Stereochemistry | ABSOLUTE |
Molecular Formula | C62H111N11O12 |
Molecular Weight | 1202.6112 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 12 / 12 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]1([C@H](O)[C@H](C)C\C=C\C)N(C)C(=O)[C@H](C(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](C)NC(=O)[C@H](C)NC(=O)[C@H](CC(C)C)N(C)C(=O)[C@@H](NC(=O)[C@H](CC(C)C)N(C)C(=O)CN(C)C(=O)[C@H](CC)NC1=O)C(C)C
InChI
InChIKey=PMATZTZNYRCHOR-CGLBZJNRSA-N
InChI=1S/C62H111N11O12/c1-25-27-28-40(15)52(75)51-56(79)65-43(26-2)58(81)67(18)33-48(74)68(19)44(29-34(3)4)55(78)66-49(38(11)12)61(84)69(20)45(30-35(5)6)54(77)63-41(16)53(76)64-42(17)57(80)70(21)46(31-36(7)8)59(82)71(22)47(32-37(9)10)60(83)72(23)50(39(13)14)62(85)73(51)24/h25,27,34-47,49-52,75H,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+,49+,50+,51+,52-/m1/s1
Cyclosporins are cyclic polypeptide macrolides that were originally derived from the soil fungus Tolypocladium inflatum. Cyclosporine (also known as cyclosporine A) was discovered by Sandoz and developed for the tretment of immune disorders. The drug was approved by FDA for such diseases as Rheumatoid Arthritis, Psoriasis (Neoral), Keratoconjunctivitis sicca (Restasis) and prevention of transplant rejections (Neoral and Sandimmune). Cyclosporine’s primary immunosuppressive mechanism of action is inhibition of T-lymphocyte function. Upon administration cyclosporine binds to cyclophilin A and thus inhibits calcineurin, leading to immune system suppression.
CNS Activity
Originator
Approval Year
Doses
AEs
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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Drug as perpetrator
Drug as victim
Tox targets
Sourcing
PubMed
Patents
Sample Use Guides
Organs transplantation: the initial oral dose of cyclosporine (Sandimmune) should be given 4 to 12 hours prior to transplantation as a single dose of 15 mg/kg. Rheumatoid Arthritis, Psoriasis: the initial dose of cyclosporine (Neoral) is 2.5 mg/kg/day, taken twice daily as a divided (BID) oral dose. Keratoconjunctivitis sicca: instill one drom twice a day in each eye, approximately 12 hours apart.
Route of Administration:
Other
Human CD4+CD25+ cells isolated from healthy donors were cultured in the presence of 40 or 400 ng/mL of cyclosporine. The suppressive activity of Treg was assessed in mixed leukocyte reactions (MLR) using CD25+ and autologous activated peripheral blood mononuclear cells (PBMC). The drug inhibited the proliferative capacity of PBMC and CD4+CD25+ Treg in a dose-dependent manner.
ACTIVE MOIETY