OXECLOSPORIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C64H115N11O14
Molecular Weight	1262.6632
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

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](COCCO)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](CC)NC1=O)C(C)C

InChI

InChIKey=XZDDMPMZGYEESG-VNHFGJPGSA-N

InChI=1S/C64H115N11O14/c1-24-26-27-42(15)54(78)53-58(82)66-44(25-2)59(83)69(17)34-50(77)70(18)46(30-36(3)4)57(81)68-51(40(11)12)63(87)71(19)47(31-37(5)6)56(80)65-43(16)55(79)67-45(35-89-29-28-76)60(84)72(20)48(32-38(7)8)61(85)73(21)49(33-39(9)10)62(86)74(22)52(41(13)14)64(88)75(53)23/h24,26,36-49,51-54,76,78H,25,27-35H2,1-23H3,(H,65,80)(H,66,82)(H,67,79)(H,68,81)/b26-24+/t42-,43+,44+,45-,46+,47+,48+,49+,51+,52+,53+,54-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C64H115N11O14
Molecular Weight	1262.6632
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	12 / 12
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7669649 | https://www.ncbi.nlm.nih.gov/pubmed/12445861 | https://adisinsight.springer.com/drugs/800002453

Oxeclosporin (previously known as SDZ IMM 125 and now called as tigderimus) was developed as an immunosuppressive drug. It was shown that the drug possessed apoptotic activity via induction of uptake of extracellular calcium. The increased intracellular calcium might directly cause apoptosis by increasing the caspase-3 activity. Oxeclosporin was studied in clinical trials in patients with severe psoriasis. In addition, it was used for the treatment of rheumatoid arthritis and transplant rejection. However, all these studies were discontinued. Besides, oxeclosporin is participating in phase II trials in Europe for the treatment of asthma and in Switzerland for the treatment of cancer. However, information about the further development of this drug is not available.

Originator

Approval Year

PubMed

Title	Date	PubMed
Absorption and disposition of SDZ IMM 125, a new cyclosporine derivative, in rats after single and repeated administration.	1994 Mar-Apr	8013274
Hepatocellular effects of cyclosporine A and its derivative SDZ IMM 125 in vitro.	1998 Mar	9495838
Isolation, identification and immunosuppressive activity of SDZ-IMM-125 metabolites from human liver microsomes.	1999 Jan-Mar	10412896
Induction of apoptosis by the O-hydroxyethyl-D(Ser)(8)-cyclosporine A derivative SDZ IMM 125 in rat hepatocytes.	2000 Apr	10734149
Role of antioxidants in the O-hydroxyethyl-D-(Ser)8-cyclosporine A (SDZ IMM125)-induced apoptosis in rat hepatocytes.	2002 Dec 15	12445861

Patents

Sample Use Guides

In Vivo Use Guide

In this multicentre, double-blind, placebo-controlled study, the efficacy and tolerability of 40, 100, 200 and 400 mg SDZ IMM (OXECLOSPORIN) 125 daily were studied in 59 patients with psoriasis

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:51:57 GMT 2023` Edited by `admin` on `Fri Dec 15 15:51:57 GMT 2023`
Record UNII	R7988D03JM
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

OXECLOSPORIN

Official Name

English

2-[O-(2-Hydroxyethyl)-D-serine]cyclosporin A

Common Name

English

SDZIMM125

Code

English

SDZ-IMM-125

Code

English

IMM125

Code

English

oxeclosporin [INN]

Common Name

English

Oxeclosporin [WHO-DD]

Common Name

English

IMM-125

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C574