Drug Information

General Information
Drug ID
DR00448
Drug Name
Cyclosporine
Synonyms
cyclosporin A; cyclosporine; Ciclosporin; Cyclosporine A; Ciclosporine; Neoral; Cyclosporin; Ciclosporinum; Ciclosporina; Sandimmune; Equoral; Neoplanta; Sandimmun; Sang-35; Gengraf; Sandimmun Neoral; UNII-83HN0GTJ6D; Antibiotic S 7481F1; Consupren; Restasis; Ramihyphin A; SangCyA; MFCD00274558; 83HN0GTJ6D; MLS001333756; CSA; S-Neoral; Cipol N; Sigmasporin Microoral; Sang 35; DSSTox_CID_365; Ciclosporinum [INN-Latin]; Ciclosporine [INN-French]; Ciclosporina [INN-Spanish]; DSSTox_RID_75541; Ciclosporin (Ciclosporin A)
Drug Type
Small molecular drug
Indication Xerophthalmia [ICD11:5B55.Y] Approved [1]
Therapeutic Class
Immunosuppressive Agents
Structure
3D MOL 2D MOL
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
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
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
XLogP
7.5
PubChem CID
5284373
PubChem SID
127280714 ,127280715 ,127280716 ,127280717 ,127280718 ,127280719 ,127280720 ,127280721 ,127280722 ,127280723 ,127280724 ,127280725 ,127280726 ,127280727 ,127280728 ,127280729 ,127280730 ,127280731 ,127280732 ,127300898 ,127300899 ,127300900 ,127300901 ,127300902 ,127300903 ,127300904 ,127300905 ,127300906 ,127300907 ,127300908 ,127300909 ,127300910 ,127300911 ,127300912 ,127300913 ,127300914 ,137018976 ,226407640
ChEBI ID
ChEBI:4031
TTD Drug ID
D0O3YF
DT(s) Transporting This Drug BCRP Transporter Info Breast cancer resistance protein Substrate [2]
MRP2 Transporter Info Multidrug resistance-associated protein 2 Substrate [3]
P-GP Transporter Info P-glycoprotein 1 Substrate [4]
Drug-Transporter Activity Data
Drug-Transporter Activity Data P-GP Transporter Info Km =0.17 microM High five cells-MDR1 [5]
P-GP Transporter Info Km =3.8 microM Human enterocyte-like 2 cells (Caco-2)-MDR1 [6]
P-GP Transporter Info Km =8.4 microM LLC-PK1 cells-MDR1 [7]
References
1 Cyclosporine was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019)
2 Mammalian drug efflux transporters of the ATP binding cassette (ABC) family in multidrug resistance: A review of the past decade. Cancer Lett. 2016 Jan 1;370(1):153-64.
3 Is cyclosporine A transport inhibited by pravastatin via multidrug resistant protein 2? Eur J Clin Pharmacol. 2010 Feb;66(2):153-8.
4 Contribution of down-regulation of intestinal and hepatic cytochrome P450 3A to increased absorption of cyclosporine A in a rat nephrosis model. J Pharmacol Exp Ther. 2008 Nov;327(2):592-9.
5 Comparative studies on in vitro methods for evaluating in vivo function of MDR1 P-glycoprotein. Pharm Res. 2001 Dec;18(12):1660-8.
6 Relevance of p-glycoprotein for the enteral absorption of cyclosporin A: in vitro-in vivo correlation. Br J Pharmacol. 1996 Aug;118(7):1841-7. Clinical Trial
7 Human P-glycoprotein transports cyclosporin A and FK506. J Biol Chem. 1993 Mar 25;268(9):6077-80.

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