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126222-34-2 molecular structure
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(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 and InChIs

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

Cite this record

CBID:97 http://www.chembase.cn/molecule-97.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
126222-34-2
PubChem SID
46507286
160963560
PubChem CID
5462340

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 cm3 Polarizability 67.33697 Å3
Polar Surface Area 161.48 Å2 Rotatable Bonds 16 
Lipinski's Rule of Five false 
Log P 2.42  LOG S -4.47 
Solubility (Water) 2.13e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
3.9 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00212 external link
Item Information
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

REFERENCES

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  • • 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
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PATENTS

PATENTS

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INTERNET

INTERNET

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