Cyclosporine (59865-13-3),Cyclosporine (59865-13-3) Manufacturers & Suppliers,Synthesis,MSDS

Basic information

Name:
Cyclosporin A
CAS No.:
59865-13-3
Molecular Structure:
Formula:
C₆₂H₁₁₁N₁₁O₁₂
Molecular Weight:
1202.84
Deleted CAS:
55126-45-9
Synonyms:
1,11-cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(E)-(2S,3R,4R)-2-amino-3-hydroxy-N,4-dimethyloct-6-enoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucine];Ciclosporin;Ciclosporinum [INN-Latin];Cipol N;Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-;Cyclosporine;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);Sang 35;Sandimmune (TN);S 7481F1;Restasis;30-ethyl-33-(1-hydroxy-2-methyl-hex-4-enyl)-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-dipropan-2-yl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone;Neoral;(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methyl-pent-3-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-3,6,9,18,24-pentakis(2-methylpropyl)-21-propan-2-yl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone;Sigmasporin Microoral;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;Consupren;cyclophorine;sandimmun;Sandimmun Neoral;Prestwick_731;Ciclosporin (JP14);Neoplanta;Neoral (TN);Sang-35;(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-dipropan-2-yl-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone;Sandimmune;Antibiotic S 7481F1;OL 27-400;
Density:
1.016 g/cm³
Melting Point:
148-151°C
Boiling Point:
1293.8 °C at 760 mmHg
Flash Point:
736.3 °C
Solubility:
ethanol: 30 mg/mL
Appearance:
White Powder
Hazard Symbols:
T， Xn
Risk Codes:
45-60-22-40
Safety Description:
53-45-36/37-24/25-22 Details

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Chemistry

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

Uses

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.

Production

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.

Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
human	TDLo	oral	12mg/kg (12mg/kg)	VASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION ENDOCRINE: ANTIDIURESIS	Journal of Hypertension. Vol. 11, Pg. 1209, 1993.
man	TDLo	oral	14286ug/kg (14.286mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: EXCITEMENT CARDIAC: ARRHYTHMIAS (INCLUDING CHANGES IN CONDUCTION)	Annals of Pharmacotherpy. Vol. 34, Pg. 405, 2000.
man	TDLo	oral	20mg/kg/2D-I (20mg/kg)	BEHAVIORAL: HEADACHE VASCULAR: ACUTE ARTERIAL OCCLUSION LUNGS, THORAX, OR RESPIRATION: CYANOSIS	Lancet. Vol. 2, Pg. 1092, 1986.
man	TDLo	parenteral	20mg/kg/5D-I (20mg/kg)	SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE SENSE ORGANS AND SPECIAL SENSES: DIPLOPIA: EYE SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE	American Journal of Ophthalmology. Vol. 126, Pg. 607, 1998.
man	TDLo	unreported	30mg/kg/4D-I (30mg/kg)	KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	Annals of Internal Medicine. Vol. 107, Pg. 786, 1987.
mouse	LD50	intravenous	96mg/kg (96mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986.
mouse	LD50	oral	2329mg/kg (2329mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Archives of Toxicology. Vol. 53, Pg. 107, 1983.
rabbit	LD50	intravenous	10mg/kg (10mg/kg)		Toxicologic Pathology. Vol. 14, Pg. 73, 1986.
rabbit	LD50	oral	> 1gm/kg (1000mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) SKIN AND APPENDAGES (SKIN): HAIR: OTHER GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"	Archives of Toxicology. Vol. 53, Pg. 107, 1983.
rat	LD50	intraperitoneal	147mg/kg (147mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986.
rat	LD50	intravenous	24mg/kg (24mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986.
rat	LD50	oral	1480mg/kg (1480mg/kg)	BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA" SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Archives of Toxicology. Vol. 53, Pg. 107, 1983.
rat	LD50	subcutaneous	286mg/kg (286mg/kg)		Iyakuhin Kenkyu. Study of Medical Supplies. Vol. 17, Pg. 365, 1986.
women	TDLo	oral	62500ug/kg/5D (62.5mg/kg)	KIDNEY, URETER, AND BLADDER: OTHER CHANGES	Lancet. Vol. 1, Pg. 1221, 1986.
women	TDLo	oral	1911mg/kg/91W (1911mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"	British Journal of Rheumatology. Vol. 33, Pg. 90, 1994.

Safety Profile

Hazard Codes of Cyclosporine (CAS NO.59865-13-3): Toxic T, Harmful 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

Specification

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 .