(R)-Metipranolol

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

What is the (R)-Metipranolol?

The molecule (R)-Metipranolol presents a molecular formula of C17H27NO4 and its IUPAC name is [4-[(2R)-2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate.

R-Metipranolol is a molecule that was first synthesized in the 1970s. It is a member of the beta-adrenergic receptor family, and acts as an antagonist at both the beta1 and beta2 subtypes. In addition to its beta-adrenergic activity, R-metipranolol also has weak alpha-adrenergic activity..

R-metipranolol has been shown to be effective in the treatment of hypertension and congestive heart failure. It has also been used in the treatment of glaucoma, although its efficacy in this indication is controversial. In addition to its use in humans, R-metipranolol has also been used in veterinary medicine..

The most common side effects of R-metipranolol are bradycardia and hypotension. More serious side effects include heart block and bronchospasm. R-metipranolol should be used with caution in patients with asthma or other pulmonary diseases..

R-metipranolol is a relatively safe and effective medication that has a wide range of uses in both human and veterinary medicine..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-Metipranolol BQIPXWYNLPYNHW-OAHLLOKOSA-N chemical compound 2D structure molecule svg
(R)-Metipranolol

 

Molecule descriptors

 
IUPAC name[4-[(2R)-2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
InChI codeInChI=1S/C17H27NO4/c1-10(2)18-8-15(20)9-21-16-7-11(3)17(22-14(6)19)13(5)12(16)4/h7,10,15,18,20H,8-9H2,1-6H3/t15-/m1/s1
InChI KeyBQIPXWYNLPYNHW-OAHLLOKOSA-N
SMILESCC(=O)Oc1c(C)cc(OC[C@H](O)CNC(C)C)c(C)c1C

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.

  • (R)-Metipranolol
  • 52849-56-6
  • Phenol, 4-[(2R)-2-hydroxy-3-[(1-methylethyl)amino]propoxy]-2,3,6-trimethyl-, 1-acetate

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC494
  • DTXSID501126220
  • SCHEMBL117702

Physico-Chemical properties

IUPAC name[4-[(2R)-2-hydroxy-3-(propan-2-ylamino)propoxy]-2,3,6-trimethylphenyl] acetate
Molecular formulaC17H27NO4
Molecular weight309.401
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity87.33
LogP2.7
Topological polar surface area67.8

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.