TOLBUTAMIDE CRYSTALLINE
Tolbutamide
CAS: 64-77-7
Molecular Formula: C12H18N2O3S
TOLBUTAMIDE CRYSTALLINE - Names and Identifiers
| Name | Tolbutamide |
| Synonyms | Tolbutamide PotassiuM channel Tolbutamide (200 mg) TOLBUTAMIDE CRYSTALLINE TOLBUTAMIDE VETRANAL, 250 MG -(p-tolyl-4-sulfonyl)-1-butylurea 3-butyl-1-(4-methylphenyl)sulfonyl-urea N-(ButylcarbaMoyl)-4-MethylbenzenesulfonaMide |
| CAS | 64-77-7 |
| EINECS | 200-594-3 |
| InChI | InChI=1/C12H18N2O3S/c1-3-4-9-13-12(15)14-18(16,17)11-7-5-10(2)6-8-11/h5-8H,3-4,9H2,1-2H3,(H2,13,14,15) |
TOLBUTAMIDE CRYSTALLINE - Physico-chemical Properties
| Molecular Formula | C12H18N2O3S |
| Molar Mass | 270.35 |
| Density | 1.2450 |
| Melting Point | 128-130°C |
| Boling Point | 430.0±38.0 °C at 760 mmHg |
| Water Solubility | 0.14g/L(25 ºC) |
| Solubility | Insoluble in water. Soluble in acetone, ethanol, chloroform and alkali solutions |
| Appearance | White crystalline powder |
| Color | White to Off-White |
| Merck | 14,9507 |
| BRN | 1984428 |
| pKa | pKa 5.32(H2Ot = 37) (Uncertain) |
| Storage Condition | Sealed in dry,Room Temperature |
| Stability | Stable. Combustible. |
| Sensitive | Photosensitivity |
| Refractive Index | 1.6360 (estimate) |
| MDL | MFCD00027169 |
| Use | Hypoglycemic agents for stable, mild to moderate adult diabetic patients |
TOLBUTAMIDE CRYSTALLINE - Risk and Safety
| Risk Codes | R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R40 - Limited evidence of a carcinogenic effect R43 - May cause sensitization by skin contact R36 - Irritating to the eyes R11 - Highly Flammable |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | YS4550000 |
| TSCA | Yes |
| HS Code | 29350090 |
| Toxicity | LD50 oral in rat: 2490mg/kg |
TOLBUTAMIDE CRYSTALLINE - Reference
| Reference Show more | 1. Wei Wenzeng, Zhao Ningning, Lin Yingyan, Wang Jin, Wang Gong. Evaluation of the effect of ethanol extract of Antrodia camphorata on the activity of human CYP450 by Cocktail probe [J]. Science and Technology Wind, 2021(03):139-140. 2. Dong Xiaoke, Liu Jinmin, Li Zhonghao, Yuan Siyuan, Wang Kaiyue, Li Lili, Zheng xiangchun. Study on the main blood components and pharmacokinetics of chaibei Zhixian decoction in rats [J]. Global Journal of Traditional Chinese Medicine, 2021,14(03):377-383. 3. Wei Wenzeng, Zhao Ningning, Lin Yingyan, Wang Jin, Wang Gong. Evaluation of the effect of ethanol extract of Antrodia camphorata on the activity of human CYP450 by Cocktail probe [J]. Science and Technology Wind, 2021(03):139-140. 4. Chen Rui, Zhou Wei, Zhang Li, Zhu Gaogao, Huang Jing, Tang Lei. In vitro inhibition of five common Cytochrome P_(450) enzymes in human liver microsomes by bevacizumab acid A [J]. China Pharmacy, 2021,32(02):195-200. 5. [IF = 2.01] Lin Li et al."Pharmacokinetic Studies of Multiple Active Components in Rat Plasma Using LC-MS/MS after Oral Administration of Shaoyao-Gancao-Fuzi decection." Rev Bras Farmacogn. 2020 Dec;30(6):810-817 6. [IF = 5.275] Kai Wang et al.Drug-drug interactions induced by Linderane based on mechanism-based inactivation of CYP2C9 and the molecular mechanism. Bioorg Chem. 2022 Jan;118:105478 7. [IF = 2.193] Zhang Tingting et al."Quantitation of Diclofenac, Tolbutamide, and Warfarin as Typical CYP2C9 Substrates in Rat Plasma by UPLC-MS/MS and Its Application to Evaluate Linderane-Mediated Herb-Drug Interactions."J Anal Methods Chem. 2022;2022:1900037 |
TOLBUTAMIDE CRYSTALLINE - Standard
Authoritative Data Verified Data
This product is 1-butyl-3-(p-tolylsulfonyl) urea. Calculated as dry product, containing C12H18N203S shall not be less than 99.0%.
Last Update：2024-01-02 23:10:35
TOLBUTAMIDE CRYSTALLINE - Trait
Authoritative Data Verified Data
- This product is white crystal or crystalline powder; Odorless.
- This product is soluble in acetone or chloroform, soluble in ethanol, almost insoluble in water; Soluble in sodium hydroxide solution.
melting point
The melting point of this product (General 0612) is 126~130°C.
absorption coefficient
take this product, precision weighing, and methanol dissolution and quantitative dilution to prepare about 10ug solution per lml, according to UV-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 229nm, and the absorption coefficient was 475 to 500.
Last Update：2022-01-01 11:37:44
TOLBUTAMIDE CRYSTALLINE - Differential diagnosis
Authoritative Data Verified Data
- take about 0.3g of this product, add 12ml of sulfuric acid solution (l-3), heat for 30 minutes, let it cool, then precipitate white precipitate, filter, and recrystallize the precipitate with a small amount of water, the melting point is about 0612°C as determined by law (General Rule 138).
- The above filtrate was taken and made alkaline by adding a 20% sodium hydroxide solution, followed by heating, I .e., the extra odor of N-butylamine occurred.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 102).
Last Update：2022-01-01 11:37:44
TOLBUTAMIDE CRYSTALLINE - Exam
Authoritative Data Verified Data
acidity
take L. 0g of this product, add 50ml of water, heat to boiling, set the ice bath to cool to below 5°C, filter; Add several drops of phenolphthalein indicator solution and sodium hydroxide titration solution (0.1mol/L)0.20, red.
Related substances
take about 37.5mg of this product, weigh it accurately, put it in a 25ml measuring flask, add 15ml of methanol, shake to dissolve, dilute it to the scale with ammonium dihydrogen phosphate solution (pH 3.5), shake, as a test solution; Precision take 1ml, 100ml flask, diluted with mobile phase to scale, shake, as a control solution. According to the high performance liquid chromatography (General rule 0512) test, with the eighteen alkyl silane bonded silica gel as filler, with ammonium dihydrogen phosphate solution (take ammonium dihydrogen phosphate 1.725g, add water 300ml to dissolve, adjust the pH value to 3.5±0.05 with phosphoric acid)-Methanol (375:625) as mobile phase, the detection wavelength was 254nm, and the number of theoretical plates was not less than 4000 based on the tolbutamide peak. 20 u1 of the test solution and the control solution were respectively injected into the liquid chromatograph, and the chromatogram was recorded to 3 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the area of a single impurity peak shall not be greater than 0.5 times (0.5%) of the area of the main peak of the control solution, the sum of each impurity peak area shall not be greater than the main peak area of the control solution (1.0%).
insolubles in alkali
take 1.0g of this product, add 5.0 of sodium hydroxide solution, should be completely dissolved.
loss on drying
take this product, dry at 105°C for 3 hours, loss of weight shall not exceed 0.5% (General rule 0831).
ignition residue
not more than 0.1% (General rule 0841).
Heavy metals
This product l.Og, inspection according to law (General Principles 0821 third law), containing heavy metals shall not exceed 10 parts per million.
Last Update：2022-01-01 11:37:45
TOLBUTAMIDE CRYSTALLINE - Content determination
Authoritative Data Verified Data
take this product 0.5g, precision weighing, add neutral ethanol (phenolphthalein indicator solution neutral) 20ml dissolved, add phenolphthalein indicator solution 3 drops, with sodium hydroxide titration solution (0.lmol/L) titration. Each 1 ml of sodium hydroxide titration solution (0.1 mol/L) corresponds to 27.04mg of c12h18n203 s.
Last Update：2022-01-01 11:37:46
TOLBUTAMIDE CRYSTALLINE - Category
Authoritative Data Verified Data
hypoglycemic drugs.
Last Update：2022-01-01 11:37:46
TOLBUTAMIDE CRYSTALLINE - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:37:46
TOLBUTAMIDE CRYSTALLINE - Tolbutamide Tablets
Authoritative Data Verified Data
This product contains tolbutamide (C12H18N2O3S) should be labeled the amount of 95.0% ~ 105.0%.
trait
This product is white tablet.
identification
- take an appropriate amount of fine powder of this product (about 0.5g of tolbutamide), add 8ml of acetone, shake to dissolve tolbutamide, filter, and evaporate the filtrate to dryness on a water bath; take 0.2g of the residue, add 12ml of sulfuric acid solution (1-3), heat and reflux for 30 minutes, let it cool down, that is, precipitate white precipitate, filter, add 20% sodium hydroxide solution to make the filtrate alkaline, and then heat it, that is, the occurrence of N-butylamine extra odor.
- the infrared light absorption spectrum of the above residue should be consistent with the spectrum of the control (Spectrum set 102).
examination
- dissolution the dissolution of this product was determined according to the dissolution and release determination method (General rule 0931 second method), and the dissolution medium was 6.8 phosphate buffer (pH), and the rotation speed was 75 revolutions per minute, operate in accordance with the law, after 30 minutes, take 10ml of the solution to filter, take 2ml of the filtrate, put it in a 100ml measuring flask, dilute it to the scale with phosphate buffer (pH 6.8), shake it well, the absorbance was measured at a wavelength of 0401 NM according to UV-Vis spectrophotometry (General rule 429), and the elution amount of each tablet was calculated as the absorption coefficient of C12Hl8N203S was. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others shall be in accordance with the relevant provisions under the item of tablets (General rule 0101).
Content determination
Take 10 tablets of this product, precision weighing, fine grinding, precision weighing appropriate amount (about 0.5g equivalent to tolbutamide), plus neutral ethanol (phenolphthalein indicator neutral) 25ml, slightly heat to dissolve tolbutamide, cool, add phenolphthalein indicator solution 3 drops, with sodium hydroxide titration solution (0.lmol/ L) titration. Each l of sodium hydroxide titration solution (0.1 mol/L) corresponds to 27.04 mg of c12h18n203 s.
category
with tolbutamide.
specification
0.5g
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:37:47
TOLBUTAMIDE CRYSTALLINE - Reference Information
| Solvent | Ethanol |
| Specific Activity | 50-60 mCi/mmol |
| Concentration | 0.1 mCi/ml |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| pharmacological action | Tolbutamide is white crystal or crystalline powder, odorless and tasteless. Soluble in acetone or chloroform, soluble in ethanol, almost insoluble in water, dissolved in sodium hydroxide solution. This product is a sulfonylurea oral hypoglycemic drugs, for normal and diabetic patients have hypoglycemic effect, but the loss of islet function without this effect. The main effect is to stimulate the secretion of insulin in pancreatic beta cells. Its mechanism of action is to specifically bind to the sulfonylurea receptor on the β cell membrane, so that the ATP-dependent K + channel is closed, causing the membrane potential to depolarize and open the Ca2 + channel, increased intracellular Ca2 + concentration promotes insulin secretion. It also enhances the hypoglycemic effect of exogenous insulin, strengthens the post-receptor effect of insulin, and the improvement of glucose tolerance can lead to the decrease of plasma insulin concentration, which will increase the number of insulin receptors, this in turn leads to increased insulin sensitivity. This product still has mild diuretic effect, but not as obvious as chlorpropamide. Oral absorption is fast, bioavailability is 85% ~ 100%, after absorption distribution of extracellular fluid, generally appear in the blood within 30 minutes, 3~4 hours blood drug concentration peak, the duration of action was 6 to 12 hours. The plasma protein binding rate is 90% ~ 95%, and the Half-Life is 4.5~6.5 hours. In the liver metabolism of chlorination and inactivation, in 24 hours about 85% of metabolites excreted by the kidney, about 8% from the feces from the bile. For patients with mild to moderate type Ⅱ diabetes who are not satisfied with the effect of diet control and physical exercise for 2 to 3 months, the islet beta cells have a certain function of secreting insulin, no acute complications such as infection, trauma, acute myocardial infarction, ketoacidosis, non-pregnant, no serious chronic complications. |
| synthetic route | N-formylation of p-methylbenzenesulfonamide with ethyl chloroformate to form p-toluenesulfonamide, tolbutamide was then prepared by aminolysis with N-butylamine. Fig.1 synthesis of tolbutamide |
| adverse reactions | 1. There may be Diarrhea, Nausea, Vomit, Head Pain, stomach pain or discomfort. 2. Rash is rare. 3. Rare and serious jaundice, liver damage, bone marrow suppression, neutropenia (manifested as sore throat, Fever, infection), thrombocytopenia (manifested as bleeding, purpura) and so on. |
| contraindicated | in patients with type I diabetes. 2. Patients with type II diabetes mellitus were accompanied by ketoacidosis, Coma, severe burns, infection, trauma and major surgery. 3. Liver and renal insufficiency. 4. Allergic to this drug or sulfa drugs. 5. Patients with leukopenia. |
| indication | 1. It is suitable for patients with mild to moderate type 2 diabetes mellitus who are not satisfied with the curative effect of diet control alone. The islet β cells have a certain function of secreting insulin and have no serious complications. This product can be used for the diagnosis of islet tumor. (2016-03-18) |
| note | 1. The following should be used with caution: physical weakness, high fever, Nausea and Vomit, hyperthyroidism, the elderly. 2. During medication should be regularly measured blood glucose, urine sugar, urine ketone body, urine protein and liver and kidney function, and eye examination. 3. Taking this class of drugs can increase body weight, aggravate the condition of obese patients with diabetes, should limit the daily intake of total calories. 4.FDA's pregnancy safety rating for this drug is C. |
| drug interaction | 1. When taken with alcohol, it can cause abdominal cramps, Nausea, Vomit, Head Pain, facial flushing and hypoglycemia. With beta blockers, can increase the risk of hypoglycemia, and can mask the symptoms of hypoglycemia, such as pulse rate increased, blood pressure increased. Small doses of selective beta-blockers such as Atenolol and metoprolol are less likely to cause this. 3. Chloramphenicol, guanethidine, insulin, monoamine oxidase inhibitor, phenylbutazone, oxybutazone, probenecid, salicylate, sulfonamides and this product used at the same time, can strengthen the hypoglycemic effect. 4. Adrenocortical hormone, epinephrine, phenytoin sodium, thiazide diuretics, thyroxine can increase blood sugar levels, with this class of drugs, may need to increase the dosage of this class of drugs. 5. When the biscoumarin anticoagulant and the drug are used together, the plasma concentration of each other initially increases, but the plasma concentration of each other decreases later, so the dosage of both needs to be adjusted. |
| Use | hypoglycemic drug, suitable for stable mild to moderate adult diabetic patients. antidiabetic drugs, hypoglycemic agonists against the secretion of islet hormones. It is metabolized by CYP2C9 (tolbutamide hydroxylase). |
| production method | is obtained by condensation of butyl isocyanate with P-toluenesulfonamide or by condensation of N-butylamine hydrochloride with toluenesulfonylurea. |
| category | toxic substances |
| toxicity grade | high toxicity |
| Acute toxicity | oral-rat LD50: 2490 mg/kg; Oral-mouse LD50: 490 mg/kg |
| flammability hazard characteristics | thermal decomposition of toxic nitrogen oxides, sulfur oxide smoke |
| storage and transportation characteristics | The warehouse is ventilated and dried at low temperature; It is stored separately from food raw materials |
| fire extinguishing agent | water, dry powder, carbon dioxide, foam |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-10 22:29:15
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