cinchophen
2-Phenylcinchoninic Acid
CAS: 132-60-5
Molecular Formula: C16H11NO2
cinchophen - Names and Identifiers
cinchophen - Physico-chemical Properties
| Molecular Formula | C16H11NO2 |
| Molar Mass | 249.26 |
| Density | 1.1426 (rough estimate) |
| Melting Point | 214-215 °C (lit.) |
| Boling Point | 392.37°C (rough estimate) |
| Water Solubility | Insoluble in water |
| Solubility | alcohol: soluble1g in 120ml(lit.) |
| Appearance | Solid |
| Color | White |
| Merck | 14,2288 |
| BRN | 192803 |
| pKa | 0.96±0.10(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Sensitive | Light Sensitive |
| Refractive Index | 1.5300 (estimate) |
| MDL | MFCD00006750 |
| Physical and Chemical Properties | White or yellowish crystalline powder. Powder point 213-216 ℃. 1g of this product is soluble in about 400ml chloroform, 100ml ether, 120ml ethanol, and almost insoluble in water. The taste is slightly bitter and almost odorless. It is easy to change in the open sun. |
| In vitro study | Cinchophen (2-phenylquinoline-4-carboxylic acid) is a powerful antibacterial agent. Veterinarians used a combination of Cinchophen and prednisolone to treat arthritis in animals. Due to the discovery that cinchophen can cause severe liver damage, the drug was discontinued in humans in the 1930s. |
| In vivo study | Cinchophen (oral gavage; 25-44 mg/kg; twice daily) combines prednisolone ( 0.125-0.220 mg/kg; twice daily) for 14 days is effective in dogs with osteoarthritis and well tolerated. The combination exhibits significantly improved lameness, weight bearing, joint mobility and stiffness scores and is similar in clinical efficacy to phenylbutazone.The kinetics and efficacy of a cinchophen prednisolone combination preparation (PLT) is tested. Cinchophen administation at a dose rate of 12.5 mg/kg intravenously exhibits a volume of distribution (V d area) of 0.13 L/kg, shows a clearance rate (Cl) of 0.15 L/h and a half-life (t 1/2β ) of 7.92 hours. The plasma concentration time curve (AUC0-∞) is 1187.0 μ/ml.h in dogs. Cinchophen administation (oral gavage; 12.5 mg/kg; single dose) exhibits a mean maximum plasma concentration (C max ) of 77.75 μg/ml and the time of Cmax (t max ) is 2.76 hours. The plasma concentration time curve (AUC 0-∞ ) is almost as large following oral as intravenous administration indicating an oral bioavailability (F) of 87.21%. |
cinchophen - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | GD4025000 |
| HS Code | 29334990 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 oral in dog: 1250mg/kg |
cinchophen - Reference Information
| brief introduction | 2-phenyl -4-quinoline carboxylic acid (drug name cinchofen) is a drug for antipyretic, analgesic and rheumatic diseases. however, clinical application shows that the drug has poor curative effect and large toxic and side effects. the Ministry of health decided to eliminate it in September 1982. Chemists from various countries have devoted themselves to the preparation and research of their biological products in order to improve their performance. |
| synthesis method | there are many synthetic routes for cinchofen. one molecule of benzaldehyde, aniline and pyruvate can be prepared in one pot by heating in ethanol solution. Or use substituted indoquinone and substituted acetophenone as raw materials, absolute ethanol as solvent, and heat reaction in the presence of potassium hydroxide to generate substituted 2-phenyl-4-quinoline carboxylic acid. The synthesis reaction formula of 2-phenyl-4-quinoline carboxylic acid is as follows: |
| biological activity | Cinchophen is an analgesic and is often used to treat gout. |
| In vitro research | Cinchophen (2-phenylquinoline-4-carboxylic acid) is a powerful antibacterial agent. Veterinarians combine Cinchophen and prednisolone to treat arthritis in animals. Due to the discovery that cinchophen can cause serious liver injury, the use of the drug in human body was stopped in 1930s. |
| in vivo study | Cinchophen (oral gavage; 25-44 mg/kg; twice daily) combines prednisolone ( 0.125-0.220 mg/kg; twice daily) for 14 days is effective in dogs with osteoarthritis and well tolerated. The combination exhibits significantly improved lameness, weight bearing, joint mobility and stiffness scores and is similar in clinical efficacy to phenylbutazone.The kinetics and efficacy of a cinchophen prednisolone combination preparation (PLT) is tested. Cinchophen administation at a dose rate of 12.5 mg/kg intravenously exhibits a volume of distribution (V d area) of 0.13 L/kg, shows a clearance rate (Cl) of 0.15 l/h and a half-life (t 1/2 β ) of 7.92 hours. The plasma concentration time curve (AUC0-∞) is 1187.0 μ/ml.h in dogs. Cinchophen administation (oral gavage; 12.5 mg/kg; single dose) exhibits a mean maximum plasma concentration (C max ) of 77.75 μg/ml and the time of cmax (t max ) is 2.76 hours. the plasma concentration time curve (AUC 0-∞) is almost as large following oral as intravenous administration indicating anoral bioavailability (F) of 87.21%. |
| chemical properties | white or light yellow crystalline powder. Powder point 213-216 ℃. 1g of this product is soluble in about 400ml chloroform, 100ml ether, 120ml ethanol, and almost insoluble in water. The taste is slightly bitter and almost odorless. It is easy to change in the open sun. |
| use | antipyretic analgesics. Used for acute and chronic arthritis, rheumatic pain, neuralgia, lumbago, gout, headache, etc. |
| Production method | Indigo is prepared into a sodium salt, which is produced by ring opening to form sodium o-aminobenzoylformate, and then cyclize with acetophenone to obtain Ciclofen sodium, acidified with acetic acid or hydrochloric acid to obtain Ciclofen. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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Mobile: 18021002903
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