Structure via PubChem · Public domain (PubChem)
cyclosporine
Sign in to saveAlso known as OLO400, ciclosporin, cyclosporine A, 1,11-cyclo[L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-(E)-(2S,3R,4R)-2-amino-3-hydroxy-N,4-dimethyloct-6-enoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucine], 30-ethyl-33-[(4E)-1-hydroxy-2-methylhex-4-en-1-yl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone, Antibiotic S 7481F1, CsA, CyA
Ciclosporin, also spelled cyclosporine and cyclosporin, is a calcineurin inhibitor, used as an immunosuppressant medication. It is taken orally or intravenously for rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, eczema, and in organ transplants to prevent rejection. It is also used as eye drops for keratoconjunctivitis sicca (dry eyes).
OverviewAI-generated
Cyclosporine is a chemical compound with the formula C₆₂H₁₁₁N₁₁O₁₂. It has a mass of 1201.841 and a weight of 1202.6. The compound is also referred to by the stylized names cycloSPORINE and SandIMMUNE.
Chemical properties of cyclosporine include an xlogp of 7.5 and a tpsa of 279. It features five hydrogen bond donors and twelve hydrogen bond acceptors, with a charge of 0. The substance is associated with a Commons category titled "Ciclosporin."
Cyclosporine is referenced by 643 other encyclopedia articles. A PubMed query for the term yields a count of 64923.
Synthesized by Vinony from 15 facts across 4 sources: Wikidata, PubMed, PubChem, Vinony graph. Generated from structured data (not the Wikipedia text) and checked against those facts — may still contain errors.
Key facts
- Drug.IUPAC_name
- (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-Ethyl-33-[(1R,2R,4E)-1-hydroxy-2-methyl-4-hexen-1-yl]-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
- Drug.C
- 62
- Drug.H
- 111
- Drug.N
- 11
- Drug.O
- 12
- Drug.SMILES
- CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](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
- Drug.StdInChI
- 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
- Drug.StdInChIKey
- PMATZTZNYRCHOR-CGLBZJNRSA-N
- Drug.IUPHAR_ligand
- 1024
- Drug.DrugBank
- DB00091
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 459588806
- Drug.image
- Ciclosporin.svg
- Drug.image_class
- skin-invert-image
- Drug.width
- 250
- Drug.image2
- Ciclosporin-A-from-xtal-3D-bs-17.png
- Drug.image_class2
- bg-transparent
via Wikipedia infobox
Chemical data
- Formula
- C62H111N11O12
- Molecular weight
- 1202.6 g/mol
- IUPAC name
- (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methylhex-4-enyl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
- SMILES
- CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](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
- InChIKey
- PMATZTZNYRCHOR-CGLBZJNRSA-N
- XLogP
- 7.5
- Polar surface area
- 279 Ų
- H-bond donors
- 5
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Protein
- First approval
- 1983
- Admin. routes
- oral, parenteral, topical
- Indications
- atopic eczema, hepatitis C virus infection, lymphoma, Aplastic anemia
via ChEMBL · EBI
Research
64,923 papersvia PubMed
Wikidata facts
- Mass
- 1201.841
- Has use
- medication
Show 11 more facts
- chemical formula
- C₆₂H₁₁₁N₁₁O₁₂
- medical condition treated
- nephrotic syndrome
- found in taxon
- Tolypocladium inflatum
- World Health Organisation international non-proprietary name
- ciclosporin
- isomeric SMILES
- CC[C@H]1C(=O)N(CC(=O)N([C@H](C(=O)N[C@H](C(=O)N([C@H](C(=O)N[C@H](C(=O)N[C@@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N([C@H](C(=O)N1)[C@@H]([C@H](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
- canonical 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)CC=CC)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
- Commons category
- Ciclosporin
- subject has role
- essential medicine
- stylized name
- SandIMMUNE
- legal status (medicine)
- boxed warning
- significant drug interaction
- tobramycin
Sources (6)
via Wikidata · CC0
~17 min read
Encyclopedic overview
18 sectionsContents
- Medical uses
- Side effects
- Pharmacology
- Mechanism of action
- Pharmacokinetics
- Biosynthesis
- Gene cluster
- History
- Society and culture
- Legal status
- Names
- Available forms
- Research
- Neuroprotection
- Cardiac disease
- Veterinary use
- References
- External links
Ciclosporin, also spelled cyclosporine and cyclosporin, is a calcineurin inhibitor, used as an immunosuppressant medication. It is taken orally or intravenously for rheumatoid arthritis, psoriasis, Crohn's disease, nephrotic syndrome, eczema, and in organ transplants to prevent rejection. It is also used as eye drops for keratoconjunctivitis sicca (dry eyes).
Common side effects include high blood pressure, headache, kidney problems, increased hair growth, and vomiting. Other severe side effects include an increased risk of infection, liver problems, and an increased risk of lymphoma. Blood levels of the medication should be checked to decrease the risk of side effects. Use during pregnancy may result in preterm birth; however, ciclosporin does not appear to cause birth defects.
Excerpted from Wikipedia’s “cyclosporine” article, available under the CC BY-SA 4.0 licence.