Thiamphenicol
thiamphenicol
CAS: 15318-45-3
Molecular Formula: C12H15Cl2NO5S
Thiamphenicol - Names and Identifiers
| Name | thiamphenicol |
| Synonyms | thiophenicol THIAMPHENICOL thiamphenicol methylsulfonyl chloramphenicol Methylsulfonyl chloramphenicol 2,2-dichloro-N-{1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]propan-2-yl}acetamide d-threo-2,2-dichloro-n-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide Acetamide, 2,2-dichloro-N-(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-4-(methylsulfonyl)phenylethyl- D-THREO-2,2-DICHLORO-N-(BETA-HYDROXY-ALPHA-[HYDROXYMETHYL]-4-[METHYLSULFONYL]PHENETHYL)ACETAMIDE D-THREO-2,2-DICHLORO-N-[BETA-HYDROXY-ALPHA-(HYDROXYMETHYL)-P-(METHYL-SULFONYL)PHENETHYL]ACETAMIDE Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-, [R-(R*,R*)]- Acetamide, 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]- (9CI) |
| CAS | 15318-45-3 |
| EINECS | 239-355-3 |
| InChI | InChI=1/C12H14Cl2N2O7S/c1-24(21,22)23-6-9(15-12(18)11(13)14)10(17)7-2-4-8(5-3-7)16(19)20/h2-5,9-11,17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1 |
| InChIKey | OTVAEFIXJLOWRX-NXEZZACHSA-N |
Thiamphenicol - Physico-chemical Properties
| Molecular Formula | C12H15Cl2NO5S |
| Molar Mass | 356.22 |
| Density | 1.3281 (rough estimate) |
| Melting Point | 163-166°C |
| Boling Point | 695.9±55.0 °C(Predicted) |
| Specific Rotation(α) | D25 +12.9° (ethanol) |
| Water Solubility | Soluble in acetonitrile or DMF. Slightly soluble in water |
| Solubility | Soluble in water and methanol, slightly soluble in ethanol, acetone, almost insoluble in ether, chloroform |
| Appearance | grayish white solid |
| Color | white to off-white |
| Merck | 14,9301 |
| BRN | 2819542 |
| pKa | 11.05±0.46(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.6000 (estimate) |
| MDL | MFCD00467983 |
| Physical and Chemical Properties | White to off-white crystalline powder or crystal. Melting point (°c) 178-180 (mixed),164-166 (dextrorotatory). |
| Use | Mainly used for the treatment of respiratory, urinary, hepatobiliary, typhoid and other intestinal surgery, obstetrics and gynecology and ENT infections and other diseases, especially in mild and moderate infections |
| In vitro study | Thiamphenicol shows a significant post-antibiotic effect (PAE) (0.33 to 2.9h) on all pathogens studied ( S. pneumoniae , S. aureus and Escherichia coli ) and a powerful bactericidal effect against β-lactamase-positive and -negative H. influenzae . Thiamphenicol MICs for the microorganisms analyzed are: 32 mg/L ( S. aureus and E. coli ), 2 mg/L ( S. pneumoniae ) and 0.25 mg/L ( H. influenzae ). Thiamphenicol shows a good in vitro activity against difficult-to-treat multiply resistant pathogens. |
| In vivo study | The pharmacokinetics of Thiamphenicol (30 mg/kg) after single intravenous (IV) and oral (PO) administration is investigated in Mulard ducks. After IV administration, for Thiamphenicol, the mean residence time is 2.83 hours, the general half-life is 1.96 hours, the clearance is 0.04 L/hr/kg. Pharmacokinetics after PO administration is very similar for IV administration. Thiamphenicol shows rapid absorption and bioavailability of more than 70%. |
Thiamphenicol - Risk and Safety
| Safety Description | S22 - Do not breathe dust. S24/25 - Avoid contact with skin and eyes. |
| WGK Germany | 2 |
| RTECS | AB6680000 |
| HS Code | 29414000 |
Thiamphenicol - Upstream Downstream Industry
Thiamphenicol - Reference
| Reference Show more | 1. [IF=7.46] Yufeng Sun et al."Voltammetric sensor for chloramphenicol determination based on a dual signal enhancement strategy with ordered mesoporous carbon@polydopamine and β-cyclodextrin."Sensor Actuat B-Chem. 2018 Feb;255:2155 2. [IF=2.082] Qin Guo et al."Synergistic inhibition effects of tea polyphenols as adjuvant of oxytetracycline on Vibrio parahaemolyticus and enhancement of Vibriosis resistance of Exopalaemon carinicauda."Aquac Res. 2021 Aug;52(8):3900-3910 3. [IF=7.514] Shuang Han et al."Preparation of mesh covalent organic framework Tppa-2-based adsorption enhanced magnetic molecularly imprinted composite for selective extraction of tetracycline residues from animal-derived foods."Food Chem. 2022 Aug;384:132601 |
Thiamphenicol - Standard
Authoritative Data Verified Data
This product is N-[1- (hydroxymethyl) -2-hydroxy-2-[4-(methylsulfonyl) phenyl] ethyl] -2, 2-dichloroacetamide. The content of C12H15C12N05S shall not be less than 98.0% calculated as the dry product.
Last Update：2024-01-02 23:10:35
Thiamphenicol - Trait
Authoritative Data Verified Data
- This product is white crystalline powder; Odorless.
- This product is soluble in N ,N-dimethylformamide, slightly soluble in anhydrous ethanol, slightly soluble in water.
melting point
The melting point of this product (General 0612) is 163~167°C.
specific rotation
take this product, precision weighing, plus N ,N-dimethylformamide dissolved and quantitatively diluted to make a solution containing about 50mg per 1 ml, determined according to law (General 0621 ), the specific rotation is from one 21 ° to one 24 °.
absorption coefficient
take this product, precision weighing, add water to dissolve (about 40°C heating dissolution) and quantitatively dilute to make a solution containing about 0.2mg per 1 ml, according to UV-Vis spectrophotometry (General rule 0401), the absorbance was measured at the wavelengths of 266nm and 273nm, and the absorption coefficients were 25-28 and 21.5-23.5, respectively; the above test solution was quantitatively diluted with water to make a solution containing about 10ug per 1 ml. The absorbance was measured at a wavelength of 224nm, and the absorption coefficient was 370 to 400.
Last Update：2022-01-01 11:37:48
Thiamphenicol - Differential diagnosis
Authoritative Data Verified Data
- take an appropriate amount of this product and the reference substance of thiamphenicol, respectively add methanol to dissolve and dilute to prepare a solution containing about 10mg per 1 ml, and test according to thin layer chromatography (General 0502), draw 5 u1 of each of the above two solutions, respectively, on the same silica gel GF254 thin layer plate, with ethyl acetate-methanol (97:3) as the developer, expand, dry, set the UV lamp (254nm) next view. The position and color of the main spot displayed by the test solution should be the same as the position and color of the main spot of the reference solution.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 594).
- take 0.1% of this product solution 5ml, add 0.lmol / L silver nitrate solution 2ml, no precipitation. Take 50mg of this product, add ethanol to make potassium hydroxide solution 2ml to dissolve, to prevent the evaporation of ethanol, heated in a water bath for 15 minutes, the solution shows chloride to identify (1) reaction (General rule 0301).
- two items (1) and (2) above can be selected as one item.
Last Update：2022-01-01 11:37:49
Thiamphenicol - Exam
Authoritative Data Verified Data
pH
take this product O.lg, add 20ml of water to dissolve, add 0.LML of bromothymol blue indicator solution; If Blue, add 0.02 ml of hydrochloric acid titration solution (0.10 mol/L), the strain is yellow; If yellow, 0.02 of sodium hydroxide titration solution (0.10 mol/L) was added, and the strain was blue.
Related substances
take this product, add mobile phase to dissolve and dilute to make a solution containing about lmg per lml as a test solution; Take lml for precision measurement and put it in a 100ml measuring flask, dilute to the scale with the mobile phase, shake, and serve as a control solution. According to the chromatographic conditions under the content determination item, 10ul of the test solution and the control solution are accurately weighed and injected into the human liquid chromatograph respectively, and the chromatogram is recorded to 3.5 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 the area of the main peak of the control solution (1.0%); the sum of each impurity peak area shall not be greater than 2 times (2.0%) of the main peak area of the control solution, and the peaks in the chromatogram of the test solution which are smaller than 0.05 times of the main peak area of the control solution are ignored.
chloride
take 0.5g of this product, add 30ml of water, shake for 5 minutes, filter, take 15ml of filtrate, add 1.5 of dilute nitric acid, and immediately add 0.1 mol / L silver nitrate solution 1ml, placed in the dark for 2 minutes, according to the law to check (General rule 0801), compared with the standard sodium chloride solution 5.0ml made of the control solution, not more concentrated (0.02%).
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 1.0% (General rule 0831).
ignition residue
This product l.O g, inspection according to law (General 0841), residue shall not exceed 0.1%.
Heavy metals
The residue left under the item of taking the ignition residue shall not contain more than 10 parts per million of heavy metal when examined by law (General Principles 0821, Law II).
Last Update：2022-01-01 11:37:50
Thiamphenicol - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
with eighteen alkyl silane bonded silica gel as filler; With water-acetonitrile (4:1) as mobile phase; The detection wavelength was 225nm, take the product 25mg, put in 25ml measuring flask, add 2ml of lmol/L sodium hydroxide solution to dissolve, place at room temperature for 10 minutes, add 2ml of lmol/L hydrochloric acid solution, dilute with mobile phase to the scale, shake well, take 5ml, put it in 50ml measuring flask, add 5mg thiamphenicol reference, dissolve with mobile phase and dilute to the scale, shake well, take 10ul injection liquid chromatograph, record chromatogram, the resolution between thiamphenicol alkaline degradation peak and thiamphenicol peak should meet the requirements.
assay
take about 0.lg of this product, weigh it accurately, put it in a 100ml measuring flask, add the mobile phase to dissolve and dilute to the scale, shake well, take 5ml accurately, put it in a 50ml measuring flask, dilute to the scale with mobile phase, shake well, as a test solution, take the precision l0ul injection liquid chromatograph, record the chromatogram; Take the appropriate amount of thiamphenicol reference, the same method for determination. According to the external standard method to calculate the peak area, that is.
Last Update：2022-01-01 11:37:50
Thiamphenicol - Category
Authoritative Data Verified Data
amide alcohol antibiotics.
Last Update：2022-01-01 11:37:51
Thiamphenicol - Storage
Authoritative Data Verified Data
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:37:51
Thiamphenicol - Thiamphenicol enteric-coated tablets
Authoritative Data Verified Data
This product contains thiamphenicol (C12H15Cl2NO5S) should be labeled the amount of 90.0% to 110.0%.
trait
This product is an enteric-coated tablet, White after removing the coating.
identification
- take the fine powder of this product, add methanol to make a solution containing 10 mg of thiamphenicol per 1 ml, filter, and filter the filtrate according to the identification (1) Test under the item of thiamphenicol, the same results are shown.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- take an appropriate amount of fine powder of this product (about 50mg of thiamphenicol), add 2ml of potassium hydroxide solution to dissolve thiamphenicol to prevent ethanol from evaporating, and heat in a water bath for 15 minutes, the filtrate shows the reaction of (1) (General 0301).
- two items (1) and (2) above can be selected as one item.
examination
- relevant substances: take an appropriate amount of fine powder of this product, dissolve it with mobile phase and dilute it to make a solution containing 1 mg of thiamphenicol per 1 ml, filter it, and take the continued filtrate as the test solution; according to the method under thiamphenicol determination. The single impurity peak area shall not be greater than the main peak area of the control solution (1.0%); The sum of each impurity peak area shall not be greater than 3 times (3.0%) of the main peak area of the control solution.
- 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 an appropriate amount (about 0.1g equivalent to thiamphenicol), put it in a 100ml measuring flask, and add an appropriate amount of mobile phase, shake to dissolve thiamphenicol and dilute to the scale with mobile phase, shake well, filter, Take 5ml of continuous filtrate precisely, put it in 50ml measuring flask, dilute to the scale with mobile phase, shake well, as a test solution. According to the method under the item of thiamphenicol, obtained.
category
Same as thiamphenicol.
specification
(1)0.125g (2)0.25g
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:37:52
Thiamphenicol - Metronidazole capsules
Authoritative Data Verified Data
This product contains thiamphenicol (C12H15C12NO5S) should be the label amount of 90.0% ~ 110.0%.
identification
- take the contents of this product, add methanol to make a solution containing 10 mg of thiamphenicol per 1 ml, filter, and filter the filtrate according to the identification (1) Test under the item of thiamphenicol, the same results are shown.
- in the chromatogram recorded under the content determination item, the retention time of the main peak of the test solution should be consistent with the retention time of the main peak of the reference solution.
- take an appropriate amount of the content of this product (about 50mg equivalent to thiamphenicol), add 2M l of potassium hydroxide solution to dissolve thiamphenicol to prevent ethanol from evaporating, after heating in a water bath for 15 minutes, the filtrate shows chloride to identify the reaction of (1) (General 0301).
- two items (1) and (2) above can be selected as one item.
examination
- relevant substances appropriate amount of the contents of this product is taken, dissolved and diluted with mobile phase to prepare a solution containing 1 mg of thiamphenicol per 1 ml, filtered, and the continued filtrate is taken as the test solution. According to the method under thiamphenicol, the peak area of a single impurity shall not be greater than the main peak area of the control solution (1.0%), the sum of the peak areas of each impurity shall not be greater than 3 times (3.0%) of the main peak area of the control solution.
- weight loss on drying the contents of this product shall be taken and dried at 105°C to constant weight, and the weight loss shall not exceed 2.0% (General rule 0831).
- dissolution of this product, according to the dissolution and release determination method (General rule 0931 The first method), with water 900ml as the dissolution medium (specification 0.125g, the amount of dissolution medium is 100), the rotation speed is rpm, and the operation is carried out according to law. After 45 minutes, the solution is taken, filtered, and the filtrate is taken as the test solution, according to UV-visible spectrophotometry (General rule 0401), measure absorbance at the wavelength of 266nm; Take appropriate amount of thiamphenicol reference substance, water was added to dissolve and quantitatively diluted to prepare a solution containing about 0.28mg per 1 ml, which was determined by the same method. The amount of dissolution of each pellet was calculated. The limit is 75% of the labeled amount and shall be in accordance with the provisions.
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
take the content under the item of loading amount difference, mix evenly, accurately weigh appropriate amount (about equivalent to thiamphenicol O.lg), put in 100ml measuring flask, add mobile phase to dissolve and dilute to the scale., shake well, filter, Take 5ml of continuous filtrate with precision, put it in 50ml measuring flask, dilute to the scale with mobile phase, shake well, as a test solution. According to the method under the item of thiamphenicol, obtained.
category
Same as thiamphenicol.
specification
(1)0.125g (2)0.25g
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 11:37:52
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Raw Materials for Thiamphenicol