Cyclosporin |
Last updated: 19/07/2024 |
(Also known as: cyclosporin A; CsA; cyclosporine; antibiotic S 7481F1 ; ciclosporin; ciclosporin A) |
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A steroid-sparing immunosuppressant veterinary medication | |
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Current | |
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1971, discovered | |
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Used mainly to treat autoimmune and inflammatory conditions including skin issues such as psoriasis, dermatitis, ulcerative colitis and rheumatoid arthritis. It is also used to used to treat dry eye conditions and pannus in dogs. | |
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Dogs; Cats; Horses |
Approval status |
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Approved | |
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Approved |
Chemical structure |
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Isomeric | |
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C₆₂H₁₁₁N₁₁O₁₂ | |
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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 | |
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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 | |
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PMATZTZNYRCHOR-CGLBZJNRSA-N | |
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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 | |
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Yes |
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Common Name | Relationship | Link |
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cyclosporin A | - |
General status |
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Medicinal drug; Fungicide | |
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Diderophore | |
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98% | |
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- | |
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Synthetic | |
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Prevents the dephosphorlyation of NF-AT by binding to cyclophilin. Calcineurin inhibitor | |
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[Calcium signal-modulating cyclophilin ligand, Binder], [Calcineurin subunit B type 2, Inhibitor], [Peptidyl-prolyl cis-trans isomerase A, inhibitor], [Peptidyl-prolyl cis-trans isomerase F, mitochondrial, Binder] | |
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59865-13-3 | |
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611-907-1 | |
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5284373 | |
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Antineoplastic & immunomodulating agents: Immunosuppressants; Sensory Organs: Ophthalmologicals | |
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QL04AD01; QS01XA18 | |
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No | |
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- | |
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1202.61 | |
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30-ethyl-33-[(E)-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 | |
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30-ethyl-33-[(E)-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 | |
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(E)-14,17,26,32-tetrabutyl-5-ethyl-8-(1-hydroxy-2-methylhex-4-enyl) -1,3,9,12,15,18,20,23,27-nonamethyl-11,29-dipropyl-1,3,6,9,12,15,18,21,24,27,30- undecaazacyclodotriacontan-2,4,7,10,13,16,19,22,25,28,31-undecaone | |
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White powdery solid |
Formulations |
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Atopica 10 mg soft capsules for dogs | Elanco GmbH | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | ||||||
Atopica 100 mg soft capsules for dogs | Novartis Animal Health | Not licensed | Not licensed | |||||||
Optimmune Ophthalmic Ointment 2mg/g Eye ointment | Schering-Plough Ltd | Not licensed | Not licensed | |||||||
Cyclavance 100 mg/ml Oral Solution for Dogs and Cats | Virbac | GB National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
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Often formulated as capsules or liquid for oral administration |
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28.6 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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200000 | Q3 Q = Miscellaneous data from online sources Ethanol3 = Unverified data of known source |
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100000 | Q3 Q = Miscellaneous data from online sources DMSO3 = Unverified data of known source |
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150 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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8.32 X 1002 | Calculated | - | |||||||
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2.92 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Degradation |
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60 | R4 R = Peer reviewed scientific publications Composed soil4 = Verified data |
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As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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- | Metabolite AM1; cyclosprorin M17 | Human (Liver) | - | ||||
- | Metabolite AM4N | Human (Liver) | - | ||||
- | Metabolite AM9 | Human (Liver) | - |
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Terrestrial ecotoxicology |
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> 1480 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Aquatic ecotoxicology |
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General |
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High (class III) | - | - | ||||||||
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> 1480 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
Moderate | ||||||||
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Intraperitoneal LD₅₀ = 147 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Subcutaneous LD₅₀ = 286 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Extensively metabolised in the liver and excreted in human bile, faeces, blood, & urine. Excreted into human breast milk | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Health issues |
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Possible liver and kidney toxicant May cause gingival hyperplasia, convulsions, peptic ulcers, pancreatitis, fever Ingestion can cause vomiting, diarrhoea, confusion & hypercholesterolemia CLP data - known carcinogen May elevate blood pressure |
Handling issues |
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Incompatible with strong oxidising agents | |||
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Health: H302, H350, H360fd | |||
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Not listed (Not listed) | |||
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Not registered | |||
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Store \at around 25 DegC. Do not refridgerate. Generally chemically stable |
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cyclosporin | ||
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ciclosporine | ||
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ciclosporina | ||
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Record last updated: | 19/07/2024 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |