] ; Richter WF, Whitby BR, Chou RC: Distribution of remikiren, a potent orally active inhibitor of human renin, in laboratory animals. Xenobiotica. 1996 Mar;26(3):243-54. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Clozel JP, Fischli W: Discovery of remikiren as the first orally active renin inhibitor. Arzneimittelforschung. 1993 Feb;43(2A):260-2. Pubmed
• Richter WF, Whitby BR, Chou RC: Distribution of remikiren, a potent orally active inhibitor of human renin, in laboratory animals. Xenobiotica. 1996 Mar;26(3):243-54. Pubmed