(R)-(+)-Ropivacaine

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

What is the (R)-(+)-Ropivacaine?

The molecule (R)-(+)-Ropivacaine presents a molecular formula of C17H26N2O and its IUPAC name is (2R)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide.

Ropivacaine is a local anesthetic and antiarrhythmic drug of the amino amide class. It is closely related to levobupivacaine and is marketed under the trade name Naropin. Ropivacaine is used for local infiltration, peripheral nerve block, sympathetic nerve block, and epidural and caudal anesthesia..

Ropivacaine is a white powder that is slightly soluble in water. It has a pKa of 8.6 and a pH of 3.5–5.5. The melting point is about 72 °C..

The (-)-enantiomer of ropivacaine is more potent and has a longer duration of action than the (+)-enantiomer. The two enantiomers are separated by chiral resolution or by enantiomeric excess synthesis..

Ropivacaine is metabolized by hepatic enzymes and is excreted in the urine..

The most common side effects of ropivacaine are dizziness, lightheadedness, and nausea. Other side effects include hypotension, hypertension, bradycardia, and tachycardia..

Ropivacaine should be used with caution in patients with liver disease or kidney disease..

3D structure

Cartesian coordinates

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

2D drawing

 

(R)-(+)-Ropivacaine ZKMNUMMKYBVTFN-OAHLLOKOSA-N chemical compound 2D structure molecule svg
(R)-(+)-Ropivacaine

 

Molecule descriptors

 
IUPAC name(2R)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
InChI codeInChI=1S/C17H26N2O/c1-4-11-19-12-6-5-10-15(19)17(20)18-16-13(2)8-7-9-14(16)3/h7-9,15H,4-6,10-12H2,1-3H3,(H,18,20)/t15-/m1/s1
InChI KeyZKMNUMMKYBVTFN-OAHLLOKOSA-N
SMILESCCCN1CCCC[C@@H]1C(=O)Nc1c(C)cccc1C

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.

  • (+)-(2R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide
  • (+)-Ropivacaine
  • (2R)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
  • (R)-(+)-Ropivacaine
  • (R)-N-(2,6-Dimethylphenyl)-1-propylpiperidine-2-carboxamide
  • (R)-ropivacaine
  • 0494L275Q6
  • 2-Piperidinecarboxamide, N-(2,6-dimethylphenyl)-1-propyl-, (2R)-
  • 98717-16-9
  • A922718
  • BDBM50505291
  • BS-18064
  • C77370
  • CS-0163000
  • MFCD06412576
  • Q27247635
  • Ropivacaine related compound B free base anhydrous
  • Ropivacaine, (R)-

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC6588
  • UNII-0494L275Q6
  • DTXSID701317045
  • CHEMBL4564685
  • SCHEMBL33293

Physico-Chemical properties

IUPAC name(2R)-N-(2,6-dimethylphenyl)-1-propylpiperidine-2-carboxamide
Molecular formulaC17H26N2O
Molecular weight274.401
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity89.03
LogP3.5
Topological polar surface area32.3

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.