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

What is the Rimonabant?

The molecule Rimonabant presents a molecular formula of C22H21Cl3N4O and its IUPAC name is 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide.

Rimonabant (INN, trade name Acomplia) is an anorectic antiobesity drug developed by Sanofi-Aventis. Rimonabant is also known as SR141716; its original developmental code name was SR141613. It was the first selective CB1 receptor blocker to be marketed..

Rimonabant was first approved in Europe in 2006 under the trade name Acomplia® by the European Medicines Agency (EMEA) for the treatment of obesity. The drug was subsequently rejected for approval by the United States Food and Drug Administration (FDA) in 2007. In October 2008, the FDA's Endocrinologic and Metabolic Drugs Advisory Committee (EMDAC) voted unanimously not to recommend approval of rimonabant for marketing in the United States. The FDA cited concerns about rimonabant's psychiatric side effects..

Rimonabant is an inverse agonist of the cannabinoid receptor CB1. It was developed for the treatment of obesity and related conditions, and acts by reducing hunger cravings. Rimonabant binds to the same brain receptors as the active ingredient in cannabis (THC), but instead of producing the "high" associated with marijuana use, rimonabant actually reduces the desire for food..

In clinical trials, rimonabant was shown to be effective in helping obese patients lose weight and keep it off. Rimonabant was also shown to help patients with type 2 diabetes improve their blood sugar control and reduce their waist size..

However, rimonabant has also been linked with a number of serious side effects, including depression, anxiety, and suicidal thoughts. For these reasons, the FDA has not approved rimonabant for use in the United States..

3D structure

Cartesian coordinates

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

2D drawing


Rimonabant JZCPYUJPEARBJL-UHFFFAOYSA-N chemical compound 2D structure molecule svg


Molecule descriptors

IUPAC name5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
InChI codeInChI=1S/C22H21Cl3N4O/c1-14-20(22(30)27-28-11-3-2-4-12-28)26-29(19-10-9-17(24)13-18(19)25)21(14)15-5-7-16(23)8-6-15/h5-10,13H,2-4,11-12H2,1H3,(H,27,30)

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.

  • (N-(Piperidin-1-yl)-5-(4-chlorophenyl)-4-methyl-1H-pyrazole-3-carboxamide
  • 158681-13-1 (HCl)
  • 168273-06-1
  • 1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-
  • 1H-Pyrazole-3-carboxamide, 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-, monohydrochloride
  • 1H-Pyrazole-3-carboxamide,5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-
  • 5-(4-Chlorophenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid piperidin-1-ylamide
  • 5-(4-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-1-piperidinyl-1H-pyrazole-3-carboxamide
  • 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1-piperidinyl)-3-pyrazolecarboxamide
  • 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(1-piperidyl)pyrazole-3-carboxamide
  • 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-(piperidin-1-yl)-1H-pyrazole-3-carboxamide
  • 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-yl-pyrazole-3-carboxamide
  • 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
  • 5-(p-Chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidinopyrazole-3-carboxamide
  • 81R131
  • A 281
  • A810956
  • AB01566860_01
  • AC-163720
  • AC-731
  • AM84578
  • AS-37280
  • AY6
  • Acomplia
  • B1429
  • BBL030198
  • BCP07803
  • BDBM21278
  • BR164345
  • CCG-269385
  • CS-0645
  • D05731
  • DB-011649
  • DB06155
  • DSSTox_CID_26453
  • DSSTox_GSID_46453
  • DSSTox_RID_81627
  • EX-A688
  • FT-0631194
  • GTPL743
  • HMS3604M05
  • HMS3657O15
  • HY-14136
  • J-010440
  • L000572
  • MFCD04034714
  • MLS004774043
  • MLS006011772
  • N-piperidino-5-(4-chlorophenyl)-1(2,4-dichlorophenyl)-4-methyl-pyrazole-3-carboxamide
  • N-piperidino-5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-3-pyrazolecarboxamide
  • NCGC00164572-01
  • NCGC00164572-02
  • NSC-791533
  • NSC791533
  • Q412529
  • R0205
  • RML78EN3XE
  • Rimonabant
  • Rimonabant (JAN/USAN/INN)
  • Rimonabant (SR141716)
  • Rimonabant - from sample
  • Rimonabant free base
  • Rimonabant(SR141716)
  • Rimonabant- Bio-X
  • Rimoslim
  • SB19549
  • SMR003500713
  • SR 141716
  • SR-01000884001
  • SR-01000884001-1
  • SR-14171
  • SR-141716
  • SR-141716A
  • SR141,716A
  • SR141716
  • SR141716A
  • STK642500
  • SW220167-1
  • Zimulti
  • [3H]SR141716A
  • s3021

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC1540228
  • CAS-168273-06-1
  • AKOS005266728
  • DTXSID3046453
  • CHEMBL111
  • CHEBI:34967
  • Tox21_112200
  • Tox21_112200_1
  • SCHEMBL38637

Physico-Chemical properties

IUPAC name5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-N-piperidin-1-ylpyrazole-3-carboxamide
Molecular formulaC22H21Cl3N4O
Molecular weight463.787
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity125.92
Topological polar surface area50.2

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.