(13cis)-15-oxidoretinal
isotretinoin
CAS: 4759-48-2
Molecular Formula: C20H28O2
(13cis)-15-oxidoretinal - Names and Identifiers
| Name | isotretinoin |
| Synonyms | Roaccutan ISOTRETINON isotretinoin 13-cis-retinoic acid Isotretinoin Capsules 13-cis-vitamin a acid (13cis)-15-oxidoretinal A different diMension acid Anti Acne Powerful Isotretinoin Powder Isotretinoin Pharmaceutical Raw Materials (2Z,4E,6E,8E)-3,7-diMethyl-9-(2,6,6-triMethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic acid 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-cis-4-trans-6-trans-8-trans-nonatetraenoic acid |
| CAS | 4759-48-2 |
| EINECS | 225-296-0 |
| InChI | InChI=1/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/p-1/b9-6+,12-11+,15-8+,16-14- |
| InChIKey | SHGAZHPCJJPHSC-YCNIQYBTSA-N |
(13cis)-15-oxidoretinal - Physico-chemical Properties
| Molecular Formula | C20H28O2 |
| Molar Mass | 300.44 |
| Density | 1.0597 (rough estimate) |
| Melting Point | 172-175 °C (lit.) |
| Boling Point | 381.66°C (rough estimate) |
| Flash Point | 350.6°C |
| Water Solubility | insoluble |
| Solubility | Soluble in chloroform (50 mg/ml), DMSO (60 mg/ml at 25 °C), water (<1 mg/ml at 25°C |
| Vapor Presure | 7.55E-10mmHg at 25°C |
| Appearance | Fine Crystalline Powder |
| Color | Yellow-orange to orange |
| Maximum wavelength(λmax) | ['354nm(EtOH)(lit.)'] |
| Merck | 14,5228 |
| pKa | 4.76±0.33(Predicted) |
| Storage Condition | -20°C |
| Stability | Stable, but probably air and light sensitive. Combustible. Incompatible with strong oxidizing agents. |
| Refractive Index | 1.4800 (estimate) |
| Physical and Chemical Properties | Melting Point 174-177°C water-soluble insoluble |
| Use | For the treatment of severe acne and other diseases |
(13cis)-15-oxidoretinal - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R61 - May cause harm to the unborn child R36/37/38 - Irritating to eyes, respiratory system and skin. R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. |
| Safety Description | S53 - Avoid exposure - obtain special instructions before use. 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. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | VH6440000 |
| TSCA | Yes |
| HS Code | 29362100 |
| Toxicity | LD50 (20 day) in mice, rats (mg/kg): 904, 901 i.p.; 3389, >4000 orally (Kamm) |
(13cis)-15-oxidoretinal - Nature
Open Data Verified Data
yellow or orange-yellow crystalline powder. The melting point was 174-175 °c. Soluble in chloroform or ether, ethanol-soluble or isopropanol, almost insoluble in water.
Last Update：2024-01-02 23:10:35
(13cis)-15-oxidoretinal - Preparation Method
Open Data Verified Data
after reacting p-ionone with ethyl magnesium chloride, it reacts with triphenylphosphine to form a triphenylphosphine salt, and then it reacts with a Cyclopentenone derivative to form isotretinoin and its 8Z isomer. After separation, it is isomerized to isotretinoin by the action of palladium nitrate.
Last Update：2022-01-01 09:24:08
(13cis)-15-oxidoretinal - Standard
Authoritative Data Verified Data
This product is 3, 7-dimethyl-9-(2,6, 6-trimethyl-1-cyclohexenyl) 2 cis -4 trans -6 trans -8 trans-nonantetraenoic acid. The content of C20H2402 shall be 98.0% ~ 102.0% calculated as dry product.
Last Update：2024-01-02 23:10:35
(13cis)-15-oxidoretinal - Trait
Authoritative Data Verified Data
- This product is yellow to orange yellow crystalline powder; Sensitive to air, heat, light, especially sensitive in solution.
- This product is dissolved in triazomethane or ether, slightly soluble in ethanol or isopropanol, and almost insoluble in water.
Last Update：2022-01-01 11:54:51
(13cis)-15-oxidoretinal - Introduction
Isotretinoin is a chemotherapy drug used to treat brain cancer, pancreatic cancer and other cancers.
Last Update：2022-10-16 17:25:22
(13cis)-15-oxidoretinal - Use
Open Data Verified Data
Roche Pharmaceutical Co., Ltd. was first launched in the United States in September 1982. It is a vitamin A antagonist, which has the function of strong and fast inhibiting the proliferation and differentiation process of skin gland cells, and is highly effective for severe nodular cystic acne. It has the functions of reducing sebaceous gland tissue, inhibiting sebaceous gland activity, reducing sebaceous gland secretion, reducing epithelial cell keratinization and reducing the number of Propionibacterium acnes, etc., and is used for severe acne, cystic acne and convergent acne that are ineffective in other drug treatments, for rosacea, ichthyosis, keratosis of hair follicle and pityriasis rubra pilaris and other skin diseases also have a certain effect.
Last Update：2022-01-01 09:24:08
(13cis)-15-oxidoretinal - Differential diagnosis
Authoritative Data Verified Data
- take 5mg of this product, add antimony trichloride solution (take 30g of antimony trichloride, wash with alcohol-free three gas methane 2 times, 15ml each time, then dissolve with alcohol-free chloroform 100ml micro-heat, shake well) 2ml, red, the gradient is purple.
- take this product, add acid Isopropanol Solution (take 0.lmol/L hydrochloric acid solution (1 ml), diluted to 0401 ml with isopropanol, then dissolved and diluted to make a solution containing about 4ug per lml, according to UV-Vis spectrophotometry (general rule) the maximum absorption was determined at a wavelength of 354 mn.
- The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 944).
Last Update：2022-01-01 11:54:52
(13cis)-15-oxidoretinal - Safety
Open Data Verified Data
mouse, rat LDso (day 20)(mg/kg): 904,901 intraperitoneal injection; 3389,>4000 orally.
Last Update：2022-01-01 09:24:09
(13cis)-15-oxidoretinal - Exam
Authoritative Data Verified Data
Related substances
operation in the dark. Take this product, precision weigh, add methanol to dissolve and quantitatively dilute to prepare a solution containing lmg per lml as a test solution; Take lml for precision measurement and put it in a 100ml measuring flask, dilute with methanol to the scale, shake, as a control solution; Another vitamin A acid control article, precision weighing, plus methanol dissolved and quantitative dilution to make 10ug per 1 mL solution, as a control solution. According to the high performance liquid chromatography (General rule 0512) test, using eighteen alkyl silane bonded silica gel as filler, methanol-water-glacial acetic acid (770:225:5) as mobile phase, the detection wavelength was 355nm. The isotretinoin reference substance was dissolved and diluted with methanol to make a solution containing about 40ug per lml, and irradiated with a light source of 3000lx illumination for 30 minutes. 20u1 was injected into the liquid chromatograph, and the chromatogram was recorded, the theoretical plate number is not less than 3000 based on the isotretinoin peak, and the separation degree of the photodegradant peak (relative retention time is about 0.93) and the isotretinoin peak should be greater than 1.5. The sample solution, the control solution and the reference solution were respectively injected with 20 u1, and the chromatogram was recorded to 2 times of the retention time of the main component peak. If there are chromatographic peaks in the chromatogram of the test solution that are consistent with the retention time of the tretinoin peak, the peak area shall be calculated according to the external standard method, and shall not exceed 1.0%; the sum of the peak areas of other impurities shall not be greater than the main peak area of the control solution (1.0%).
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
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 20 parts per million of heavy metal when examined by law (General rule 0821, Law II).
Last Update：2022-01-01 11:54:53
(13cis)-15-oxidoretinal - Content determination
Authoritative Data Verified Data
take this product about 0.2g, precision weighing, add acetone 70ml dissolved, according to the potentiometric titration method (General 0701), with tetrabutylammonium hydroxide titration solution (0.1 mol /L) titration, and the results of the titration were corrected with a blank test. Each 1 ml of tetrabutylammonium hydroxide titrant (0.1 mol/L) corresponds to 30.04 mg of C20H2802.
Last Update：2022-01-01 11:54:53
(13cis)-15-oxidoretinal - Category
Authoritative Data Verified Data
keratolytic drug.
Last Update：2022-01-01 11:54:54
(13cis)-15-oxidoretinal - Storage
Authoritative Data Verified Data
light shielding, filled with inert gas. Sealed storage at 0-5°C.
Last Update：2022-01-01 11:54:54
(13cis)-15-oxidoretinal - Isotretinoin soft capsules
Authoritative Data Verified Data
This product contains isotretinoin (C20H2302) should be labeled the amount of 90.0% ~ 110.0%.
trait
This product is a dark brown soft capsule with an orange-yellow oily suspension.
identification
take the contents of this product, add acid Isopropanol Solution (take 0.lmol/L hydrochloric acid solution (1 ml), diluted to 0401 ml with isopropanol, then dissolved and diluted to make a solution containing about 4ug per lml, according to UV-Vis spectrophotometry (general rule) the maximum absorption was measured at a wavelength of 354nm.
examination
- Content uniformity protected from light. Take 1 capsule of this product, carefully pierce the top with scissors, squeeze the contents into a 50ml measuring flask, cut open the rubber shell, and place it in a 25ml small beaker, wash the scissors and the contents of the shell with 10ml methane, mix the washing solution in a 50ml measuring flask, shake to dissolve isotretinoin, dilute to the scale with isooctane, and shake well, take 2ml accurately, put it in another 100ml measuring flask, dilute it with isooctane to the scale, shake it well, and determine the content according to the method under the content determination item, which shall comply with the regulations (General rule 0941).
- others should comply with the relevant provisions under the capsule (General 0103).
Content determination
operation in the dark. Take the contents of 20 granules of this product, mix them evenly, weigh an appropriate amount (about 10 mg of isotretinoin) accurately, put it in a 50ml measuring flask, add 5ml of dimethanone, shake to dissolve the isotretinoin, add isooctane to dilute to the scale, shake well, take 2ml accurately, put it in another 100ml measuring flask, dilute it to the scale with isooctane, shake well, according to UV-visible spectrophotometry (General rule 0401), the absorbance was measured at the wavelength of 361nm, isooctane was added to dissolve and quantitatively dilute to make a solution containing 4ug per 1 ml, which was determined and calculated by the same method.
category
isotretinoin.
specification
lOmg
storage
sealed and stored in a cool and dry place.
Last Update：2022-01-01 11:54:55
(13cis)-15-oxidoretinal - Isotretinoin gel
Authoritative Data Verified Data
This product contains isotretinoin (C20H23O2) should be labeled the amount of 90.0% to 110.0%.
trait
This product is a water-soluble light yellow translucent thick liquid.
identification
- take an appropriate amount of this product, add acid Isopropanol Solution (take 0.1ml of 1 mol/L hydrochloric acid solution, diluted to 1000ml with isopropanol, and then dissolved and diluted with isotretinoin to make a solution containing 4ug of isotretinoin per 1ml, there is an absorption maximum at a wavelength of 0401 nm as determined by UV-Vis spectrophotometry (general).
- 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.
examination
- pH value of this product l.Og, add water 20ml, stir to dissolve, measured according to law (General 0631),pH value should be 4.5~7.5 related substances to avoid light operation. Take lg of this product, put it in a 25ml measuring flask, add an appropriate amount of methanol, ultrasonic to dissolve isotretinoin, let it cool, dilute it with methanol to the scale, shake well; Take 10ml and put it in a plug centrifuge tube, the sample was centrifuged at 4000 rpm for 15 minutes, and the supernatant was taken as a test solution (injection immediately). Take 1 ml of the sample solution, put it in a 100ml measuring flask, dilute it to the scale with methanol, shake it, and use it as a control solution, methanol was added to dissolve and quantitatively diluted to prepare a solution containing 10ug per 1 ml as a control solution. According to the chromatographic conditions under the content determination item, accurately measure 20ml of each of the above three solutions, respectively inject human liquid chromatography, record the chromatogram to 2 times of the retention time of the main component peak, if there are chromatographic peaks in the chromatogram of the test solution that are consistent with the retention time of the tretinoin peak, the peak area shall be calculated according to the external standard method, and shall not exceed 1.0%; the sum of the peak areas of other impurities (the peak area before the retention time of 3 minutes is not excluded) shall not be greater than the main peak area of the control solution (1.0%).
- others shall comply with the relevant provisions under the item of gel (General rule 0114).
Content determination
- light-shielding operation. Determined by high performance liquid chromatography (General 0512).
- chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica gel as filler; Acetonitrile-methanol -0.1 mol/L ammonium acetate (adjusted to pH 2.5 with trifluoroacetic acid) (70:10:20) as mobile phase, the detection wavelength was 355nm. The isotretinoin reference substance is dissolved and diluted with methanol to make a solution containing about 40ug per lml, and irradiated with a 3000LX illuminance light source for 30 minutes as a solution for system suitability test; take 20u1 injection human liquid chromatograph, record chromatogram, the number of theoretical plate according to isotretinoin peak is not less than 3000, photodegradation * Peak (relative retention time is about 0.93) and isotretinoin peak separation degree should be greater than 1.5.
- determination method: take about 0.5g of this product, weigh it accurately, put it in a 25ml measuring flask, add an appropriate amount of methanol, shake it, sonicate it to dissolve isotretinoin, let it cool, and dilute it to the scale with methanol, shake well, take 10ml, put it in a plug centrifuge tube, centrifuge at 4000 rpm for 15 minutes, and take the supernatant as the test solution. Accurately take 20ug of the sample solution and inject it into the liquid chromatograph, record the chromatogram; Take an appropriate amount of isotretinoin reference substance, accurately weigh it, add methanol to dissolve and quantitatively dilute it to make a solution containing 10ug per lml, the same method of determination, according to the external standard method to calculate the peak area, that is.
category
isotretinoin.
specification
10g:5mg
storage
protect from light, seal, and store in a cool place.
Last Update：2022-01-01 11:54:56
(13cis)-15-oxidoretinal - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| Pharmacological effects | Isotretinoin belongs to the first generation of tretinoin, which is a stereoisomer of all-trans tretinoin. Oral administration has anti-oil effect and has special curative effect on severe acne. The mechanism of action is as follows: ① It has the effects of reducing sebaceous glands, inhibiting sebaceous gland activity, and reducing sebaceous gland secretion, thereby inhibiting the growth of Propionibacterium acnes that depends on the lipid environment. ② It has the effects of anti-keratinization, inhibiting the excessive proliferation of epidermal cells and promoting their differentiation, and can reduce the keratinization of hair follicle mouth and sebaceous gland duct. ③ It can also affect the function of monocytes and lymphocytes, inhibit the chemotaxis of neutrophils and have anti-inflammatory activity. ④ selectively bind to retinoic acid nuclear receptor to play a therapeutic role. Inhibits the proliferation of Corynebacterium brevis, has an immunostimulatory effect at low doses, and has an immunosuppressive effect at high doses. ⑤ can inhibit the formation of collagenase and gelatinase in skin, and can inhibit the activity of ornithine decarboxylase. Because the induction of ornithine decarboxylase can play a major role in skin mutation, isotretinoin can also inhibit the occurrence of tumors. ⑥ When using topical medicine, the mechanism of action of this product is similar to that of retinoic acid. It can induce epidermal cell proliferation, promote the differentiation of epidermal cell granular layer into the stratum corneum, and regulate the abnormal keratinization process of hair follicle sebum epithelium. Keratinous plug, thereby playing a therapeutic role. Figure 1 shows the structural formula of isotretinoin. |
| pharmacokinetics | this product is absorbed rapidly after oral administration, reaching the peak blood drug concentration in 2~4 hours, with low oral bioavailability, and postprandial medication can increase bioavailability. The binding rate with plasma protein is greater than 99%. It is mainly metabolized in the liver or intestinal wall, and enters the intestinal and liver circulation with prototype and metabolites. Unchanged prototype drugs are excreted from feces, and metabolites are excreted through urine. The elimination half-life is 10 to 20 hours. |
| indications | 1. isotretinoin is the first choice for refractory acne, especially for patients with severe nodular, cystic and inflammatory acne who are ineffective in traditional treatment. 2. generalized flat warts or verrucous epidermal dysplasia; 3. keratinizing abnormal skin diseases; 4. cutaneous lupus erythematosus; 5. Lichen planus, sclerosing atrophic moss. |
| clinical application | isotretinoin is an effective drug for the treatment of acne. it plays a role from the four links of acne onset and prevents the formation of acne lesions: ① inhibit sebaceous gland secretion; (2) inhibit the growth of Acne bacillus; (3) inhibit sebaceous gland hyperplasia; (4) anti-inflammatory effect. Isotretinoin has no affinity with tretinoin receptor, and the exact mechanism of its action is not very clear. The anti-acne effect of isotretinoin may be related to its or its metabolites inhibiting the proliferation and differentiation of sebaceous glands. Reduce the volume of sebaceous glands, reduce the skin of dihydrotestosterone, down-regulate the skin androgen receptor related. Other mechanisms include reduction of hair follicle keratosis, antibacterial effect, anti-inflammatory effect, etc. In the 1980s, isotretinoin was only used in severe nodular cystic acne. Now isotretinoin is also used in some less serious acne. These patients are often insensitive to conventional treatment, especially for some long-term use In patients with antibiotics, Acne bacillus has developed resistance to many drugs (such as erythromycin, tetracycline). It can also be used in the treatment of acne patients who are prone to scar. when isotretinoin is used to treat acne, the dosage is too large, 1 mg/(kg d), but most patients have poor compliance due to adverse drug reactions. Later, it was found that 0.5 mg/(kg d) can also obtain similar therapeutic effects. In order to achieve a suitable cumulative amount, the drug use time can be prolonged. The cumulative dose of isotretinoin is calculated by dividing the total amount of the drug taken by the patient's body weight (mg/kg). Generally speaking, when the cumulative dose reaches 120mg/kg, the disease is not easy to repeat. The maximum cumulative amount taken is generally not more than 150mg/kg. Since the drug has a period of retention in the body, the condition of some patients continues to improve after stopping the drug, so maintenance treatment is not necessary until all skin lesions subside. Approximately 1/3 of the patients require retreatment (due to persistence or recurrence of the condition). The two conditions of resistance to isotretinoin are closed acne and small cystic acne. In the first 1 to 2 weeks of treatment, some patients' skin lesions will worsen, and some cystic acne will become pyogenic granuloma-like skin lesions. This is due to the destruction of the normal barrier function of the skin after taking isotretinoin, and the increase in the number of Staphylococcus aureus colonization. If women are resistant to isotretinoin treatment or recurrent attacks, attention should be paid to whether the patient has hirsutism and whether the menstrual cycle is normal, and ovarian and adrenal function should be checked. Abnormal adrenal function or high expression level of 5 α-reductase can lead to this situation. |
| toxicity | (1) adverse reactions of skin and mucosa: this is the most common adverse reaction of oral isotretinoin. the larger the oral dose, the higher the incidence of adverse reactions. Cheilitis is the most common, and the incidence is 100%. It is manifested as dry, chapped, peeling, and bleeding of the lips and mucous membranes, similar to exfoliative dermatitis; nearly 30%-50% patients have dry nasal mucosa, bleeding, reversible alopecia, dry and itchy skin, Dry eyes, especially for patients with allergies and xerosis. Contact lenses should not be used or should not be worn during the application of this product. (2) teratogenic effect: animal experiments have proved that oral isotretinoin can lead to developmental malformation, abortion and stillbirth. Administration in the early stage of fetal organ formation can lead to abnormal development of the central nervous system and cardiovascular system; administration in the third trimester can lead to fetal limb shortage and urinary system defects. (3) Effect on bones: Long-term application of isotretinoin can cause bone hypertrophy, tendon ligament calcification, osteoporosis, epiphyseal atresia, thus affecting the growth of children and adolescents. Bone hypertrophy and calcification of tendon and ligament are the most common, and their incidence is related to drug dosage and medication time. When treating acne with oral isotretinoin at a dose of 1-2mg per kilogram of body weight per day and a course of 4-5 months, about 10% of patients can detect bone hypertrophy. (4) effect on mental activity: people suffering from acne are often depressed or have a tendency to depression. after taking isotretinoin, this tendency will be aggravated. It is reported in the literature that from 1982 to May 2000, the U.S. Food and Drug Administration (FDA) has reported 431 cases of mental disorders after taking isoretinoic acid, of which 37 patients committed suicide, 110 patients were hospitalized with emotional depression, suicidal thoughts or suicidal tendencies, and 284 patients were depressed but not hospitalized. The effect of oral isoretinoic acid on mental activity is related to the time of drug use; after stopping or psychiatric treatment, symptoms can be reduced; symptoms can be aggravated after remedication. (5) abnormal laboratory examination: oral isotretinoin can cause serum triglyceride and cholesterol to rise. |
| drug interaction | 1. combined with warfarin can enhance the latter effect. 2. The combination of acitretin, tretinoin or tretinoin can increase the incidence and severity of adverse reactions. 3. when combined with methotrexate, it can aggravate the liver damage due to the increase of the blood concentration of the latter. 4. when combined with tetracycline, it can cause brain pseudotumor and cause benign brain pressure to increase. the clinical manifestations are hypertension, dizziness and visual impairment accompanied by headache. 5. The combination with carbamazepine can lead to a decrease in the blood concentration of the latter. 6. combined with light sensitive drugs, can add heavy light sensitive effect. (2015-09-23) |
| contraindications | 1. pregnant women, lactation, severe liver and kidney dysfunction. 2. Hyperlipidemia, diabetes, severe osteoporosis should be used with caution. 3. Avoid taking with vitamin A, tetracycline and aspirin. |
| adverse reactions | 1. skin and mucous membrane changes, including cheilitis, dry mouth, facial erythema, dry eyes, conjunctivitis, etc.; 2. long-term application can cause liver and kidney damage; 3. long-term application of isotretinoin can cause osteoporosis, epiphyseal atresia, osteogenesis retardation, etc., the incidence is <15%; 4. teratogenic effect is one of the more serious adverse reactions. |
| preparation method | 1. preparation by reaction of C15 monophosphonate alkyl ester with 5-hydroxy -4-methyl -2-furanone; 2. preparation by reaction of C15 aldehyde and 3,3-dimethacrylate; 3. preparation by condensation reaction of Cl5 aldehyde and diethyl propanoic acid and decarboxylation; 4. Preparation by reaction of C15-triphenylquaternary phosphine salt with 5-hydroxy -4-methyl -2-furanone: |
| use | is a vitamin a drug, which has the function of strong and fast inhibiting the proliferation and differentiation process of skin gland cells, and is highly effective for severe jointed cystic acne. This product has good gastrointestinal absorption, but local medication is ineffective. It is used for severe acne, cystic acne, and acne that are ineffective in other drug treatments. It also has a certain effect on skin diseases such as rosacea, ichthyosis, follicular keratosis and pityriasis rubra. Used for severe acne, etc. Anti-skin keratosis abnormal drug. used to treat severe acne and other diseases |
| Production method | After β-violet ketone reacts with ethylmagnesium chloride, it reacts with triphenylphosphine to form a triphenyl engrazed salt, and then reacts with cyclopentenone derivatives to form isoretinoic acid and its 8Z isomer. After the separation of its 8Z isomer, it is isomerized into isoretinoic acid by palladium nitrate. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:52:54
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