10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride
Oxytetracycline HCL
CAS: 2058-46-0
Molecular Formula: C22H25ClN2O9
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Names and Identifiers
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Physico-chemical Properties
| Molecular Formula | C22H25ClN2O9 |
| Molar Mass | 496.89 |
| Melting Point | 180°C |
| Boling Point | 845.6°C at 760 mmHg |
| Specific Rotation(α) | -188～-200°(D/20℃)(c=1,0.1mol/l HCl) (calculated on the dried basis) |
| Flash Point | 465.2°C |
| Water Solubility | >100 g/L |
| Solubility | Freely soluble in water, sparingly soluble in ethanol (96 per cent). Solutions in water become turbid on standing, owing to the precipitation of oxytetracycline. |
| Vapor Presure | 2.17E-30mmHg at 25°C |
| Appearance | crystalline |
| Color | yellow |
| Maximum wavelength(λmax) | ['360nm(H2O)(lit.)'] |
| Merck | 14,6976 |
| BRN | 3853107 |
| PH | 2.0～3.0 (10g/l, 25℃) |
| Storage Condition | 0-6°C |
| Stability | Hygroscopic |
| Sensitive | Light Sensitive |
| MDL | MFCD00135815 |
| Physical and Chemical Properties | Melting Point: 180°C water-soluble> 100g/L |
| Use | Belongs to broad-spectrum antibiotics, its antibacterial spectrum and antibacterial principle are basically the same as tetracycline |
| In vitro study | Oxytetracycline is an important member of the bacterial aromatic polyketide family, which is a structurally diverse class of natural products. Oxytetracycline is synthesized by a type II polyketide synthase that generates the poly-beta-ketone backbone through successive decarboxylative condensation of malonyl-CoA extender units, followed by modifications by cyclases, oxygenases, transferases, and additional tailoring enzymes. |
| In vivo study | The effects of administration a therapeutic dose of Oxytetracycline (82.8 mg/kg of bw to 1 % bw/day) for 10 days are species specific. Oxytetracycline increases the relative liver weight in Morone chrysops x M. saxatilis , the enzymatic activity of CYP3A4 in Ictalurus punctatus, protein expression of CYP3A4 in Oreochromis niloticus and depleted the hepatic CYP3A4 in the latter. For Oxytetracycline, the limits are 100 μg/kg in muscle and milk, 200 μg/kg in egg, 300 μg/kg in liver and 600 μg/kg in kidney. Oxytetracycline (OTC) is administered to fish as medicated feed at concentrations ranging from 35 to 75 mg a.i kg-1 biomass day-1 for 7-14 days. |
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Risk and Safety
| Risk Codes | 63 - Possible risk of harm to the unborn child |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S53 - Avoid exposure - obtain special instructions before use. S36/37/39 - Wear suitable protective clothing, gloves and eye/face protection. |
| WGK Germany | 2 |
| RTECS | QI8225000 |
| FLUKA BRAND F CODES | 8-10-23 |
| TSCA | Yes |
| HS Code | 29413000 |
| Toxicity | LD50 oral in mouse: 6696mg/kg |
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Upstream Downstream Industry
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Reference
| Reference Show more | 1. Ma Zhenzhen, Zhao Tao, He Jinxing. Preparation of Tetracycline Molecularly Imprinted-Biochar Composites by Pickering Emulsion Polymerization [C]// Abstracts of 15th Annual Meeting of China Food Science and Technology Society. 2018. 2. Liu Hui, Li Jingshi, Zhu Xiaomei, et al. Study on Photodegradation of Oxytetracycline under Simulated Sunlight [J]. China Science and Technology Papers, 2015, 000(021):2477-2480. 3. He, Baoshan, et al. "Aptamer-based thin film gold electrode modified with gold nanoparticles and carboxylated multi-walled carbon nanotubes for detecting oxytetracycline in chicken samples." Food chemistry 300 (2019): 125179.https://doi.org/10.1016/j.foodc 4. [IF = 2.896] Bao-Shan He et al. "Electrochemical aptasensor based on aptamer-complimentary strand conjugate and thionine for sensitive detection of tetracycline with multi-walled carbon nanotubes and gold nanoparticles amplification." Anal Methods-Uk. 2018 Feb;10(7):783 5. [IF = 13.273] Panpan Wang et al. "Photocatalytic degradation of tetracyclines in liquid digestate: Optimization, kinetics and correlation studies." Chem Eng J. 2021 Apr;410:128327 6. [IF = 10.588] Qiaopeng Tian et al. "Characterization of a robust cold-adapted and thermostable laccase from Pycnoporus sp. SYBC-L10 with a strong ability for the degradation of tetracycline and oxytetracycline by laccase-mediated oxidation." J Hazard Mater. 2020 Jan;382: 7. [IF = 7.514] Baoshan He et al. "Aptamer-based thin film gold electrode modified with gold nanoparticles and carboxylated multi-walled carbon nanotubes for detecting oxytetracycline in chicken samples." Food Chem. 2019 Dec;300:125179 8. [IF = 4.616] Mengru Ti et al. "A ratiometric nanoprobe based on carboxylated graphitic carbon nitride nanosheets and Eu3 for the detection of tetracyclines." Analyst. 2021 Feb;146(3):1065-1073 9. [IF = 5.882] Zi-Jian Zheng et al. "MALDI-TOF MS for rapid detection and differentiation between Tet(X)-producers and non-Tet(X)-producing tetracycline-resistant Gram-negative bacteria." Virulence. 2022;13(1):77-88 |
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Standard
Authoritative Data Verified Data
This product is 6-methyl -4-(dimethylamino)-3,5,6,10,12, 12a-hexahydroxy-l, ll-dioxo-l,4,4a,5,5a,6,ll, 12a-octahydro -2-tetrabenzamide hydrochloride. Calculated as anhydrous, containing no less oxytetracycline (C22H24N09)
In 88.0%.
Last Update：2024-01-02 23:10:35
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Trait
Authoritative Data Verified Data
- This product is yellow crystalline powder; Odorless, hygroscopic; Darkened in the sun, easy to break in the alkali solution failure.
- This product is soluble in water, slightly soluble in methanol or ethanol, insoluble in ether.
specific rotation
take this product, precision weighing, add hydrochloric acid solution (9-1000) dissolved and quantitatively diluted to make a solution containing about 10 mg per 1 ml, determined according to law (General 0621), the specific rotation is from one to 188 ° to one to 200 °.
Last Update：2022-01-01 14:20:13
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Differential diagnosis
Authoritative Data Verified Data
- take about 0.5mg of this product, add 2ml sulfuric acid, that is deep red; Then add 1ml water, the solution turns yellow.
- take this product and oxytetracycline reference, add methanol to dissolve and dilute to make a solution containing about 1 mg per 1 ml, as the test solution and the reference solution; Take oxytetracycline and tetracycline hydrochloride reference, add methanol to dissolve and dilute to prepare a mixed solution containing about 1 mg in each lml, and extract each lul of the above three solutions as tested by thin layer chromatography (General 0502), respectively, in the same silica gel G(H)F254 thin layer plate, with water-methanol-dichloromethane (6:35:59) solution as the developer, expand, dry, set the UV lamp (365nm) next, the mixed solution should show two completely separated spots, and the position and fluorescence of the main spot displayed by the test solution should be the same as the position and fluorescence of the main spot of the control 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 aqueous solution of this product was chloride identification (1) of the reaction (General 0301).
- two items (2) and (3) above can be selected as one item.
Last Update：2022-01-01 14:20:14
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Exam
Authoritative Data Verified Data
acidity
take this product, add water to make a solution containing lOmg per lml, and determine it according to law (General 0631). The pH value should be 2.3~2.9.
Related substances
take an appropriate amount of this product, add 0. The Olmol/L hydrochloric acid solution is dissolved and made into a solution containing about 0.5mg per 1 ml as a test solution; 2ml is accurately measured, and the solution is placed in a 100ml measuring flask, and 0.Olmol/L hydrochloric acid solution was diluted to the scale and shaken to serve as a control solution. Take 2ml of the control solution, put it in a 100ml measuring flask, dilute it to the scale with 0.01 mol/L hydrochloric acid solution, and shake it to be used as a sensitivity solution. According to the chromatographic condition test under the content determination item, the sensitivity solution 10u1 is injected into the liquid chromatograph, and the chromatogram is recorded. The signal-to-noise ratio of the high peak of the main component should be greater than 10. Accurately take the test solution and the control solution and inject the human liquid chromatograph respectively, record the chromatogram to 4 times of the retention time of the main component peak, and the chromatogram of the test solution should have impurity peaks, the Peak area of 2-acetyl-2-doxycycline shall not be greater than 1.75 times (3.5%) of the main peak area of the control solution, and the sum of the peak areas of other impurities shall not be greater than the main peak area of the control solution (2.0%). The peaks in the chromatogram of the test solution which are smaller than the main peak area of the sensitivity solution are ignored.
absorbance of impurities
take this product, add 0.1 mol/L hydrochloric acid methanol solution (1-100) was dissolved and quantitatively diluted to prepare 2.0 mg of the solution, according to UV-visible spectrophotometry (General rule 0401), in 1 hours, at a wavelength of 430nm, absorbance should not exceed 0.50. Separately take this product, add the above hydrochloric acid methanol solution to dissolve and quantitatively dilute to make a solution containing lOmg per lml, and measure at the wavelength of 490nm, and the absorbance shall not exceed 0.20.
moisture
take this product, according to the determination of moisture (General 0832 first method 1), the water content shall not exceed 2.0%.
Last Update：2022-01-01 14:20:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Content determination
Authoritative Data Verified Data
measured by high performance liquid chromatography (General 0512).
chromatographic conditions and system suitability test
silica gel bonded with octylsilane as filler; Ammonium acetate solution [0.25mol/L ammonium acetate solution ~ 0.05mol/L ethylene diamine tetraacetic acid disodium solution-triethylamine (100:10:1), with acetic acid to adjust the pH value to 7.5]-acetonitrile (88:12) as mobile phase; Detection wavelength was 280nm. Take an appropriate amount of 4-axis tetracycline control and add 0.Olmol/L hydrochloric acid solution was dissolved and diluted to make a solution containing about 0.5mg per 1 ml; An appropriate amount of oxytetracycline reference substance (containing about 3% of 2-acetyl-2-deamidooxytetracycline) was taken, add a small amount of 0.1 mol/L hydrochloric acid solution dissolved, diluted with water to make a solution containing 0.5mg of oxytetracycline per 1 ml, take the above two solutions (1:24) A mixed solution containing about 20ug of 4-heterotetracycline and 480ug of oxytetracycline (about 14.5ug of 2-acetyl-2-deoxytetracycline) per 1 ml was prepared as a resolution solution. 10ul of the solution was injected into the human liquid chromatograph, and the chromatogram was recorded. The peak sequence was tetracycline peak (relative retention time of oxytetracycline peak was about 0.9), oxytetracycline peak, 2-acetyl-2-deamidooxytetracycline peak (relative retention time to oxytetracycline peak approximately 1.1). The retention time of the oxytetracycline peak was approximately 12 minutes. The degree of separation between the 4-episomal tetracycline peak and the oxytetracycline peak should be greater than 2.0, and the degree of separation between the oxytetracycline peak and the 2-acetyl-2-deoxytetracycline peak should be greater than 2.5.
assay
take this product about 25mg, precision weighing, put 50ml measuring bottle, add 0.Olmol/L hydrochloric acid solution dissolved and diluted to the scale, shake, precision take 5ml, put 25ml flask, with 0.Olmol/L hydrochloric acid solution was diluted to scale, and then shaken well. As the test solution, a 10ul injection liquid chromatograph was used for precise measurement, and the chromatogram was recorded. The content of C22H24N209 in the sample was calculated by peak area according to external standard method.
Last Update：2022-01-01 14:20:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Category
Authoritative Data Verified Data
Tetracycline antibiotics.
Last Update：2022-01-01 14:20:16
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Storage
Authoritative Data Verified Data
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 14:20:16
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Oxytetracycline hydrochloride tablets
Authoritative Data Verified Data
This product contains oxytetracycline hydrochloride according to oxytetracycline (C22H24N209) calculation, should be 90.0% ~ 110.0% of the label amount.
trait
This product is yellow or sugar-coated; It shows yellow color after removing the coating.
identification
take an appropriate amount of the fine powder of this product (about 25mg of oxytetracycline hydrochloride), Heat 25ml of ethanol, soak for 20 minutes, filter, and evaporate the filtrate on a water bath, the residue showed the same result according to the identification test under the item oxytetracycline hydrochloride.
examination
- Related substances take an appropriate amount of the fine powder of this product (about 50mg equivalent to oxytetracycline), put it in a 100ml measuring flask, add 0.1 mol/L hydrochloric acid solution oxytetracycline hydrochloride was dissolved and diluted to the scale, shaken, filtered, and the filtrate was taken as a test solution. According to oxytetracycline hydrochloride under the determination of the method should comply 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 0.25g equivalent to oxytetracycline), put it in a 500ml measuring flask, add O.Olmol/L hydrochloric acid solution to dissolve oxytetracycline hydrochloride and diluted to the scale, shake, filter, precision take the filtrate 5ml, put 25ml flask, with 0. The Olmol/L hydrochloric acid solution was diluted to the scale, and shaken well. As a test solution, it was obtained by measuring according to the method under the item of oxytetracycline hydrochloride.
category
with oxytetracycline hydrochloride.
specification
Based on C22H24N209 (l)0.125g (2)0.25g
storage
light-shielded, sealed, and stored in a dry place.
Last Update：2022-01-01 14:20:16
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Introduction
Tetracycline antibiotics. Alias: doxycycline, oxytetracycline. This product is a broad-spectrum bacteriostatic agent, many Rickettsia, Mycoplasma, chlamydia, spirochete, amoebic protozoan and some Plasmodium are also sensitive to this product. Enterococcus is resistant to it. Others such as Actinomyces, Bacillus anthracis, Listeria monocytogenes, Clostridium, Nocardia, Vibrio, Brucella, Campylobacter, Yersinia, etc. are sensitive to this product.
Last Update：2024-04-10 22:29:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Safety terminology
- after contact with the eyes, please immediately rinse with plenty of water and seek the advice of your doctor.
- wear appropriate protective clothing, gloves, and goggles or masks.
Last Update：2024-04-10 22:29:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Trait
This product is yellow crystalline powder; Odorless, slightly bitter taste; Micro-hygroscopicity; Dark color in the sun, easy to break failure in alkali dissolution. This product is soluble in water, slightly soluble in ethanol, insoluble in chloroform or ether. Take this product with specific rotation, weigh it accurately, dissolve it with hydrochloric acid (9 & rarr;1000) and dilute it into a solution containing 10mg per 1ml, place it in the dark for 1 hour, and determine it according to law, the specific rotation ranged from -188 degrees to -200 degrees.
Last Update：2024-04-10 22:29:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Adverse reactions
- digestive system: gastrointestinal symptoms such as Nausea, Vomit, upper abdominal discomfort, abdominal distension, Diarrhea, occasional reports of pancreatitis, esophagitis and esophageal ulcer, mostly occurred in patients who were bed immediately after taking the drug.
- liver toxicity: usually fatty liver degeneration, liver toxicity is likely to occur in pregnant women and patients with previous renal impairment, but liver toxicity can also occur in patients who do not have the above conditions.
- allergic reactions: mostly maculopapular rash and erythema, in addition to visible urticaria, angioneurotic edema, allergic purpura, pericarditis and systemic lupus erythematosus exacerbation, exfoliative dermatitis is not common. Anaphylactic shock and asthma occurred occasionally. Some patients with tetracycline have photosensitivity when exposed to the sun. Therefore, patients should be advised not to be directly exposed to sunlight or ultraviolet light, and should be discontinued as soon as skin erythema occurs.
- Blood system: Occasionally, it can cause hemolytic anemia, thrombocytopenia, neutropenia and eosinophil decrease.
- Central nervous system: Occasionally, it can cause benign intracranial hypertension, with Head Pain, Vomit, papilledema, etc.
- nephrotoxicity: patients with preexisting significant renal impairment may develop aggravation of azotemia, hyperphosphatemia, and acidosis.
- double infection: Long-term application of this product can occur resistant Staphylococcus aureus, gram-negative bacilli and fungi and other digestive tract, respiratory tract and urinary tract infections, severe cases can cause sepsis.
- This product can be deposited in the teeth and bones, causing varying degrees of tooth discoloration, yellow staining, enamel dysplasia and dental caries, and can cause bone dysplasia.
- application of this product can reduce the normal flora in the human body, resulting in vitamin B deficiency, fungal reproduction, dry mouth, sore throat, angular cheilitis and glossitis.
Last Update：2024-04-10 22:29:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Dosage instructions
oral, 0.5g, 3~4 times a day, 8 years old children over 30~40mg per kilogram of body weight per day, divided into 3~4 times.
pregnant and lactating women
This product can enter the fetal body through the placental barrier and deposit in the calcium area of teeth and bone, causing discoloration of fetal teeth, poor enamel regeneration and inhibition of fetal bone growth, in addition, this kind of drug has teratogenic effect in animal experiments, so pregnant women should not use this product. This product can be secreted from milk, milk concentration is higher, there is a potential for the occurrence of serious adverse reactions to the breast milk, lactating women should suspend the application of lactation.
Children
This product can form stable calcium compounds in any bone tissue, resulting in yellow staining of permanent teeth, enamel dysplasia and bone growth inhibition, so children under 8 years of age should not use this product.
use in elderly patients
elderly patients often accompanied by renal dysfunction, the application of this product, easy to cause liver toxicity, so the elderly patients should be based on the degree of renal dysfunction to adjust the dose.
Last Update：2024-04-10 22:29:15
10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| biological activity | Oxytetracycline hydrochloride is a tetracycline antibiotic. Oxytetracycline hydrochloride strongly inhibit Gram-negative and Gram-positive bacteria. Oxytetracycline hydrochloride is a protein synthesis inhibitor that prevents aminoacil-tRNA from binding to complex ribosomal RNA. Oxytetracycline hydrochloride also has anti-HSV-1 activity. |
| use | is a broad-spectrum antibiotic, and its antibacterial spectrum and antibacterial principle are basically the same as tetracycline mainly for gram-positive bacteria, meningococcus, gonococcus and other gram-negative bacteria have antibacterial activity by preventing aminoacyl-tRNA from binding to 30S subunit Inhibit protein synthesis. Antibacterial spectrum: Gram-negative and positive bacteria. Patterns of resistance: loss of activity, ribosome protection, tetracycline inactivation. |
Last Update：2024-04-09 21:01:54
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Raw Materials for 10,12,12a-hexahydroxy-6-methyl-1,11-dioxo-monohydrochloride