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CAS No 59865-13-3 , Cyclosporin A

  • Name: Cyclosporin A
  • Synonyms: Antibiotic S 7481F1; Cyclosporine, Trichoderma polysporum; ciclosporin;Cyclosporine A; Cyclosporine;Cyclosporin A;
  • CAS Registry Number:
  • Melting Point: 148-151ºC
  • Flash Point: 736.3ºC
  • Boiling Point: 1293.8ºC at 760 mmHg
  • Density: 1.016 g/cm3
  • Water Solubility: ethanol: 30 mg/mL
  • Safety Statements: R45;R60;R22
  • Hazard Symbols: T: Toxic;
  • Flash Point: 736.3ºC
  • Molecular Weight: 1202.62
  • InChI: InChI=1/C62H111N11O12/c1-25-27-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-49(74)68(19)44(28-34(3)4)55(78)66-50(39(13)14)62(85)69(20)45(29-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(30-36(7)8)59(82)71(22)47(31-37(9)10)60(83)72(23)48(32-38(11)12)61(84)73(51)24/h25,27,34-48,50-52,75H,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+,48+,50+,51+,52-/m1/s1
  • Risk Statements: S53;S45
  • Molecular Formula: C62H111N11O12
  • Molecular Structure:CAS No:59865-13-3 Cyclosporin A

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  • Cyclosporin A 59865-13-3 Name: Cyclosporin A 59865-13-3 Appearance:white powder Cas No:59865-13-3 EINECS:NA Formula:C62H111N11O12 Molecular Weight:1202.84 Melting Point:1293.8 °C Boiling Point: 595 °C Flash Point: 736.3 °C Usage:immunosuppressant Tes...
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References of Cyclosporin A
Title: Cyclosporins
Literature References: Group of nonpolar cyclic oligopeptides with immunosuppressant activity; produced by Tolypocladium inflatum Gams (formerly designated as Trichoderma polysporum [Link ex Pers.] Rifai) and other fungi imperfecti. Cyclosporins A through Z have been identified with A being the major component. Characterized by a C9-amino acid, MeBmt, q.v., cyclosporins bind to the cytosolic protein, cyclophilin, to form an active complex which inhibits the enzyme, calcineurin, a key component of T-cell activation. Isoln of A and C, structure of A: A. Rüegger et al., Helv. Chim. Acta 59, 1075 (1976); structure of C: R. Traber et al., ibid. 60, 1247 (1977). Production of A and C: E. H?rri et al., US 4117118 (1978 to Sandoz). Review of isoln, structure elucidation, synthesis and bioactivity: A. von Wartburg, R. Traber, Prog. Med. Chem. 25, 1-33 (1988); of biosynthesis and mode of action: A. Lawen, ibid. 33, 53-97 (1996). Review of role of calcineurin on bioactivity of cyclosporins: K. A. Jorgensen et al., Scand. J. Immunol. 57, 93-98 (2003). HPLC separation of components from fungal fermentation samples: J. Tuominen et al., Rapid Commun. Mass Spectrom. 12, 1085 (1998). HPLC-MS determn in blood: B. Vollenbroeker et al., Transplant. Proc. 37, 1741 (2005).
 
Derivative Type: Cyclosporin A
CAS Registry Number: 59865-13-3
Synonyms: Cyclosporine; ciclosporin
Manufacturers' Codes: 27-400
Trademarks: Atopica (Novartis); Sandimmun(e) (Novartis); Neoral (Novartis); Optimmune (Schering-Plough); Restasis (Allergan)
Molecular Formula: C62H111N11O12
Molecular Weight: 1202.61
Percent Composition: C 61.92%, H 9.30%, N 12.81%, O 15.96%
Literature References: Comprehensive description: M. M. Hassan, M. A. Al-Yahya, Anal. Profiles Drug Subs. 16, 145-206 (1987). Toxicological evaluation: B. Ryffel et al., Arch. Toxicol. 53, 107 (1983). Symposium on therapeutic use in dermatology: J. Am. Acad. Dermatol. 23, part 2, 1241-1334 (1990). Review of use in canine skin diseases: E. Guaguere et al., Vet. Dermatol. 15, 61-74 (2004). Review of clinical experience in organ transplantation: C. J. Dunn et al., Drugs 61, 1957-2016 (2001); in treatment of dry eye: H. D. Perry, E. D. Donnenfeld, Expert Opin. Pharmacother. 5, 2099-2107 (2004).
Properties: White prismatic needles from acetone at -15°. mp 148-151°. [a]D20 -244° (c = 0.6 in chloroform); [a]D20 -189° (c = 0.5 in methanol). Sol in methanol, ethanol, acetone, ether, chloroform; slightly sol in water and saturated hydrocarbons. LD50 in mice, rats, rabbits (mg/kg): 107, 25, >10 i.v.; 2329, 1480, >1000 orally (Ryffel).
Melting point: mp 148-151°
Optical Rotation: [a]D20 -244° (c = 0.6 in chloroform); [a]D20 -189° (c = 0.5 in methanol)
Toxicity data: LD50 in mice, rats, rabbits (mg/kg): 107, 25, >10 i.v.; 2329, 1480, >1000 orally (Ryffel)
 
Derivative Type: Cyclosporin B
CAS Registry Number: 63775-95-1
Synonyms: Ala2-cyclosporine
Molecular Formula: C61H109N11O12
Molecular Weight: 1188.58
Percent Composition: C 61.64%, H 9.24%, N 12.96%, O 16.15%
Properties: Amorphous white powder, mp 149-152°. [a]D20 -238° (c = 0.62 in chloroform). [a]D20 -168° (c = 0.56 in methanol).
Melting point: mp 149-152°
Optical Rotation: [a]D20 -238° (c = 0.62 in chloroform); [a]D20 -168° (c = 0.56 in methanol)
 
Derivative Type: Cyclosporin C
CAS Registry Number: 59787-61-0
Synonyms: Thr2-cyclosporine
Molecular Formula: C62H111N11O13
Molecular Weight: 1218.61
Percent Composition: C 61.11%, H 9.18%, N 12.64%, O 17.07%
Properties: Colorless prismatic needles from acetone at -15°. mp 152-155°. [a]D20 -255° (c = 0.5 in chloroform). [a]D20 -182° (c = 0.5 in methanol). Solubility similar to cyclosporin A.
Melting point: mp 152-155°
Optical Rotation: [a]D20 -255° (c = 0.5 in chloroform); [a]D20 -182° (c = 0.5 in methanol)
 
Derivative Type: Cyclosporin D
CAS Registry Number: 63775-96-2
Synonyms: Val2-cyclosporine
Molecular Formula: C63H113N11O12
Molecular Weight: 1216.64
Percent Composition: C 62.19%, H 9.36%, N 12.66%, O 15.78%
Properties: Colorless prisms from acetone at -15°. mp 148-151°. [a]D20 -245° (c = 0.52 in CHCl3). [a]D20 -211° (c = 0.51 in methanol).
Melting point: mp 148-151°
Optical Rotation: [a]D20 -245° (c = 0.52 in CHCl3); [a]D20 -211° (c = 0.51 in methanol)
 
Derivative Type: Cyclosporin G
CAS Registry Number: 74436-00-3
CAS Name: 7-L-Norvaline cyclosporin A
Synonyms: Nva2-cyclosporine
Molecular Formula: C63H113N11O12
Molecular Weight: 1216.64
Percent Composition: C 62.19%, H 9.36%, N 12.66%, O 15.78%
Literature References: Immunosuppressive profile: P. C. Hiestand et al., Transplant. Proc. 17, 1362 (1985); eidem, Immunology 55, 249 (1985).
Properties: Colorless, polyhedric crystals from ether + petroleum ether, mp 196-197°. [a]D20 -245° (c = 1.0 in chloroform). [a]D20 -191° (c = 1.04 in methanol).
Melting point: mp 196-197°
Optical Rotation: [a]D20 -245° (c = 1.0 in chloroform); [a]D20 -191° (c = 1.04 in methanol)
 
CAUTION: Cyclosporin A is listed as a known human carcinogen: Report on Carcinogens, Eleventh Edition (PB2005-104914, 2004) p III-75.
Therap-Cat: Cyclosporin A as immunosuppressant.
Therap-Cat-Vet: In the control of canine atopic dermatitis and immune-mediated dermatological diseases.
Keywords: Immunosuppressant.