Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H24N4O3 |
Molecular Weight | 404.4617 |
Optical Activity | ( - ) |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C)OC1=CC=C(C=C1C#N)C2=NC(=NO2)C3=C4CC[C@H](NCCO)C4=CC=C3
InChI
InChIKey=XRVDGNKRPOAQTN-FQEVSTJZSA-N
InChI=1S/C23H24N4O3/c1-14(2)29-21-9-6-15(12-16(21)13-24)23-26-22(27-30-23)19-5-3-4-18-17(19)7-8-20(18)25-10-11-28/h3-6,9,12,14,20,25,28H,7-8,10-11H2,1-2H3/t20-/m0/s1
Molecular Formula | C23H24N4O3 |
Molecular Weight | 404.4617 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/26990079
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26990079
Ozanimod (previously known as RPC-1063) is a selective immune-inflammatory modulator of the G protein-coupled receptors sphingosine 1-phosphate 1 and 5, which are part of the sphingosine 1-phosphate (S1P) receptor family. Treatment with S1P receptor modulators interferes with S1P signaling and blocks the response of lymphocytes (a type of white blood cell) to exit signals from the lymph nodes, sequestering them within the nodes. The result is a downward modulation of circulating lymphocytes and anti-inflammatory activity by inhibiting cell migration to sites of inflammation. Ozanimod is currently in phase III clinical trials for the treatment of relapsing multiple sclerosis (RMS) and ulcerative colitis, and also in phase II clinical trials to determine whether it is effective in the treatment of Crohn's disease.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26990079
Curator's Comment: effectively crossing the blood–brain barrier resulting in exposure in the brain
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P21453 Gene ID: 1901.0 Gene Symbol: S1PR1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26990079 |
0.41 nM [EC50] | ||
Target ID: Q9H228 Gene ID: 53637.0 Gene Symbol: S1PR5 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/26990079 |
11.0 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.409 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28398597 |
1.5 mg 1 times / day steady-state, oral dose: 1.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
OZANIMOD plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7.66 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28398597 |
1.5 mg 1 times / day steady-state, oral dose: 1.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
OZANIMOD plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28398597 |
1.5 mg 1 times / day steady-state, oral dose: 1.5 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
OZANIMOD plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Other AEs: Nasopharyngitis, Headache... Other AEs: Nasopharyngitis (9.7%) Sources: Headache (6%) Upper respiratory tract infection (6.8%) Alanine aminotransferase increased (2.6%) Back pain (2.2%) Gamma-glutamyltransferase increased (2.2%) Respiratory tract infection viral (2.2%) Urinary tract infection (1.8%) Hypercholesterolaemia (1.3%) Hypertension (2.4%) Pharyngitis (1.3%) Rhinitis (1.8%) Upper abdominal pain (2%) |
1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Other AEs: Nasopharyngitis, Headache... Other AEs: Nasopharyngitis (6.7%) Sources: Headache (7.6%) Upper respiratory tract infection (4%) Alanine aminotransferase increased (4.7%) Back pain (3.8%) Gamma-glutamyltransferase increased (3.3%) Respiratory tract infection viral (3.3%) Urinary tract infection (3.8%) Hypercholesterolaemia (2.5%) Hypertension (1.3%) Pharyngitis (2.5%) Rhinitis (2%) Upper abdominal pain (1.3%) |
0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Other AEs: Upper respiratory infection, Transaminases increased... Other AEs: Upper respiratory infection (26%) Sources: Transaminases increased (10%) Orthostatic hypotension (4%) Urinary tract infection (4%) Back pain (4%) Hypertension (4%) Abdominal pain upper (2%) |
0.92 mg 1 times / day multiple, oral Recommended Dose: 0.92 mg, 1 times / day Route: oral Route: multiple Dose: 0.92 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Disc. AE: Hepatic enzymes increased... AEs leading to discontinuation/dose reduction: Hepatic enzymes increased (1%) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Hypercholesterolaemia | 1.3% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Pharyngitis | 1.3% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Rhinitis | 1.8% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Urinary tract infection | 1.8% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Upper abdominal pain | 2% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Back pain | 2.2% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Gamma-glutamyltransferase increased | 2.2% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Respiratory tract infection viral | 2.2% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Hypertension | 2.4% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Alanine aminotransferase increased | 2.6% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Headache | 6% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Upper respiratory tract infection | 6.8% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Nasopharyngitis | 9.7% | 0.5 mg 1 times / day multiple, oral Recommended Dose: 0.5 mg, 1 times / day Route: oral Route: multiple Dose: 0.5 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Hypertension | 1.3% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Upper abdominal pain | 1.3% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Rhinitis | 2% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Hypercholesterolaemia | 2.5% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Pharyngitis | 2.5% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Gamma-glutamyltransferase increased | 3.3% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Respiratory tract infection viral | 3.3% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Back pain | 3.8% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Urinary tract infection | 3.8% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Upper respiratory tract infection | 4% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Alanine aminotransferase increased | 4.7% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Nasopharyngitis | 6.7% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Headache | 7.6% | 1 mg 1 times / day multiple, oral Recommended Dose: 1 mg, 1 times / day Route: oral Route: multiple Dose: 1 mg, 1 times / day Sources: |
unhealthy, 18 - 55 years Health Status: unhealthy Age Group: 18 - 55 years Sex: M+F Sources: |
Transaminases increased | 10% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Abdominal pain upper | 2% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Upper respiratory infection | 26% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Back pain | 4% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Hypertension | 4% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Orthostatic hypotension | 4% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Urinary tract infection | 4% | 0.84 mg 1 times / day multiple, oral Recommended Dose: 0.84 mg, 1 times / day Route: oral Route: multiple Dose: 0.84 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Hepatic enzymes increased | 1% Disc. AE |
0.92 mg 1 times / day multiple, oral Recommended Dose: 0.92 mg, 1 times / day Route: oral Route: multiple Dose: 0.92 mg, 1 times / day Sources: |
unhealthy, mean age 35.4 years Health Status: unhealthy Age Group: mean age 35.4 years Sex: M+F Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Drug as victim
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/209899Orig1s000PharmR.pdf#page=30 Page: 30.0 |
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Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2020/209899Orig1s000PharmR.pdf#page=30 Page: 30.0 |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02576717
Multiple Sclerosis: 1 mg RPC1063 (Ozanimod) oral capsule daily
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26990079
Ozanimod (RPC1063) is a specific agonist for sphingosine-1-phosphate receptor subtypes 1 (S1P1) and S1P5 receptors. The EC50 values were 0.16 nM and 0.41 nM for S1P1 receptors in the inhibition of cAMP generation and [35S]-GTPγS binding. The 83% Emax value of ozanimod against S1P5 receptor was 11 nM. RPC1063 demonstrated a dose‐dependent effect on S1P1 receptor re‐expression on the cell surface, with near complete and sustained loss of cell surface receptor expression at concentrations above 10 nM in S1P1 receptor-HEK293T cells after 1 h incubation.
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:01:23 GMT 2025
by
admin
on
Mon Mar 31 19:01:23 GMT 2025
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Record UNII |
Z80293URPV
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Record Status |
Validated (UNII)
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Record Version |
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Preferred Name | English | ||
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Code | English | ||
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Common Name | English |
Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
499515
Created by
admin on Mon Mar 31 19:01:23 GMT 2025 , Edited by admin on Mon Mar 31 19:01:23 GMT 2025
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WHO-ATC |
L04AA38
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admin on Mon Mar 31 19:01:23 GMT 2025 , Edited by admin on Mon Mar 31 19:01:23 GMT 2025
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FDA ORPHAN DRUG |
611517
Created by
admin on Mon Mar 31 19:01:23 GMT 2025 , Edited by admin on Mon Mar 31 19:01:23 GMT 2025
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5383
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m12197
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DB12612
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C170279
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Ozanimod
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Z80293URPV
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100000167014
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Ozanimod
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Z80293URPV
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52938427
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CD-21
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10057
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SUB181335
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DTXSID501026488
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1306760-87-1
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2288236
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Related Record | Type | Details | ||
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TARGET -> AGONIST |
SELECTIVE
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METABOLIC ENZYME -> SUBSTRATE | |||
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EXCRETED UNCHANGED |
Ozanimod was not present in feces. Ozanimod concentration in urine was negligible.
FECAL; URINE
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
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BINDER->LIGAND |
BINDING
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> AGONIST |
SELECTIVE
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SALT/SOLVATE -> PARENT |
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
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METABOLITE ACTIVE -> PARENT |
PLASMA
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METABOLITE ACTIVE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE ACTIVE -> PARENT |
PLASMA
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METABOLITE INACTIVE -> PARENT |
URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
FECAL
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METABOLITE ACTIVE -> PARENT |
PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
FECAL; PLASMA; URINE
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METABOLITE INACTIVE -> PARENT |
MAJOR
FECAL
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METABOLITE ACTIVE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
FECAL
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METABOLITE INACTIVE -> PARENT |
MAJOR
URINE
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Biological Half-life | PHARMACOKINETIC |
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Volume of Distribution | PHARMACOKINETIC |
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Tmax | PHARMACOKINETIC |
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AT STEADY-STATE |
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