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CYCLOSPORIN

Cyclosporine A

CAS: 79217-60-0;59865-13-3

Molecular Formula: C62H111N11O12

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CYCLOSPORIN - Names and Identifiers

Name Cyclosporine A
Synonyms Restasis
Cyclosporin
CYCLOSPORIN
CYCLOSPRINE
CYCLOSPORINE
Cyclosporine
Cyclosporins
cyclosporin A
Cyclosporine A
Antibiotic S 7481F1
Cyclosporine (Neoral)
Cyclosporine (cyclosporin A)
30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-3,21-bis(1-methylethyl)-6,9,18,24-tetrakis(2-methylpropyl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-3,21-bis(1-methylethyl)-6,9,18,24-tetrakis(2-methylpropyl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
CAS 79217-60-0
59865-13-3
EINECS 1312995-182-4
InChI InChI=1/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,26,28-33H2,1-24H3,(H,63,77)(H,64,76)(H,65,79)(H,66,78)/b27-25+/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1

CYCLOSPORIN - Physico-chemical Properties

Molecular FormulaC62H111N11O12
Molar Mass1202.61
Density1.016g/cm3
Melting Point151°C
Boling Point1293.8°C at 760 mmHg
Specific Rotation(α)D20 -244° (c = 0.6 in chloroform); D20 -189° (c = 0.5 in methano
Flash Point736.3°C
Solubility Soluble in methanol, ethanol, acetone, ether or chloroform, slightly soluble in water
Vapor Presure0mmHg at 25°C
AppearanceWhite needle crystal
Storage Condition2-8℃
Refractive Index1.467
MDLMFCD00274558
UseFor the treatment of leukemia, cancer, kidney transplantation, tuberculosis, etc
In vitro studyCyclosporine induces phenotypic transformation through cell-autonomous mechanisms, including infiltration of non-transformed cells. Treatment of tumor cells with Cyclosporine resulted in significant morphological changes, including fluctuations in cell membrane margins and numerous pseudopodia protrusions, increased cell motility, and matrix-independent (infiltrative) growth. Cyclosporine (CsA) has potent immunosuppressive properties, suggesting its role in blocking cytokine gene transcription in activated T cells. Cyclosporine inhibits the phosphatase activity of calcineurin by forming a complex with cyclophilin, which regulates nuclear transport and subsequent activation of NFAT transcription factors. Cyclosporine also blocks the activation of JNK and p38 caused by antigen recognition, making CsA a highly specific inhibitor of T cell activation. Cyclosporine-mediated inhibition of biliary excretion of MPAG via the Mrp2 transporter is a reactive mechanism of interaction between Cyclosporine and mycophenate mofetil (MMF). Cyclosporine inhibits the biochemical and morphological differentiation of skeletal muscle cells and has minimal effect on proliferation.
In vivo studyCyclosporine enhances tumor growth in immunodeficient SCID light brown mice. Cyclosporine inhibits induced post-traumatic muscle regeneration in mice. Cyclosporine reached the highest concentration at 1H in blood, spleen, and kidney, with higher concentrations in spleen and kidney than in blood.

CYCLOSPORIN - Reference

Reference
Show more
1. Li Qian, Wang Ming, Deng Cheng-Cheng et al. Cytotoxicity and cellular uptake of amphiphilic block copolymer Pluronic [J]. Chinese Journal of Hospital Pharmacy, 2017, 37(12): 1104-1128.
2. Zhao, Jing. Effects of ginsenoside Rg_1 on inflammation and TGF β/Smad signaling pathway in Glomerular mesangial cells induced by glycosylation end products [J]. Chinese pharmacist, 2018, 21(11):1919-423.
3. Deng Chengcheng, Li Qian, Tang Jun, etc. Effect of Pluronic on cytotoxicity and uptake of docetaxel-resistant human breast cancer cells [J]. China pharmacist, 2018, 21(008):1325-1330.
4. Liang Yuanyuan, Ma Lin, Cui Lili, etc. Effect of positive electret and azone on penetration of cyclosporine A in vitro [J]. Academic Journal of Second Military Medical University, 2012, 26 (06):617-620.
5. Ping Huang, Yan Shi, Xin Guo, et al. Open-circuit thermally stimulated discharge of cyclosporine A patch with positive electret [J]. High voltage technology, 2015.
6. Li Fangyuan, Liu Daoxu, Liu Miao, et al. Protective effects of reactive oxygen species-responsive cyclosporine A loaded nanoparticles on cardiomyocytes injured by hypoxia/reoxygenation [J]. Northwest Pharmaceutical Journal, 2020, 035(002):229-233.
7. Zuo xia, Guo Lihong, Li Li. Effect of Bailing Capsule on renal function and rejection in renal transplantation rats [J]. Journal of Modern integrative medicine, 2015(12):1279-1282.
8. Meng Zhiping, Lu Manqi, Su Wenqiang, etc. Preparation of berberine hydrochloride powder spray and its effect on Staphylococcus aureus Pneumonia [J]. Chinese herbal medicine, 2020, v.51;No.661(02):73-80.
9. Guo Xin, Cui Lili, Liang Yuanyuan, etc. Piezoelectric properties of negative electret Cyclosporin A patch [J]. High voltage Technology, 2014, 040(006):1916-1920.
10. Liu Hongyue, Jiang Jian, Ma Lin, et al. Effect of electret combined with azone on Percutaneous penetration of Cyclosporin A in vitro [J]. Journal of Pharmaceutical Practice, 2012, 30(006):440-442.
11. Guo Xin, Wang Tao, Shi Yan, et al. Effect of electret external electrostatic field on the polarization characteristics of Cyclosporin A patch with different parameters [J]. Journal of Beijing Institute of Technology, 2017, 37(002):191-195.
12. Lin Lin, Cao Junchang, Yang Zheng, Feng Chunyan. Experimental study of 0.05% cyclosporine A nanoparticle eye drops in the treatment of dry eye [J]. Chinese Journal of eye ear nose and throat, 2021,11(01):1-5.
13. Feng, Baihua, et al. "Exposure to a 50-Hz magnetic field induced mitochondrial permeability transition through the ROS/GSK-3β signaling pathway." International journal of radiation biology 92.3 (2016): 148-155.https://doi.org/10.3109/09553002.2016.1135261
14. [IF=10.435] Zhang Chang-xiong et al."Mitochondria-targeted cyclosporin A delivery system to treat myocardial ischemia reperfusion injury of rats."J Nanobiotechnol. 2019 Dec;17(1):1-16
15. [IF=4.411] Xu Zhang et al."In Vitro and In Situ Characterization of the Intestinal Absorption of Capilliposide B and Capilliposide C from Lysimachia capillipes Hemsl."Molecules. 2019 Jan;24(7):1227
16. [IF=2.368] Baihuan Feng et al."Exposure to a 50-Hz magnetic field induced mitochondrial permeability transition through the ROS/GSK-3β signaling pathway."Int J Radiat Biol. 2016;92(3):148-155
17. [IF=1.627] Yanming Xia et al."Transport mechanism of ursodeoxycholic acid in human placental BeWo cells."Biopharm Drug Dispos. 2018 Jul;39(7):335-343
18. [IF=5.923] Yue Gao et al."Human IL-23R Cytokine-Binding Homology Region-Fc Fusion Protein Ameliorates Psoriasis via the Decrease of Systemic Th17 and ILC3 Cell Responses."Int J Mol Sci. 2019 Jan;20(17):4170
19. [IF=3.981] Xiao-Hang Liu et al."Comparison of the permeability between conjugated estrogens and atenolol in rat in situ single-pass intestinal perfusions model and in Caco-2 cell monolayers."J Drug Deliv Sci Tec. 2022 Feb;68:102786

CYCLOSPORIN - Nature

Open Data Verified Data

White needle-like crystals were obtained from acetone at -15 °c. Melting point of 148~151 ° C, soluble in methanol, ethanol, acetone, ether or chloroform, water-soluble.

Last Update：2025-06-10 22:55:16

CYCLOSPORIN - Preparation Method

Open Data Verified Data

with the production strain of the fungus. Each cyclosporine fermentation broth was prepared, and extracted by adding ethyl acetate to the fermentation broth. The organic layer was separated and evaporated under reduced pressure to obtain a crude product. After purification treatment available.

Last Update：2025-06-10 22:55:16

CYCLOSPORIN - Standard

Authoritative Data Verified Data

This product is cyclic [[(E)-(2S,3R, 4r-3-methyl-2-(methylamino)]-6-octenoyl]-L-2-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-gamma-N-methyl-L-Leucyl-L-alanyl-D-alanyl-JV-methyl-L-leucyl-N-methyl-L-leucine-N-methyl-L-Valyl]. According to the dry product calculation, containing cyclosporine (C62H111N11O12) not less than 98.5%.

Last Update：2024-01-02 23:10:35

CYCLOSPORIN - Trait

Authoritative Data Verified Data
  • This product is white or off-white powder; Odorless.
  • This product is easily soluble in methanol, ethanol or acetonitrile, soluble in ethyl acetate, soluble in acetone or ether, and almost insoluble in water.

specific rotation

take this product, precision weighing, add methanol to dissolve and quantitatively dilute to make a solution containing about 10 mg per lml, and determine according to law (General 0621), the specific rotation was -185 ° to -193 °.

Last Update：2022-01-01 13:32:23

CYCLOSPORIN - Introduction

Odorless and tasteless. This product is easily soluble in methanol, ethanol or acetonitrile, soluble in ethyl acetate, soluble in acetone or ether, and almost insoluble in water.
Last Update：2022-10-16 17:28:56

CYCLOSPORIN - Quality standards-Chinese Pharmacopoeia 2005 edition

Authoritative Data Verified Data

The weight loss on drying shall not be less than 98.5% l of cyclosporine (C2H111N11012), calculated as dry product, heated at 60 ℃ for 3H, the loss on drying should not be more than 2.0% l heavy metal content should be less than 0. 00226.

Last Update：2022-01-01 08:52:47

CYCLOSPORIN - Differential diagnosis

Authoritative Data Verified Data
  1. take about 5mg of this product, add 5ml of methanol to dissolve, add 1 drop of potassium permanganate test solution, place, the purple color should gradually disappear.
  2. 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.
  3. The infrared absorption spectrum of this product should be consistent with that of the control (Spectrum set 784).
Last Update：2022-01-01 13:32:24

CYCLOSPORIN - Application

Open Data Verified Data

developed by Swiss Mountain Taoist company, put into the market in lunar January. Immunosuppressant. A cyclic polypeptide consisting of eleven amino acids. Can inhibit lymphocyte production of interferon. It has no effect on the phagocytic cells of the reticuloendothelial system. Unlike cytotoxic drugs, ciclosporin only inhibits T cell-mediated cellular immunity without significantly affecting the general defenses of the body. It inhibits humoral and cellular transmission of immune function, without inhibiting the bone marrow, does not reduce the number of white blood cells. Can prevent the rejection of the transplanted tissue or organ. In addition, it has a certain effect on autoimmune diseases and schistosomiasis, malaria, diabetes, AIDS, etc., as well as anti-inflammatory properties. Cyclosporine is mainly used to prevent adverse immune reactions such as rejection in allogeneic organ or bone marrow transplantation, and is often combined with glucocorticoids.

Last Update：2025-08-19 16:24:40

CYCLOSPORIN - Exam

Authoritative Data Verified Data

Related substances

take an appropriate amount of this product, precision weighing, add 50% acetonitrile solution to dissolve and quantitatively dilute to make a solution containing about 2.5mg per lml, as a test solution; Take cyclosporine reference substance, precision weighing, adding 50% acetonitrile solution to dissolve and quantitatively dilute to make a solution containing about 25ug per 1 ml as a control solution. According to the chromatographic conditions under the content determination item, 20 u1 of the test solution and the control solution are accurately measured, and the human liquid chromatograph is injected respectively, and the chromatogram is recorded to 2 times of the retention time of the main component peak. If there are impurity peaks in the chromatogram of the test solution, the peak area of cyclosporine shall be calculated according to the external standard method, and the single impurity shall not exceed 0.7% and the total amount of impurity shall not exceed 1.5%. The peaks in the chromatogram of the test solution which were 0.05 times smaller than the main peak area of the control solution were ignored.

loss on drying

take 0.5g of this product, take phosphorus pentoxide as desiccant, dry under reduced pressure at 60°C for 3 hours, and the weight loss shall not exceed 2.0% (General rule 0831).

Heavy metals

take this product 0.5g, inspection according to law (General Principles 0821 second law), containing heavy metals shall not exceed 20 parts per million.

Last Update：2022-01-01 13:32:25

CYCLOSPORIN - Safety

Open Data Verified Data

mice, rats, rabbits intravenous LDso( mg/kg):107, 25,> 10; Oral: 2329. 1480. >1000.

Last Update：2025-06-10 22:55:16

CYCLOSPORIN - Content determination

Authoritative Data Verified Data

measured by high performance liquid chromatography (General 0512).

chromatographic conditions and system suitability test

silica gel bonded with octanoalkyl silane as filler (0.25mm x 430 stainless steel tube connected in front of column); Acetonitrile-water-tert-butyl methyl ether-phosphoric acid (520:: 50:1) mobile phase; Detection wavelength of 210mn; Stainless steel tube and column temperature 70°C. Take appropriate amount of cyclosporine system applicable reference substance, add 50% acetonitrile solution to dissolve and dilute to make a solution containing 2.5mg per lml, and inject 20u1 into the liquid chromatograph. The chromatogram recorded should be consistent with the standard spectrum.

assay

take an appropriate amount of this product, precision weighing, add 50% acetonitrile solution to dissolve and quantitatively dilute to prepare a solution containing about mg per 1 ml as a test solution, the chromatogram was recorded by injection of 20u1 into human Liquid Chromatograph. The appropriate amount of cyclosporine reference substance was taken and determined by the same method. According to the external standard method to calculate the peak area, that is.

Last Update：2022-01-01 13:32:25

CYCLOSPORIN - Category

Authoritative Data Verified Data

immunosuppressant.

Last Update：2022-01-01 13:32:25

CYCLOSPORIN - Storage

Authoritative Data Verified Data

light shielding, sealed storage.

Last Update：2022-01-01 13:32:25

CYCLOSPORIN - Cyclosporin Oral Solution

Authoritative Data Verified Data

This product contains the Ring (C62H111N11O12) should be the standard amount of 90.0% ~ 110.0%.

trait

This product is light yellow or yellow clear oily liquid.

identification

  1. a solution containing 1 mg per 1 ml was prepared by adding a methanol solution of 20% chloroform to each appropriate amount of the product and the control substance of cyclosporine as the test solution and the control solution. According to the thin layer chromatography (General 0502) test, absorb the above two solutions of 10 u1, respectively, on the same silica gel G thin layer plate, with ether as the developing agent, after spreading, dry, move the other cylinder, and use ethyl acetate-butanone-water-methanol (60:40:2:1) as the developing solvent. After spreading, dry, spray with bismuth potassium iodide solution, then immediately sprayed with hydrogen peroxide solution for color development. The position and color of the main spot displayed by the test solution should be the same as the position and color of the main spot of the reference solution.
  2. 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.
  3. two items (1) and (2) above can be selected as one item.

examination

  • amount of ethanol the appropriate amount of test solution and ethanol shall be taken, quantitatively diluted with butanol to a certain concentration, and checked according to law (General rule 0711). The ethanol content shall be 80.0% ~ 120.0% of the labeled amount.
  • others should comply with the relevant provisions under the item of oral solution (General rule 0123).

Content determination

  • measured by high performance liquid chromatography (General 0512).
  • chromatographic conditions and system suitability test using eighteen alkyl silane bonded silica as filler; Acetonitrile-water-methanol-phosphoric acid (550:400:50:0.5) as mobile phase; the detection wavelength was 210nm; The column temperature was 50-70°C. Take appropriate amount of cyclosporine system applicable reference substance, add acetonitrile-water (1:1) mixed solution to dissolve and dilute to make 2.5mg solution per 1 ml, take 20u1 injection human liquid chromatograph, the recorded chromatograms should be consistent with the standard chromatograms.
  • determination precision weigh appropriate amount of this product, add 20% chloroform methanol solution quantitative dilution to prepare a solution containing about 1 mg of cyclosporine per 1 ml, as a test solution, 20u1 was injected into human liquid chromatograph, and the chromatogram was recorded. Appropriate amount of cyclosporine reference substance was taken and determined by the same method. Calculated by peak area according to external standard method, and photographed, the relative density measured by densitometry (General 0601) at the same temperature as the content measurement is converted.

category

Same as cyclosporine.

specification

50ml:5g

storage

shade, seal, and store in a cool place.

Last Update：2022-01-01 13:32:26
CYCLOSPORIN
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