Cyclosporin A

Molecular Structure:

Molecular Formula: C₆₂H₁₁₁N₁₁O₁₂
Molecular Weight: 1202.6112
IUPAC Name: (2S,5S,8S,11S,14R,17S,20S,23S,26S,32S)-32-ethyl-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
Classification Code: Anti-Infective Agents ; Antifungal agents ; Antirheumatic agents ; Dermatologic agents ; Drug / Therapeutic Agent ; Enzyme inhibitors ; Human Data ; Immunologic Factors ; Immunosuppressant ; Immunosuppressive agents ; Mutation data ; Reproductive Effect ; Tumor data
Melting point: 148-151°C 
Index of Refraction: 1.467
Molar Refractivity: 328.83 cm³
Molar Volume: 1183.6 cm³
Surface Tension: 31.6 dyne/cm
Density: 1.016 g/cm³
Flash Point: 736.3 °C
Enthalpy of Vaporization: 218.52 kJ/mol
Boiling Point: 1293.8 °C at 760 mmHg

 Cyclosporine (CAS NO.59865-13-3) is an immunosuppressant drug widely used in post-allogeneic organ transplant to reduce the activity of the patient's immune system and, so, the risk of organ rejection. It has been studied in transplants of skin, heart, kidney, liver, lung, pancreas, bone marrow, and small intestine.

 Cyclosporine (CAS NO.59865-13-3) is synthesized by a nonribosomal peptide synthetase, cyclosporine synthetase. The enzyme contains an adenylation domain, a thiolation domain, a condensation domain, and an N-methyltransferase domain. The adenylation domain is responsible for substrate recognition and activation, whereas the thiolation domain covalently binds the adenylated amino acids to phosphopantetheine and the condensation domain elongates the peptide chain. Cyclosporine synthetase substrates include L-VALINE, l-LEUCINE, l-ALANINE, L-Glycine, 2-aminobutyric acid, 4-methylThreonine, and D-alanine. With the adenylation domain, cyclosporine synthetase generates the acyl-adenylated amino acids, then covalently binds the amino acid to phosphopantetheine through a thioester linkage. Some of the amino acid substrates become N-methylated by S-Adenosyl methionine. The cyclization step releases cyclosporine A from the enzyme.  Amino acids such as D-Ala and butenyl-methyl-L-Threonine indicates that cyclosporine synthetase requires the action of other enzymes such as a D-alanine racemase. The racemization of L-Ala to D-Ala is pyridoxal phosphate-dependent. The formation of butenyl-methyl-L-Threonine is performed by a butenyl-methyl-L-Threonine polyketide synthase that utilizes acetate/malonate as its starting material.

Hazard Codes of Cyclosporine (CAS NO.59865-13-3): T,Xn
Risk Statements: 45-60-22-40 
R45: May cause cancer. 
R60: May impair fertility. 
R22: Harmful if swallowed. 
R40: Limited evidence of a carcinogenic effect.
Safety Statements: 53-45-36/37-24/25-22 
S53: Avoid exposure - obtain special instructions before use. 
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37: Wear suitable protective clothing and gloves. 
S24/25: Avoid contact with skin and eyes. 
S22: Do not breathe dust.
WGK Germany: 3
RTECS: GZ4120000

 Synonyms of Cyclosporin A (CAS NO.59865-13-3) are (R-(R*,R*-(E)))-Cyclic(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-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl) ; Abrammune ; Antibiotic S 7481F1 ; Arpimune ME ; CCRIS 1590 ; Cicloral ; Cicloral (antibiotic) ;  Cyclo(((E)-(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl)-L-2-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl) ; Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl) ; Cyclosporin rine ; DRG-0275 ; Debio088 ; Equoral ; Gengraf ; HSDB 6881 ; Imusporin ; NSC 290193 ; Neoplanta ; Neoral ; OL 27-400 ; Optimmune ; Papilock Mini ; Ramihyphin A ; Restasis ; S 7481F1 ; S-Neoral ; SDZ-OXL 400 ; Sandimmun ; Sandimmun Neoral ; Sandimmune ; Sandimmune Neoral ; Sang 35 ; Sang-35 ; Sangcya ; Sigmasporin Microoral ; UNII-83HN0GTJ6D ; Zinograf ME .