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| CAS No.: | 59865-13-3 |
|---|---|
| Name: | Cyclosporin A |
| Molecular Structure: | |
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| 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: |
 T，  Xn
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| Risk Codes: | 45-60-22-40 |
| Safety: | 53-45-36/37-24/25-22 |
| PSA: | 278.80000 |
| LogP: | 4.14950 |
cyclosporin A
| Conditions | Yield |
|---|---|
| With Cyclohexyl isocyanide; benzotriazol-1-ol In tetrahydrofuran; dichloromethane at 23℃; for 24h; Inert atmosphere; | 55% |
| Conditions | Yield |
|---|---|
| pH=7.4; Reactivity; |
cyclosporin A
| Conditions | Yield |
|---|---|
| With Cyclohexyl isocyanide; benzotriazol-1-ol In tetrahydrofuran at 70℃; for 16h; Inert atmosphere; Microwave irradiation; | 6.4 mg |
cyclosporin A
| Conditions | Yield |
|---|---|
| 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 |
cyclosporin A
| Conditions | Yield |
|---|---|
| With Cyclohexyl isocyanide; benzotriazol-1-ol In tetrahydrofuran; dichloromethane at 70℃; for 20h; Inert atmosphere; Microwave irradiation; | 8.6 mg |
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| With 2,6-dimethylpyridine In dichloromethane at 20℃; for 12h; | 100% |
| Conditions | Yield |
|---|---|
| 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; |
| Conditions | Yield |
|---|---|
| (1,3-Bis-(2,4,6-trimethylphenyl)-2-imidazolidinylidene)dichloro(o-isopropoxyphenylmethylene)ruthenium In dichloromethane for 16h; Heating / reflux; | 98% |
| Conditions | Yield |
|---|---|
| (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; |
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Molecular Structure:
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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.
| 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. |
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 .
