Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0321)
Drug Name
Ciclosporin
Synonyms
Ciclosporin; Ciclosporin (Ciclosporin A); Ciclosporina; Ciclosporina [INN-Spanish]; Ciclosporine; Ciclosporine [INN-French]; Ciclosporinum; Ciclosporinum [INN-Latin]; Cipol N; Consupren; Cyclosporin; Cyclosporine A; Equoral; Antibiotic S 7481F1; Gengraf; Neoplanta; Neoral; Ramihyphin A; Restasis; S-Neoral; Sandimmun; Sandimmun Neoral; Sandimmune; Sang 35; Sang-35; SangCyA; Sigmasporin Microoral; cyclosporin A; cyclosporine; 59865-13-3; 83HN0GTJ6D; CHEBI:4031; CSA; DSSTox_CID_365; DSSTox_RID_75541; MFCD00274558; MLS001333756; UNII-83HN0GTJ6D
Indication Viral hepatitis [ICD11: 1E51] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 1202.6 Topological Polar Surface Area 279
Heavy Atom Count 85 Rotatable Bond Count 15
Hydrogen Bond Donor Count 5 Hydrogen Bond Acceptor Count 12
Cross-matching ID
PubChem CID
5284373
ChEBI ID
CHEBI:4031
CAS Number
59865-13-3
Formula
C62H111N11O12
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
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
AM1 DM017053 N. A. Oxidation - Oxidation 1 [6]
AM4N DM001840
11115853
Oxidation - Oxidation 1 [6]
AM9 DM017064 N. A. Oxidation - Hydroxylation 1 [7]
AM11d DM017061 N. A. Unclear - Unclear 2 [6]
AM19 DM017062 N. A. Oxidation - Hydroxylation 2 [7]
AM19 DM017062 N. A. Unclear - Unclear 2 [6]
AM1AL DM017054 N. A. Unclear - Unclear 2 [6]
AM1c DM017057 N. A. Unclear - Unclear 2 [6]
AM49 DM017066 N. A. Unclear - Unclear 2 [6]
AM4N9 DM017063 N. A. Unclear - Unclear 2 [6]
AM69 DM017065 N. A. Unclear - Unclear 2 [6]
AM1A DM017055 N. A. Unclear - Unclear 3 [6]
AM1c9 DM017058 N. A. Unclear - Unclear 3 [6]
AM1A4N DM017056 N. A. Unclear - Unclear 4 [6]
AM1c4N9 DM017059 N. A. Unclear - Unclear 4 [6]
⏷ Show the Full List of 15  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR014160 Ciclosporin AM1 Oxidation - Oxidation CYP3A4 ... [6]
MR014164 Ciclosporin AM9 Oxidation - Hydroxylation Unclear [7]
MR014166 Ciclosporin AM4N Oxidation - Oxidation CYP3A4 ... [6]
MR014163 AM1 AM19 Oxidation - Hydroxylation Unclear [7]
MR014181 AM1 AM1AL Unclear - Unclear Unclear [6]
MR014184 AM1 AM1c Unclear - Unclear Unclear [6]
MR014185 AM1 AM11d Unclear - Unclear Unclear [6]
MR014189 AM4N AM4N9 Unclear - Unclear Unclear [6]
MR014165 AM9 AM19 Unclear - Unclear Unclear [6]
MR014186 AM9 AM4N9 Unclear - Unclear Unclear [6]
MR014187 AM9 AM49 Unclear - Unclear Unclear [6]
MR014188 AM9 AM69 Unclear - Unclear Unclear [6]
MR014182 AM1AL AM1A Unclear - Unclear Unclear [6]
MR014161 AM1c AM1c9 Unclear - Unclear Unclear [6]
MR014183 AM1A AM1A4N Unclear - Unclear Unclear [6]
MR014162 AM1c9 AM1c4N9 Unclear - Unclear Unclear [6]
⏷ Show the Full List of 16 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[4]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
References
1 Ciclosporin was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Dasatinib significantly reduced in vivo exposure to cyclosporine in a rat model: The possible involvement of CYP3A induction. Pharmacol Rep. 2019 Apr;71(2):201-205.
3 CYP3A4*18B and CYP3A5*3 polymorphisms contribute to pharmacokinetic variability of cyclosporine among healthy Chinese subjects. Eur J Pharm Sci. 2015 Aug 30;76:238-44.
4 Metabolic Pathway of Cyclosporine A and Its Correlation with Nephrotoxicity
5 CYP3A7, CYP3A5, CYP3A4, and ABCB1 genetic polymorphisms, cyclosporine concentration, and dose requirement in transplant recipients. Ther Drug Monit. 2008 Dec;30(6):689-99.
6 Cyclosporin metabolism in transplant patients
7 High-performance liquid chromatographic method for the simultaneous determination of cyclosporine A and its four major metabolites in whole blood Talanta. 2005 Feb 15;65(3):638-43. doi: 10.1016/j.talanta.2004.07.048.

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