DIRUCOTIDE ACETATE

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C92H141N25O26.4C2H4O2
Molecular Weight	2253.4637
Optical Activity	UNSPECIFIED
Defined Stereocenters	20 / 20
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(O)=O.CC(O)=O.CC(O)=O.CC(O)=O.CC[C@H](C)[C@H](NC(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCCCN)NC(=O)[C@H](CC1=CC=CC=C1)NC(=O)[C@H](CC2=CC=CC=C2)NC(=O)[C@H](CC3=CNC=N3)NC(=O)[C@@H](NC(=O)[C@@H](NC(=O)[C@@H]4CCCN4C(=O)[C@H](CC(N)=O)NC(=O)[C@H](CCC(O)=O)NC(=O)[C@@H](N)CC(O)=O)C(C)C)C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H]([C@@H](C)O)C(=O)N5CCC[C@H]5C(=O)N[C@@H](CCCNC(N)=N)C(=O)N[C@@H]([C@@H](C)O)C(O)=O

InChI

InChIKey=AGWHZYPHHINWPT-WPDHDECSSA-N

InChI=1S/C92H141N25O26.4C2H4O2/c1-11-48(8)72(88(139)112-71(47(6)7)87(138)114-73(49(9)118)90(141)117-36-22-29-63(117)83(134)104-56(28-20-34-100-92(97)98)78(129)115-74(50(10)119)91(142)143)113-82(133)61(41-65(95)120)107-76(127)55(27-18-19-33-93)103-79(130)58(37-51-23-14-12-15-24-51)105-80(131)59(38-52-25-16-13-17-26-52)106-81(132)60(39-53-43-99-44-101-53)108-85(136)69(45(2)3)111-86(137)70(46(4)5)110-84(135)64-30-21-35-116(64)89(140)62(42-66(96)121)109-77(128)57(31-32-67(122)123)102-75(126)54(94)40-68(124)125;4*1-2(3)4/h12-17,23-26,43-50,54-64,69-74,118-119H,11,18-22,27-42,93-94H2,1-10H3,(H2,95,120)(H2,96,121)(H,99,101)(H,102,126)(H,103,130)(H,104,134)(H,105,131)(H,106,132)(H,107,127)(H,108,136)(H,109,128)(H,110,135)(H,111,137)(H,112,139)(H,113,133)(H,114,138)(H,115,129)(H,122,123)(H,124,125)(H,142,143)(H4,97,98,100);4*1H3,(H,3,4)/t48-,49+,50+,54-,55-,56-,57-,58-,59-,60-,61-,62-,63-,64-,69-,70-,71-,72-,73-,74-;;;;/m0..../s1

HIDE SMILES / InChI

Molecular Formula	C92H141N25O26
Molecular Weight	2013.2558
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	20 / 20
E/Z Centers	8
Optical Activity	UNSPECIFIED

Molecular Formula	C2H4O2
Molecular Weight	60.052
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.mstrust.org.uk/a-z/dirucotide-mbp8298 | https://investor.lilly.com/news-releases/news-release-details/dirucotide-does-not-meet-primary-endpoint-phase-iii-maestro-01 | http://www.io.nihr.ac.uk/report/dirucotide-mbp-8298-for-secondary-progressive-multiple-sclerosis-spms/

Dirucotide (MBP 8298) is a synthetic myelin basic protein (MBP) peptide designed to decrease type 2 helper T cells (TH2)-mediated B-cell signalling of auto-reactive T-cells thereby reducing the production of specific antibodies that target endogenous MBP. MBP is the dominant site of attack in patients with multiple sclerosis and haplotype (HLA) DR2 or DR4. Dirucotide did not meet the primary endpoint of delaying disease progression, as measured by the Expanded Disability Status Scale (EDSS), during the two-year MAESTRO-01 Phase III trial in patients with secondary progressive multiple sclerosis (SPMS). In addition, there were no statistically significant differences between dirucotide and placebo on the secondary endpoints of the study. After disappointing trial results, development of the drug was ended in 2009.

Approval Year

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:50:09 GMT 2025` Edited by `admin` on `Mon Mar 31 18:50:09 GMT 2025`
Record UNII	48G1L28581
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIRUCOTIDE ACETATE

Official Name

English

SF-328

Preferred Name

English

SF328

Code

English

L-THREONINE, L-.ALPHA.-ASPARTYL-L.ALPHA.-GLUTAMYL-L-ASPARAGINYL-L-PROLYL-L-VALYL-L-VALYL-L-HISTIDYL-L- PHENYLALANYL-L-PHENYLALANYL-L-LYSYL-L-ASPARAGINYL-L-ISOLEUCYL-L-VALYL-L-THREONYL-L-PROLYL- L-ARGINYL-, TETRAACETATE (SALT)

Common Name

English

Dirucotide acetate [WHO-DD]

Common Name

English

DIRUCOTIDE ACETATE [USAN]

Common Name

English

HUMAN MYELIN BASIC PROTEIN-(216-232)-PEPTIDE (MAJOR 18.5 KDA ISOFORM-(82-98)- PEPTIDE) TETRAACETATE (SALT)

Common Name

English

Code System Code Type Description

CAS

781666-30-6