Cyclosporin (CED0000882)

Record Information
Version1.0
Creation Date2009-07-30 17:58:49 UTC
Update Date2026-05-14 16:23:58 UTC
SynCED IDCED0000882
Secondary Accession Numbers
  • CHEM002512
  • T3D3498
Identification
Common NameCyclosporin
ClassSmall Molecule
Description
Cyclosporin (C62H111N11O12) is an exogenous solid at room temperature. Cyclosporin belongs to the peptoid-peptide hybrids, a subclass of peptidomimetics within the organic compounds. With an average molecular weight of 1,203 g/mol, Cyclosporin is a heavy molecule. It functions as a metabolite and is utilized as an immunosuppressive agent, antifungal agent, antirheumatic drug, dermatologic drug, and anti-asthmatic drug. Biologically, it acts as a carcinogenic agent and an EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor. The compound is found in healthcare, pharmaceuticals, and veterinary products, specifically within ophthalmologicals and immunosuppressants, as well as in electrical and electronic equipment such as antennas. Exposure routes include oral, intravenous, topical, and ophthalmic administration. Cyclosporin interacts with seven protein targets, including the ATP-dependent translocase ABCB1, the solute carrier organic anion transporter family member 1B3 (SLCO1B3), the guided entry of tail-anchored proteins factor CAMLG, and the peptidyl-prolyl cis-trans isomerase A (PPIA) and F, mitochondrial (PPIF). It also targets the protein phosphatase 3 catalytic subunit alpha (PPP3CA) and calcineurin subunit B type 2 (PPP3R2). Cyclosporine binds to cyclophillin to form a complex that inhibits calcineurin, which typically activates the transcription of interleukin 2. Additionally, it inhibits interleukin release and lymphokine production. In ophthalmic applications, where the precise mechanism of action is unknown, cyclosporine emulsion is thought to act as a partial immunomodulator for patients with keratoconjunctivitis sicca whose tear production is presumed to be suppressed due to ocular inflammation.
Contaminant Type
  • Amide
  • Amine
  • Antifungal Agent
  • Antirheumatic Agent
  • Dermatologic Agent
  • Drug
  • Enzyme Inhibitor
  • Fungal Toxin
  • Human Neurotoxin
  • Immunomodulatory Agent
  • Immunosuppressive Agent
  • Natural Compound
  • Organic Compound
Chemical Structure
Synonyms
ValueSource
CiclosporinKegg
CyclosporineKegg
GengrafKegg
NeoralKegg
RestasisKegg
SandimmuneKegg
CsANeoralMeSH
CsA neoralMeSH
CsA-neoralMeSH
CyA NOFMeSH
Cyclosporine aMeSH
SandimmunMeSH
CyA-NOFMeSH
CyclosporinMeSH
Sandimmun neoralMeSH
Chemical FormulaC62H111N11O12
Average Molecular Mass1202.611 g/mol
Monoisotopic Mass1201.841 g/mol
CAS Registry Number59865-13-3
IUPAC Name30-ethyl-14,17,23,32-tetrahydroxy-33-[(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-bis(propan-2-yl)-1,4,7,10,13,16,19,22,25,28,31-undecaazacyclotritriaconta-13,16,22,31-tetraene-2,5,8,11,20,26,29-heptone
Traditional Name30-ethyl-14,17,23,32-tetrahydroxy-33-[(4E)-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-undecaazacyclotritriaconta-13,16,22,31-tetraene-2,5,8,11,20,26,29-heptone
SMILES[H]\C(C)=C(\[H])CC(C)C(O)C1N(C)C(=O)C(C(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(CC(C)C)N(C)C(=O)C(C)N=C(O)C(C)N=C(O)C(CC(C)C)N(C)C(=O)C(N=C(O)C(CC(C)C)N(C)C(=O)CN(C)C(=O)C(CC)N=C1O)C(C)C
InChI IdentifierInChI=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+
InChI KeyPMATZTZNYRCHOR-IMVLJIQESA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as cyclosporins. These are cyclic depsipeptides containing the cyclosporin backbone.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassPeptidomimetics
Sub ClassPeptoid-peptide hybrids
Direct ParentCyclosporins
Alternative Parents
Substituents
  • Cyclosporin-backbone
  • Alpha-oligopeptide
  • Macrolactam
  • Alpha-amino acid or derivatives
  • Tertiary carboxylic acid amide
  • Carboxamide group
  • Lactam
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Carboxylic acid derivative
  • Azacycle
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Alcohol
  • Organic oxygen compound
  • Carbonyl group
  • Organooxygen compound
  • Organic nitrogen compound
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
  • Non-ribosomal peptide/polyketide hybrids (C05086 )
  • Non-ribosomal peptide/polyketide hybrids (LMPK14000003 )
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point148-151°C
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0058 g/LALOGPS
logP4.37ALOGPS
logP6.92ChemAxon
logS-5.3ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
pKa (Strongest Basic)1.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count16ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area292.76 ŲChemAxon
Rotatable Bond Count15ChemAxon
Refractivity329.23 m³·mol⁻¹ChemAxon
Polarizability131.92 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
Toxicity Profile
Toxicity ValuesNot Available
Toxicity / Toxin ClassNot Available
Mechanism of ToxicityCyclosporine binds to cyclophilin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca. The oral LD50 is 2329 mg/kg in mice, 1480 mg/kg in rats, and > 1000 mg/kg in rabbits. The I.V. LD50 is 148 mg/kg in mice, 104 mg/kg in rats, and 46 mg/kg in rabbits.
Carcinogenicity (IARC Classification)1, carcinogenic to humans. (3)
Minimum Risk LevelNot Available
SymptomsThe oral LD50 is 2329 mg/kg in mice, 1480 mg/kg in rats, and > 1000 mg/kg in rabbits. The I.V. LD50 is 148 mg/kg in mice, 104 mg/kg in rats, and 46 mg/kg in rabbits.
TreatmentNot Available
Health Effects
Health EffectRelationshipDirectionDescriptionReference
hypertensionAssociated With?increaseA disorder characterized by a pathological increase in blood pressure; a repeatedly elevation in the blood pressure exceeding 140 over 90 mm Hg. (NCI CTCAE)PMC6357920
hypertensionAssociated With?Not AvailableA disorder characterized by a pathological increase in blood pressure; a repeatedly elevation in the blood pressure exceeding 140 over 90 mm Hg. (NCI CTCAE)PMC12678558 , PMC12678558
inflammationNot AvailableNot AvailableNot AvailablePMC12598623
inflammationHas Therapeutic Effect OnNot AvailableNot AvailablePMC11859051 , PMC3237613
kidney diseaseAssociated With?increaseA urinary system disease that is located in the kidney. (DO)PMC11853432
kidney diseaseAssociated With?Not AvailableA urinary system disease that is located in the kidney. (DO)PMC3237613
feverNot AvailableNot AvailableA disorder characterized by an abnormally high body temperature.PMC4718299
painNot AvailableNot AvailableA disorder characterized by the sensation of marked discomfort, distress or agony. (NCI CTCAE)PMC4718299
painHas Therapeutic Effect OnNot AvailableA disorder characterized by the sensation of marked discomfort, distress or agony. (NCI CTCAE)PMC10562155
headacheAssociated With?Not AvailableA disorder characterized by a sensation of marked discomfort in various parts of the head, not confined to the area of distribution of any nerve. (NCI CTCAE)PMC10921011
psoriasisNot AvailableNot AvailableA disorder characterized by a quicker life span of skin cells causing cells to build up rapidly on the surface of the skin.PMC9372960 , PMC11665659
psoriasisHas Therapeutic Effect OnNot AvailableA disorder characterized by a quicker life span of skin cells causing cells to build up rapidly on the surface of the skin.PMC4834511
edemaNot AvailableNot AvailableA disorder characterized by swelling due to an excessive accumulation of fluid (NCI CTCAE)PMC12307128
hyperuricemiaAssociated With?Not AvailableA disorder characterized by laboratory test results that indicate an elevation in the concentration of uric acid. (NCI CTCAE)PMC10921011
paresthesiaAssociated With?Not AvailableNot AvailablePMC10921011
osteoarthritisHas Therapeutic Effect OnNot AvailableAn arthritis that has material basis in worn out cartilage located in joint. (DO)PMC6696379
arrhythmiaHas Therapeutic Effect OnNot AvailableNot AvailablePMC9313001
cholestasisAssociated With?Not AvailableImpairment of the bile flow caused by obstruction within the liver, or outside the liver in the bile duct system.PMC12678558 , PMC9968698
hepatic steatosisAssociated With?Not AvailableNot AvailablePMC9968698
kidney failureAssociated With?increaseNot AvailablePMC6357920
kidney failureAssociated With?Not AvailableNot AvailablePMC5595648
alopeciaNot AvailableNot AvailableA disorder characterized by the partial or complete lack of hair growth.PMC7470034
leukopeniaAssociated With?increaseNot AvailablePMC6357920
graft-versus-host diseaseNot AvailableNot AvailableNot AvailablePMC4718299 , PMC3611089
interstitial cystitisNot AvailableNot AvailableNot AvailablePMC5595648
autoimmune diseaseNot AvailableNot AvailableAn autoimmune disease is a condition arising from an abnormal immune response to a functioning body part. There are at least 80 types of autoimmune diseases. Nearly any body part can be involved. Common symptoms include low grade fever and feeling tired. Some autoimmune diseases such as lupus run in families, and certain cases may be triggered by infections or other environmental factors. Some common diseases that are generally considered autoimmune include celiac disease, diabetes mellitus type 1, Graves' disease, inflammatory bowel disease, multiple sclerosis, psoriasis, rheumatoid arthritis, and systemic lupus erythematosus. About 24 million (7%) people in the United States are affected by an autoimmune disease. Women are more commonly affected than men.PMC9476466 , PMC5385174
vitiligoNot AvailableNot AvailableA hypersensitivity reaction type II disease that causes depigmentation of patches of skin resulting from loss of function or death of melanoctyes. (DO)PMC10921011 , PMC10921011
Cell DeathNot AvailableNot AvailableNot AvailablePMC12347410
HyperkalemiaAssociated With?Not AvailableNot AvailablePMC9866503
Endoplasmic Reticulum StressAssociated With?Not AvailableNot AvailablePMC3572937
infectious diseaseAssociated With?increaseNot AvailablePMC6357920
RhabdomyolysisAssociated With?increaseNot AvailablePMC1492602
NeurodegenerationHas Therapeutic Effect OnNot AvailableNot AvailablePMC12732708
fetal growth restrictionAssociated With?increaseNot AvailablePMC4834511
ischemia reperfusion injuryHas Therapeutic Effect OnNot AvailableNot AvailablePMC12732708
dyspepsiaAssociated With?Not AvailableNot AvailablePMC10921011
bilirubin metabolic disorderAssociated With?Not AvailableNot AvailablePMC7465333 , PMC10921011
mpoxNot AvailableNot AvailableNot AvailablePMC13115161
Unusual cystitisHas Therapeutic Effect OnNot AvailableNot AvailablePMC5123821
GranulomaNot AvailableNot AvailableNot AvailablePMC7152448
Immunosuppression TherapyAssociated With?Not AvailableNot AvailablePMC12678558 , PMC10441638
Immunosuppression TherapyNot AvailableNot AvailableNot AvailablePMC3460365 , PMC9226287
MyalgiaAssociated With?Not AvailableNot AvailablePMC10921011
dry eye syndromeNot AvailableNot AvailableNot AvailablePMC10146824 , PMC13030595
Graft RejectionNot AvailableNot AvailableNot AvailablePMC4464443
hemophagocytic lymphohistiocytosisNot AvailableNot AvailableNot AvailablePMC4718299
Increased susceptibility to fracturesAssociated With?Not AvailableNot AvailablePMC10150014
Alveolar Bone LossAssociated With?Not AvailableNot AvailablePMC7595528 , PMC7595528
Alveolar Bone LossAssociated With?decreaseNot AvailablePMC7595528
thrombotic microangiopathyAssociated With?Not AvailableNot AvailablePMC7152208
hypertrichosisAssociated With?Not AvailableNot AvailablePMC10921011
Disease-Free SurvivalAssociated With?increaseNot AvailablePMC6161255
transplant rejectionAssociated With?Not AvailableNot AvailablePMC3583015
transplant rejectionNot AvailableNot AvailableNot AvailablePMC12285105
gingival hypertrophyAssociated With?Not AvailableNot AvailablePMC3237613
Gingival overgrowthAssociated With?Not AvailableNot AvailablePMC10921011 , PMC7595528
Myocardial necrosisHas Therapeutic Effect OnNot AvailableNot AvailablePMC4443500
Exposure Sources
Source IDSourceSectorReference
CEDs000010Insecticides?Insecticides are synthetic chemicals designed to control or eliminate insect pests that threaten crops and other agricultural products.Agriculture & land managementPubChem
CEDs000115Drinking water?Drinking water can be a medium for synthetic chemical contamination, often originating from various industrial processes and agricultural practices.Drinking water & water supplyPMC9682362
CEDs000362Immunosuppressants?Immunosuppressants are synthetic chemicals used to inhibit the immune response, primarily in patients undergoing organ transplants or those with autoimmune disorders.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000405Ophthalmologicals?Ophthalmologicals are a category of synthetic chemicals used primarily for the treatment of eye disorders, including medications such as anti-inflammatories, antibiotics, and lubricants.Healthcare, pharmaceuticals & veterinary productsNot Available
CEDs000506Antennas?Antennas, commonly used in communication technologies, can be a source of synthetic chemical contamination through the materials and coatings used in their construction.Electrical & Electronic EquipmentPubChem
CEDs000511Conductors Or Conductive Bodies Characterised By The Conductive Materials?Conductors, or conductive bodies, are materials that allow the flow of electrical current, typically made from metals such as copper, aluminum, or silver.Electrical & Electronic EquipmentPubChem
CEDs000514Discharge Lamps?Discharge lamps, including fluorescent and high-intensity discharge (HID) lamps, are commonly used for lighting applications due to their energy efficiency and brightness.Electrical & Electronic EquipmentPubChem
CEDs000519Electrodes?Electrodes, used in various electrical and electronic applications, can be a source of synthetic chemical contamination due to the materials from which they are constructed and the processes involved in their manufacturing.Electrical & Electronic EquipmentPubChem
CEDs000521Fixed Capacitors And Their Manufacture?Fixed capacitors are passive electronic components used to store and release electrical energy, playing a critical role in various circuits.Electrical & Electronic EquipmentPubChem
CEDs000530Radio Transmission Systems?Radio transmission systems utilize a variety of synthetic chemicals in their manufacturing and maintenance processes.Electrical & Electronic EquipmentPubChem
CEDs000537Television Systems?Television systems can be a source of synthetic chemical contamination due to the various materials and components used in their manufacture and operation.Electrical & Electronic EquipmentPubChem
CEDs000544Fermentation Processes For Beer?Fermentation processes for beer involve the conversion of sugars into alcohol and carbon dioxide by yeast.Food, food processing & cookwarePubChem
CEDs000545Food Preservation?Food preservation often involves the use of synthetic chemicals, such as preservatives, flavor enhancers, and color additives, to extend shelf life and enhance the sensory qualities of food products.Food, food processing & cookwarePubChem
CEDs000552Processing Meats?Processing meats can lead to synthetic chemical contamination primarily through the use of additives and preservatives.Food, food processing & cookwarePubChem
CEDs000555Bleaching Agents?Bleaching agents are chemical substances used to whiten or lighten materials, often employed in various cleaning products for their stain removal and disinfecting properties.Household cleaning & consumer productsPubChem
CEDs000561Perfumes Within Detergents And Soaps?Perfumes within detergents and soaps are synthetic fragrance compounds added to enhance the sensory experience of cleaning products.Household cleaning & consumer productsPubChem
CEDs000569Tobacco Smoke Filters?Tobacco smoke filters are designed to reduce the inhalation of harmful substances in cigarette smoke, including tar and other particulate matter.Household cleaning & consumer productsPubChem
CEDs000580Manufacture Preparation Of Tobacco Products?The manufacture and preparation of tobacco products involve various processes that can result in the introduction of synthetic chemicals into the environment.Industrial manufacturing & chemical processingPubChem
CEDs000609Aftershave?Aftershave is a grooming product typically used to soothe and protect the skin following shaving.Personal care & cosmeticsPubChem
CEDs000610Aftersun Products?Aftersun products are designed to soothe and hydrate the skin after sun exposure, often containing various synthetic chemicals such as emollients, preservatives, and fragrances.Personal care & cosmeticsPubChem
CEDs000611Anti Perspirants Or Body Deoderants?Antiperspirants and body deodorants commonly contain synthetic chemicals such as aluminum compounds, parabens, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000613Depilatories?Depilatories are products designed to remove unwanted hair through the application of synthetic chemicals that break down the protein structure of hair, facilitating its removal.Personal care & cosmeticsPubChem
CEDs000614Essential Oils Or Perfumes?Essential oils and perfumes are complex mixtures of volatile compounds derived from natural or synthetic sources, commonly used for their aromatic properties.Personal care & cosmeticsPubChem
CEDs000615Eye Makeup Products?Eye makeup products, including mascaras, eyeliners, and eyeshadows, often contain a variety of synthetic chemicals such as pigments, preservatives, and film-forming agents.Personal care & cosmeticsPubChem
CEDs000617Lip Care Products?Lip care products, including lipsticks, balms, and glosses, often contain a variety of synthetic chemicals such as parabens, phthalates, and synthetic fragrances.Personal care & cosmeticsPubChem
CEDs000618Lip Makeup Products?Lip makeup products, such as lipsticks, lip glosses, and lip liners, often contain a variety of synthetic chemicals, including pigments, preservatives, and emollients.Personal care & cosmeticsPubChem
CEDs000632Apparel?Apparel production often involves the use of various synthetic chemicals, including dyes, finishing agents, and preservatives.Textiles, leather & furnishingsPubChem
CEDs000642Footwear?Footwear production often involves the use of various synthetic chemicals, such as adhesives, dyes, and treatments, which can contribute to environmental contamination.Textiles, leather & furnishingsPubChem
CEDs000650Purses Luggage Hand Bags?Purses, luggage, and handbags are often manufactured using synthetic materials such as polyvinyl chloride (PVC), polyurethane, and various types of nylon.Textiles, leather & furnishingsPubChem
CEDs000685Ceramics?Ceramics can be a source of synthetic chemical contamination through various additives and processing agents used in their production.Building & ConstructionPubChem
CEDs000688Glass Coatings?Glass coatings are synthetic chemical formulations applied to glass surfaces to enhance properties such as durability, UV resistance, and aesthetic appeal.Building & ConstructionPubChem
CEDs000696Nanotechnology?Nanotechnology involves the manipulation of materials at the molecular or atomic level, typically within the range of 1 to 100 nanometers.Industrial manufacturing & chemical processingPubChem
CEDs000739Inks?Inks are complex mixtures composed of pigments or dyes, solvents, resins, and additives used primarily for printing and writing applications.Paper, pulp & fiber productsPubChem
CEDs000744Water, Wastewater, & Sewage Treatment?Water, wastewater, and sewage treatment processes are critical for managing and mitigating pollutants in water systems.Wastewater, sanitation & biosolidsPubChem
CEDs01231WinesFood, food processing & cookwarePMC9682362
CEDs01346Milk PowderFood, food processing & cookwarePMC8691421
CEDs01386Pet FoodFood, food processing & cookwarePMC8691421
CEDs02255WaterAquatic systems & sedimentsPMC8691421 , PMC8691421
CEDs02257WatersAquatic systems & sedimentsPMC8691421
CEDs02265River WaterAquatic systems & sedimentsPMC8691421
CEDs02270RiverAquatic systems & sedimentsPMC8691421
CEDs02339River Water SampleAquatic systems & sedimentsPMC8691421
CEDs02423River Water SamplesAquatic systems & sedimentsPMC8691421
CEDs02752Cement SlurryBuilding & ConstructionPMC10707400
CEDs03435Swimming Pool WaterRecreation & sports surfacesPMC8691421
Pathways
1 pathwayPathway Source: PathBank
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Peptidyl-prolyl cis-trans isomerase F, mitochondrial structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase F, mitochondrialP30405HumansKnownNot Available
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansKnownNot Available
Solute carrier family 15 member 1 structureClick to view 3D structureSolute carrier family 15 member 1P46059HumansKnownNot Available
Cytochrome P450 3A5 structureClick to view 3D structureCytochrome P450 3A5P20815HumansKnownNot Available
Interleukin-2 structureClick to view 3D structureInterleukin-2P04351Mus musculusPredicted (SEA)
Prediction Confidence Score
0.548
Applicability Domain
0.57
Statistical Significance
2.80e-04
Supporting Reference Compounds
2
E-value
2.17978
Peptidyl-prolyl cis-trans isomerase A structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase AP62937HumansPredicted (SEA)
Prediction Confidence Score
0.513
Applicability Domain
0.57
Statistical Significance
2.90e-04
Supporting Reference Compounds
23
E-value
2.25763
Peptidyl-prolyl cis-trans isomerase B structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase BP23284HumansPredicted (SEA)
Prediction Confidence Score
0.493
Applicability Domain
0.57
Statistical Significance
3.00e-04
Supporting Reference Compounds
13
E-value
2.33548
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansPredicted (SEA)
Prediction Confidence Score
0.485
Applicability Domain
0.57
Statistical Significance
5.90e-04
Supporting Reference Compounds
139
E-value
4.5931
Peptidyl-prolyl cis-trans isomerase F, mitochondrial structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase F, mitochondrialP30405HumansPredicted (SEA)
Prediction Confidence Score
0.479
Applicability Domain
0.57
Statistical Significance
2.90e-04
Supporting Reference Compounds
7
E-value
2.25763
Solute carrier organic anion transporter family member 1B1 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B1Q9Y6L6HumansPredicted (SEA)
Prediction Confidence Score
0.471
Applicability Domain
0.57
Statistical Significance
3.70e-04
Supporting Reference Compounds
82
E-value
2.88042
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansPredicted (SEA)
Prediction Confidence Score
0.405
Applicability Domain
0.57
Statistical Significance
3.40e-04
Supporting Reference Compounds
51
E-value
2.64687
Bile salt export pump structureClick to view 3D structureBile salt export pumpO95342HumansPredicted (SEA)
Prediction Confidence Score
0.402
Applicability Domain
0.57
Statistical Significance
4.60e-04
Supporting Reference Compounds
104
E-value
3.58106
Peptidyl-prolyl cis-trans isomerase C structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase CP45877HumansPredicted (SEA)
Prediction Confidence Score
0.385
Applicability Domain
0.385
Statistical Significance
3.00e-04
Supporting Reference Compounds
1
E-value
2.33548
Protein phosphatase 3 catalytic subunit alpha structureClick to view 3D structureProtein phosphatase 3 catalytic subunit alphaQ08209HumansPredicted (SEA)
Prediction Confidence Score
0.344
Applicability Domain
0.57
Statistical Significance
4.00e-04
Supporting Reference Compounds
7
E-value
3.11397
Reverse transcriptase/RNaseH structureClick to view 3D structureReverse transcriptase/RNaseHQ72547Human immunodeficiency virus 1Predicted (SEA)
Prediction Confidence Score
0.324
Applicability Domain
0.57
Statistical Significance
0.003
Supporting Reference Compounds
79
E-value
23.5883
Broad substrate specificity ATP-binding cassette transporter ABCG2 structureClick to view 3D structureBroad substrate specificity ATP-binding cassette transporter ABCG2Q9UNQ0HumansPredicted (SEA)
Prediction Confidence Score
0.29
Applicability Domain
0.57
Statistical Significance
0.0232
Supporting Reference Compounds
126
E-value
180.766
fMet-Leu-Phe receptor structureClick to view 3D structurefMet-Leu-Phe receptorP21462HumansPredicted (SEA)
Prediction Confidence Score
0.281
Applicability Domain
0.57
Statistical Significance
0.0072
Supporting Reference Compounds
42
E-value
56.1293
Peptidyl-prolyl cis-trans isomerase FKBP1B structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase FKBP1BP68106HumansPredicted (SEA)
Prediction Confidence Score
0.277
Applicability Domain
0.57
Statistical Significance
6.30e-04
Supporting Reference Compounds
8
E-value
4.9045
Cytochrome P450 3A4 structureClick to view 3D structureCytochrome P450 3A4P08684HumansPredicted (SEA)
Prediction Confidence Score
0.244
Applicability Domain
0.57
Statistical Significance
0.6254
Supporting Reference Compounds
1538
E-value
4868.85
Hepatic sodium/bile acid cotransporter structureClick to view 3D structureHepatic sodium/bile acid cotransporterQ14973HumansPredicted (SEA)
Prediction Confidence Score
0.229
Applicability Domain
0.57
Statistical Significance
0.004
Supporting Reference Compounds
17
E-value
31.3732
ATP-dependent Clp protease ATP-binding subunit ClpC1 structureClick to view 3D structureATP-dependent Clp protease ATP-binding subunit ClpC1P9WPC9Mycobacterium tuberculosisPredicted (SEA)
Prediction Confidence Score
0.216
Applicability Domain
0.216 Low confidence
Statistical Significance
0.0026
Supporting Reference Compounds
1
E-value
20.0072
Peptidyl-prolyl cis-trans isomerase FKBP1A structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase FKBP1AP62942HumansPredicted (SEA)
Prediction Confidence Score
0.216
Applicability Domain
0.57
Statistical Significance
0.0191
Supporting Reference Compounds
21
E-value
148.77
Substance-K receptor structureClick to view 3D structureSubstance-K receptorP21452HumansPredicted (SEA)
Prediction Confidence Score
0.211
Applicability Domain
0.57
Statistical Significance
0.2641
Supporting Reference Compounds
118
E-value
2055.69
Click to view 3D structureAureobasidin-resistance proteinQ9Y745Neosartorya fumigata (Aspergillus fumigatus)Predicted (SEA)
Prediction Confidence Score
0.211
Applicability Domain
0.211 Low confidence
Statistical Significance
0.0061
Supporting Reference Compounds
1
E-value
47.2545
Cytochrome P450 2C19 structureClick to view 3D structureCytochrome P450 2C19P33261HumansPredicted (SEA)
Prediction Confidence Score
0.211
Applicability Domain
0.57
Statistical Significance
0.8266
Supporting Reference Compounds
825
E-value
6435.09
Click to view 3D structurePhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit gamma isoformQ9JHG7Mus musculusPredicted (SEA)
Prediction Confidence Score
0.209
Applicability Domain
0.57
Statistical Significance
0.0164
Supporting Reference Compounds
23
E-value
127.673
Multidrug resistance-associated protein 1 structureClick to view 3D structureMultidrug resistance-associated protein 1P33527HumansPredicted (SEA)
Prediction Confidence Score
0.202
Applicability Domain
0.57
Statistical Significance
0.171
Supporting Reference Compounds
49
E-value
1331.61
Click to view 3D structureATP-dependent translocase ABCB1P06795Mus musculusPredicted (SEA)
Prediction Confidence Score
0.202
Applicability Domain
0.57
Statistical Significance
0.0843
Supporting Reference Compounds
22
E-value
655.958
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P21447Mus musculusPredicted (SEA)
Prediction Confidence Score
0.2
Applicability Domain
0.57
Statistical Significance
0.0243
Supporting Reference Compounds
23
E-value
189.563
ATP-dependent translocase ABCB1 structureClick to view 3D structureATP-dependent translocase ABCB1P08183HumansKnownCyclosporine binds to cyclophillin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca.
Peptidyl-prolyl cis-trans isomerase A structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase AP62937HumansKnownCyclosporine binds to cyclophillin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca.
Click to view 3D structureCalcineurin subunit B type 2Q96LZ3HumansKnownCyclosporine binds to cyclophillin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca.
Guided entry of tail-anchored proteins factor CAMLG structureClick to view 3D structureGuided entry of tail-anchored proteins factor CAMLGP49069HumansKnownCyclosporine binds to cyclophillin. The complex then inhibits calcineurin which is normally responsible for activating transcription of interleukin 2. Cyclosporine also inhibits lymphokine production and interleukin release. In ophthalmic applications, the precise mechanism of action is not known. Cyclosporine emulsion is thought to act as a partial immunomodulator in patients whose tear production is presumed to be suppressed due to ocular inflammation associated with keratoconjunctivitis sicca.
Peptidyl-prolyl cis-trans isomerase F, mitochondrial structureClick to view 3D structurePeptidyl-prolyl cis-trans isomerase F, mitochondrialP30405HumansKnownNot Available
Solute carrier organic anion transporter family member 1B3 structureClick to view 3D structureSolute carrier organic anion transporter family member 1B3Q9NPD5HumansKnownNot Available
Concentrations
Not Available
External Links
DrugBank IDNot Available
HMDB IDNot Available
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDC00001517
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCiclosporin
Chemspider IDNot Available
ChEBI IDNot Available
PubChem Compound ID5280754
Kegg Compound IDC05086
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Hans Dietl, “Pharmaceutical preparation containing cyclosporine(s) for intravenous administration and a process for its production.” U.S. Patent US5527537, issued October, 1990.

MSDSNot Available
General References
  1. Lichtiger S, Present DH, Kornbluth A, Gelernt I, Bauer J, Galler G, Michelassi F, Hanauer S: Cyclosporine in severe ulcerative colitis refractory to steroid therapy. N Engl J Med. 1994 Jun 30;330(26):1841-5. [PubMed: 8196726]
  2. Husi H, Schorgendorfer K, Stempfer G, Taylor P, Walkinshaw MD: Prediction of substrate-specific pockets in cyclosporin synthetase. FEBS Lett. 1997 Sep 15;414(3):532-6. [PubMed: 9323029]
  3. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. - http://monographs.iarc.fr/index.php
  4. Drugs.com - http://www.drugs.com/cons/Cyclosporine.html
  5. Patent Genius (2006). Cyclosporin with improved activity profile. - http://www.patentgenius.com/patent/6927208.html
  6. Pubmed - http://www.ncbi.nlm.nih.gov/pubmed/9323029