UNIL-088

Name: UNIL-088
CAS#: 473545-11-8
Chemical Formula: C73H128N13O22P
Exact Mass: 1569.9034
Molecular Weight: 1570.8698
Elemental Analysis: C, 55.82; H, 8.21; N, 11.59; O, 22.41; P, 1.97

Description: UNIL088 is a water-soluble prodrug of cyclosporine A (CsA) designed for topical ocular delivery. The pro-moiety is grafted via an ester function to CsA and the solubilizing group is a phosphate ion. UNIL-088 can be rapidly hydrolysed under physiological conditions, and can retain a long shelf-life in aqueous media. UNIL-088 is more stable at pH 5 than at pH 7 with conversion rate constant of 3.2 x 10(-3) and 26.0 x 10(-3)days(-1), respectively.

IUPAC/Chemical Name: (1R,2R,E)-1-((2S,5S,11S,14S,17S,20S,23R,26S,29S,32S)-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-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2-yl)-2-methylhex-4-en-1-yl N-(N-((1-acetoxyethoxy)carbonyl)-O-phosphono-L-seryl)-N-methylglycinate

InChi Key: INYOUNWJPIAZGW-VITLZLMDSA-N

InChi Code: InChI=1S/C73H128N13O22P/c1-28-30-31-45(15)61(108-57(89)37-80(21)68(96)51(38-105-109(102,103)104)77-73(101)107-49(19)106-48(18)87)60-65(93)76-50(29-2)67(95)79(20)36-56(88)81(22)52(32-39(3)4)64(92)78-58(43(11)12)71(99)82(23)53(33-40(5)6)63(91)74-46(16)62(90)75-47(17)66(94)83(24)54(34-41(7)8)69(97)84(25)55(35-42(9)10)70(98)85(26)59(44(13)14)72(100)86(60)27/h28,30,39-47,49-55,58-61H,29,31-38H2,1-27H3,(H,74,91)(H,75,90)(H,76,93)(H,77,101)(H,78,92)(H2,102,103,104)/b30-28+/t45-,46+,47-,49?,50+,51+,52+,53+,54+,55+,58+,59+,60+,61-/m1/s1

SMILES Code: O=C(O[C@H]([C@@H](C/C=C/C)C)[C@@H](C(N1)=O)N(C)C([C@H](C(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@H](CC(C)C)N(C)C([C@@H](C)NC([C@H](C)NC([C@H](CC(C)C)N(C)C([C@H](C(C)C)NC([C@H](CC(C)C)N(C)C(CN(C)C([C@@H]1CC)=O)=O)=O)=O)=O)=O)=O)=O)=O)=O)CN(C([C@H](COP(O)(O)=O)NC(OC(OC(C)=O)C)=O)=O)C

Appearance: Solid powder