CYCLOSPORIN C

5S,8S,11S,14R,17S,20S,23S,26S,32S)-32-[(1R)-1-hydroxyethyl]-2-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]- 3,6,9,12,14,17,21,27,30-nonamethyl-8, 11,20,26-tetrakis(2- methylpropyl)- 5,23-di(propan-2-yl)-3,6,9, 12,15,18, 21,24,27,30,33-undecazacyclotritriacontane-1,4,7,10,13,16,19,22,25,28, 31-undecone; Cyclo(L-alanyl- D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4- dimethyl-L- 2-amino- 6-octenoyl-L-threonyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl); [Thr2]CsA; 7-Threonine-cyclosporin A; [Thr2-Cyclosporin A];

CYCLOSPORIN C

 

PRODUCT IDENTIFICATION

CAS RN

59787-61-0

EINECS RN

 

FORMULA

C62H111N11O13

MOLE WEIGHT

1218.61

 

PHYSICAL AND CHEMICAL PROPERTIES

PHYSICAL STATE

white crystalline powder

MELTING POINT

152 - 155 C

BOILING POINT

 

DENSITY

 

SOLUBILITY IN WATER

Insoluble (soluble in ethanol, organic solvents)

pH

 

VAPOR DENSITY

 

REFRACTIVE INDEX

 

FLASH POINT

 

 

STABILITY AND REACTIVITY
STABILITY Stable under normal conditions

INCOMPATIBLE MATERIALS

Strong acids, Alkali metals, Aluminum,

DECOMPOSITION PRODUCTS

Carbon oxides. Nitrogen oxides.

POLYMERIZATION Has not been reported

NFPA RATINGS

Health: 1, Flammability: 0, Reactivity: 0

 

SAFETY

HAZARD NOTES

Target Organ Effect, Harmful by ingestion., Carcinogen. Target Organs: Immune system., Kidney, Liver, Blood.

EYE

May cause eye irritation.

SKIN

May be harmful if absorbed through skin. May cause skin irritation.

INGESTION

Harmful if swallowed.

INHALATION

May be harmful if inhaled. May cause respiratory tract irritation.

CHRONIC

 

 

TRANSPORT & REGULATORY INFORMATION

UN NO.

 
HAZARD CLASS

 

PACKING GROUP

 

HAZARD CODE

T

RISK STATEMENTS

45-60-22

SAFETY STATEMENTS

53-45

 

EXTERNAL LINKS & GENERAL INFORMATION

Cyclosporin A (CAS No. 59865-13-3) is a strong immunosuppressant agent (Laupacis et al., 1982; Wagner, 1983) used for the treatment of kidney, liver, heart, and other organ transplantation; rheumatoid arthritis; and psoriasis (Faulds et al., 1993). Cyclosporin A is a non-polar cyclic polypeptide consisting of 11 amino acids produced by multiple fungal species (Petcher et al., 1976; Krensky et al., 2006; Budavari et al., 1996). Cyclosporin A is a white to off white crystalline solid that is slightly soluble in water and soluble in organic solvents (Budavari et al., 1996). (http://www.vcu.edu/)

Cyclosporin (brand names Sandimmun and Neoral) is a medicine used to treat rheumatoid arthritis and other rheumatic conditions such as systemic lupus erythematosus (lupus/SLE) and polymyositis (muscle inflammation). Cyclosporin is used in rheumatoid arthritis when other treatments have been unsuccessful. It is also used to prevent the rejection of transplanted organs. Cyclosporin is an immunosuppressive medicine, which means that it works by reducing the activity of the immune system. In rheumatoid arthritis, this action helps to reduce inflammation and thus reduce pain and swelling. It also limits damage to the joints and helps to prevent disability in the long term. Because cyclosporin reduces the damage to the joints, rather than just relieving the pain, it belongs to the group of medicines called disease modifying antirheumatic drugs (DMARDS). (http://www.rheumatology.org.au/)

Discovery of immunosuppression by cyclosporin in 1976 is attributed to J. F. Borel, see Figure 5. In 1983 cyclosporin was approved for clinical use to prevent graft rejection in transplantation. Most of the surgical problems of allograft transplantation had already been solved by this time. Since 1961 the standard method of achieving immunosuppression had been a combination of azathioprine and corticosteroids. Azathioprine inhibits cell proliferation non-selectively. Its main unwanted side effect is depression of the bone marrow, other toxic effects include increased susceptibility to infections, a mild hepatotoxicity, skin eruptions, nausea and vomiting. Corticosteroids inhibit T lymphocytes and have an anti-inflammatory effect. Side effects include diabetes, avascular necrosis of bones and increased tendency to infections. Cyclosporin was the strongest immunosuppressor to be discovered so far, it also overcame many of the risk factors associated with azathioprine and is relatively non-toxic to bone marrow. With the introduction of cyclosporin patient morbidity fell. It became possible to transplant organs with a one year success of 20% higher than previously, and to transplant organs successfully which previously had only been done in experimentation: the heart, the liver, the lung and combined heart lung transplants. As well as transplantation, cyclosporin has been used in most autoimmune diseases. In the 1980’s experimental treatment with cyclosporin of insulin-dependent diabetes mellitus, inflammatory bowel disease, chronic asthma, atopic dermatitis, aplastic anaemia and psoriasis supported evidence of their T cell mediated nature. (http://www.world-of-fungi.org/)

Cyclosporins

Product

CAS RN.

Cyclosporin C

59787-61-0

Cyclosporine 59865-13-3
Dihydrocyclosporin A 59865-15-5
Isocyclosporin A 59865-16-6
Dihydrocyclosporin C 63556-15-0
Dihydrocyclosporin D 63775-91-7
Isocyclosporin D 63775-93-9
Cyclosporin B 63775-95-1
Cyclosporin D 63775-96-2
Geclosporin 74436-00-3
Cyclosporin 79217-60-0
Cyclosporin F 83574-28-1
Cyclosporin H 83602-39-5
Cyclosporine A acetate 83602-41-9
8-(N-Methylalanine)cyclosporin A 108466-41-7
11-(N-Methyl-L-alanine)cyclosporin A 111710-61-3
N-Methyl-4-((E)-2-butenyl)-4,4-dimethylthreonine cyclosporin A 114865-22-4
Cyclosporin lactam(3,4) 115141-85-0
Valspodar 121584-18-7
8-Hydroxy-6,7-dihydro-(4-(2-butenyl)-4,N-dimethylthreonine)cyclosporin 121886-75-7
N(epsilon)-(Diazotrifluoroethyl)benzoyl-lys(8)-cyclosporin 126871-92-9
9-Hydroxy-9-desmethylcyclosporine 132362-39-1
Dansylisocyclosporin A 134998-06-4
Oxeclosporin 135548-15-1
9-(N-Methyl-L-isoleucine)cyclosporin A 143205-42-9
4-(L-Leucine-7-L-threonine-10-L-leucine)cyclosporin A 153049-50-4
Tricyclic cyclosporin A 153475-57-1
6-(Threo-3-hydroxy-N-methyl-L-leucine)cyclosporin A 154334-72-2
N-Methyl-valyl-4-cyclosporin A 159605-70-6
5-(N-Methyl-D-valine)-6-(threo-3-hydroxy-N-methyl- L-leucine)cyclosporin A 166733-03-5
6-((2S,3R,4R)-3-Hydroxy-4-methyl-2-(methylamino)-6, 8-nonadienoic acid) cyclosporin A 515814-00-3

 

SALES SPECIFICATION

APPEARANCE

white crystalline powder

ASSAY

98.5% - 101.5%

LOSS ON DRYING

2.0% max

HEAVY METALS

10ppm max

MELTING POINT

152 - 155 C

 

PRICE INFORMATION

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