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Details

Stereochemistry ACHIRAL
Molecular Formula C31H37N5O3.ClH
Molecular Weight 564.118
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DORAMAPIMOD HYDROCHLORIDE

SMILES

Cl.CC1=CC=C(C=C1)N2N=C(C=C2NC(=O)NC3=CC=C(OCCN4CCOCC4)C5=CC=CC=C35)C(C)(C)C

InChI

InChIKey=WVPYACKQYUYZGC-UHFFFAOYSA-N
InChI=1S/C31H37N5O3.ClH/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);1H

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
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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

Boehringer Ingelheim
130
Curator's Comment: # Boehringer Ingelheim Pharmaceuticals

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
 0.1 nM [Kd]
Inhibitor
8504
 65.0 nM [IC50]
Inhibitor
8504
 0.2 µM [IC50]
Inhibitor
8504
 0.52 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Primary
Phase II
1147
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1108 ng/mL
EXPERIMENT
https://www.jacionline.org/article/S0091-6749(02)82128-5/pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DORAMAPIMOD plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5924 ng × h/mL
EXPERIMENT
https://www.jacionline.org/article/S0091-6749(02)82128-5/pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DORAMAPIMOD plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.1 h
EXPERIMENT
https://www.jacionline.org/article/S0091-6749(02)82128-5/pdf
150 mg 1 times / day steady-state, oral
dose: 150 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
DORAMAPIMOD plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
Ambeed
A103377
http://www.ambeed.com/search/Search.html?keyword=A103377
AOBIOUS INC
AOB1672
http://aobious.com/aobious/search?search_query=AOB1672
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
BioSynth
Q-101419
https://www.biosynth.com/en/products/life-science/other-biochemicals/products/Q-101419
BOC Sciences
285983-48-4
http://www.bocsci.com/description.asp?cas=285983-48-4
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
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
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
mcule
MCULE-9036074972
https://mcule.com/MCULE-9036074972/
mcule
MCULE-9717887012
https://mcule.com/MCULE-9717887012/
MedChem Express
HY-10320
https://www.medchemexpress.com/search.html?q=HY-10320&ft=&fa=&fp=
Molnova
M13869
https://www.molnova.com/en/serch-list.html?keywords=M13869
MolPort
MolPort-006-168-795
https://www.molport.com/shop/molecule-link/MolPort-006-168-795
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
PubMed

PubMed

TitleDatePubMed
Gene expression profiles in engineered cardiac tissues respond to mechanical loading and inhibition of tyrosine kinases.
2013-10
Discovery of a novel class of non-ATP site DFG-out state p38 inhibitors utilizing computationally assisted virtual fragment-based drug design (vFBDD).
2011-12-01
Comprehensive analysis of kinase inhibitor selectivity.
2011-10-30
A possible mechanism for hepatotoxicity induced by BIRB-796, an orally active p38 mitogen-activated protein kinase inhibitor.
2011-10
Activation state-dependent binding of small molecule kinase inhibitors: structural insights from biochemistry.
2010-11-24
Mitogen-activated protein kinase phosphatase-1 negatively regulates the expression of interleukin-6, interleukin-8, and cyclooxygenase-2 in A549 human lung epithelial cells.
2010-04
Role of protein haptenation in triggering maturation events in the dendritic cell surrogate cell line THP-1.
2009-07-15
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.
2007-11-08
P38 mitogen activated protein kinase is involved in the downregulation of granulocyte CXC chemokine receptors 1 and 2 during human endotoxemia.
2004-01
Structure-activity relationships of the p38alpha MAP kinase inhibitor 1-(5-tert-butyl-2-p-tolyl-2H-pyrazol-3-yl)-3-[4-(2-morpholin-4-yl-ethoxy)naph- thalen-1-yl]urea (BIRB 796).
2003-10-23
Inhibition of p38 MAP kinase by utilizing a novel allosteric binding site.
2002-04
Patents

Patents

US20030118575
2
US20070203141
2
WO2005009367A2
2

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 Mon Mar 31 23:18:00 GMT 2025
Edited
by admin
on Mon Mar 31 23:18:00 GMT 2025
Record UNII
X9BAM4UVNT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DORAMAPIMOD HYDROCHLORIDE
Common Name English
UREA, N-(3-(1,1-DIMETHYLETHYL)-1-(4-METHYLPHENYL)-1H-PYRAZOL-5-YL)-N'-(4-(2-(4-MORPHOLINYL)ETHOXY)-1-NAPHTHALENYL)-, HYDROCHLORIDE (1:1)
Preferred Name English
Code System Code Type Description
FDA UNII
X9BAM4UVNT
Created by admin on Mon Mar 31 23:18:00 GMT 2025 , Edited by admin on Mon Mar 31 23:18:00 GMT 2025
PRIMARY
CAS
1283526-53-3
Created by admin on Mon Mar 31 23:18:00 GMT 2025 , Edited by admin on Mon Mar 31 23:18:00 GMT 2025
PRIMARY
PUBCHEM
68107492
Created by admin on Mon Mar 31 23:18:00 GMT 2025 , Edited by admin on Mon Mar 31 23:18:00 GMT 2025
PRIMARY
Related Record Type Details
Structure of DORAMAPIMOD
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of DORAMAPIMOD
ACTIVE MOIETY
NIH
NCATS
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