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Drug Details

General Information of the Drug (ID: DR8350)
Name
Cyclosporin
Synonyms
cyclosporin A; cyclosporine; Ciclosporin; 59865-13-3; Cyclosporine A; Sandimmune; Sandimmun; Neoral; Cyclosporin; Ciclosporine; Gengraf; Ramihyphin A; Sandimmun Neoral; Sang-35; Ciclosporina; Ciclosporinum; Consupren; Equoral; Neoplanta; UNII-83HN0GTJ6D; Antibiotic S 7481F1; SangCyA; MFCD00274558; 83HN0GTJ6D; MLS001333756; CHEBI:4031; CSA; S-Neoral; Cipol N; Sigmasporin Microoral; Cyclosporin A solution; DSSTox_CID_365; Ciclosporin (Ciclosporin A); DSSTox_RID_75541; DSSTox_GSID_20365; (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; SDZ-OXL 400; Ciclosporin A; OL 27-400; Abrammune; Imusporin; Optimmune; Seciera; Vekacia; Papilock Mini; Arpimune ME; Zinograf ME; Sandimmune Neoral; Ciclosporina Germed; (R-(R*,R*-(E)))-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl); CYA; SMR000058578; Cicloral (antibiotic); Debio088; Sang 35; Cyclosporine [USAN:USP]; Ciclosporine [INN-French]; Ciclosporinum [INN-Latin]; Ciclosporina [INN-Spanish]; Cyclospori; Sigmasporin; Cyclokat; Mitogard; Papilock; Pulminiq; Zyclorin; CicloMulsion; Ciclosporin;; CCRIS 1590; Ciclosporin DT; Consupren S; NSC290193; Modusik-A; HSDB 6881; NeuroSTAT; 1cyn; 2wfj; 4jjm; NSC-290193; Cipol-N; NCGC00016890-01; (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R,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-2,5,8,11,14,17,20,23,2; (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,2R,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; (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(E,1R,2R)-1-hydroxy-2-methyl-hex-4-enyl]-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-undecazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone; (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; (R-[R*,R*-(E)])-Cyclic(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-3-hydroxy-N,4-dimethyl-L-2-amino-6-octenoyl-L-alpha-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl); Cyclo(((E)-(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl)-L-2-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl); Cyclo[[(E)-(2S,3R,4R)-3-hydroxy-4-methyl-2-(methylamino)-6-octenoyl]-L-2-aminobutyryl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methyl-L-leucyl-L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl]; DRG-0275; Prestwick_731; Ciclosporin [INN]; CAS-59865-13-3; NSC 290193; CsA & IFN.alpha.; 1c5f; 2z6w; S 7481F1; Cyclosporine manufacturer; Prestwick2_000435; Prestwick3_000435; CHEMBL160; Sang-2000; SCHEMBL3491; SCHEMBL4442; Nova-22007; Ikervis (opthalmic solution); BSPBio_000450; Cyclosporin A & IFN.alpha.; MLS000028376; MLS002153454; MLS002207033; Verkazia (opthalmic solution); SDZ-OXL-400; BPBio1_000496; GTPL1024; ANTIBIOTIC S-7481F1; DTXSID0020365; CHEBI:92233; AOB2581; ATH-002; OLO-400; CB-01-09 MMX; HMS1569G12; HMS2089A09; HMS2096G12; HMS2230M14; HMS3713G12; 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-(1-hydroxy-2-methyl-hex-4-enyl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,25,28-nonamethyl-1,4,7,10,13,16,19,22,25,28,31undecaaza-cyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone; 30-ethyl-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-undecaazacyclotritriacontane-2,5,8,11,14,17,20,23,26,29,32-undecone; 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; Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl)-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl); Cyclosporin A, Ready Made Solution; EX-A4110; HY-B0579; Tox21_110667; Tox21_301849; BDBM50022815; DE-076; ST-603; Cyclosporin A, >=98.5% (TLC); AKOS015969287; Tox21_110667_1; CCG-208184; DB00091; EBD2126862; KS-1257; SDCCGSBI-0050230.P004; NCGC00093704-12; NCGC00164258-01; NCGC00164258-02; NCGC00164258-03; NCGC00255232-01; AT-12519; C042; Cyclo(L-alanyl-D-alanyl-N-methyl-L-leucyl-N-methyl-L-leucyl-N-methyl-L-valyl-((3R,4R,6E)-6,7-didehydro-3-hydroxy-N,4-dimethyl-L-2-aminooctanoyl-L-2-aminobutanoyl-N-methylglycyl-N-methyl-L-leucyl-L-valyl-N-methylleucyl); OL-27400; SBI-0050230.P003; AB0090560; OL-27-400; 5946-EP0930075A1; 5946-EP2289877A1; 5946-EP2292601A1; 5946-EP2292602A1; 5946-EP2292603A1; 5946-EP2292604A2; 5946-EP2292618A1; 5946-EP2293650A1; 5946-EP2298737A1; 5946-EP2298739A1; 5946-EP2298740A1; 5946-EP2298741A1; 5946-EP2298771A2; 5946-EP2301920A1; 5946-EP2301940A1; 5946-EP2308843A1; 5946-EP2308861A1; J10181; J90049; 865C133; Cyclosporin A, VETRANAL(TM), analytical standard; Q367700; SR-01000780563; Q-200913; SR-01000780563-3; BRD-K03222093-001-01-8; BRD-K13533483-001-03-0; Ciclosporin, European Pharmacopoeia (EP) Reference Standard; Cyclosporin A, from Tolypocladium inflatum, >=95% (HPLC), solid; Cyclosporine, United States Pharmacopeia (USP) Reference Standard; Ciclosporin for system suitability, European Pharmacopoeia (EP) Reference Standard; Cyclosporin A, from Tolypocladium inflatum, BioReagent, for molecular biology, >=95%; Cyclosporine, Pharmaceutical Secondary Standard; Certified Reference Material; (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-((1R,2R,E)-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-undecaazacyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone; (3S,6S,9S,12R,15S,18S,21S,24S,30S,33S)-30-ethyl-33-[(1R,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-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; (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; 104250-72-8; 30-Ethyl-33-((E)-1-hydroxy-2-methyl-hex-4-enyl)-6,9,18,24-tetraisobutyl-3,21-diisopropyl-1,4,7,10,12,15,19,28-octamethyl-1,4,7,10,13,16,19,22,25,28,31undecaaza-cyclotritriacontan-2,5,8,11,14,17,20,23,26,29,32-undecaone
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Molecular Type
Small molecule
Disease Plaque psoriasis [ICD-11: EA90] Approved [1]
Structure
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2D MOL

3D MOL

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Formula
C62H111N11O12
PubChem CID
5284373
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
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
InChIKey
PMATZTZNYRCHOR-CGLBZJNRSA-N
CAS Number
CAS 59865-13-3
ChEBI ID
CHEBI:4031
TTD Drug ID
D0O3YF
DrugBank ID
DB00091
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Acarbose      Actinoplanes utahensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression IL17  Molecule Info 
Pathway MAP
Down-regulation Expression IL22  Molecule Info 
Pathway MAP
Down-regulation Expression IL23  Molecule Info 
Pathway MAP
Down-regulation Expression TNF  Molecule Info 
Pathway MAP
                    In-vivo Model Male BALB/c mice aged 6 weeks were used in this study.
                    Experimental
                    Result(s)
Acar and low-dose CsA in combination alleviates psoriatic skin lesions by inhibiting inflammation.
          Mycophenolate mofetil      Penicillium stoloniferum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical Trial
                    Experimental
                    Result(s)
The introduction of MMF combined with the reduction of at least 50% of CNI dose allowed the renal function of liver transplant recipients to significantly improve at 1 year, without any rejection episode and without significant secondary effects.
          Mycophenolate mofetil + Corticosteroid     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model Clinical trial
                    Experimental
                    Result(s)
Triple immunosuppressive therapy significantly reduced proteinuria and preserved renal function in refractory NS patients.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Schisandrol B      Schisandra chinensis     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Down-regulation Expression LDHA  Molecule Info 
Pathway MAP
                    Biological
                    Regulation
Increase ATP generation
Induction ROS generation
                    In-vitro Model HK2 CVCL_0302 Healthy Homo sapiens
                    Experimental
                    Result(s)
Sch B appears to protect against CsA-induced nephrotoxicity by decreasing oxidative stress and cell death.
Target and Pathway
Target(s) Calcineurin (PPP3CA)  Molecule Info  [1]
KEGG Pathway MAPK signaling pathway Click to Show/Hide
2 Calcium signaling pathway
3 cGMP-PKG signaling pathway
4 Oocyte meiosis
5 Apoptosis
6 Wnt signaling pathway
7 Axon guidance
8 VEGF signaling pathway
9 Osteoclast differentiation
10 Natural killer cell mediated cytotoxicity
11 T cell receptor signaling pathway
12 B cell receptor signaling pathway
13 Long-term potentiation
14 Glutamatergic synapse
15 Dopaminergic synapse
16 Oxytocin signaling pathway
17 Glucagon signaling pathway
18 Alzheimer's disease
19 Amyotrophic lateral sclerosis (ALS)
20 Amphetamine addiction
21 Tuberculosis
22 HTLV-I infection
Reactome DARPP-32 events Click to Show/Hide
2 FCERI mediated Ca+2 mobilization
3 Ca2+ pathway
WikiPathways Mitochondrial Gene Expression Click to Show/Hide
2 MAPK Signaling Pathway
3 G Protein Signaling Pathways
4 Cardiac Hypertrophic Response
5 Fc epsilon receptor (FCERI) signaling
6 Signaling by the B Cell Receptor (BCR)
7 T-Cell Receptor and Co-stimulatory Signaling
8 Amyotrophic lateral sclerosis (ALS)
9 Spinal Cord Injury
10 Alzheimers Disease
11 miR-targeted genes in muscle cell - TarBase
12 miR-targeted genes in lymphocytes - TarBase
13 Opioid Signalling
14 MicroRNAs in cardiomyocyte hypertrophy
15 Physiological and Pathological Hypertrophy of the Heart
References
Reference 1 Why Choose Cyclosporin A as First-line Therapy in COVID-19 Pneumonia. Reumatol Clin. 2020 Apr 16;S1699-258X(20)30044-9.
Reference 2 Combination Therapy of Acarbose and Cyclosporine a Ameliorates Imiquimod-Induced Psoriasis-Like Dermatitis in Mice. Molecules. 2020 Apr 16;25(8):1822.
Reference 3 Mycophenolate mofetil in combination with reduction of calcineurin inhibitors for chronic renal dysfunction after liver transplantation. Liver Transpl. 2006 Dec;12(12):1755-60.
Reference 4 Protective effect of schisandrin B against cyclosporine A-induced nephrotoxicity in vitro and in vivo. Am J Chin Med. 2012;40(3):551-66.
Reference 5 Combination treatment with corticosteroid, cyclosporine A, and mycophenolate in refractory nephrotic syndrome. Clin Nephrol. 2011 Jun;75(6):511-7.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China