Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C34H52N18O2 |
| Molecular Weight | 744.8961 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 4 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
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=PWDYHMBTPGXCSN-VCBMUGGBSA-N
InChI=1S/C34H52N18O2/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/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)/b45-19+,46-20+,47-21+,48-22+
| 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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/14758776 | http://adisinsight.springer.com/drugs/800007268Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/27194788
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14758776 | http://adisinsight.springer.com/drugs/800007268
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23147695 | https://www.ncbi.nlm.nih.gov/pubmed/21593565
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
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
6.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11297238 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11297238 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
432 μg × min/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11297238 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11297238 |
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.42 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11297238 |
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 EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11297238 |
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
| Dose | Population | Adverse 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
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
Sample Use Guides
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 18:30:01 UTC 2023
by
admin
on
Fri Dec 15 18:30:01 UTC 2023
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| Record UNII |
9SGW2H1K8P
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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Code | English |
| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C2149
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| Code System | Code | Type | Description | ||
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SEMAPIMOD
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DTXSID70870333
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5745214
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100000175237
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9SGW2H1K8P
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8349
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C96535
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CHEMBL2107779
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DB12094
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352513-83-8
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C097256
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SALT/SOLVATE -> PARENT |
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TARGET -> INHIBITOR |
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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TARGET -> AGONIST |
CNI-1493 was found to be effective for resolving of endotoxic shock in a rat model. In a clinical trial, CNI-1493 was examined as a drug for the treatment of Crohn’s disease, a disease associated with inflammation. The investigators reported no plausible effect for CNI-1493 single and 3 day dosing. However, cumulative dosing brings some positive effects to Crohn’s disease therapy.
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ACTIVE MOIETY |
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