Rapamycin
Title: Rapamycin
CAS Registry Number: 53123-88-9
Additional Names: Sirolimus; RAPA; RPM
Manufacturers' Codes: AY-22989; NSC-226080
Trademarks: Rapamune (Wyeth)
Molecular Formula: C51H79NO13
Molecular Weight: 914.17
Percent Composition: C 67.01%, H 8.71%, N 1.53%, O 22.75%
Literature References: Triene macrolide antibiotic isolated from Streptomyces hygroscopicus. Name derived from the native word for Easter Island, Rapa Nui. Isoln: S. N. Sehgal et al., DE 2347682; eidem, US 3929992 (1974, 1975 both to Ayerst McKenna Harrison); purification and characterization: C. Vézina et al., J. Antibiot. 28, 721 (1975); S. N. Sehgal et al., ibid. 727. Inhibition of immune response: R. R. Martel et al., Can. J. Physiol. Pharmacol. 55, 48 (1977); of graft rejection in mice: C. P. Eng et al., Transplant. Proc. 23, 868 (1991). Total synthesis: K. C. Nicolaou et al., J. Am. Chem. Soc. 115, 4419 (1993); D. Romo et al., ibid. 7906. Series of articles on therapeutic monitoring and pharmacokinetics: Clin. Ther. 22, Suppl. 2, B1-B132 (2000); on pharmacology and clinical experience in transplantation: Transplant. Proc. 35, Suppl. 1, S1-S233 (2003). Clinical trial in prevention of coronary restenosis: D. R. Holmes, Jr. et al., Circulation 109, 634 (2004).
Properties: Colorless crystalline solid from ether, mp 183-185°. uv max (95% ethanol): 267, 277, 288 nm (E1%1cm 417, 541, 416). [a]D25 -58.2° (methanol). Sol in ether, chloroform, acetone, methanol and DMF; very sparingly sol in hexane and petr ether. Substantially insol in water. LD50 in mice (mg/kg): »600 i.p.; >2,500 orally (Vézina).
Melting point: mp 183-185°
Optical Rotation: [a]D25 -58.2° (methanol)
Absorption maximum: uv max (95% ethanol): 267, 277, 288 nm (E1%1cm 417, 541, 416)
Toxicity data: LD50 in mice (mg/kg): »600 i.p.; >2,500 orally (Vézina)
Use: Tool for immunochemistry.
Therap-Cat: Immunosuppressant; antirestenotic.
Keywords: Immunosuppressant; Antirestenotic.

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