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Doramapimod

CAS No.
285983-48-4
Chemical Name:
Doramapimod
Synonyms
BIRB 796 (DoraMapiMod);CS-379;CS-1863;BIBR-796;BIRB 796;BIRB 796BS;doramapimod;BIRB-796;BIRB796;DoraMapin BIBR796;BIBR-796(DoraMapiMod)
CBNumber:
CB2855127
Molecular Formula:
C31H37N5O3
Molecular Weight:
527.66
MDL Number:
MFCD09752957
MOL File:
285983-48-4.mol
Last updated:2025-07-24 18:13:48

Doramapimod Properties

Melting point 142-143 °C
Boiling point 631.6±55.0 °C(Predicted)
Density 1.20±0.1 g/cm3(Predicted)
storage temp. Sealed in dry,Store in freezer, under -20°C
solubility Soluble in DMSO (up to 50 mg/ml) or in Ethanol (up to 30 mg/ml).
pka 13.47±0.70(Predicted)
form solid
color White or off-white
Stability Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 2 months.
FDA UNII HO1A8B3YVV
UNSPSC Code 12352200
NACRES NA.77

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H319-H335-H302+H312+H332-H315
Precautionary statements  P301+P312-P302+P352-P305+P351+P338
HS Code  2934999090

Doramapimod price More Price(55)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 506172 p38 MAP Kinase Inhibitor X, BIRB 796 - CAS 285983-48-4 - Calbiochem 285983-48-4 10mg $172 2024-03-01 Buy
Cayman Chemical 10460 Doramapimod ≥98% 285983-48-4 1mg $26 2024-03-01 Buy
Cayman Chemical 10460 Doramapimod ≥98% 285983-48-4 5mg $50 2024-03-01 Buy
Cayman Chemical 10460 Doramapimod ≥98% 285983-48-4 10mg $87 2024-03-01 Buy
Cayman Chemical 10460 Doramapimod ≥98% 285983-48-4 25mg $153 2024-03-01 Buy
Product number Packaging Price Buy
506172 10mg $172 Buy
10460 1mg $26 Buy
10460 5mg $50 Buy
10460 10mg $87 Buy
10460 25mg $153 Buy

Doramapimod Chemical Properties,Uses,Production

Description

Doramapimod (285983-48-4) potently and selectively inhibits p38 MAPK by simultaneously binding to the ATP-binding domain and an allosteric site.1?(IC50=18 nM). Displays anti-inflammatory activity2?but differential effects on inflammatory genes3. Cell permeable.

Chemical Properties

Pale Beige Solid

Uses

Doramapimod is a highly potent inhibitor of p38 mitogen-activated protein kinase (MAPK). Doramapimod is a potential agent for the treatment of inflammatory diseases. Doramapimod blocks baseline and bortezomib-triggered upregulation of p38 MAPK and Hsp27 phosphorylation leading to enhanced cytotoxicity and caspase activation.

Definition

ChEBI: A member of the class of pyrazoles that is an immunomodulator used for treatment of rheumatoid arthritis, Crohn's disease and psoriasis.

Synthesis

2,2,2-trichloroethyl 3-tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-ylcarbamate

317806-87-4

4-[2-(4-NITRONAPHTHALEN-1-YLOXY)ETHYL]MORPHOLINE

317806-88-5

Doramapimod

285983-48-4

Step 4 Synthesis of 1-(3-tert-butyl-1-tosyl-1H-pyrazol-5-yl)-3-(4-(2-morpholinoethoxy)naphthalen-1-yl)urea (Compound 4): to a mixed solution of 4-(2-((4-nitronaphthalen-1-yl)oxy)ethyl)morpholine (11.18 g, 36.9 mmol) in methanol (90 mL) and THF (30 mL) , 5% palladium/activated carbon (0.500 g) was added. The resulting mixture was stirred at room temperature in a hydrogen atmosphere for 23 hours. Upon completion of the reaction, the insoluble material was removed by filtration and the solvent was evaporated under reduced pressure. The resulting residue was mixed with 2,2,2-trichloroethyl (3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)carbamate (16.1 g, 39.7 mmol), N,N-diisopropylethylamine (8.50 mL) and DMSO (30 mL) and stirred at 60 °C for 18 hours. After completion of the reaction, the reaction solution was cooled to room temperature and saturated brine was added. The aqueous layer was extracted with ethyl acetate and the organic phase was dried with anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate/hexane=50/50 to ethyl acetate/methanol=90/10) to afford 13.58 g of the target product 1-(3-(tert-butyl)-1-(p-tolyl)-1H-pyrazol-5-yl)-3-(4-(2-morpholinoethoxy)naphthalen-1-yl)urea in 69% yield.

in vitro

birb 796 is a picomolar inhibitor of human p38 map kinase with a 12,000-fold increase in binding affinity. moreover, birb 796 behavors as one of the most potent and slowest dissociating human p38 map kinase inhibitors now known [1].

in vivo

in a lps-stimulated tnf-α synthesis mouse model, a 65% inhibition of tnf-α synthesis was observed when birb 796 was dosed orally at 10 mg/kg. in a model of established collagen-induced arthritis using b10.riii mice, birb 796 showed a 63% inhibition of arthritis severity when dosed orally at 30 mg/kg qd [2].

storage

Store at -20°C

References

1) Pargellis?et al. (2002),?Inhibition of p38 MAP kinase by utilizing a novel allosteric binding site; Nat. Struct. Biol.,?9?268 2) Branger?et al.?(2002),?Anti-inflammatory effects of a p38 mitogen-activated protein kinase inhibitor during human endotoxemia; J. Immunol.,?168?4070 3) Joos?et al. (2010),?Differential effects of p38MAP kinase inhibitors on the expression of inflammation-associated genes in primary, interleukin-1 beta-stimulated human chondrocytes; Br. J. Pharmacol.,?160?1252

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View Lastest Price from Doramapimod manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Doramapimod pictures 2025-04-04 Doramapimod
285983-48-4
US $0.00-0.00 / kg 1kg 98% 1Ton Henan Aochuang Chemical Co.,Ltd.
Doramapimod pictures 2021-07-13 Doramapimod
285983-48-4
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
Doramapimod pictures 2021-07-10 Doramapimod
285983-48-4
US $15.00-10.00 / KG 1KG 99%+ HPLC Monthly supply of 1 ton Zhuozhou Wenxi import and Export Co., Ltd
  • Doramapimod pictures
  • Doramapimod
    285983-48-4
  • US $0.00-0.00 / kg
  • 98%
  • Henan Aochuang Chemical Co.,Ltd.
  • Doramapimod pictures
  • Doramapimod
    285983-48-4
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd
  • Doramapimod pictures
  • Doramapimod
    285983-48-4
  • US $15.00-10.00 / KG
  • 99%+ HPLC
  • Zhuozhou Wenxi import and Export Co., Ltd

Doramapimod Spectrum

1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholinoethoxy)-1-naphthyl]urea 1-[5-tert-butyl-2-(4-methylphenyl)pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea BIRB 796; BIRB-796; BIRB796; CS-379 BIRB 796 - BIRB 0796 | Doramapimod CS-1863 BIBR-796 1-(3-tert-butyl-1-p-tolyl-1H-pyrazol-5-yl)-3-(4-(2-morpholinoethoxy)naphthalen-1-yl)urea DoraMapiMod, BIBR-796 BIBR-796(DoraMapiMod) BIRB 796 (DoraMapiMod) BIRB 796BS N-[3-(1,1-DiMethylethyl)-1-(4-Methylphenyl)-1H-pyrazol-5-yl]-N'-[4-[2-(4-Morpholinyl)ethoxy]-1-naphthalenyl]urea DoraMapin BIBR796 DoraMapiMod (BIRB-796) BIRB 796 doramapimod Urea, N-[3-(1,1-dimethylethyl)-1-(4-methylphenyl)-1H-pyrazol-5-yl]-N'-[4-[2-(4-morpholinyl)ethoxy]-1-naphthalenyl]- 1-[2-(4-Methylphenyl)-5-tert-butyl-pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea BIRB 796 (Doramapimod) Doramapimod 1-(3-(1,1-Dimethylethyl)-1-(4-methylphenyl)-1H-pyrazol-5-yl)-3-(4-(2-(morpholin-4-yl)ethoxy)naphthalen-1-yl)urea DORAMAPIMOD;BIRB 796;BIRB796 3-[3-Tert-butyl-1-(4-methylphenyl)-1H-pyrazol-5-yl]-1-{4-[2-(morpholin-4-yl)ethoxy]naphthalen-1-yl}urea 1-[2-(4-methylphenyl)-5-tert-butyl-pyrazol-3-yl]-3-[4-(2-morpholin-4-ylethoxy)naphthalen-1-yl]urea 1-(3-(1,1-dimethylethyl)-1-(4-methylphenyl)-1h-pyrazol-5-yl)-3-(4-(2-(morpholin-4-yl)ethoxy)naphthalen-1-yl)urea BIRB-796;BIRB796 Doramapimod USP/EP/BP p38 MAP Kinase Inhibitor X BIRB-796 Doramapimod 1-[3-(tert-Butyl)-1-(p-tolyl)-5-pyrazolyl]-3-[4-(2-morpholinoethoxy)-1-naphthyl]urea Doramapimod, p38 MAPK inhibitor Doramapimod, 10 mM in DMSO 285983-48-4 C31H37N5O3 Anti-cancer&immunity Aromatics Heterocycles Intermediates & Fine Chemicals Pharmaceuticals Protein Kinase Inhibitors and Activators MAPK Inhibitors