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59865-13-3

Basic Information
CAS No.: 59865-13-3
Name: Cyclosporin A
Article Data: 18
Cas Database
Molecular Structure:
Molecular Structure of 59865-13-3 (Cyclosporin A)
Formula: C62H111N11O12
Molecular Weight: 1202.63
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;
EINECS: 200-835-2
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: ToxicT, HarmfulXn
Risk Codes: 45-60-22-40
Safety: 53-45-36/37-24/25-22
Transport Information: N/A
PSA: 278.80000
LogP: 4.14950
Synthetic route

H-D-Ala-MeLeu-MeLeu-MeVal-MeBmt-Abu-Sar-MeLeu-Val-MeLeu-Ala-SH

59865-13-3

cyclosporin A

Conditions
ConditionsYield
With Cyclohexyl isocyanide; benzotriazol-1-ol In tetrahydrofuran; dichloromethane at 23℃; for 24h; Inert atmosphere;55%
324077-04-5

C117H209N41O23

A

C55H98N30O11

B

59865-13-3

cyclosporin A

Conditions
ConditionsYield
pH=7.4; Reactivity;

7,8-Secocyclosporin-7-carboxylic acid

59865-13-3

cyclosporin A

Conditions
ConditionsYield
With Cyclohexyl isocyanide; benzotriazol-1-ol In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Microwave irradiation;6.4 mg

C67H121N11O15

59865-13-3

cyclosporin A

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: chlorotriisopropylsilane; trifluoroacetic acid / dichloromethane / 1 h / -20 °C
2: Cyclohexyl isocyanide; benzotriazol-1-ol / tetrahydrofuran; dichloromethane / 20 h / 70 °C / Inert atmosphere; Microwave irradiation
View Scheme

C62H113N11O13

59865-13-3

cyclosporin A

Conditions
ConditionsYield
With Cyclohexyl isocyanide; benzotriazol-1-ol In tetrahydrofuran; dichloromethane at 70℃; for 20h; Inert atmosphere; Microwave irradiation;8.6 mg
59865-13-3

cyclosporin A

108-24-7

acetic anhydride

83602-41-9

O-acetyl-cyclosporin A

Conditions
ConditionsYield
With pyridine; dmap In dichloromethane at 0 - 20℃; for 48h; Inert atmosphere;100%
With dmap at 20℃;96%
With dmap In dichloromethane at 20℃;95%
80522-42-5

triisopropylsilyl trifluoromethanesulfonate

59865-13-3

cyclosporin A

C71H131N11O12Si

Conditions
ConditionsYield
With 2,6-dimethylpyridine In dichloromethane at 20℃; for 12h;100%
583-04-0

vinyl benzoate

59865-13-3

cyclosporin A

A

benzoic acid 6-(5-ethyl-11,17,26,29-tetraisobutyl-14,32-diisopropyl-1,7,10,16,20,23,25,28,31-nonamethyl-3,6,9,12,15,18,21,24,27,30,33-undecaoxo-1,4,7,10,13,16,19,22,25,28,31undecaaza-cyclotritriacont-2-yl)-6-hydroxy-5-methyl-hex-2-enyl ester

B

benzoylated-MeBMT-CsA

Conditions
ConditionsYield
With 1,3-dimesityl-4,5-dihydroimidazol-2-ylidenetricyclohexylphos; phine benzylidene ruthenium dichloride In dichloromethane at 45℃; for 12h; Title compound not separated from byproducts;A n/a
B 99%
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 45℃; Title compound not separated from byproducts;
23939-49-3

S-(4-vinylphenyl) thioacetate

59865-13-3

cyclosporin A

C69H115N11O13S

Conditions
ConditionsYield
(1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium In dichloromethane for 16h; Heating / reflux;98%
1663-39-4

tert-Butyl acrylate

59865-13-3

cyclosporin A

C66H117N11O14

Conditions
ConditionsYield
(1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium In dichloromethane for 16h; Heating / reflux;93%
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 70℃; for 4h; Inert atmosphere; Sealed tube; Microwave irradiation;
With Hoveyda-Grubbs catalyst second generation In 1,2-dichloro-ethane at 23 - 70℃; for 4h; Inert atmosphere; Sealed tube;
Downstream Products
59865-15-5
121584-52-9
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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): ToxicT,HarmfulXn
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 .