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Details

Stereochemistry ACHIRAL
Molecular Formula C34H52N18O2.4CH4O3S
Molecular Weight 1129.319
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 4
Charge 0

SHOW SMILES / InChI
Structure of SEMAPIMOD MESYLATE

SMILES

CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.CS(O)(=O)=O.C\C(=N/NC(N)=N)C1=CC(=CC(NC(=O)CCCCCCCCC(=O)NC2=CC(=CC(=C2)C(\C)=N\NC(N)=N)C(\C)=N\NC(N)=N)=C1)C(\C)=N\NC(N)=N

InChI

InChIKey=CKWNYVLFZNKVGX-RTQZJKMDSA-N
InChI=1S/C34H52N18O2.4CH4O3S/c1-19(45-49-31(35)36)23-13-24(20(2)46-50-32(37)38)16-27(15-23)43-29(53)11-9-7-5-6-8-10-12-30(54)44-28-17-25(21(3)47-51-33(39)40)14-26(18-28)22(4)48-52-34(41)42;4*1-5(2,3)4/h13-18H,5-12H2,1-4H3,(H,43,53)(H,44,54)(H4,35,36,49)(H4,37,38,50)(H4,39,40,51)(H4,41,42,52);4*1H3,(H,2,3,4)/b45-19+,46-20+,47-21+,48-22+;;;;

HIDE SMILES / InChI

Molecular Formula C34H52N18O2
Molecular Weight 744.8961
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 4
Optical Activity NONE

Molecular Formula CH4O3S
Molecular Weight 96.106
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/27194788

Semapimod (CNI-1493) is a cytokine inhibitor and synthetic guanylhydrazone mitogen-activated protein kinase blocker, is being developed by Cytokine PharmaSciences as a potential treatment for Crohn's disease and other inflammatory conditions. As of December 2001, a phase I study demonstrating the safety of the compound had been completed and phase II trials for psoriasis and Crohn's disease were ongoing. In April 2003, preclinical and early clinical studies were underway for a variety of indications, including congestive heart failure and pancreatitis. Semapimod inhibits activation of p38 MAPK and NF-κB and induction of cyclooxygenase-2 by TLR ligands, but not by IL-1β or stresses. Semapimod inhibits TLR4 signaling (IC50 ≈0.3 umol) and acts by desensitizing cells to LPS; it fails to block responses to LPS concentrations of ≥5 ug/ml. Semapimod had been in phase II clinical trials by Ferring Pharmaceuticals for the treatment of Crohn's disease. However, this research has been discontinued. Semapimod is in phase I clinical trials for the treatment of autoimmune disorders and inflammation.

CNS Activity

Curator's Comment: The neuroprotective effect of Semapimod suggests that CNI-1493 might be a valuable neuroprotective candidate in the future treatment of PD.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
6.2 μg/mL
32 mg/m² single, intravenous
dose: 32 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SEMAPIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3.8 μg/mL
32 mg/m² 1 times / day multiple, intravenous
dose: 32 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
SEMAPIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
432 μg × min/L
32 mg/m² single, intravenous
dose: 32 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SEMAPIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
246 μg × min/mL
32 mg/m² 1 times / day multiple, intravenous
dose: 32 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
SEMAPIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.42 h
32 mg/m² single, intravenous
dose: 32 mg/m²
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SEMAPIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.02 h
32 mg/m² 1 times / day multiple, intravenous
dose: 32 mg/m²
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
SEMAPIMOD plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
16 mg/m2 1 times / day multiple, intravenous
MTD
Dose: 16 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 16 mg/m2, 1 times / day
Co-administed with::
Interleukin-2
Sources: Page: p.489
unhealthy, ADOLESCENT
n = 7
Health Status: unhealthy
Condition: melanoma
Age Group: ADOLESCENT
Sex: M+F
Food Status: UNKNOWN
Population Size: 7
Sources: Page: p.489
60 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 60 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg, 1 times / day
Sources: Page: p,763
unhealthy, ADULT
n = 51
Health Status: unhealthy
Condition: Crohn's disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 51
Sources: Page: p,763
Disc. AE: Infusion site reaction...
AEs leading to
discontinuation/dose reduction:
Infusion site reaction (3.9%)
Sources: Page: p,763
32 mg/m2 1 times / day multiple, intravenous
Studied dose
Dose: 32 mg/m2, 1 times / day
Route: intravenous
Route: multiple
Dose: 32 mg/m2, 1 times / day
Sources: Page: p.489
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: melanoma
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 6
Sources: Page: p.489
AEs

AEs

AESignificanceDosePopulation
Infusion site reaction 3.9%
Disc. AE
60 mg 1 times / day multiple, intravenous
Highest studied dose
Dose: 60 mg, 1 times / day
Route: intravenous
Route: multiple
Dose: 60 mg, 1 times / day
Sources: Page: p,763
unhealthy, ADULT
n = 51
Health Status: unhealthy
Condition: Crohn's disease
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 51
Sources: Page: p,763
PubMed

PubMed

TitleDatePubMed
Identification of cellular deoxyhypusine synthase as a novel target for antiretroviral therapy.
2005 Jan
High-mobility group box 1 protein is an inflammatory mediator in necrotizing enterocolitis: protective effect of the macrophage deactivator semapimod.
2005 Oct
Patents

Sample Use Guides

Semapimod 60 mg IV q 6 - 10 weeks
Route of Administration: Intravenous
Semapimod inhibits degradation of IkBa induced by LPS concentrations up to 1 ug/ml, but is ineffective at 5 ug/ml in IEC-6 cells. Semapimod (2 umol) blocks LPS-induced recruitment of MyD88 to cell surface.
Substance Class Chemical
Created
by admin
on Sat Dec 16 04:53:13 GMT 2023
Edited
by admin
on Sat Dec 16 04:53:13 GMT 2023
Record UNII
8W415THB21
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SEMAPIMOD MESYLATE
Common Name English
SEMAPIMOD TETRAMESYLATE
Common Name English
DECANEDIAMIDE, N1,N10-BIS(3,5-BIS(1-(2-(AMINOIMINOMETHYL)HYDRAZINYLIDENE)ETHYL)PHENYL)-, METHANESULFONATE
Common Name English
Code System Code Type Description
PUBCHEM
72941930
Created by admin on Sat Dec 16 04:53:14 GMT 2023 , Edited by admin on Sat Dec 16 04:53:14 GMT 2023
PRIMARY
DRUG BANK
DBSALT002135
Created by admin on Sat Dec 16 04:53:13 GMT 2023 , Edited by admin on Sat Dec 16 04:53:13 GMT 2023
PRIMARY
CAS
872830-80-3
Created by admin on Sat Dec 16 04:53:13 GMT 2023 , Edited by admin on Sat Dec 16 04:53:13 GMT 2023
NON-SPECIFIC STOICHIOMETRY
FDA UNII
8W415THB21
Created by admin on Sat Dec 16 04:53:14 GMT 2023 , Edited by admin on Sat Dec 16 04:53:14 GMT 2023
PRIMARY
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ACTIVE MOIETY