Protopic
Tacrolimus
CAS: 104987-11-3
Molecular Formula: C44 H69 N O12
Protopic - Names and Identifiers
Protopic - Physico-chemical Properties
| Molecular Formula | C44 H69 N O12 |
| Molar Mass | 804.02 |
| Density | 1.19±0.1 g/cm3(Predicted) |
| Melting Point | 113-115°C |
| Boling Point | 871.7±75.0 °C(Predicted) |
| Specific Rotation(α) | -84.4 (c, 1.02 in CHCl3) |
| Flash Point | 2℃ |
| Water Solubility | Freely soluble in DMSO or ethanol. Poorly soluble in water.Soluble in dimethyl sulfoxide, ethanol, water, acetone, chloroform, ethyl acetate, ether, methanol and dimethyl formamide. |
| Solubility | Soluble in methanol, ethanol, acetone, ethyl acetate, chloroform or ether, insoluble in hexane or petroleum ether, insoluble in water. |
| Vapor Presure | 1.73E-35mmHg at 25°C |
| Appearance | Powder |
| Color | white |
| pKa | 9.97±0.70(Predicted) |
| Storage Condition | Sealed in dry,Store in freezer, under -20°C |
| Stability | Stable for 2 years from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months. |
| Refractive Index | 1.549 |
| MDL | MFCD11045918 |
| Physical and Chemical Properties | Monohydrate: C44H69NO12? H2O. Colorless prisms from acetonitrile, melting point 127~129 °c. [Α] D20-84.4 °(C = 1.02, chloroform). Soluble in methanol, ethanol, acetone, ethyl acetate, chloroform or ether, insoluble in hexane or petroleum ether, insoluble in water. Acute toxicity LD50 mice (mg/kg):>200 intraperitoneal injection. Acute toxicity LD50 male and female rats (mg/kg):57.0,23.6 intravenous; 134,194 oral. |
Protopic - Risk and Safety
| Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R36 - Irritating to the eyes R20/21/22 - Harmful by inhalation, in contact with skin and if swallowed. R11 - Highly Flammable |
| Safety Description | S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S16 - Keep away from sources of ignition. S60 - This material and its container must be disposed of as hazardous waste. S20 - When using, do not eat or drink. |
| UN IDs | UN 2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | KD4201200 |
| HS Code | 29349990 |
| Hazard Class | 6.1 |
Protopic - Reference Information
| overview | tacrolimus is a macrolide drug isolated from Streptomyces. it has a strong immunosuppressive effect, can specifically bind and inhibit calmodulin phosphatase activity, inhibit IL-2 signal transcription, thus inhibiting T cell activation, TNF-α, IL-1β and IL-6 production, and T cell-dependent B cell proliferation. Compared with cyclosporine, another calmodulin phosphatase inhibitor, tacrolimus has a stronger inhibitory effect on T cell activation and fewer adverse reactions. Tacrolimus (also known as FK506, trade name: Placoft) is widely used in anti-rejection treatment after various organ transplants, as well as in the treatment of autoimmune diseases, kidney diseases, and blood system diseases. However, there are great individual differences in the use of tacrolimus, and a variety of drugs and foods may affect the blood concentration of tacrolimus in all aspects of medication. |
| immunosuppressive effect | tacrolimus (Tarolimus,Tac, also known as FK506), a calcineurin inhibitor (CNI), became the cornerstone of most immunosuppressive programs in solid organ transplantation (SOT) after its introduction in the field of transplantation in the 1990s. The immunosuppressive mechanism of tacrolimus is mainly through binding to FK506 receptor binding protein -12(FKBP-12) in T lymphocytes to form a Tac-FKBP-12 complex, which binds to calcineurin and inhibits the activation of the latter, Interfering with and inhibiting the synthesis of interleukin 2(IL-2) at the molecular level, inhibiting the infiltration of cytotoxic T lymphocytes into the graft, so as to achieve the purpose of preventing and treating rejection. Compared with cyclosporine, the use of tacrolimus has completely changed the future of kidney transplantation because of its higher graft survival rate, higher drug tolerance, lower rejection rate and fewer side effects. KDIGO has recommended tacrolimus as the first-line CNI for kidney transplantation in 2009 as an initial and long-term maintenance immunosuppressive therapy. However, tacrolimus concentration monitoring is still complicated. Insufficient dosage will increase the risk of rejection, while excessive dosage will increase the risk of side effects, mainly nephrotoxicity, neurotoxicity, infection, malignant tumors, diabetes and gastrointestinal discomfort. |
| drug monitoring | tacrolimus is not completely absorbed in gastrointestinal tract after oral administration, and individual differences are large. Some patients are rapidly absorbed after oral administration, reaching the highest blood concentration at 0.5h, and some patients reach the peak at 1-3 h. Tacrolimus can be widely distributed in the body after absorption, and the blood concentration is higher in the heart, liver, kidney and other tissues. Tacrolimus is mainly metabolized by the liver. At least 9 metabolites have been found. Among them, the methyl-deficient group is considered to be the main metabolite of liver microsomes. After its metabolism, it is mainly excreted from bile through feces. The therapeutic window of tacrolimus is narrow, and its therapeutic dose is close to the toxic dose. The pharmacokinetic characteristics and bioavailability of different individuals are quite different. Therefore, it is necessary to monitor the blood concentration of tacrolimus and perform according to the monitoring results. The dosage is adjusted to reach the target blood drug concentration as soon as possible within a certain period of time. |
| Drug interaction | Tacrolimus is mainly metabolized by the liver CYP enzyme system and is also an inhibitor of CYP enzyme. Therefore, drugs that are also metabolized by CYP enzyme Or drugs that have an impact on CYP enzyme will cause the concentration of tacrolimus to fluctuate. Increase blood drug concentration-antifungal drugs (ketoconazole, fluconazole, itraconazole, voriconazole), macrolide antibacterial drugs (erythromycin, clarithromycin), calcium channel blockers Hepatic enzyme inhibitors such as antihypertensive drugs (diltiazem) can significantly increase the blood concentration of tacrolimus; various aluminum-containing and magnesium-containing drugs such as aluminum hydroxide, aluminum phosphate, magnesium hydroxide, and magnesium oxide can increase the exposure of tacrolimus and should also be avoided. Reducing the blood concentration-liver drug enzyme inducers such as rifampicin and glucocorticoids will significantly reduce the blood concentration of tacrolimus. Schisandrin A (the main ingredient of pentaester capsules), berberine (berberine hydrochloride), rhubarb, compound glycyrrhizin (licorice), phellinus, bifendate, hypericum perforatum and other traditional Chinese medicine ingredients can affect tacrolimus Blood concentration should be avoided at the same time. Therefore, during taking tacrolimus, adding any western medicine or proprietary Chinese medicine, it is necessary to closely monitor the concentration of tacrolimus. In addition, due to the complex composition of Chinese herbal medicine, we should try to avoid taking Chinese herbal medicine and ointment. |
| use | macrolide antibiotics. Immunosuppressants. The mechanism of action is the same as that of cyclosporin, mainly inhibiting the synthesis of interleukin-2. Rejection for organ transplantation. A macrolide that can bind to FK506 binding protein (FKBP) to form a complex, thereby reducing the activity of peptidyl prolyl isomerase in T cells. |
| production method | obtained from Streptomyces tsukubaensis fermentation. The fermentation process is as follows: 100m1 seed solution (containing 1% glycerol, 1% corn starch, 0.5% glucose, 1% cotton seed powder, 0.5% corn impregnation solution and 0.2% calcium carbonate, pH = 6.5) is transferred into a 500ml bottle and disinfected at 120 ℃ for 30min. A circle of S.Tsukubaensis No.9993 seeds cultured by inclined plane was connected and cultured at 30 ℃ for 4 days. The culture solution was transferred into the 201. The same seed liquid was cultured in a 30L fermenter that had been disinfected at 120 ℃ for 30min for 2 days at 30 ℃, and the air was drummed for 2L/min and stirred for 300r /min. 16L of the culture solution was implanted into 2000L containing 1600L of fermentation broth (containing 4.5% soluble starch, 1% corn impregnation solution, 1% dry yeast, 0.1% calcium carbonate and 0.1% Adekancd,pH = 6.8), which had been disinfected at 120 ℃ for 30min, and fermented in a tank at 30 ℃, 170r/min stirring and 1600L/min air flow for 4 days. Separation: 1500L fermentation broth was filtered with 25kg diatomite. The filter cake is extracted with 500L acetone, and the extract and filtrate (1350L) are combined by containing 100LDiaion HP-20 non-ionic absorption resin (Mitsubishi Industries Ltd,. Japan products) pillars. After washing with 300L of water and 300L of 50% acetone aqueous solution, elution with 75% acetone aqueous solution. The eluent was concentrated under reduced pressure to about 300L of aqueous solution, and then extracted 3 times with 20L of ethyl acetate. The extracts are combined and concentrated under reduced pressure to the remaining oil. The oily residue is mixed with 2 times the weight of acidic silica gel (special silica gelgrade 12,Fuji(9evision Co,Japan product) and immersed in ethyl acetate. The solvent was distilled, and the remaining dry powder was used for chromatography with 8L of the same acidic silica gel column, and eluted with 30L of n-hexane, 30L of n-hexane and ethyl acetate (4:1) mixture and 30L of ethyl acetate. The eluent containing fulgemycin was collected and concentrated under reduced pressure. The oily residue is mixed with 2 times the weight of acidic silica gel and immersed in ethyl acetate. The solvent was distilled, and the resulting dry powder was subjected to 3.5L acidic silica gel column chromatography, eluted with 10L n-hexane, 10L n-hexane and ethyl acetate (4:1) mixture, and 10L ethyl acetate. The eluent containing fulgemycin was collected and concentrated under reduced pressure. The obtained yellow oily residue was dissolved in a mixture of 300ml of n-hexane and ethyl acetate (1:1), column chromatography with 2L silica gel (230~400 μm,Merck Co.,Ltd.IJSA product), eluted with n-hexane, ethyl acetate (10L 1:1, 6L 1:2) and 6L ethyl acetate. The eluent containing fulgemycin was collected and concentrated under reduced pressure to obtain 34g of white powdered fulgemycin. Dissolve it in acetonitrile and concentrate under reduced pressure. The concentrated solution was left overnight at 5 ℃ to obtain 22.7g prismatic crystals. Then recrystallize with acetonitrile to obtain 13.6g of pure fujimycin with colorless prismatic crystals. |
| 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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