DORAMAPIMOD

Details

Stereochemistry	ACHIRAL
Molecular Formula	C31H37N5O3
Molecular Weight	527.6572
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=C(C=C1)N2N=C(C=C2NC(=O)NC3=CC=C(OCCN4CCOCC4)C5=C3C=CC=C5)C(C)(C)C

InChI

InChIKey=MVCOAUNKQVWQHZ-UHFFFAOYSA-N

InChI=1S/C31H37N5O3/c1-22-9-11-23(12-10-22)36-29(21-28(34-36)31(2,3)4)33-30(37)32-26-13-14-27(25-8-6-5-7-24(25)26)39-20-17-35-15-18-38-19-16-35/h5-14,21H,15-20H2,1-4H3,(H2,32,33,37)

HIDE SMILES / InChI

Molecular Formula	C31H37N5O3
Molecular Weight	527.6572
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11896401
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15755732 | https://www.ncbi.nlm.nih.gov/pubmed/11937566 | https://trials.boehringer-ingelheim.com/trial_results/clinical_trials_overview/clinical_trial_result.c=n.i=68.html

Doramapimod (BIRB-796) is a p38 MAPK inhibitor, relatively potent against alpha isoform. Oral doramapimod exerts anti-inflammatory potential in humans in vivo. Doramapimod has entered clinical trials for the treatment of autoimmune diseases.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
MAP kinase p38 alpha 35 Target ID: CHEMBL260 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11896401 \| https://www.ncbi.nlm.nih.gov/pubmed/15755732	Inhibitor 8297	0.1 nM [Kd]
MAP kinase p38 beta 11 Target ID: CHEMBL3961 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15755732	Inhibitor 8297	65.0 nM [IC50]
MAP kinase p38 gamma 2 Target ID: CHEMBL4674 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15755732	Inhibitor 8297	0.2 µM [IC50]
MAP kinase p38 delta 2 Target ID: CHEMBL2939 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15755732	Inhibitor 8297	0.52 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316 Sources: https://trials.boehringer-ingelheim.com/trial_results/clinical_trials_overview/clinical_trial_result.c=n.i=68.html https://clinicaltrials.gov/ct2/show/NCT02209779	Primary	Phase II 1132	Unknown Approved Use Unknown
Crohn's disease 42 Sources: https://trials.boehringer-ingelheim.com/trial_results/clinical_trials_overview/clinical_trial_result.c=n.i=68.html https://clinicaltrials.gov/ct2/show/NCT02209792	Primary	Phase II 1132	Unknown Approved Use Unknown
Psoriasis 84 Sources: https://trials.boehringer-ingelheim.com/trial_results/clinical_trials_overview/clinical_trial_result.c=n.i=68.html https://clinicaltrials.gov/ct2/show/NCT02209753	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P002W9Z	https://www.1pchem.com/search?query=1P002W9Z
A2B Chem	AB34343	http://a2bchem.com/prod/AB34343
AK Scientific	X7401	https://aksci.com/item_detail.php?cat=X7401
AOBIOUS INC	AOB1672	http://aobious.com/aobious/search?search_query=AOB1672
Ambeed	A103377	http://www.ambeed.com/search/Search.html?keyword=A103377
ApexBio Technology	A5639	https://www.apexbt.com/catalogsearch/result/?q=A5639
AstaTech	41137	http://astatechinc.com/CPSResult.php?CRNO=41137
Axon MedChem	1358	https://www.axonmedchem.com/product/1358
BOC Sciences	285983-48-4	http://www.bocsci.com/description.asp?cas=285983-48-4
BioSynth	Q-101419	https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-101419
Capot Chemical	18416	https://www.capotchem.com/search.do?q=18416
Cayman Chemical	10460	http://www.caymanchem.com/app/template/Product.vm/catalog/10460
Chem Scene	CS-0219	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0219
ChemShuttle	129033	https://www.chemshuttle.com/catalogsearch/result/?q=129033
Combi-Blocks	QJ-3549	http://www.combi-blocks.com/cgi-bin/find.cgi?QJ-3549
Hairui	HR114596	http://www.hairuichem.com/en/product/search.do?q=HR114596
KeyOrganics	AS-19375	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-19375
Lab Seeker	SC-19868	http://www.labseeker.com/search.php?keywords=SC-19868&category=0
LabSeeker	SC-19868	http://www.labseeker.com/search.php?keywords=SC-19868&category=0
Matrix Scientific	90569	http://www.matrixscientific.com/090569.html
MedChem Express	HY-10320	https://www.medchemexpress.com/search.html?q=HY-10320&ft=&fa=&fp=
MolPort	MolPort-006-168-795	https://www.molport.com/shop/molecule-link/MolPort-006-168-795
Molnova	M13869	https://www.molnova.com/en/serch-list.html?keywords=M13869
MuseChem	I002974	https://www.musechem.com/product/I002974.html
Nanjing Raymon Biotech Co Ltd	R0013R	http://www.raymonbio.com/en/search.html?key=R0013R&type=code
ShangHai Biochempartner	BCP000174	http://www.biochempartner.com/search_BCP000174
ShangHai Biochempartner	BCP01896	http://www.biochempartner.com/search_BCP01896
TargetMol	T6277	https://www.targetmol.com/search?keyword=T6277
Tetrahedron	TS93639	http://www.thsci.com/search.do?q=TS93639
Toronto Research Chemicals	A633357	https://www.trc-canada.com/product-detail/?CatNum=A633357
Toronto Research Chemicals	D534250	https://www.trc-canada.com/product-detail/?CatNum=D534250
eMolecules	85163665	https://orderbb.emolecules.com/search/#?query=85163665
eMolecules	901477	https://orderbb.emolecules.com/search/#?query=901477
eNovation Chemicals	D501848	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D501848&searchbtn.x=0&searchbtn.y=0
mcule	MCULE-9036074972	https://mcule.com/MCULE-9036074972/
mcule	MCULE-9717887012	https://mcule.com/MCULE-9717887012/

PubMed

Title	Date	PubMed
		252160078
The role of IFN-gamma in regulation of IFN-gamma-inducible protein 10 (IP-10) expression in lung epithelial cell and peripheral blood mononuclear cell co-cultures.	2007 Nov 8	17996064
Discovery of a novel class of non-ATP site DFG-out state p38 inhibitors utilizing computationally assisted virtual fragment-based drug design (vFBDD).	2011 Dec 1	22014550
A possible mechanism for hepatotoxicity induced by BIRB-796, an orally active p38 mitogen-activated protein kinase inhibitor.	2011 Oct	21328587

Patents

Sample Use Guides

In Vivo Use Guide

A randomised, parallel, double-blind, placebo-controlled study investigated efficacy and safety of different doses (5, 10, 20 and 30 mg) of doramapimod (BIRB-796) administered twice a day orally over 4 weeks in patients with active rheumatoid arthritis

Route of Administration: Oral

In Vitro Use Guide

1-1000 nM doramapimod (BIRB-796) inhibited LPS-induced phosphorylation of p38 MAPK in human peripheral blood mononuclear cells in a dose-related fashion

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:40:45 GMT 2023` Edited by `admin` on `Fri Dec 15 15:40:45 GMT 2023`
Record UNII	HO1A8B3YVV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DORAMAPIMOD

Official Name

English

doramapimod [INN]

Common Name

English

Doramapimod [WHO-DD]

Common Name

English

UREA, N-(3-(1,1-DIMETHYLETHYL)-1-(4-METHYLPHENYL)-1H-PYRAZOL-5-YL)-N'-(4-(2-(4-MORPHOLINYL)ETHOXY)-1-NAPHTHALENYL)-

Systematic Name

English

BIRB-796

Code

English

BIRB-796 BS

Code

English

BIRB 796 BS

Code

English

1-[3-(1,1-Dimethylethyl)-1-(4-methylphenyl)-1H-pyrazol-5-yl]-3-[4-[2-(morpholin-4-yl)ethoxy]naphthalen-1-yl]urea

Systematic Name

English

DORAMAPIMOD [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2149