Cyclosporine

Therapeutic

Cyclosporine is approved for a variety of conditions. Firstly, it is approved for the prophylaxis of organ rejection in allogeneic kidney, liver, and heart transplants. It is also used to prevent bone marrow transplant rejection. Secondly, cyclosporine is used for the treatment of patients with severe active rheumatoid arthritis (RA) when they no longer respond to methotrexate alone. Off-label, cyclosporine is commonly used for the treatment of various autoimmune and inflammatory conditions such as atopic dermatitis, blistering disorders, ulcerative colitis, juvenile rheumatoid arthritis, uveitis, connective tissue diseases, as well as idiopathic thrombocytopenic purpura

Structural features

SMILES

CCC1C(=O)N(CC(=O)N(C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N(C(C(=O)N1)C(C(C)C/C=C/C)O)C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)CC(C)C)C)C(C)C)CC(C)C)C)C

Sequence

XXXXVXAaXXX

Molar mass

1202.635 g/mol

Constitutional members:

11

Natural amino acids

2

D-Amino acids

1

N-terminus

cycle

C-terminus

cycle

Cyclic

yes

Members/cycle

11

Bond to form cycle

head-to-tail

Lipidation

no

Glycosylation

no

Route of administration

TOPICAL, OPHTALMIC, IV, ORAL

Terminal half-life

19 hours

Protein binding

About 50% of the administered dose is taken up by erythrocytes while about 34% is bound to lipoproteins. Prescribing information for Sandimmune states that 90% is mainly bound to lipoproteins.

Absorption and Bioavailability

0.3

References