trimethoprim
trimethoprim
CAS: 738-70-5
Molecular Formula: C14H18N4O3
trimethoprim - Names and Identifiers
| Name | trimethoprim |
| Synonyms | trimethoprim TRIMETHOPRIM BP Trimethopim(TMP) Antibiotic synergist trimethoprim crystalline TRIMETHOPRIM, CRYSTALLIZED methoxybenzyl aminopyrimidine TRIMETHOPRIM VETRANAL, 250 MG 5-(3,4,5-trimethoxybenzyl)pyrimidine-2,4-diyldiamine 5-((3,4,5-trimethoxyphenyl)methyl)-2,4-pyrimidinediamine |
| CAS | 738-70-5 |
| EINECS | 212-006-2 |
| InChI | InChI=1/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18) |
trimethoprim - Physico-chemical Properties
| Molecular Formula | C14H18N4O3 |
| Molar Mass | 290.32 |
| Density | 1.1648 (rough estimate) |
| Melting Point | 199-203 °C |
| Boling Point | 432.41°C (rough estimate) |
| Water Solubility | <0.1 g/100 mL at 24 ºC |
| Solubility | chloroform/ethanol (1:1): soluble 50 mg/mL;DMSO: soluble |
| Appearance | white to off-white(white powder) |
| Color | colorless or white |
| Merck | 14,9709 |
| BRN | 625127 |
| pKa | 6.6(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable. Incompatible with strong oxidizing agents, acids. |
| Sensitive | Sensitive to light and humidity |
| Refractive Index | 1.6000 (estimate) |
| MDL | MFCD00036761 |
| Physical and Chemical Properties | Melting point 199-203°C water-soluble <0.1g/100 mL at 24°C |
| Use | Antibacterial Synergist, used alone for respiratory tract infection, urinary tract infection, intestinal infection and other diseases |
trimethoprim - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | 25 - Toxic if swallowed |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S24/25 - Avoid contact with skin and eyes. |
| UN IDs | 3249 |
| WGK Germany | 3 |
| RTECS | UV8225000 |
| FLUKA BRAND F CODES | 8-10-21 |
| HS Code | 29335995 |
| Hazard Class | 6.1(b) |
| Packing Group | III |
| Toxicity | LD50 orally in mice: 7000 mg/kg (Yamamoto) |
trimethoprim - Upstream Downstream Industry
| Raw Materials | Acrylonitrile Acetic acid Sodium methoxide Potassium ferricyanide Guanidine nitrate Ethyl Alcohol Ethyl acetate |
trimethoprim - Reference
| Reference Show more | 1. Chen Shu-Xin, Wang Jing, He Shi-Chong, Liu Yan-Zheng, Feng Huajun, Mu Peng-Qian. Determination of 17 antibiotics in water by ultra performance liquid chromatography-tandem mass spectrometry [J]. China Environmental Monitoring, 2020,36(06):119-126. 2. [IF = 5.548] Jing Hu et al."A high sensitive visual sensor for 100% in food samples by a double-signal response nano hybrid." Food Control. 108:106832 3. [IF = 4.098] Xiao Ying Yuan et al."Silicon nanoparticles-based proportional fluorescence platform: Real-time visual sensing to ciprofloxacin and Cu2 ." Spectrochim Acta A. 2021 May;253:119599 4. [IF = 6.498] Jingyun Shi et al."Groundwater antibiotics and microplastics in a drinking-water source area, northern China: Occurrence, spatial distribution, risk assessment, and correlation."Environ Res. 2022 Jul;210:112855 |
trimethoprim - Standard
Authoritative Data Verified Data
This product is 5-[(3,4, 5-trimethoxyphenyl) methyl]-2, 4-pyrimidine diamine. Calculated as dried product, containing no less than 99.0% of C14H18N403.
Last Update：2024-01-02 23:10:35
trimethoprim - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless.
- This product is slightly soluble in trioxymethane, slightly soluble in ethanol or acetone, almost insoluble in water; Soluble in glacial acetic acid.
melting point
The melting point of this product (General 0612) is 199~203°C.
absorption coefficient
take this product, precision weighing, and dilute acetic acid dissolved and quantitatively diluted to make a solution containing about lOOug per lml, and then dilute with water to make a solution containing about 20ug per lml. The absorbance was measured at a wavelength of 0401 NM according to ultraviolet-visible spectrophotometry (General rule 198), and the absorption coefficient was 210.
Last Update：2022-01-01 11:37:59
trimethoprim - Differential diagnosis
Authoritative Data Verified Data
- take about 20mg of this product, add 2ml of dilute sulfuric acid to dissolve, and add 2 drops of Iodine test solution to generate brown precipitate.
- Take 20mg of this product, precision weighing, add 5ml of ethanol to dissolve, and then add 0.4% sodium hydroxide solution to make a solution containing 20ug per 1 ml. According to UV-visible spectrophotometry (General rule 0401), there is a maximum absorption at the wavelength of 287mn, and its absorbance is about 0.49.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 103).
Last Update：2022-01-01 11:37:59
trimethoprim - Exam
Authoritative Data Verified Data
alkalinity
take 0.50g of this product, add 50ml of water, shake, filter. Take the filtrate, according to the law (General 0631),pH value should be 7.5~8.5. Acid solution clarity and color take this product l.Og, add acetic acid 0.5 to dissolve, the solution should be clear and colorless; If the color is colored, compared with the yellow No. 0901 Standard Colorimetric solution (General rule first method), not deeper.
Related substances
take about 50mg of this product, put it in a 50ml measuring flask, add an appropriate amount of mobile phase, shake to dissolve, dilute to the scale with mobile phase, shake well, and use it as a test solution; an appropriate amount was taken in a precise amount, and a solution containing 2ug per 1 ml was prepared by dilution with the mobile phase, and used as a control solution. According to the test of high performance liquid chromatography (General 0512), silica gel bonded with eighteen alkyl silane as filler; Acetonitrile-water-triethylamine (200:799:1)(With sodium hydroxide solution or glacial acetic acid to adjust the pH value to 6.4) as mobile phase; The detection wavelength was 280nm. Take appropriate amounts of trimethoprim control and ditrimethoprim control, add mobile phase, dissolve and dilute to prepare a solution containing 2 tons of trimethoprim and lug of dimethoprim per 1 ml, as the system applicable solution, take 20u1 injection human liquid chromatograph and record chromatogram. The number of theoretical plates shall not be less than 5000 based on trimethoprim peak, and the separation degree between trimethoprim peak and dimethoprim peak shall be greater than 2.5. 2 u1 of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatogram was recorded to 4 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 (0.2% ) , the sum of each impurity peak area shall not be greater than 2 times (0.4%) of the main peak area of the control solution. Peaks in the chromatogram of the test solution that are 0.05 times smaller than the main peak area of the control solution are negligible.
loss on drying
take this product, dry to constant weight at 105°C, weight loss shall not exceed 0.5% (General rule 0831).
ignition residue
not more than 0.1% (General rule 0841).
Last Update：2022-01-01 11:38:00
trimethoprim - Content determination
Authoritative Data Verified Data
take this product about 0.2g, precision weighing, add glacial acetic acid 20ml, warm to dissolve, cool, add crystal violet indicator solution 1 drop, with perchloric acid titration solution (0.1 mol/L) titration to a blue color of the solution, and the results of the titration were corrected by a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 29.03mg of C14H18N4O3.
Last Update：2022-01-01 11:38:00
trimethoprim - Category
Authoritative Data Verified Data
antibacterial drugs.
Last Update：2022-01-01 11:38:01
trimethoprim - Storage
Authoritative Data Verified Data
light shielding, sealed storage.
Last Update：2022-01-01 11:38:01
trimethoprim - Trimethoprim tablets
Authoritative Data Verified Data
This product contains trimethoprim C14H18N403 should be 95.0% to 105.0% of the label.
trait
This product is white tablet.
identification
take an appropriate amount of fine powder of this product (about equivalent to trimethoprim O.lg), add 10ml of ethanol, shake, filter, distill off the ethanol, and the residue is dried at 105°C and measured according to law (General rule 0612), with a melting point of 198-203°C; the remaining residue showed the same reaction according to the trimethoprim identification (1) test.
examination
- dissolution of this product, according to the dissolution and release determination method (General 0931 second method), with 0.Olmol / L hydrochloric acid solution 900ml as the dissolution medium, the speed is 50 revolutions per minute, according to the law, after 45 minutes, take 10ml of solution filtration, precision amount of filtrate 2ml, in a 10ml measuring flask, use 0. Dilute Olmol / L hydrochloric acid solution to the scale, shake well, as the test solution; Take the trimethoprim control about 10 mg, precision weighing, put in 100ml measuring flask, add 0.Olmol / L hydrochloric acid solution dissolved and diluted to the scale (if necessary, ultrasonic treatment), shake, precision take 5ml, put 25ml flask, with 0.Olmol / L hydrochloric acid solution diluted to the scale, shake, as a reference solution. The test solution and the reference solution were taken, and the absorbance at the wavelength of 271nm was measured by ultraviolet-visible spectrophotometry (General rule 0401), and the dissolution amount of each piece was calculated. 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 20 tablets of this product, precision weighing, fine grinding, precision weighing an appropriate amount (about 50mg equivalent to trimethoprim), put it in a 250ml measuring flask, add about 150ml of dilute acetic acid, fully shake to dissolve trimethoprim, dilute to the scale with dilute acetic acid, shake well, filter, take 10ml filtrate accurately, put it in 100ml children's bottle, add 10ml dilute acetic acid, dilute to the scale with water, shake well and measure absorbance at 271nm by UV-Vis spectrophotometry (General rule 0401), dilute acetic acid is added to dissolve and quantitatively dilute to make a solution containing about 20ug per lml, which is determined and calculated by the same method.
category
Same as trimethoprim.
specification
O.lg
storage
light shielding, sealed storage.
Last Update：2022-01-01 11:38:02
trimethoprim - Trimethoprim injection
Authoritative Data Verified Data
This product is a sterilized aqueous solution of trimethoprim. Trimethoprim-containing (C14Hl8N403) shall be between 95.0% and 105.0% of the labeled amount.
trait
This product is colorless to yellowish clear liquid.
identification
- take 1~2 drops of this product, add nitric acid solution (1-2)lml, that is red, the gradient is Brown yellow.
- the solution under the content measurement was measured by ultraviolet-visible spectrophotometry (General 0401), and the maximum absorption was found at a wavelength of 271mn.
examination
- the pH value should be 3.5 to 5.5 (General 0631).
- Related substances take 1ml of this product, put it in a 50ml measuring flask, dilute it to the scale with mobile phase, shake it, and use it as a sample solution, A solution containing 2ug of trimethoprim per 1ml was prepared by dilution with the mobile phase as a control solution. 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 (0.2% ) , the sum of each impurity peak area shall not be greater than 2.5 times (0.5%) of the main peak area of the control solution. Peaks in the chromatogram of the test solution that are 0.05 times smaller than the main peak area of the control solution are negligible.
- bacterial endotoxin this product, according to the law inspection (General 1143), each 1 mg trimethoprim containing endotoxin amount should be less than 3.0EU.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
take 1ml of this product with precision, put it in a 25ml measuring flask, dilute it to the scale with dilute acetic acid, shake it well, take 1ml with precision, put it in a 100ml measuring flask, dilute it to the scale with dilute acetic acid, shake well and measure the absorbance at a wavelength of 271nm by UV-visible spectrophotometry (General rule 0401). Another appropriate amount of trimethoprim reference substance was carefully weighed, dissolved with dilute acetic acid and quantitatively diluted to prepare a solution containing about 20% of each lml, which was determined and calculated by the same method.
category
Same as trimethoprim.
specification
2ml:0.lg
storage
light shielding, closed storage.
Last Update：2022-01-01 11:38:02
trimethoprim - Reference Information
| NIST chemical information | information provided by: webbook.nist.gov (external link) |
| EPA chemical substance information | information provided by: ofmpeb.epa.gov (external link) |
| pyrimethamine bacteriostatic agent | trimethoprim is a lipophilic weak alkaline pyrimethamine bacteriostatic agent, also known as sulfanilamide Synergist, trimethoprim, antibacterial Synergist, trimethoprim, trimethoprim, trimethoprim, trimethoprim, trimethoprim, white or off-white crystalline powder at room temperature, odorless, bitter, slightly soluble in chloroform, slightly soluble in ethanol or acetone, almost insoluble in water, soluble in glacial acetic acid. The antibacterial spectrum and sulfa drugs are similar, but the antibacterial effect is strong, and it is effective against Escherichia coli, Proteus mirabilis, Pneumonia Bacillus, Staphylococcus saprophyticus, a variety of gram-positive and negative bacteria, but ineffective against Pseudomonas aeruginosa infection, the minimum inhibitory concentration is often lower than 10mg/L, single use is easy to cause bacterial resistance, so it is generally not used alone, mainly with sulfa drugs to form a compound preparation, clinically used for the treatment of urinary tract infection, intestinal infection, respiratory tract infection, bacillary dysentery, enteritis, typhoid fever, meningitis, otitis media, meningitis, septicemia and soft tissue infection. Typhoid, paratyphoid not less than ampicillin, can also be combined with long-acting sulfonamides for the prevention and treatment of drug-resistant falciparum malaria. The antibacterial principle of trimethoprim is to interfere with the folate metabolism of bacteria. The main mechanism of action is selective inhibition of bacterial dihydrofolate reductase activity, so that dihydrofolic acid can not be reduced to tetrahydrofolic acid, and synthesis of folic acid is the main component of nucleic acid biosynthesis, therefore, this product prevents the synthesis of bacterial nucleic acid and protein, and the combination of the two hydrogen folate reductase (TMP) and the bacteria is 5 to 60,000 times that of the mammalian enzyme. The combination with sulfa drugs can double block the folic acid anabolism of bacteria, and has a synergistic effect, so that the antibacterial activity of sulfa drugs is enhanced, and the antibacterial effect can be turned into bactericidal effect, and the drug resistant strains can be reduced. In addition, this product can also enhance the antibacterial effect of a variety of antibiotics (such as tetracycline, gentamicin, etc.). |
| antibacterial effect | trimethoprim is a bacterial dihydrofolate reductase inhibitor, and its antibacterial effect is based on interfering with bacterial folate metabolism. antibacterial spectrum: Streptococcus genus contains Pneumonia Streptococcus, Escherichia coli, salmonella, Proteus mirabilis, Pneumonia Bacillus, Shigella, Salmonella Typhi, Bordetella pertussis and so on, which are sensitive to trimethoprim. In addition, trimethoprim on malaria parasites and certain fungi, such as Nocardia, group of bacteria, yeast also have a role. Good antibacterial activity against Vibrio cholerae and Chlamydia trachomatis in vitro. Trimethoprim had no antibacterial effect on Pseudomonas aeruginosa, Meningococcus and Alcaligenes. |
| preparation method of trimethoprim solution | as a selective inhibitor, trimethoprim is commonly used in the preparation of selective medium, such as campylobacter selective medium, legionella selective medium, Clostridium botulinum selective medium, etc. working concentration: preparation of selective medium: 2.5~20mg/L screening campylobacter 10 or 20mg/L Legionella 2.5mg/L Clostridium botulinum 4mg/L preparation method of trimethoprim solution: 1. First, all the instruments used are sterilized at high temperature, and the surface of the instrument and the table top Disinfection are used. Weigh 0.500g of trimethoprim powder on an analytical balance and dissolve in 10 mL DMSO (or lactic acid solution, acetic acid solution). 3. Filter sterilizing with a 0.2 micron filter into a sterile container and then sub-load into a 1.5 mL EP tube. It is not recommended to use the screw cap pipe, which is easy to be contaminated. -20 degree preservation. to avoid pollution and repeated freezing and thawing, it is recommended to pack into small specifications, such as 500 uL. |
| adverse reactions | trimethoprim (TMP) has low toxicity, and common dose adverse reactions are rare. Because this product can interfere with the metabolism of folic acid, patients may appear anemia, leukopenia and thrombocytopenia and other blood system reactions, more common in excessive doses, long course of treatment. Therefore, hemogram should be checked frequently during medication. The maximum daily dosage of this product should not exceed 0.5g, and the continuous medication time should not exceed 1 week. When the adverse reactions of the blood system are obvious, the oral folic acid preparation can be corrected. This product should not be used with anti-tumor drugs, anti-epileptic drugs and other folic acid antagonists at the same time; When TMP is combined with SMZ or SD, it can cause crystallization urine. Other adverse reactions were rash and mild gastrointestinal reactions. |
| Use | as an antibacterial Synergist, it can also treat bacterial infections and coccidiosis in poultry. new oral broad-spectrum antibiotics. The antibacterial spectrum is similar to that of sulfonamides, and is effective against a variety of Gram positive and negative bacteria. Because the bacteria will be easy to produce drug resistance to this product, it should not be used alone as an antibacterial drug. Trimethoprim and sulfa drug combination can enhance the antibacterial effect of several times to tens of times. This product is mainly used as a synergistic drug of sulfa drugs. It is generally used in a ratio of 1:5. It can also be used as a veterinary medicine to treat septicemia caused by coliliver bacteria, Pullorum, Fowl typhoid fever, cholera, and secondary bacterial infection of respiratory system. It can also be used for the treatment of coccidiosis. use: antibacterial Synergist, used alone for respiratory tract infection, urinary tract infection, intestinal infection and other diseases preferred as an antibacterial agent, dihydrofolate reductase inhibitor with prokaryotic enzyme selectivity; Specific dosage form inhibitor, widely used in the study of dihydrofolate reductase; Inhibition of tetrahydrofolate synthesis by prokaryote-specific dihydrofolate reductase (DHFR) |
| production method | trimethoxybenzaldehyde is obtained by condensation and cyclization. The trimethoxybenzaldehyde is first condensed with methoxypropionitrile to form 3'4'5 '-trimethoxy-2 cyano-3-methoxypropene, and then cyclized with guanidine nitrate in methanol/sodium methoxide. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:21:28
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View History
trimethoprim
619-64-7
Eucarvon
429-60-7
Mercurous bromide
NAXAINE CO
12-Iodododecane
activox b
Oxiracetam Impurity 12
9014-76-0
619-64-7
Eucarvon
429-60-7
Mercurous bromide
NAXAINE CO
12-Iodododecane
activox b
Oxiracetam Impurity 12
9014-76-0
Raw Materials for trimethoprim