Tolcapone

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

What is the Tolcapone?

The molecule Tolcapone presents a molecular formula of C14H11NO5 and its IUPAC name is (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone.

Tolcapone (INN) is a catechol-o-methyltransferase (COMT) inhibitor used as an adjunct to levodopa in the treatment of Parkinson's disease. Tolcapone improves the conversion of levodopa to dopamine, thereby increasing dopamine levels in the brain..

Tolcapone was discovered by scientists at Merck & Co. in the early 1970s. It was approved for use in the United States in 1997 and is marketed under the brand name Tasmar. In Europe, it is marketed under the brand name Stalevo..

Tolcapone is a white to off-white powder that is insoluble in water. The molecule has a molecular weight of 369.38 and the following chemical structure:.

Tolcapone inhibits the catechol-O-methyltransferase (COMT) enzyme. COMT is responsible for the breakdown of dopamine in the brain. By inhibiting COMT, tolcapone increases the levels of dopamine in the brain..

Dopamine is a neurotransmitter that participes in the control of movement, emotion, and cognition. Parkinson's disease is characterized by a loss of dopamine-producing cells in the brain..

Levodopa is the precursor to dopamine. It is converted to dopamine by the enzyme dopa decarboxylase. Levodopa is administered in the treatment of Parkinson's disease to replace the lost dopamine..

Tolcapone is used as an adjunct to levodopa in the treatment of Parkinson's disease. It improves the conversion of levodopa to dopamine, thereby increasing dopamine levels in the brain..

The most common side effects of tolcapone are gastrointestinal in nature, such as nausea, vomiting, diarrhea, and abdominal pain. Other side effects include headache, dizziness, drowsiness, and skin rash..

Tolcapone should be used with caution in patients with liver disease or liver dysfunction. It is metabolized by the liver and excreted by the kidney..

Patients taking tolcapone should be monitored for signs and symptoms of liver injury, such as fatigue, anorexia, nausea, vomiting, dark urine, and jaundice. Liver function tests should be performed prior to initiation of tolcapone and periodically thereafter..

Tolcapone should be used with caution in patients with a history of psychiatric illness. It can cause or worsen psychiatric symptoms such as psychosis, mania, and depression..

Patients taking tolcapone should be monitored for signs and symptoms of psychiatric illness, such as changes in mood, behavior, or thinking. Psychiatric evaluation should be performed prior to initiation of tolcapone and periodically thereafter..

Tolcapone should be used with caution in pregnant women. It is not known if tolcapone crosses the placenta..

Tolcapone should be used with caution in breastfeeding women. It is not known if tolcapone is excreted in human milk..

The safety and efficacy of tolcapone in children has not been established..

Tolcapone is a prescription medication. It exists as a tablet..

3D structure

Cartesian coordinates

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

2D drawing

 

Tolcapone MIQPIUSUKVNLNT-UHFFFAOYSA-N chemical compound 2D structure molecule svg
Tolcapone

 

Molecule descriptors

 
IUPAC name(3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
InChI codeInChI=1S/C14H11NO5/c1-8-2-4-9(5-3-8)13(17)10-6-11(15(19)20)14(18)12(16)7-10/h2-7,16,18H,1H3
InChI KeyMIQPIUSUKVNLNT-UHFFFAOYSA-N
SMILESCc1ccc(C(=O)c2cc(O)c(O)c([N+](=O)[O-])c2)cc1

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.

  • (3,4-Dihydroxy-5-nitro-phenyl)-p-tolyl-methanone
  • (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone
  • (3,4-dihydroxy-5-nitrophenyl)(p-tolyl)methanone
  • (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
  • 134308-13-7
  • 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone
  • 3,4-dihydroxy-4 inverted exclamation mark -methyl-5-nitrobenzophenone
  • 3,4-dihydroxy-5-nitro-4'-methylbenzophenone
  • 308T137
  • 3s68
  • 4'-methyl-3,4-dihydroxy-5-nitrobenzophenone
  • 5-[(4-METHYLPHENYL)CARBONYL]-3-NITROBENZENE-1,2-DIOL
  • AB01275441-01
  • AB01275441_02
  • AC-791
  • AS-7085
  • BCP09156
  • BDBM50108877
  • BIDD:GT0032
  • BT164481
  • C07949
  • CCG-221217
  • CCRIS 7904
  • CIF6334OLY
  • CS-1173
  • D00786
  • DB-013561
  • DB00323
  • DSSTox_CID_3685
  • DSSTox_GSID_23685
  • DSSTox_RID_77146
  • FT-0631149
  • GTPL6646
  • HMS2089K14
  • HMS3652M17
  • HMS3715D16
  • HMS3872F03
  • HMS3885G18
  • HY-17406
  • KS-1314
  • MFCD00866569
  • MLS006012044
  • Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-
  • Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)-
  • NCGC00181767-01
  • NCGC00181767-02
  • NCGC00181767-03
  • NCGC00255188-01
  • O10068
  • Q-201840
  • Q413840
  • Ro 40-7592
  • Ro-40-7592
  • Ro-407592
  • SMR001614567
  • SR-05000001444
  • SR-05000001444-1
  • SW219511-1
  • SY102278
  • T3856
  • TCW
  • Talcapone
  • Tasmar
  • Tolcapone
  • Tolcapone (JAN/USP/INN)
  • Tolcapone- Bio-X
  • s4021

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC35342789
  • CAS-134308-13-7
  • UNII-CIF6334OLY
  • AKOS015902328
  • BRD-K10852020-001-01-1
  • DTXSID3023685
  • CHEMBL1324
  • CHEBI:63630
  • Tox21_112963
  • Tox21_302414
  • Tox21_112963_1
  • SCHEMBL33869

Physico-Chemical properties

IUPAC name(3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone
Molecular formulaC14H11NO5
Molecular weight273.241
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity74.15
LogP3.1
Topological polar surface area103.4

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.