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Details

Stereochemistry ABSOLUTE
Molecular Formula C27H30ClFN4O3
Molecular Weight 513.004
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TALMAPIMOD

SMILES

C[C@H]1CN([C@H](C)CN1CC2=CC=C(F)C=C2)C(=O)C3=C(Cl)C=C4N(C)C=C(C(=O)C(=O)N(C)C)C4=C3

InChI

InChIKey=ZMELOYOKMZBMRB-DLBZAZTESA-N
InChI=1S/C27H30ClFN4O3/c1-16-13-33(17(2)12-32(16)14-18-6-8-19(29)9-7-18)26(35)21-10-20-22(25(34)27(36)30(3)4)15-31(5)24(20)11-23(21)28/h6-11,15-17H,12-14H2,1-5H3/t16-,17+/m0/s1

HIDE SMILES / InChI
Molecular Formula C27H30ClFN4O3
Molecular Weight 513.004
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Talmapimod is a p38 MAPK kinase inhibitor that inhibits p38 alpha with IC50 value of 9 nM which is 10-times lower then IC50 for p38 beta. Talmapimod was under clinical development for the treatment of Myelodysplastic Syndromes, Multiple Myeloma and Rheumatoid Arthritis (phase II), however, it seems to be discontinued as no longer presents in Janssen's pipeline.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
 9.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
360 mg multiple, oral
Highest studied dose
Dose: 360 mg
Route: oral
Route: multiple
Dose: 360 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
unhealthy, ADULT
n = 17
Health Status: unhealthy
Condition: myelodysplastic syndrome
Age Group: ADULT
Sex: M+F
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
Disc. AE: ALT increased, Atrial fibrillation...
AEs leading to
discontinuation/dose reduction:
ALT increased (5.9%)
Atrial fibrillation (5.9%)
ALT increased (grade 3, 5.9%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
AEs

AEs

AESignificanceDosePopulation
ALT increased 5.9%
Disc. AE
360 mg multiple, oral
Highest studied dose
Dose: 360 mg
Route: oral
Route: multiple
Dose: 360 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
unhealthy, ADULT
n = 17
Health Status: unhealthy
Condition: myelodysplastic syndrome
Age Group: ADULT
Sex: M+F
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
Atrial fibrillation 5.9%
Disc. AE
360 mg multiple, oral
Highest studied dose
Dose: 360 mg
Route: oral
Route: multiple
Dose: 360 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
unhealthy, ADULT
n = 17
Health Status: unhealthy
Condition: myelodysplastic syndrome
Age Group: ADULT
Sex: M+F
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
ALT increased grade 3, 5.9%
Disc. AE
360 mg multiple, oral
Highest studied dose
Dose: 360 mg
Route: oral
Route: multiple
Dose: 360 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
unhealthy, ADULT
n = 17
Health Status: unhealthy
Condition: myelodysplastic syndrome
Age Group: ADULT
Sex: M+F
Population Size: 17
Sources:
https://pubmed.ncbi.nlm.nih.gov/23032694
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P0032B5
https://www.1pchem.com/search?query=1P0032B5
Axon MedChem
1671
https://www.axonmedchem.com/product/1671
BLD Pharm
BD630630
http://www.bldpharm.com/search/Search.html?keyword=BD630630
BOC Sciences
309913-83-5
http://www.bocsci.com/description.asp?cas=309913-83-5
Chem Scene
CS-5645
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-5645
Hairui
HR106412
http://www.hairuichem.com/en/product/search.do?q=HR106412
MedChem Express
HY-10406
https://www.medchemexpress.com/search.html?q=HY-10406&ft=&fa=&fp=
MolPort
MolPort-023-276-837
https://www.molport.com/shop/molecule-link/MolPort-023-276-837
MolPort
MolPort-042-665-734
https://www.molport.com/shop/molecule-link/MolPort-042-665-734
Molnova
M13991
https://www.molnova.com/en/serch-list.html?keywords=M13991
MuseChem
I003096
https://www.musechem.com/product/I003096.html
MuseChem
I012013
https://www.musechem.com/product/I012013.html
Tocris
3528
https://www.tocris.com/search.php?Type=QuickSearch&Value=3528
Toronto Research Chemicals
H972833
https://www.trc-canada.com/product-detail/?CatNum=H972833
Toronto Research Chemicals
L487913
https://www.trc-canada.com/product-detail/?CatNum=L487913
Toronto Research Chemicals
T005540
https://www.trc-canada.com/product-detail/?CatNum=T005540
Toronto Research Chemicals
T005550
https://www.trc-canada.com/product-detail/?CatNum=T005550
eMolecules
275056809
https://orderbb.emolecules.com/search/#?query=275056809
eMolecules
275092015
https://orderbb.emolecules.com/search/#?query=275092015
eMolecules
300491795
https://orderbb.emolecules.com/search/#?query=300491795
eMolecules
300492051
https://orderbb.emolecules.com/search/#?query=300492051
eMolecules
36745704
https://orderbb.emolecules.com/search/#?query=36745704
mcule
MCULE-4653964554
https://mcule.com/MCULE-4653964554/
PubMed

PubMed

TitleDatePubMed
Patents

Patents

20030092717
2
20030144520
2
20030158417
2
20030162970
2
20030195355
2

Sample Use Guides

In Vivo Use Guide
Myelodysplastic Syndromes: tablets should be administered orally at a dose of 30, 60, 90 or 120 mg thrice daily for 16 weeks. Multiple Myeloma: two 30-mg capsules three times daily. Rheumatoid Arthritis: 30 mg, 60 mg, 90 mg administered dailly for 30 days or 60 mg for one week followed by 120 for one week followed by 180 mg for two weeks.
Route of Administration: Oral
In Vitro Use Guide
Bone marrow mononuclear cells (BMMNC) (1 × 10(6)) were cultured in the absence or presence of increasing concentrations of talmapimod (0, 10, 20, 50, 100, 500 nM) for 24h without or with 10 ng/mL LPS. The drug was shown to potently inhibit the secretion of TNFalpha from both basal or LPS-induced cell cultures with an IC50 of 50 nM.
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:03:03 GMT 2023
Edited
by admin
on Sat Dec 16 18:03:03 GMT 2023
Record UNII
B1E00KQ6NT
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TALMAPIMOD
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
TALMAPIMOD [USAN]
Common Name English
Talmapimod [WHO-DD]
Common Name English
talmapimod [INN]
Common Name English
SCIO 469
Code English
SCIO-469
Code English
2-[6-Chloro-5-[[(2R,5S)-4-(4-fluorobenzyl)-2,5-dimethylpiperazin-1-yl]carbonyl]-1-methyl-1H-indol-3-yl]-N,N-dimethyl-2-oxoacetamide
Systematic Name English
1H-INDOLE-3-ACETAMIDE, 6-CHLORO-5-(((2R,5S)-4-((4-FLUOROPHENYL)METHYL)-2,5-DIMETHYL-1-PIPERAZINYL)CARBONYL)-N,N,1-TRIMETHYL-.ALPHA.-OXO-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C2149
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
NCI_THESAURUS C129825
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
Code System Code Type Description
SMS_ID
100000174942
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
USAN
SS-75
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
PUBCHEM
9871074
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL514201
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
CAS
309913-83-5
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
FDA UNII
B1E00KQ6NT
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
NCI_THESAURUS
C79841
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
INN
8957
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID10953119
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
CHEBI
90683
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
DRUG BANK
DB05412
Created by admin on Sat Dec 16 18:03:03 GMT 2023 , Edited by admin on Sat Dec 16 18:03:03 GMT 2023
PRIMARY
Related Record Type Details
MITOGEN-ACTIVATED PROTEIN KINASE 14
TARGET -> INHIBITOR
MITOGEN-ACTIVATED PROTEIN KINASE 11
TARGET -> INHIBITOR
Structure of TALMAPIMOD HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of TALMAPIMOD
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