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Details

Stereochemistry ABSOLUTE
Molecular Formula C63H113N11O12
Molecular Weight 1216.6378
Optical Activity UNSPECIFIED
Defined Stereocenters 12 / 12
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of GECLOSPORIN

SMILES

[H][C@@]1([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)C(=O)[C@H](CCC)NC1=O)C(C)C

InChI

InChIKey=ZMKGDQSIRSGUDJ-VSROPUKISA-N
InChI=1S/C63H113N11O12/c1-25-27-29-41(15)53(76)52-57(80)66-44(28-26-2)59(82)68(18)34-49(75)69(19)45(30-35(3)4)56(79)67-50(39(11)12)62(85)70(20)46(31-36(5)6)55(78)64-42(16)54(77)65-43(17)58(81)71(21)47(32-37(7)8)60(83)72(22)48(33-38(9)10)61(84)73(23)51(40(13)14)63(86)74(52)24/h25,27,35-48,50-53,76H,26,28-34H2,1-24H3,(H,64,78)(H,65,77)(H,66,80)(H,67,79)/b27-25+/t41-,42+,43-,44+,45+,46+,47+,48+,50+,51+,52+,53-/m1/s1

HIDE SMILES / InChI

Molecular Formula C63H113N11O12
Molecular Weight 1216.6378
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 12 / 12
E/Z Centers 1
Optical Activity UNSPECIFIED

Geclosporin (Cyclosporine) is an immunosuppressive agent, that is used to prevent rejection of a transplanted organ by the body. Geclosporin is isolated from a fungus, Beauveria nivea, and was first discovered in 1970. By suppressing the immune system, this drug prevents white blood cells from rejecting the transplanted organ. Geclosporin primarily does this by suppressing T cells and T cell cytokine production, but also acts in other ways, for example by inhibiting growth and activation of B cells and antigen presenting cells, and by reducing antibody production. Geclosporin is usually combined with other compounds, and has been studied as potential treatment for a large range of disorders. It is used for the treatment of several other conditions, such as severe recalcitrant plaque psoriasis, severe active rheumatoid artritis, and to prevent rejection of donor cells as a result of bone marrow transplantation. Relapse after discontinuation of this compound is to be expected, and therefore, patients should receive maintenance therapy at the lowest effective dosage. The most common adverse events are hypertrichosis, gingival hyperplasia, and neurological and gastrointestinal effects. Renal dysfunction is also possible, but irreversible damage is rare.

Approval Year

PubMed

PubMed

TitleDatePubMed
Characterization of anti-Toxoplasma activity of SDZ 215-918, a cyclosporin derivative lacking immunosuppressive and peptidyl-prolyl-isomerase-inhibiting activity: possible role of a P glycoprotein in Toxoplasma physiology.
1997 Sep
Inhibition of vaccinia virus replication by cyclosporin A analogues correlates with their affinity for cellular cyclophilins.
1998 Feb
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 18:54:23 UTC 2023
Edited
by admin
on Fri Dec 15 18:54:23 UTC 2023
Record UNII
UA3JNW70T9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GECLOSPORIN
INN  
INN  
Official Name English
CYCLOSPORIN G [MI]
Common Name English
SDZ37325
Code English
CYCLOSPORINE G
Common Name English
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-NORVALYL-N-METHYLGLYCYL-N-METHYL-L-LEUCYL-L-VALYL-N-METHYL-L-LEUCYL)
Systematic Name English
CYCLOSPORIN A, 7-L-NORVALINE-
Common Name English
OG37325
Code English
CYCLOSPORIN-G
Common Name English
CYCLO(((2S,3R,4R,6E)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOYL)-L-NORVALYL-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)
Systematic Name English
OG-37-325
Code English
geclosporin [INN]
Common Name English
CYCLO((2S,3R,4R,6E)-3-HYDROXY-4-METHYL-2-(METHYLAMINO)-6-OCTENOYL-L-NORVALYL-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)
Systematic Name English
CYCLOSPORIN G
MI  
Common Name English
SDZ-37-325
Code English
Code System Code Type Description
CAS
74436-00-3
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
ChEMBL
CHEMBL2107422
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
MESH
C045571
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
MERCK INDEX
m4020
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY Merck Index
INN
7182
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
EVMPD
SUB07887MIG
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
PUBCHEM
6475296
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
SMS_ID
100000084518
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
FDA UNII
UA3JNW70T9
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
NCI_THESAURUS
C170024
Created by admin on Fri Dec 15 18:54:23 UTC 2023 , Edited by admin on Fri Dec 15 18:54:23 UTC 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY