CAS 126222-34-2|(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|Remikiren|Ro 42-589...

General Information

Structure

Molecular Formula

C₃₃H₅₀N₄O₆S

Molecular Mass

630.8383

Exact Mass

630.34510634

Charge

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

Canonic 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

Isomeric 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

Calculated Properties

JChem

Acid pKa

12.323535

H Acceptors

H Donor

LogD (pH = 5.5)

1.840877

LogD (pH = 7.4)

2.3054776

Log P

2.368043

Molar Refractivity

169.5993

Polarizability

67.33697

Polar Surface Area

161.48

Rotatable Bonds

Lipinski's Rule of Five

false

ALOGPS 2.1

Log P

2.42

LOG S

-4.47

Solubility (Water)

2.13e-02 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

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

RemikirenRo 42-5892

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

Names and Identifiers

Registration numbers

PubChem SID

16096356046507286

CAS Number

126222-34-2

PubChem CID

5462340

Registration numbers

Properties

Physical Property

Hydrophobicity(logP)

3.9

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule 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]

Molecule Details

References

PubChem Literature

From Data Sources

• 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

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data