Details
Stereochemistry | ACHIRAL |
Molecular Formula | 2C29H35F3N2O3.C4H4O4 |
Molecular Weight | 1149.2622 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 3 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C(O)=O.CCC1=CC(=CC=C1CN2CC(C2)C(O)=O)C(\C)=N\OCC3=CC=C(C4CCCCC4)C(=C3)C(F)(F)F.CCC5=CC(=CC=C5CN6CC(C6)C(O)=O)C(\C)=N\OCC7=CC=C(C8CCCCC8)C(=C7)C(F)(F)F
InChI
InChIKey=JNLIKIBISICTMS-PEJBKAKVSA-N
InChI=1S/2C29H35F3N2O3.C4H4O4/c2*1-3-21-14-23(10-11-24(21)15-34-16-25(17-34)28(35)36)19(2)33-37-18-20-9-12-26(22-7-5-4-6-8-22)27(13-20)29(30,31)32;5-3(6)1-2-4(7)8/h2*9-14,22,25H,3-8,15-18H2,1-2H3,(H,35,36);1-2H,(H,5,6)(H,7,8)/b2*33-19+;2-1+
Siponimod (BAF312) is a dual agonist at the sphingosine-1 phosphate receptors, S1PR1 and S1PR5. The S1P receptor is commonly found on the surface of specific cells residing in the central nervous system (CNS), that are responsible for causing CNS damage that drives loss of function in secondary progressive multiple sclerosis (SPMS). Siponimod (BAF312) enters the brain and by binding to these specific receptors, may prevent the activation of these harmful cells, helping to reduce the loss of physical and cognitive function associated with SPMS.
CNS Activity
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22646698
Curator's Comment: # Novartis Pharma AG
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL4333 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22646698 |
0.39 nM [EC50] | ||
Target ID: CHEMBL2274 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22646698 |
0.98 nM [EC50] | ||
Target ID: CHEMBL3230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22646698 |
750.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | SIPONIMOD Approved UseUnknown |
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Palliative | SIPONIMOD Approved UseUnknown |
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Palliative | SIPONIMOD Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30.4 ng/mL |
2 mg 1 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SIPONIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
558 ng × h/mL |
2 mg 1 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SIPONIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
30 h |
2 mg 1 times / day steady-state, oral dose: 2 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
SIPONIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Other AEs: Feeling hot, Dizziness... Other AEs: Feeling hot (5.9%) Sources: Dizziness (5.9%) Headache (5.9%) Presyncope (5.9%) Blurred vision (5.9%) Dry lips (5.9%) Nasopharyngitis (5.9%) Vaginal discharge (5.9%) |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: |
Disc. AE: Headache, Transaminases increased... AEs leading to discontinuation/dose reduction: Headache (0.1%) Sources: Transaminases increased (0.9%) |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: |
Disc. AE: Hypertension... AEs leading to discontinuation/dose reduction: Hypertension (10%) Sources: |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Disc. AE: Macular edema, ALT increased... AEs leading to discontinuation/dose reduction: Macular edema (1%) Sources: Page: p. 109ALT increased (0.5%) Bradycardia (0.3%) GGT increased (0.3%) AST increased (0.3%) Depression (0.3%) Dizziness (0.3%) Fatigue (0.3%) Pulmonary function test decreased (0.3%) Angina pectoris (0.2%) Edema peripheral (0.2%) Seminoma (0.2%) Uveitis (0.2%) Lymphopenia (0.1%) Urinary tract infection (0.1%) |
20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Other AEs: Headache, Dizziness... Other AEs: Headache (20.8%) Sources: Page: p. 38Dizziness (5.7%) Nausea (4.2%) |
75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Other AEs: Headache, Dizziness... Other AEs: Headache (32%) Sources: Page: p. 38Dizziness (12.1%) Nausea (5.5%) |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Disc. AE: Macular edema, ALT increased... AEs leading to discontinuation/dose reduction: Macular edema (2%) Sources: Page: p. 109ALT increased (2%) ALT increased (2%) AST increased (2%) Dizziness (4%) Edema peripheral (2%) Headache (2%) Lymphopenia (4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Blurred vision | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Dizziness | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Dry lips | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Feeling hot | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Headache | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Nasopharyngitis | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Presyncope | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Vaginal discharge | 5.9% | 1 mg single, intravenous Dose: 1 mg Route: intravenous Route: single Dose: 1 mg Sources: |
healthy, 18-50 years n = 17 Health Status: healthy Age Group: 18-50 years Population Size: 17 Sources: |
Headache | 0.1% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: |
Transaminases increased | 0.9% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: |
Hypertension | 10% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: |
Lymphopenia | 0.1% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Urinary tract infection | 0.1% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Angina pectoris | 0.2% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Edema peripheral | 0.2% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Seminoma | 0.2% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Uveitis | 0.2% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
AST increased | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Bradycardia | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Depression | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Dizziness | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Fatigue | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
GGT increased | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Pulmonary function test decreased | 0.3% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
ALT increased | 0.5% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Macular edema | 1% Disc. AE |
2 mg 1 times / day steady, oral Recommended Dose: 2 mg, 1 times / day Route: oral Route: steady Dose: 2 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, 49.0 years n = 1148 Health Status: unhealthy Condition: secondary progressive multiple sclerosis Age Group: 49.0 years Sex: M+F Population Size: 1148 Sources: Page: p. 109 |
Headache | 20.8% | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Nausea | 4.2% | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Dizziness | 5.7% | 20 mg 1 times / day multiple, oral Highest studied dose Dose: 20 mg, 1 times / day Route: oral Route: multiple Dose: 20 mg, 1 times / day Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Dizziness | 12.1% | 75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Headache | 32% | 75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
Nausea | 5.5% | 75 mg single, oral Highest studied dose Dose: 75 mg Route: oral Route: single Dose: 75 mg Sources: Page: p. 38 |
healthy, adult Health Status: healthy Age Group: adult Sources: Page: p. 38 |
ALT increased | 2% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
ALT increased | 2% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
AST increased | 2% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Edema peripheral | 2% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Headache | 2% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Macular edema | 2% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Dizziness | 4% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Lymphopenia | 4% Disc. AE |
10 mg 1 times / day multiple, oral Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: Page: p. 109 |
unhealthy, adult n = 50 Health Status: unhealthy Age Group: adult Population Size: 50 Sources: Page: p. 109 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209884Orig1s000ClinPharmR.pdf#page=11 Page: 11.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209884Orig1s000ClinPharmR.pdf#page=11 Page: 11.0 |
no | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209884Orig1s000ClinPharmR.pdf#page=11 Page: 11.0 |
no | |||
Page: 16.0 |
yes | yes (co-administration study) Comment: administered with fluconazole (moderate CYP2C9 and CYP3A4 dual inhibitor): increased siponimod’s Cmax by 10% and the AUC 2-fold; administered with rifampin (strong CYP3A4 and moderate CYP2C9 dual inducer) decreased siponimod AUCtau,ss and Cmax,ss by 57% and 45%, respectively. Page: 16.0 |
||
yes | yes (pharmacogenomic study) Comment: administered with fluconazole (moderate CYP2C9 and CYP3A4 dual inhibitor): increased siponimod’s Cmax by 10% and the AUC 2-fold; administered with rifampin (strong CYP3A4 and moderate CYP2C9 dual inducer) decreased siponimod AUCtau,ss and Cmax,ss by 57% and 45%, respectively. Page: 16.0 |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2019/209884Orig1s000PharmR.pdf#page=23 Page: 23.0 |
Sample Use Guides
Patients received 2 mg once daily siponimod (following initial dose titration starting at 0.25 mg).
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22646698
The selectivity of siponimod (BAF312) for receptor subtypes S1P1 and S1P5, sparing activity on the S1P2, S1P3 and S1P4 receptors, was demonstrated by measuring agonist efficacy in the GTPγ[35S] binding assay. The half-maximal effective concentration (EC50) values were in the sub-nanomolar range for S1P1 (0.39 ± 0.07 nM) and S1P5 (0.98 ± 0.43 nM) receptors, with Emax levels of approximately 100% (full agonist).
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100000178213
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46700777
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C170378
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Z7G02XZ0M6
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ACTIVE MOIETY
SUBSTANCE RECORD