CAS 134308-13-7|Tolcapone
| Common Name | Tolcapone | ||
|---|---|---|---|
| CAS Number | 134308-13-7 | Molecular Weight | 273.241 |
| Density | 1.4±0.1 g/cm3 | Boiling Point | 485.6±45.0 °C at 760 mmHg |
| Molecular Formula | C14H11NO5 | Melting Point | 126-128ºC |
| MSDS | ChineseUSA | Flash Point | 205.7±17.2 °C |
| Symbol | GHS09 | Signal Word | Warning |
Names
| Name | (3,4-dihydroxy-5-nitrophenyl)-(4-methylphenyl)methanone |
|---|---|
| Synonym | More Synonyms |
Tolcapone BiologicalActivity
| Description | Tolcapone(Ro 40-7592) is an orally active selective, potent catechol-O-methyltransferase (COMT) inhibitor. IC50 value:Target: COMTTolcapone inhibits both central and peripheral COMT. Tolcapone caused a rapid and reversible inhibition of COMT activity in erythrocytes in parallel with a dose-dependent decrease in the formation of 3-OMD. Tolcapone increased the area under the concentration-time curve and elimination half-life of levodopa. Tolcapone crosses the blood-brain barrier, and has been used for L-DOPA adjunct therapy in the treatment of Parkinson's disease. |
|---|---|
| Related Catalog | Signaling Pathways >>Metabolic Enzyme/Protease >>COMTSignaling Pathways >>Neuronal Signaling >>COMTResearch Areas >>Neurological Disease |
| References | [1]. Neil E. Paterson, Jennifer Ricciardi, Caitlin Wetzler, et al. Sub-optimal performance in the 5-choice serial reaction time task in rats was sensitive to methylphenidate, atomoxetine and d-amphetamine, but unaffected by the COMT inhibitor tolcapone. Neuros [2]. Saviana Di Giovanni, Simona Eleuteri, Katerina E. Paleologou, et al. Entacapone and Tolcapone, Two Catechol O-Methyltransferase Inhibitors, Block Fibril Formation of α-Synuclein and β-Amyloid and Protect against Amyloid-induced Toxicity. The Journal of Bi [3]. Panos Bitsios, Panos Roussos1. Tolcapone, COMT polymorphisms and pharmacogenomic treatment of schizophrenia. Pharmacogenomics. 2001,12 (4): 559-566. [4]. M.A. Vieira-Coelho, P. Soares-da-Silva. Ontogenic aspects of liver and kidney catechol-O- methyltransferase sensitivity to tolcapone. British Journal of Pharmacology.1996,117 (3):516-520. [5]. J. Dingemanse, K. Jorga, G. Zurcher,et al. Pharmacokinetic-pharmacodynamic interaction between the COMT inhibitor tolcapone and single-dose levodopa. British Journal of Clinical Pharmacology 1995, 40 (3):253-262. |
Chemical & Physical Properties
| Density | 1.4±0.1 g/cm3 |
|---|---|
| Boiling Point | 485.6±45.0 °C at 760 mmHg |
| Melting Point | 126-128ºC |
| Molecular Formula | C14H11NO5 |
| Molecular Weight | 273.241 |
| Flash Point | 205.7±17.2 °C |
| Exact Mass | 273.063721 |
| PSA | 103.35000 |
| LogP | 4.07 |
| Vapour Pressure | 0.0±1.3 mmHg at 25°C |
| Index of Refraction | 1.661 |
| InChIKey | MIQPIUSUKVNLNT-UHFFFAOYSA-N |
| SMILES | Cc1ccc(C(=O)c2cc(O)c(O)c([N+](=O)[O-])c2)cc1 |
| Storage condition | -20°C Freezer |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- >2 gm/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1513,199
- TYPE OF TEST :
- LD50 - Lethal dose, 50 percent kill
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - mouse
- DOSE/DURATION :
- 1600 mg/kg
- TOXIC EFFECTS :
- Behavioral - somnolence (general depressed activity) Behavioral - ataxia Lungs, Thorax, or Respiration - respiratory depression
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1513,199 ** OTHER MULTIPLE DOSE TOXICITY DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 9300 mg/kg/4W-I
- TOXIC EFFECTS :
- Liver - changes in liver weight Related to Chronic Data - death
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1521,199
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Rodent - rat
- DOSE/DURATION :
- 91 gm/kg/26W-C
- TOXIC EFFECTS :
- Nutritional and Gross Metabolic - weight loss or decreased weight gain
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1557,199
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 1120 mg/kg/4W-I
- TOXIC EFFECTS :
- Gastrointestinal - alteration in gastric secretion Kidney, Ureter, Bladder - other changes
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1537,199
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 25830 mg/kg/26W-I
- TOXIC EFFECTS :
- Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1585,199
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- SPECIES OBSERVED :
- Mammal - dog
- DOSE/DURATION :
- 1760 mg/kg/15D-I
- TOXIC EFFECTS :
- Gastrointestinal - hypermotility, diarrhea Gastrointestinal - nausea or vomiting
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1513,199 ** REPRODUCTIVE DATA **
- TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Oral
- DOSE :
- 3 gm/kg
- SEX/DURATION :
- female 6-15 day(s) after conception
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - other effects
- REFERENCE :
- YACHDS Yakuri to Chiryo. Pharmacology and Therapeutics. (Raifu Saiensu Shuppan K.K., 2-5-13, Yaesu, Chuo-ku, Tokyo 104, Japan) V.1- 1972- Volume(issue)/page/year: 24(Suppl 10),S1631,199
Safety Information
| Symbol | GHS09 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H400 |
| Precautionary Statements | P273 |
| Hazard Codes | N |
| Risk Phrases | 50 |
| Safety Phrases | 61 |
| RIDADR | UN 3077 9 / PGIII |
| RTECS | PC4952500 |
Articles44
More Articles| Real-time concurrent monitoring of apoptosis, cytosolic calcium, and mitochondria permeability transition for hypermulticolor high-content screening of drug-induced mitochondrial dysfunction-mediated hepatotoxicity. Toxicol. Lett. 214(2) , 175-81, (2012) A quantitative high-content screening (HCS) was suggested for the real-time monitoring of drug-induced mitochondrial dysfunction-mediated hepatotoxicity. This HCS is very advantageous in that it allow... | |
| Telescoping phenomenon in pathological gambling: association with gender and comorbidities. J. Nerv. Ment. Dis. 200(11) , 996-8, (2012) The course of pathological gambling (PG) in women has been described as having a later age of initiation but a shorter time to problematic gambling ("telescoped"). This study examined evidence for tel... | |
| Capture compound mass spectrometry sheds light on the molecular mechanisms of liver toxicity of two Parkinson drugs. Toxicol. Sci. 113(1) , 243-53, (2010) Capture compound mass spectrometry (CCMS) is a novel technology that helps understand the molecular mechanism of the mode of action of small molecules. The Capture Compounds are trifunctional probes: ... |
Synonyms
| UNII-CIF6334OLY |
| 1-(3,4-dihydroxy-5-nitrophenyl)-1-(4-methylphenyl)methanone |
| tolcapone |
| Methanone, (3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl)- |
| tolcapone [INN_en] |
| 3,4-Dihydroxy-4'-methyl-5-nitrobenzophenone |
| 4'-methyl-3,4-dihydroxy-5-nitro-benzophenone |
| [14C]-Tolcapone |
| Tasmar (TN) |
| MFCD00866569 |
| Methanone,(3,4-dihydroxy-5-nitrophenyl)(4-methylphenyl) |
| Tasmar |
| (3,4-Dihydroxy-5-nitrophenyl)(4-methylphenyl)methanone |
| Ro 40-7592 |
