BIRD-PRD_000142: Cyclosporin A

Basic information

• Entry: Database: Biologically Interesting Molecule Reference Dictionary (BIRD) / ID: PRD_000142
• Status: Status: REF ONLY
• Name: Cyclosporin A

BIRD information

• Type: Cyclic peptide / Immunosuppressant

Details

• CYCLOSPORIN IS A CYCLIC UNDECAPEPTIDE. HERE, CYCLOSPORIN A IS REPRESENTED BY THE SEQUENCE (SEQRES)
• CYCLOSPORIN IS A CYCLIC UNDECAPEPTIDE. CYCLIZATION IS ACHIEVED BY LINKING THE N- AND THE C- TERMINI.

• Downloads: Molecular definition / Chemical definition / Family definition

Synonyms

• (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 (ChemSpider)
• Abrammune (SciFinder)
• Antibiotic S 7481F1 (SciFinder, ChemSpider)
• Apo-Cyclosporine (ChemBank)
• Arpimune ME (SciFinder)
• Atopica (Merck, ChemBank)
• CYCLOSPORIN (PDB)
• Cicloral (SciFinder)
• Cicloral (antibiotic) (SciFinder)
• Ciclosporin (SciFinder, KEGG, DrugBank, PubChem, ChemBank)
• Ciclosporina Germed (SciFinder)
• Cipol N (SciFinder, ChemSpider, ChemBank)
• Consupren (SciFinder, PubChem, ChemSpider, ChemBank)
• Consupren S (ChemSpider)
• Cyclokat (PubChem)
• Cyclosporin (DrugBank, PubChem)
• Cyclosporin A (KEGG, DrugBank, ChemBank)
• Cyclosporine (SciFinder, KEGG, ChemSpider, ChemBank)
• Cyclosporine A (SciFinder, PubChem, ChemBank)
• Debio088 (SciFinder)
• Equoral (SciFinder, ChemSpider)
• Gengraf (SciFinder, KEGG, DrugBank, ChemSpider, ChemBank)
• Imusporin (SciFinder)
• Modusik-A (ChemSpider)
• NSC 290193 (SciFinder)
• Neoplanta (SciFinder, ChemSpider, ChemBank)
• Neoral (SciFinder, Merck, KEGG, DrugBank, ChemSpider, ChemBank)
• OL 27-400 (SciFinder)
• Optimmune (Merck, ChemSpider, ChemBank)
• Papilock (ChemSpider)
• Papilock Mini (SciFinder)
• Pulminiq (ChemSpider, ChemBank)
• Ramihyphin A (SciFinder, PubChem, ChemSpider, ChemBank)
• Restasis (SciFinder, Merck, KEGG, DrugBank, ChemBank)
• Rhoxal-cyclosporine (ChemBank)
• S 7481F1 (ChemSpider)
• S-Neoral (SciFinder, ChemSpider)
• SDZ-OXL 400 (SciFinder)
• Sandimmun (SciFinder, ChemBank)
• Sandimmun Neoral (SciFinder, ChemBank)
• Sandimmune (SciFinder, Merck, KEGG, DrugBank, PubChem, ChemSpider, ChemBank)
• Sandimmune I.V. (ChemBank)
• Sandimmune Neoral (SciFinder)
• Sandoz-cyclosporine (ChemBank)
• Sang 35 (ChemBank)
• Sang-35 (SciFinder)
• SangCyA (SciFinder)
• SangCya (ChemBank)
• Sangcya (DrugBank)
• Sigmasporin (PubChem)
• Sigmasporin Microoral (SciFinder)
• Zinograf ME (SciFinder)
• ciclosporin (Merck, Norine)
• ciclosporine (Norine)
• cyclosporin A (PubChem)
• cyclosporine (Merck, Norine, PubChem)

Annotation

• Function: immunosuppressant / Info source: KEGG
• Function: immunosuppressant / Info source: DrugBank
• Function: binds to cyclophilin and forms a complex to inhibit calcineurin, which is normally responsible for activating transcription of interleukin 2 / Info source: DrugBank
• Function: inhibitor of T-lymphocytes in the G0 or G1 phase of cell cycle / Info source: DrugBank
• Function: inhibitor of lymphokine production and Interleukin release / Info source: DrugBank
• Function: used in organ and tissue transplants for prophylactic treatment / Info source: DrugBank
• Function: Immunomodulating, antibiotic / Info source: Norine
• Function: used to prevent rejections in organ and bone marrow transplants / Info source: Norine
• Mechanism of action: Binds to cyclophilin and suppresses its proline rotamase activity. The CsA-cyclophilin complex inhibits calcineurin, a type 2B phosphatase - it inhibits mitochondrial permeability transition pore opening however, pore inhibition becomes less efficient at increasing Ca2+ loads and inhibition is transient. / Info source: www.enzolifesciences.com
• Application: Important diagnostic tool for the characterization of permeability transition-related phenomena. / Info source: www.enzolifesciences.com
• Mechanism of action: Weak immunosuppressor. Potent inhibitor of tumor promoting phorbol ester TPA/PMA (Prod. No. BML-PE160) in vivo. Potent inhibitor of Ca2+/calmodulin dependent EF-2 phosphorylation in vitro. / Info source: www.enzolifesciences.com
• Function: immunosuppressive agent / Info source: ChemBank
• Function: anti-fungal / Info source: ChemBank
• Function: immunosuppressive drug, binds cyclosporin A (PEPTIDYL-PROLYL CIS-TRANS ISOMERASE A), EC: 5.2.1.8EC: immunosuppressive drug, binds cyclosporin A (PEPTIDYL-PROLYL CIS-TRANS ISOMERASE A), EC: 5.2.1.8 / Info source: PubMed: 8075981

Source

• Cylindrocarpon lucidum (fungus), KEGG: C05086
• Tolypocladium inflatum (fungus), KEGG: C05086
• Tolypocladium inflatum (fungus), NORINE: NOR00033

External info

• ATC: L04AD01
• Beilstein: 3586354
• Beilstein: 3647785
• ChemBank: 460
• ChemDB: 9491791
• DrugBank: DB00091
• Merck: 14:2752
• ChemSpider: 4447449
• Norine: NOR00033
• ChEBI: 4031
• PubChem: 5284373
• PubChem: 6436251
• CAS: 114865-22-4
• CAS: 59865-13-3
• [BRITE_Hierarchy] KEGG: br08301
• [BRITE_Hierarchy] KEGG: br08302
• [BRITE_Hierarchy] KEGG: br08303
• [FunctionalOntology] ChEBI: 24613
• [KEGG_Compound_ID] KEGG: C05086
• [KEGG_Drug_ID] KEGG: D00184
• [MESH_Unique_ID] MESH: D016572
• [StructuralOntology] ChEBI: 35705
• [StructuralOntology] ChEBI: 35718
• [StructuralOntology] ChEBI: 35842
• [StructuralOntology] ChEBI: 50177
• [Therapeutic_Category] KEGG: 1319
• [Therapeutic_Category] KEGG: 3999
• world-of-fungi.org: Harriet_Upton.htm
• NADB: 490276
• NADB: 420231
• NADB: 420107
• NADB: 450030
• wikipedia: Cyclosporine
• RXLIST: sandimmune-drug.htm
• Drugs.Com: Cyclosporine
• wikipedia

Family

Cyclosporin

Cyclosporin A / Cyclosporin D / Cyclosporin C / CYCLOSPORIN D, 5,7 mutation / CYCLOSPORIN A, 5 mutation / CYCLOSPORIN A, 6 mutation / CYCLOSPORIN A, 7 mutation / CYCLOSPORIN A, 8 mutation / Cyclosporin A variant, MLE 8 to MNL / Cyclosporin D variant, MSA 7 to MAA / Cyclosporin C variant (DAL 1 to VAD, MLE 3 to LEU, VAL 9 to LEU) / Mutant CYCLOSPORIN D

Related structures

• Iodo-cyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: ICYSPA / Reference
• Cyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: DEKSAN / Reference
• Cyclosporin A monohydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: KEPNAU / Reference
• (-4-PSI-5-,CS-NH,-7-PSI-8-,CS-NH)-Cyclosporin A diethyl ether solvate, seqres C11 ALA*-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: JOKMAX / Reference
• methyl((4S)-METHYL)NORLEU-4 Cyclosporin cyclophilin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LIKNIC / Reference
• cyclo-(alanyl-d-alanyl-n-methylleucyl-n-methylleucyl-N-methylvalyl-alpha-(1-oxo-2-methylhex-4-enyl)sarcosyl-valyl-sarcosyl-N-methylleucyl-valyl-N-methylleucyl), seqres C11 ALA-ALA-LEU*-LEU*-VAL*-SAR*-VAL*-SAR-LEU*-VAL-LEU*- / CCDC: ZADRIF / Reference
• sulfhydryl cyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: ZAJDUJ / Reference
• isocyclosporin A acetone solvate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*,GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: NAMPIA / Reference
• cyclosporin A dimethylisosorbide solvate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: TECRIC / Reference
• cyclosporin E acetone solveate monohydrate clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: SUQNUN / Reference
• O-acetyl-(4R)-4-(E-2-butenyl)-4,N-dimethyl-L-threonylcyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: CUQRUB / Reference
• O-acetyl-(4R)-4-(4-bromobutyl)-4,N-dimethyl-L-threonylcyclosporin A, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: CUQSAI / Reference
• cyclosporin H diethyl ether solvate monohydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: DUDQAU / Reference
• cyclosporin V t-butyl methyl ether clathrate, seqres C11 GLY*-ALA-LEU*-LEU*-VAL*-THR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: HUCVIK / Reference
• dihydrocyclosporin A t-butyl methyl ether clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: HUCVOQ / Reference
• cyclosporin A tetrahydrofuran clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOWGOT / Reference
• cyclosporin A di-n-butyl ether clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOWHAG / Reference
• cyclosporin A di-n-butyl ether clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOWHAG01 / Reference
• cyclosporin G methanol solvate hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-NVA-SAR-LEU*-VAL-LEU*- / CCDC: GABWOW / Reference
• cyclosporin G methanol solvate hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-NVA-SAR-LEU*-VAL-LEU*- / CCDC: GABWUC / Reference
• cyclosporin H hexahydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: GABXAJ / Reference
• cyclosporin H hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: GABXEN / Reference
• cyclosporin A acetone monohydrate clathrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-SAR*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: KADFOL / Reference
• cyclo-(alanyl-D-alanyl-N-methylleucyl-N-methylleucyl-N-methylvalyl-alpha-(1-oxo-2-methylhex-4-enyl)sarcosyl-valyl-sarcosyl-N-methylleucyl-valyl-N-methylleucyl) di-isopropyl ether solvate hemihydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-SAR*-VAL*-SAR-LEU*-VAL-LEU*- / CCDC: ZADREB / Reference
• Cyclosporin A monohydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: KEPNAU01
• Cyclosporin A hydrate, seqres C11 ALA-ALA-LEU*-LEU*-VAL*-GLY*-GLY*-SAR-LEU*-VAL-LEU*- / CCDC: LOSLEL

Chemical information

Composition

Formula: C₆₂H₁₁₁N₁₁O₁₂ / Formula weight: 1202.611

• Others: Type: peptide-like

History

• External links: UniChem / ChemSpider / Wikipedia search / Google search

Details

SMILES

• ACDLabs 12.01: O=C1N(C)C(C(=O)NC(C(=O)N(C(C(=O)NC(C(=O)NC(C(=O)N(C)C(C(=O)N(C)C(C(=O)N(C)C(C(=O)N(C)C(C(=O)NC(C(=O)N(C)C1)CC)C(O)C(C)C\C=C/C)C(C)C)CC(C)C)CC(C)C)C)C)CC(C)C)C)C(C)C)CC(C)C
• CACTVS 3.370: CC[CH]1NC(=O)[CH]([CH](O)[CH](C)CC=CC)N(C)C(=O)[CH](C(C)C)N(C)C(=O)[CH](CC(C)C)N(C)C(=O)[CH](CC(C)C)N(C)C(=O)[CH](C)NC(=O)[CH](C)NC(=O)[CH](CC(C)C)N(C)C(=O)[CH](NC(=O)[CH](CC(C)C)N(C)C(=O)CN(C)C1=O)C(C)C
• OpenEye OEToolkits 1.7.6: 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

SMILES CANONICAL

• CACTVS 3.370: CC[C@@H]1NC(=O)[C@H]([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)C1=O)C(C)C
• OpenEye OEToolkits 1.7.6: 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

InChI

• InChI 1.03: 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)

InChIKey

• InChI 1.03: PMATZTZNYRCHOR-UHFFFAOYSA-N

SYSTEMATIC NAME

• ACDLabs 12.01: (3R,6S,9R,12R,15R,18R,21S,24R,30R,33S)-30-ethyl-33-[(1S,2R,4E)-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-di(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone
• OpenEye OEToolkits 1.7.6: (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-1,4,7,10,12,15,19,25,28-nonamethyl-33-[(E,1R,2R)-2-methyl-1-oxidanyl-hex-4-enyl]-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

PDB entries

Showing all 30 items

1c5f

1csa

1cwa

1cya

1cyb

1ikf

1m63

1mf8

1qng

1qnh

1xq7

2esl

2oju

2poy

2rma

2rmc

2wfj

2x2c

2x7k

2z6w

3bo7

3cys

3eov

3pmp

4dgc

4hy7

4jjm

4yv9

7pcj

8b58