Aliskiren

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Aliskiren are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Aliskiren?

The molecule Aliskiren presents a molecular formula of C30H53N3O6 and its IUPAC name is (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide.

Aliskiren (trade names Tekamlo, Rasilez) is a direct renin inhibitor medication used to treat hypertension. It is the first in a new class of antihypertensive agents. Aliskiren was discovered by Swiss company Novartis. It is marketed as Tekamlo in the United States by Abbott Laboratories and as Rasilez in Europe and other countries by Novartis..

Aliskiren works by directly inhibiting renin, a key enzyme in the renin-angiotensin-aldosterone system (RAAS). The RAAS is a hormone system that regulates blood pressure and fluid balance in the body. By inhibiting renin, aliskiren reduces blood pressure by preventing the production of angiotensin II, a hormone that causes blood vessels to constrict..

Aliskiren is generally well-tolerated, with the most common side effects being dizziness, headache, and nausea. It is not recommended for use in pregnant or breastfeeding women..

Aliskiren is a promising new treatment for hypertension, but more research is needed to determine its long-term safety and efficacy..

3D structure

Cartesian coordinates

Geometry of Aliskiren in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Aliskiren UXOWGYHJODZGMF-QORCZRPOSA-N chemical compound 2D structure molecule svg
Aliskiren

 

Molecule descriptors

 
IUPAC name(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide
InChI codeInChI=1S/C30H53N3O6/c1-19(2)22(14-21-10-11-26(38-8)27(15-21)39-13-9-12-37-7)16-24(31)25(34)17-23(20(3)4)28(35)33-18-30(5,6)29(32)36/h10-11,15,19-20,22-25,34H,9,12-14,16-18,31H2,1-8H3,(H2,32,36)(H,33,35)/t22-,23-,24-,25-/m0/s1
InChI KeyUXOWGYHJODZGMF-QORCZRPOSA-N
SMILESCOCCCOc1cc(C[C@@H](C[C@H](N)[C@@H](O)C[C@H](C(=O)NCC(C)(C)C(N)=O)C(C)C)C(C)C)ccc1OC

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (2S,4S,5S,7S)-5-AMINO-N-(2-CARBAMOYL-2-METHYLPROPYL)-4-HYDROXY-2-ISOPROPYL-7-[4-METHOXY-3-(3-METHOXYPROPOXY)BENZYL]-8-METHYLNONANAMIDE
  • (2S,4S,5S,7S)-5-Amino-N-(2-carbamoyl)-2-methylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonamide
  • (2S,4S,5S,7S)-5-Amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide
  • (2S,4S,5S,7S)-5-amino-N-(2-carbamoyl-2,2-dimethylethyl)-4-hydroxy-7-{[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl}-8-methyl-2-(propan-2-yl)nonanamide
  • (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxo-propyl)-4-hydroxy-2-isopropyl-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-nonanamide
  • (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methyl-2-(1-methylethyl)nonanamide
  • (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methyl-2-(propan-2-yl)nonanamide
  • (2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide
  • (2S,4S,5S,7S)-5-amino-N-[2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide
  • (2s,4s,5s,7s)-5-amino-N-(2-carbamoyl-2-methylpropyl)-4-hydroxy-2-isopropyl-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-8-methylnonanamide
  • (2s,4s,5s,7s)-7-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-amino-n-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-8-methylnonanamide
  • 1327153-71-8
  • 173334-57-1
  • 173334-58-2
  • 2(S),4(S),5(S),7(S)-N-(2-carbamoyl-2-methylpropyl)-5-amino-4-hydroxy-2,7-diisopropyl-8-(4-methoxy-3-(3-methoxypropoxy)phenyl)octanamid hemifumarate
  • 334A582
  • 5(S)-Amino-4(S)-hydroxy-2(S),7(S)-diisopropyl-8-[4-methoxy-3-(3-methoxypropyloxy)-phenyl]-octanoic acid N-(2-carbamoyl-2,2-dimethyl-ethyl)-amide
  • 5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-2-isopropyl-7-[4-methoxy-3-(3-methoxypropoxy)benzyl]-8-methylnonanamide fumarate
  • 502FWN4Q32
  • AB01274865-01
  • AB01274865_02
  • AB01274865_03
  • AS-80517
  • Aliskiren
  • Aliskiren (USAN/INN)
  • Aliskiren fumarate
  • Aliskiren(CGP 60536)
  • Aliskiren-hemifumarate
  • BDBM17950
  • Benzeneoctanamide, delta-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-gamma-hydroxy-4-methoxy-3-(3-methoxypropoxy)-alpha,zeta-bis(1-methylethyl)-, (alphaS,gammaS,deltaS,zetaS)-
  • Benzeneoctanamide, delta-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-gamma-hydroxy-4-methoxy-3-(3-methoxypropoxy)-alpha,zeta-bis-(1-methylethyl)-, (alphaS,gammaS,deltaS,zetaS)-
  • C41
  • CGP 60536
  • CGP-060536B
  • CGP60536B
  • CS-0443
  • D03208
  • DB09026
  • GTPL4812
  • HSDB 7843
  • HY-12176
  • MFCD09839018
  • NCGC00186464-01
  • NCGC00186464-02
  • Q414904
  • Rasilez
  • SBI-0206888.P001
  • SPP 100
  • SPP-100
  • SPP100
  • STL386835
  • benzeneoctanamide, delta-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-gamma-hydroxy-4-methoxy-3-(3-methoxypropoxy)-alpha,zeta-bis(1-methylethyl)-, (alphaS,gammaS,deltaS,zetaS)-, fumarate
  • s5767

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC4393164
  • UNII-502FWN4Q32
  • AKOS015852572
  • AKOS015888741
  • ALBB-027274
  • BRD-K30020243-051-01-7
  • DTXSID40891494
  • CHEMBL1639
  • CHEBI:601027
  • SCHEMBL455490

Physico-Chemical properties

IUPAC name(2S,4S,5S,7S)-5-amino-N-(3-amino-2,2-dimethyl-3-oxopropyl)-4-hydroxy-7-[[4-methoxy-3-(3-methoxypropoxy)phenyl]methyl]-8-methyl-2-propan-2-ylnonanamide
Molecular formulaC30H53N3O6
Molecular weight551.758
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity155.94
LogP5.1
Topological polar surface area146.1

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.