CYCLOSPORIN C
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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];
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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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