alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano
ornidazole
CAS: 16773-42-5
Molecular Formula: C7H10ClN3O3
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Names and Identifiers
| Name | ornidazole |
| Synonyms | ro7-0207 ornidazole Ornidazole 0.1 Ornidazole (Tiberal) 1(3-chloro-2-hydroxypropyl)-2-methyl-5-nitro imidazole alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano alpha-(chlormethyl)-2-methyl-5-nitro-imidazol-1-aethanol 1-chloro-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propan-2-ol 1-Chloro-3-(2-Methyl-5-nitro-1H-iMidazol-1-yl)propan-2-ol alpha-(chloromethyl)-2-methyl-5-nitro-1h-imidazole-1-ethano alpha-(chloromethyl)-2-methyl-5-nitro-1H-Imidazole-1-ethanol Ornidazol a-(ChloroMethyl)-2-Methyl-5-nitro-1H-iMidazole-1-ethanol |
| CAS | 16773-42-5 |
| EINECS | 240-826-0 |
| InChI | InChI=1/C7H10ClN3O3/c1-5-9-3-7(11(13)14)10(5)4-6(12)2-8/h3,6,12H,2,4H2,1H3 |
| InChIKey | IPWKIXLWTCNBKN-UHFFFAOYSA-N |
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Physico-chemical Properties
| Molecular Formula | C7H10ClN3O3 |
| Molar Mass | 219.63 |
| Density | 1.6545 (rough estimate) |
| Melting Point | 85-90°C |
| Boling Point | 443.2±40.0 °C(Predicted) |
| Flash Point | 221.9°C |
| Solubility | Soluble in Chloroform and Methanol |
| Vapor Presure | 1.23E-08mmHg at 25°C |
| Appearance | Crystalline solid |
| Color | Crystals from toluene |
| Maximum wavelength(λmax) | ['276nm(H2SO4 aq.)(lit.)'] |
| Merck | 14,6872 |
| pKa | 2.4 ± 0.1(at 25℃) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.6000 (estimate) |
| MDL | MFCD00057960 |
| Physical and Chemical Properties | Melting point 85-90°C |
| Use | Used as anti-anaerobic bacteria and antigenic insect drug |
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | NI5460000 |
| Hazard Class | IRRITANT |
| Toxicity | LD50 in rats, mice (mg/kg): 1780, 1420 orally (Grunberg); LD50 in mice (mg/kg): >2000 orally, >2000 i.p. (Hoffer, Grunberg) |
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Standard
Authoritative Data Verified Data
This product is S-(-) + (3-chloro-2-hydroxypropyl)-2-methyl-5-nitroimidazole. Calculated as the dried product, the content of C7H10C1N303 shall not be less than 99.0%.
Last Update：2024-01-02 23:10:35
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Trait
Authoritative Data Verified Data
- This product is white or off-white crystalline powder; Odorless.
- This product is soluble in ethanol or chloroform, slightly soluble in water.
melting point
The melting point of this product (General rule 0612) is 92~97°C.
absorption coefficient
take this product, precision weighing, add anhydrous ethanol to dissolve and dilute to make a solution containing about 10ug per lml, according to UV-visible spectrophotometry (General 0401), the absorbance was measured at a wavelength of 310MN, and the absorption coefficient was 388-412.
Last Update：2022-01-01 11:36:03
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Differential diagnosis
Authoritative Data Verified Data
- Take 10mg of this product, add 2ml of sodium hydroxide test solution, warm, that is, orange red solution; Dropwise add dilute hydrochloric acid to make it acidic and then turn yellow, then drop excess sodium hydroxide test solution to turn orange red.
- take about O.lg of this product, add 5ml of sulfuric acid solution (3-100) to dissolve, and add 2ml of trinitrophenol test solution to produce yellow precipitate.
- in the chromatogram recorded under the right ornidazole item, the retention time of the main peak of the test solution should be consistent with the retention time of the left ornidazole peak (after) in the main peak of the control solution.
- the solution under the item of absorption coefficient has the maximum absorption at the wavelength of 310nm as determined by UV-visible spectrophotometry (General rule 0401), there is minimal absorption at a wavelength of 263nm.
- The infrared absorption spectrum of this product should be consistent with that of the reference product (General rule 0402).
Last Update：2022-01-01 11:36:03
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Exam
Authoritative Data Verified Data
pH
take this product, add water to make a solution containing about 5mg per lml, according to the law (General 0631),pH value should be 5.5~7.5.
clarity and color of ethanol solution
take this product O.lg, after dissolving with 0902 of ethanol, the solution should be clear and colorless; If it is turbid, it should not be more concentrated compared with No. 1 turbidity standard solution (General rule method 1); If it is colored, no deeper than the yellow or yellow-green No. 2 Standard Colorimetric solution (General rule 0901 method 1).
chloride
take 0.25g of this product, add 2M l of ethyl yeast to dissolve, add water to 25ml, check according to law (General rule 0801), and compare with the control solution made of 5.0ml of standard gasification sodium solution, no more concentrated (0.02%).
sulfate
take 1.0g of this product, Add 10ml of ethanol to dissolve, add water to 40ml, check according to law (General rule 0802), and standard potassium sulfate solution 2.0ml of the control solution should not be more concentrated (0.02%).
ammonium salt
take this product 67mg, according to the law inspection (General 0808), should comply with the provisions (0.03%).
Related substances
take an appropriate amount of this product, add the mobile phase to dissolve and dilute to make a solution containing about 0.5mg per lml as a test solution; Take an appropriate amount for precision measurement, as a control solution, a solution containing about 0.5ug per 1 ml was prepared by dilution with mobile phase. Weigh 2-methyl-5-nitroimidazole (impurity I) control, 1-(2, 3-epoxypropyl)-2-methyl-5-nitroimidazole (impurity II) 1-(2, 3-dihydroxypropyl)-2-methyl-5-nitroimidazole (impurity II), the mobile phase was added and dissolved and diluted to prepare a solution containing about 50ug each per 1 ml as a system-suitable solution. According to the high performance liquid chromatography (General 0512) test, silica gel bonded with eighteen alkyl silane was used as the filler; Methanol-water (20:80) was used as the mobile phase; The detection wavelength was 318mn. 20M1 of the applicable solution of the system is injected into the liquid chromatograph, and the chromatogram is recorded. The number of theoretical plates is not less than 3000 based on the left ornidazole peak. The separation degree between impurity I peak and impurity IE peak shall meet the requirements, the resolution between other peaks should be greater than 3.0. Accurately take 20 u1 of the test solution and the control solution, respectively inject human liquid chromatography, record the chromatogram to 2.5 times 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 (0.1%), the sum of each impurity peak area shall not be greater than 5 times (0.5%) of the main peak area of the control solution.
right ornidazole
take an appropriate amount of this product, add the mobile phase to dissolve and dilute to make a solution containing about 0.2 mg per 1 ml, as a test solution; Take the appropriate child with a precise amount, as a control solution, a solution containing about 1ug per 1 ml was prepared by dilution with mobile phase. According to the high performance liquid chromatography (General 0512) test, cellulose tribenzoate was used as the filler, n-hexane-ethanol-glacial acetic acid (90:10:0.1) as the mobile phase, and the detection wavelength was 3 l0nm; the theoretical plate number is not less than 2000 based on the left ornidazole peak. An appropriate amount of ornidazole reference is taken, dissolved and diluted with mobile phase to make a solution containing about 0.4mg per 1 ml. 20ul is injected into human liquid chromatograph to record the chromatogram. The peak order is right ornidazole peak and left ornidazole peak, and the separation degree between left ornidazole peak and right ornidazole peak should meet the requirements. 20 u1 of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatograms were recorded. The right ornidazole peak area in the chromatogram of the test solution shall not be greater than the main peak area of the control solution (0.5%).
residual solvent
take this product l. In a 10ml measuring flask, dissolve in dimethyl sulfoxide and dilute to the scale. Shake well to be used as a sample solution, A solution containing about 8% per 1 ml was prepared by diluting with dimethyl methylene as a control solution. According to the test for determination of residual solvents (General Principle 0861 third method), a capillary column with 5% phenyl-95% methyl polysiloxane (or similar polarity) as the stationary liquid is used as the column; The initial temperature is 40°C and the retention time is 6 minutes, increase to 150°C at a rate of 40°C per minute for 2 minutes; The detector is a hydrogen flame ionization (FID) detector with a detector temperature of 240°C; The inlet temperature is 100°C, the carrier gas was nitrogen. 1ul of the test solution and the reference solution were injected into the human gas chromatograph respectively, and the chromatogram was recorded. According to the external standard method to calculate the peak area, the residual amount of toluene should comply with the provisions.
loss on drying
take this product, with phosphorus pentoxide as desiccant, under reduced pressure drying to constant weight, weight loss should not exceed 0.5% (General rule 0831).
ignition residue
take l.Og of this product and check it according to law (General rule 0841). The residue left 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 11:36:04
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Content determination
Authoritative Data Verified Data
take this product 0.16g, precision weighing, add acetic anhydride 20ml to dissolve, according to the potential titration method (General 0701), with high gas acid titration solution (0.1 mol/L) titration, and the titration results were corrected with a blank test. Each 1 ml of perchloric acid titration solution (0.1 mol/L) corresponds to 21.96mg of C7H10ClN3O30.
Last Update：2022-01-01 11:36:05
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Category
Authoritative Data Verified Data
Anti-anaerobic drugs.
Last Update：2022-01-01 11:36:05
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Storage
Authoritative Data Verified Data
shade, seal, and store in a cool place.
Last Update：2022-01-01 11:36:05
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Left Ornidzole and Sodium Chloride Injection
Authoritative Data Verified Data
This product is a sterilized aqueous solution of ornidazole and gasified sodium. The content of levornidazole (C7H10C1N303) shall be 93.0% to 107.0% of the label; The content of sodium chloride (NaCl) shall be 95.0% to 105.0% of the label.
trait
This product is a clear liquid from colorless to yellowish green.
identification
- take 50ml of this product, place it in a separatory funnel, add 20ml of chloroform, shake, stand, take the three-gas methane layer, and steam dry on a hot water bath, take appropriate amount of residue (about 20mg of ornidazole), add 2ml of sodium hydroxide solution and warm it to obtain orange-red solution; Add dilute hydrochloric acid Dropwise to make it acidic and yellow, then add excess sodium hydroxide solution dropwise, became orange-red.
- 2ml of a sulfuric acid solution (3-100) was added to dissolve the remaining residue, and 2 to 3 drops of the trinitrophenol test solution were added dropwise, thereby generating a yellow precipitate.
- in the chromatogram recorded under the right ornidazole item, the retention time of the main peak of the test solution should be consistent with the retention time of the left ornidazole peak (after) in the main peak of the control solution.
- take this product and dilute it with water to make a solution containing 10ug of ornidazole per 1 ml, and measure it by UV-Vis spectrophotometry (General 0401), there is a maximum absorption at a wavelength of 318nm and a minimum absorption at a wavelength of 263nm.
- This product shows the reaction of sodium salt identification (1) and chloride identification (1) (General rule 0301).
examination
- the pH value should be 3.2 to 4.5 (General 0631).
- the color of this product, compared with the yellow-green No. 2 Standard Colorimetric liquid (General Principles 0901 first method), shall not be deeper.
- appropriate amount of related substances should be taken and diluted with mobile phase to prepare a solution containing about 0.5mg of ornidazole per 1 ml as a sample solution, A solution containing about 1% of ornidazole per 1 ml was prepared as a control solution by quantitative dilution with mobile phase. According to the chromatographic conditions under the content determination item, 20ul of the test solution and the control solution are respectively injected into the liquid chromatograph, and the chromatogram is recorded to 2.5 times of the retention time of the main component peak. If there is a chromatographic peak in the chromatogram of the test solution that is consistent with the retention time of the impurity ID peak in the system applicable solution, the peak area shall not be greater than 5 times (1.0%) of the main peak area of the control solution, other single impurity peak area shall not be greater than 0.5 times (0.1%) of the main peak area of the control solution, and the sum of each impurity peak area shall not be greater than 7.5 times (1.5%) of the main peak area of the control solution.
- right ornidazole take an appropriate amount of this product and dilute it with isopropyl alcohol to make a solution containing about 0.2mg of left ornidazole per 1 ml as a test solution; Take an appropriate amount for precision measurement, as a control solution, a solution containing about 2ug of levo-ornidazole per 1 ml was prepared by dilution with isopropanol. According to the high performance liquid chromatography (General rule 0512) test, cellulose tribenzoate was used as the filler; N-hexane-ethanol-glacial acetic acid (90:10:0.1) was used as the mobile phase; The detection wavelength was 310nm; an appropriate amount of ornidazole reference substance was taken, dissolved and diluted with isopropramine to make a solution containing about 0.4mg of ornidazole per 1 ml. 20ul was injected into the liquid chromatograph and the chromatogram was recorded. The peak order is right ornidazole peak and left ornidazole peak, and the separation degree between left ornidazole peak and right ornidazole peak should meet the requirements. 20 u1 of the test solution and the control solution were respectively injected into the human liquid chromatograph, and the chromatograms were recorded. The right ornidazole peak area in the chromatogram of the test solution shall not be greater than the main peak area of the control solution (1.0%).
- Heavy Metal take 3.5 of this product, evaporate to about 0821, let it cool, add acetate buffer (pH) 2ml, and check according to law (General Principles first method), heavy metals should not exceed three million.
- The osmolality shall be 0632 ~ 320mOsmol/kg when the product is taken for inspection according to law (General Rule 260).
- bacterial endotoxin this product, according to the law to check (General 1143), the amount of endotoxin per lml should be less than 0.50EU.
- sterile take this product, after membrane filtration treatment, with pH 7.0 sterile gasification sodium-peptone buffer washing (1000ml per membrane), with clostridium sporogenes as positive control bacteria, inspection in accordance with the law (General rule 1101), should comply with the provisions.
- others should comply with the relevant provisions under injection (General 0102).
Content determination
- levornidazole was measured by HPLC (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler, methanol-water (20:80) as mobile phase; The detection wavelength was 318mn. Weigh the appropriate amount of each reference substance of impurity I, impurity II, impurity III and ornidazole, add mobile phase to dissolve and dilute to prepare a solution containing about 50ug in each lml, which is used as the applicable solution for the system, take 20u1 injection liquid chromatograph and record chromatogram. The number of theoretical plates shall not be less than 3000 based on left ornidazole peak. The separation degree between impurity I peak and impurity II peak shall meet the requirements, the resolution between other peaks should be greater than 3.0.
- determination of precision take an appropriate amount of this product, diluted with mobile phase made of each lml containing about 0.lmg solution, accurately take 20u1 injection liquid chromatograph, record chromatogram; Another appropriate amount of left ornidazole reference substance, precision weighing, plus mobile phase dissolution and quantitative dilution to make about 0 per lml. lmg solution, the same method of determination, according to the external standard method to calculate the peak area, that is.
- sodium chloride precision measure 20ml of this product, Add 30ml of water, add 5ml of 2% dextrin solution, 2ml of 2.5% borax solution and 5~8 drops of fluorescein indicator solution, and use silver nitrate titration solution (0.lmol/L) titration. Each l of silver nitrate titration solution (0.1 mol/L) corresponds to 5.844mg of NaCl.
category
Same as ornidazole.
specification
100ml: ornidazole 0.5g with sodium chloride 0.83g
storage
sealed and kept in a cool dark place.
Last Update：2022-01-01 11:36:07
alpha-(chloromethyl)-2-methyl-5-nitro-imidazole-1-ethano - Reference Information
| nitroimidazole drugs | ornidazole is the third generation nitroimidazole drugs, which has obvious antibacterial advantages over metronidazole and tinidazole. The efficacy of ornidazole lasts for a long time, and its plasma elimination half-life is 14.4 hours, which is higher than 8.4 hours of metronidazole and 12.7 hours of tinidazole, so it can reduce the number of patients taking drugs and make it more convenient to use. It acts on the DNA of anaerobic bacteria, amoeba, flagellates and trichomonas cells to break the spiral structure or prevent its transcription and replication, resulting in the death of pathogenic bacteria. The blood drug peak concentration can be reached 2 hours after oral administration, and the bioavailability is about 90%. ornidazole structure contains a chiral carbon atom with hydroxyl group, so it has optical activity, and the racemate is left ornidazole and right ornidazole. The two are mainly manifested as the difference in elimination. There is no significant difference in urine excretion, plasma protein binding rate, distribution in the brain, blood-brain barrier permeability, metabolites, etc., but left ornidazole is eliminated faster than right ornidazole. This significantly reduces the incidence of total clinical adverse reactions of left ornidazole, while right ornidazole is prone to neurotoxicity. Levornidazole has now been marketed in my country, mainly for the treatment of various infectious diseases caused by sensitive anaerobic bacteria, and the prevention of infection before surgery. |
| pharmacological effects | ornidazole (ornidazole) is the third generation of nitroimidazole anti-anaerobic drugs widely used clinically after metronidazole and tinidazole. Pharmacodynamics Ornidazole mainly uses drug prototypes or active metabolites to interact with cellular components, resulting in the death of pathogenic bacteria. Preliminary studies have shown that this drug is effective for Crohn's disease, but the comparative study between this drug and other nitroimidazole drugs is limited. The mechanism of action is in the body. This drug is a prototype or active metabolite with cytotoxic effects. It acts on the DNA of anaerobic bacteria, amoeba, Giardia and Trichomonas cells to break its spiral structure or block its transcription and replication, resulting in its death, achieving the purpose of antibacterial and antiprotoplasm. Antibacterial spectrum Anaerobic bacteria: Bacteroides fragilis, Bacteroides dixii, Bacteroides oval, Bacteroides polymorpha, Bacteroides vulgare, Clostridium, Eubacillus, Digestive cocci and Digestive Streptococcus, Helicobacter pylori, Bacteroides melanoides, Fusobacterium, CO2 Bacteroides, Bacillus gingivalis. Parasites: Trichomonas, Giardia, Amoeba. |
| pharmacokinetics | this product is easy to absorb after oral administration, and its bioavailability is greater than 90%. A single dose of 1.5g was taken orally, and the peak blood drug concentration was 30mg/L at 2 hours, 9mg/L at 24 hours and 2.5mg/L at 48 hours. Oral administration of 0.5g reached the peak blood drug concentration of 10.9mg/L. It can also be absorbed through the vagina. The blood drug peak concentration is about 5mg/L at 12 hours after the suppository is given 0.5g. After absorption, the drug is widely distributed in the body. It is close to the blood concentration in saliva, bile, vaginal secretions, urine, and pus, and can penetrate the blood-brain barrier, and the plasma protein binding rate does not exceed 15%. Metabolized in the liver, its active metabolites are M1 [1-(3-chloro-2-propyl)-2-hydroxymethyl-5-nitroimidazole] and M2[1-(3-hydroxy-2-hydroxypropyl)-2-methyl-5-nitroimidazole]. The original removal half-life of this product is 11~14 hours, and the elimination half-lives of M1 and M2 are 5 hours and 6 hours respectively. The renal clearance rate of this product is 45~50ml/min, most of which are excreted from urine by free or metabolite through kidney, less than 4% are excreted in the original form of drug, and the rest 22% are excreted from feces. This product can be removed by dialysis. |
| indication | this product is suitable for infections caused by sensitive microorganisms and anaerobic bacteria. 1. Genitourinary tract infections in men and women caused by Trichomonas. 2. Intestinal and hepatic amebic disease (including amebic dysentery and amebic liver abscess) caused by amoeba protozoa. 3. Giardiasis. 4. Anaerobic infection: such as sepsis, meningitis, peritonitis, post-operative wound infection, postpartum sepsis, septic abortion, endometritis and other infections caused by sensitive bacteria. 5. Prevent anaerobic bacteria infection after various operations. |
| drug interaction | 1. when combined with oral anticoagulants such as warfarin, this product can inhibit the metabolism of the latter, prolong the half-life and enhance the efficacy of anticoagulants. if the two drugs are the same, attention should be paid to observe the prothrombin time and adjust the dosage. 2. The combination of barbiturates, ranitidine and cimetidine can accelerate the elimination and reduce the effect of this product, and it is not suitable for the same use. 3. This product can prolong the muscle relaxation effect of vecuronium and reduce its curative effect. It is not suitable for full use. 4. There is no obvious interaction between this product and fleroxacin. 5. This product is different from other nitroimidazole drugs. This product may have no interaction with alcohol, which needs further research to confirm. |
| precautions | 1. those who are allergic to this product and other nitroimidazole drugs, patients with brain and spinal cord lesions, patients with various organ sclerosis, low hematopoietic function and chronic alcoholism are prohibited. 2. For patients with central nervous system diseases (such as epilepsy), use dispersible tablets with caution. Use with caution for patients with liver disease and alcoholics. Children under 3.3 years old should not use injections, and children should use them with caution. It is not suitable for pregnant women (especially in early pregnancy) and nursing women. 4. Check whole blood cells before and after medication. 5. In order to reduce gastrointestinal reactions, this product should be taken after meals or taken with food. 6. Before using this product injection, it should be diluted appropriately. When using this powder for injection, it should be dissolved with 50-100ml of 0.9% sodium chloride injection or 5% glucose injection, and finally diluted into 2.5-5 mg/ml solution, then slowly instilled for not less than 30 minutes. |
| adverse reactions | this product is well tolerated, and the following adverse reactions may occur during medication. 1. Central nervous system: headache, fatigue, rigidity, drowsiness, dizziness, tremor, numbness of limbs, cramps, seizures, motor disorders and neurological disorders, short-term disappearance of consciousness, etc.; peripheral neuropathy can also be seen. 2. Digestive system: mild stomach discomfort, nausea, vomiting, stomachache, oral odor, abnormal liver function, etc. 3. Allergic reactions: visible rash, itching, etc. 4. Others: local injection has stabbing sensation, pain, etc. There is still leukopenia, etc. (2016-03-18) |
| use | antiparasitic drugs. used as anti-anaerobic bacteria and antigenic insect medicine |
Last Update：2024-04-09 19:05:10
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Product Name: 1-(3-Chloro-2-Hydroxypropyl)-2-Methyl-5-Nitroimidazole Visit Supplier Webpage Request for quotationCAS: 16773-42-5
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Spot supply
Product Name: Ornidazole Visit Supplier Webpage Request for quotationCAS: 16773-42-5
Tel: 0714-3999186
Email: 2853786052@qq.com
Mobile: 86+15671228036
QQ: 2853786052
Wechat: 15671228036
Multiple SpecificationsSpot supply
Product Name: 1-(3-Chloro-2-Hydroxypropyl)-2-Methyl-5-Nitroimidazole Visit Supplier Webpage Request for quotationCAS: 16773-42-5
Tel: 18301782025
Email: 3008007409@qq.com
Mobile: 18021002903
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