(3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone

• ChemBase ID: 126592
• Molecular Formular: C62H111N11O12
• Molecular Mass: 1202.61124
• Monoisotopic Mass: 1201.84136805
• 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: C/C=C/C[C@H]([C@H]([C@H]1C(=O)N[C@H](CC)C(=O)N(C)CC(=O)N(C)[C@@H](CC(C)C)C(=O)N[C@H](C(C)C)C(=O)N(C)[C@@H](CC(C)C)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)N1C)C(C)C)C)CC(C)C)C)CC(C)C)C)C)C)O)C
• InChI: 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)/t40-,41+,42-,43+,44+,45+,46+,47+,49+,50+,51+,52-/m1/s1
• InChIKey: PMATZTZNYRCHOR-HHPJSCBPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R)-1-hydroxy-2-methylhex-4-en-1-yl]-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-3,21-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
• IUPAC Traditional name: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R)-1-hydroxy-2-methylhex-4-en-1-yl]-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-6,9,18,24-tetrakis(2-methylpropyl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecone
• Brand Name: Neoral, Sandimmune
• Synonyms: Antibiotic S 7481F1; Cyclosporine; Cyclosporin A; Ciclosporin; 抗生素 S 7481F1; 环孢霉素; 环孢菌素 A

Database IDs

• CAS Number: 59865-13-3
• MDL Number: MFCD00274558
• Beilstein Number: 3647785
• PubChem SID: 162220922; 24858080
• PubChem CID: 5284373
• ATC CODE: S01XA18; L04AD01
• CHEMBL: 160
• Chemspider ID: 4447449
• DrugBank ID: DB00091
• KEGG ID: D00184
• Unique Ingredient Identifier: 83HN0GTJ6D
• Wikipedia Title: Ciclosporin
• Medline Plus: a601207

CALCULATED PROPERTIES

• Acid pKa: 11.825702
• H Acceptors: 12
• H Donor: 5
• LogD (pH = 5.5): 3.6381571
• LogD (pH = 7.4): 3.6381428
• Log P: 3.6381574
• Molar Refractivity: 327.1417 cm^3
• Polarizability: 127.97144 Å^3
• Polar Surface Area: 278.8 Å^2
• Rotatable Bonds: 15
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• RTECS: GZ4120000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 45-60-22
• Safety Statements: 53-45
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H302-H350-H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Admin Routes: Oral, IV, ophthalmic
• Bioavailability: Variable
• Excretion: Biliary
• Half Life: Variable (about 24 hours)
• Metabolism: Hepatic
• Legal Status: POM (UK); Rx-only (US); S4 (Australia)
• Pregnancy Category: C (Australia); C (US)

Product Information

• Purity: ≥98.5% (TLC)
• Grade: VETRANAL™, analytical standard
• Pharmacopeia Traceability: traceable to PhEur C2163000; traceable to USP 1158504
• Empirical Formula (Hill Notation): C62H111N11O12

DETAILS

Sigma Aldrich - 30024

Application
Cyclosporin A is used for immunosuppressive studies 1,2.
Biochem/physiol Actions
A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A-cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.

Sigma Aldrich - 80688

Biochem/physiol Actions
A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A-cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.

Sigma Aldrich - 32425

Biochem/physiol Actions
A fungal metabolite possessing potent immunosuppressive properties. It inhibits the T-cell receptor signal transduction pathway via the formation of cyclosporin A-cyclophilin complex that inhibits calcineurin (protein phosphatase 2B). Inhibits nitric oxide synthesis induced by interleukin 1α, lipopolysaccharides and TNFα. Can block cytochrome c release from mitochondria.
Legal Information
VETRANAL is a trademark of Sigma-Aldrich Co. LLC