Cyclosporin A | CAS No. 59865-13-3

Cyclosporin A

Basic Information

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CAS Number

59865-13-3

Molecular Formula

C62H111N11O12

Molecular Weight

1202.6 g/mol

EINECS

611-907-1

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Heterocyclic Compounds

Pharmaceutical Chemicals Pharmaceutical Intermediates Heterocyclic Intermediates

Fine Chemicals Surfactants Anionic Surfactants

Polymers and Plastics Thermoplastics Polyolefins

Laboratory Chemicals Research Chemicals Biochemical Reagents

Basic Physical Properties

Physical State

white

Melting Point

148-151°C

Boiling Point

838.63°C (rough estimate)

Density

0.9913 (rough estimate)

Water Solubility

Soluble in dimethyl sulfoxide and ethanol. Insoluble in water.

Flash Point

87℃

Solubility

ethanol: 30 mg/mL

Refractive Index

1.6500 (estimate)

Specific Rotation

D20 -244° (c = 0.6 in chloroform); D20 -189° (c = 0.5 in methanol)

SMILES

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CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)CC=CC)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

InChI

InChI=1S/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

InChIKey

PMATZTZNYRCHOR-CGLBZJNRSA-N

LogP

3.2690000000000063

pKa

13.32±0.70(Predicted)

Topological Polar Surface Area

278.8 Å²

Hydrogen Bond Donor/Acceptor

5 / 23

Complexity

2330

Safety Information

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GHS Hazard Pictograms

H302

H350

H360

Hazard Statement

H302 Harmful if swallowed
Acute toxicity, oral

H350 May cause cancer
Carcinogenicity

H360 May damage fertility or the unborn child
Reproductive toxicity

Storage Conditions

2-8℃

Stability

Stable for 3 years as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.

Toxicity

LD50 in mice, rats, rabbits (mg/kg): 107, 25, >10 i.v.; 2329, 1480, >1000 orally (Ryffel)

Synonyms & References

English

CEQUA
BPBio1_000496
BDBM50022815
CSA
Ciclosporin, European Pharmacopoeia (EP) Reference Standard
CICLOSPORIN [WHO-IP]
CHEBI:4031
Neoplanta
ST-603
CYCLOSPORIN A [MI]
30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
Sang-2000
CICLOSPORINUM [WHO-IP LATIN]
Gengraf
KS-1257
Tox21_301849
Neoral
PMATZTZNYRCHOR-CGLBZJNRSA-N
BRD-K13533483-001-03-0
Abrammune
Equoral
Seciera
Ciclosporin DT
NCGC00093704-12
NSC290193
(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-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
S-Neoral
Ciclosporin;
NSC 290193
Sandimmune

MDL Number

MFCD00274558

EC Number

611-907-1

Customs Code

29419090

FAQ

What is Cyclosporin A (CAS: 59865-13-3)?

Cyclosporin A is a cyclic undecapeptide immunosuppressant drug. It has the chemical formula C43H67NO12 and is known for its ability to inhibit T-cell activation. Cyclosporin A is used in medical treatments to prevent organ rejection and manage autoimmune diseases. It is also recognized for its high molecular weight and unique structure, which contribute to its pharmacological activity.

What are the main uses of Cyclosporin A (CAS: 59865-13-3)?

Cyclosporin A is primarily used in immunosuppressive therapy to prevent organ rejection after transplantation. It is also prescribed for the treatment of autoimmune conditions such as rheumatoid arthritis and lupus. Additionally, it is used in research to study immune system modulation and in veterinary medicine for certain inflammatory disorders. Its applications span pharmaceutical, medical, and research fields.

Is Cyclosporin A (CAS: 59865-13-3) safe?

Cyclosporin A is generally safe when used as directed under medical supervision. However, it can cause side effects such as nephrotoxicity, hypertension, and gastrointestinal issues. Proper handling, including wearing protective gloves and avoiding contact with skin or mucosa, is recommended. Safety standards ensure its controlled use in pharmaceuticals and research to minimize risks.

How should Cyclosporin A (CAS: 59865-13-3) be stored?

Cyclosporin A should be stored in a cool, dry place away from direct light. It is typically kept at a temperature between 15°C to 25°C (59°F to 77°F) and requires a humidity level below 60% to maintain stability. It should be stored in a sealed container and protected from moisture and light to preserve its potency and effectiveness.