Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C14H12N6O |
| Molecular Weight | 280.2847 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@@H]1CC(=O)NN=C1C2=CC=C(NN=C(C#N)C#N)C=C2
InChI
InChIKey=WHXMKTBCFHIYNQ-SECBINFHSA-N
InChI=1S/C14H12N6O/c1-9-6-13(21)19-20-14(9)10-2-4-11(5-3-10)17-18-12(7-15)8-16/h2-5,9,17H,6H2,1H3,(H,19,21)/t9-/m1/s1
Levosimendan (Simdax) is a novel intravenous agent that exerts inotropic effects through sensitization of myofilaments to calcium and vasodilator effects by binding to cardiac troponin C in a calcium-dependent manner. It also has a vasodilatory effect, by opening adenosine triphosphate (ATP)-sensitive potassium channels in vascular smooth muscle to cause smooth muscle relaxation. Unlike other calcium sensitizing compounds, the binding of levosimendan is highly dependent on the intracellular concentration of calcium, such that calcium sensitivity is enhanced only when the calcium level is elevated. Levosimendan is licensed for the treatment of decompensated heart failure in many countries but not in North America. This drug also passed phase III clinical trials for the prevention of low cardiac output syndrome in pediatric patients after open heart surgery.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P63316 Gene ID: 7134.0 Gene Symbol: TNNC1 Target Organism: Homo sapiens (Human) |
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Target ID: Q14654 Gene ID: 3767.0 Gene Symbol: KCNJ11 Target Organism: Homo sapiens (Human) |
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Target ID: Q15842 Gene ID: 3764.0 Gene Symbol: KCNJ8 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Simdax Approved UseUnknown |
|||
| Preventing | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
256.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27122803/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
7.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
18.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
9.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
17.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
38 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 3 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
25 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 4 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
5.2 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
15.3 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 3 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
7.7 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 4 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
6.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
16.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 3 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
8.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
17.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 4 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
207.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27122803/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
2510 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5970 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1650 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3950 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
2370 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3890 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
91 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
57 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 3 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
56 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
56 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 4 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
40 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
113 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 3 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
59 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
120 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 4 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
47 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 1 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
126 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 3 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
65 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 2 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
128 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15342615/ |
2 mg 4 times / day multiple, oral dose: 2 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27122803/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
1.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
72.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
78.4 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
81.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
81.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.1 μg/kg/min 1 times / week steady-state, intravenous dose: 0.1 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
0.85% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/27122803/ |
2 mg single, intravenous dose: 2 mg route of administration: Intravenous experiment type: SINGLE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
|
3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
LEVOSIMENDAN plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
58% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1855 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
61% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15025738/ |
0.05 μg/kg/min 1 times / week steady-state, intravenous dose: 0.05 μg/kg/min route of administration: Intravenous experiment type: STEADY-STATE co-administered: |
OR-1896 plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
4 mg 1 times / day multiple, intravenous Highest studied dose Dose: 4 mg, 1 times / day Route: intravenous Route: multiple Dose: 4 mg, 1 times / day Sources: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: |
|
5 mg single, intravenous Highest studied dose Dose: 5 mg Route: intravenous Route: single Dose: 5 mg Sources: |
healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| inconclusive [IC50 13.8029 uM] | ||||
| inconclusive | ||||
| no | ||||
| no | ||||
| yes [IC50 0.9772 uM] | ||||
| yes [IC50 17.3768 uM] |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sample Use Guides
0.2 micrograms/kg/min is administered intravenously without bolus for 6 hours every two weeks.
Route of Administration:
Intravenous
Levosimendan down-regulates the expression of the pro-thrombotic and anti-fibrinolytic biomolecules TF and PAI-1 in activated human endothelial cells. Human heart microvascular endothelial cells (HHMEC) and human umbilical vein endothelial cells (HUVEC) were treated with interleukin-1β (IL-1β) (200U/mL) or thrombin (5U/mL) and co-treated with or without levosimendan (0.1-10μM) for 2-24h. In addition, flow experiments were performed. Effects on plasminogen activator inhibitor-1 (PAI-1) and tissue factor (TF) expression and activity were measured by rt-PCR, specific ELISA and flow cytometry.
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Code | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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WHO-ATC |
C01CX08
Created by
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WHO-VATC |
QC01CX08
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FDA ORPHAN DRUG |
495515
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EU-Orphan Drug |
EU/3/18/1980
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1576
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SUB08493MIG
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KK-60
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C6T4514L4E
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73107
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DTXSID9046445
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m6795
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DB00922
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3033825
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7020
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141505-33-1
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CHEMBL2051955
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100000092487
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LEVOSIMENDAN
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C174653
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759644
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50567
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ACTIVE MOIETY
METABOLITE ACTIVE (PARENT)
