This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Ozanimod
Accession Number
DB12612
Type
Small Molecule
Groups
Approved
Description

Ozanimod is a sphingosine 1-phosphate receptor modulator for the treatment of relapsing Multiple Sclerosis (MS) and inflammatory bowel disease. It was developed by Celgene(now acquired by Bristol-Myers Squibb)7 and was approved by the FDA on March 26 2020.8,9

MS is a devastating inflammatory disease that often progresses and causes severe neurological, physical, and cognitive effects.4 Inflammatory bowel disease also a chronic inflammatory condition and can cause persistent abdominal pain, diarrhea, bloody stools, and vomiting.5

In clinical trials, Ozanimod has been shown to be well-tolerated and has resulted in a higher decrease in the rate of MS relapses than with intramuscular interferon beta-1a, a current standard in MS therapy. Studies involving patients with inflammatory bowel disease have also shown promising results.1,6

Structure
Thumb
Synonyms
  • Ozanimod
  • Ozanimodum
External IDs
RPC 1063 / RPC-1063 / RPC1063
Product Ingredients
IngredientUNIICASInChI Key
Ozanimod hydrochloride3UPR33JAAM1618636-37-5HAOOCAKHSFYDBU-BDQAORGHSA-N
Categories
UNII
Z80293URPV
CAS number
1306760-87-1
Weight
Average: 404.47
Monoisotopic: 404.184840649
Chemical Formula
C23H24N4O3
InChI Key
XRVDGNKRPOAQTN-FQEVSTJZSA-N
InChI
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
IUPAC Name
5-{3-[(1S)-1-[(2-hydroxyethyl)amino]-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl}-2-(propan-2-yloxy)benzonitrile
SMILES
CC(C)OC1=C(C=C(C=C1)C1=NC(=NO1)C1=C2CC[C@H](NCCO)C2=CC=C1)C#N

Pharmacology

Indication

Ozanimod is indicated for adults in the treatment of relapsing forms of MS, which may include relapsing-remitting disease, clinically isolated syndrome, and active secondary progressive MS.9

Associated Conditions
Pharmacodynamics

Ozanimod reduces the neuroinflammation associated with MS, reducing debilitating symptoms and possibly disease progression. During clinical trials, ozanimod reduced MS-associated brain volume loss in several areas.1,9

Mechanism of action

Sphingosine‐1‐phosphate (S1P) is an important phospholipid that binds to various G‐protein‐coupled receptor subtypes, which can be identified as S1P1–5R. S1P and the receptors it binds to perform regular functions in the immune, cardiovascular, pulmonary, and nervous system. S1P can be expressed ubiquitously. S1P1R, S1P2R, and S1P3R receptors can be found in the cardiovascular, immune, and central nervous systems. S1P4R is found on lymphocytic and hematopoietic cells, while S1P5R expression is found only on the spleen (on natural killer cells) or in the central nervous system.

Ozanimod (RPC1063) is an oral selective modulator of S1P receptors that is selective for binding to the S1P1R and S1P5R subtypes.3 The mechanism of action of ozanimod is not fully understood, but this drug likely reduces the migration of lymphocytes, which aggravate MS.9

TargetActionsOrganism
ASphingosine 1-phosphate receptor 1
agonist
Humans
ASphingosine 1-phosphate receptor 5
agonist
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Ozanimod.
9-(N-methyl-L-isoleucine)-cyclosporin AThe risk or severity of adverse effects can be increased when Ozanimod is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.
AbataceptThe risk or severity of adverse effects can be increased when Abatacept is combined with Ozanimod.
AbetimusThe risk or severity of adverse effects can be increased when Abetimus is combined with Ozanimod.
ActeosideThe risk or severity of adverse effects can be increased when Ozanimod is combined with Acteoside.
AdalimumabThe risk or severity of adverse effects can be increased when Adalimumab is combined with Ozanimod.
Adenovirus type 7 vaccine liveThe risk or severity of infection can be increased when Adenovirus type 7 vaccine live is combined with Ozanimod.
AfelimomabThe risk or severity of adverse effects can be increased when Afelimomab is combined with Ozanimod.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Ozanimod.
AldosteroneThe risk or severity of adverse effects can be increased when Aldosterone is combined with Ozanimod.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food.

References

Synthesis Reference

Florian Uthoff, Jana Löwe, Christina Harms, Kai Donsbach, Harald Gröger. Chemoenzymatic Synthesis of a Chiral Ozanimod Key Intermediate Starting from Naphthalene as Cheap Petrochemical Feedstock. April 2019. The Journal of Organic Chemistry. DOI: 10.1021/acs.joc.8b03290

General References
  1. Cohen JA, Comi G, Selmaj KW, Bar-Or A, Arnold DL, Steinman L, Hartung HP, Montalban X, Kubala Havrdova E, Cree BAC, Sheffield JK, Minton N, Raghupathi K, Huang V, Kappos L: Safety and efficacy of ozanimod versus interferon beta-1a in relapsing multiple sclerosis (RADIANCE): a multicentre, randomised, 24-month, phase 3 trial. Lancet Neurol. 2019 Nov;18(11):1021-1033. doi: 10.1016/S1474-4422(19)30238-8. Epub 2019 Sep 3. [PubMed:31492652]
  2. Tran JQ, Hartung JP, Peach RJ, Boehm MF, Rosen H, Smith H, Brooks JL, Timony GA, Olson AD, Gujrathi S, Frohna PA: Results From the First-in-Human Study With Ozanimod, a Novel, Selective Sphingosine-1-Phosphate Receptor Modulator. J Clin Pharmacol. 2017 Aug;57(8):988-996. doi: 10.1002/jcph.887. Epub 2017 Apr 11. [PubMed:28398597]
  3. Tran JQ, Hartung JP, Tompkins CA, Frohna PA: Effects of High- and Low-Fat Meals on the Pharmacokinetics of Ozanimod, a Novel Sphingosine-1-Phosphate Receptor Modulator. Clin Pharmacol Drug Dev. 2018 Aug;7(6):634-640. doi: 10.1002/cpdd.409. Epub 2017 Nov 10. [PubMed:29125718]
  4. Ghasemi N, Razavi S, Nikzad E: Multiple Sclerosis: Pathogenesis, Symptoms, Diagnoses and Cell-Based Therapy. Cell J. 2017 Apr-Jun;19(1):1-10. Epub 2016 Dec 21. [PubMed:28367411]
  5. Fakhoury M, Negrulj R, Mooranian A, Al-Salami H: Inflammatory bowel disease: clinical aspects and treatments. J Inflamm Res. 2014 Jun 23;7:113-20. doi: 10.2147/JIR.S65979. eCollection 2014. [PubMed:25075198]
  6. Vetter M, Neurath MF: Emerging oral targeted therapies in inflammatory bowel diseases: opportunities and challenges. Therap Adv Gastroenterol. 2017 Oct;10(10):773-790. doi: 10.1177/1756283X17727388. Epub 2017 Sep 5. [PubMed:29051788]
  7. Celgene: Press releases archive [Link]
  8. AJMC: FDA approves Zeposia (Ozanimod) for patients with RMS [Link]
  9. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
External Links
PubChem Compound
52938427
PubChem Substance
347828826
ChemSpider
34979946
ChEMBL
CHEMBL3707247
ZINC
ZINC000116109867
Wikipedia
Ozanimod
ATC Codes
L04AA38 — Ozanimod
FDA label
Download (369 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1Active Not RecruitingBasic ScienceDisseminated Sclerosis1
1CompletedBasic ScienceHealthy Volunteers3
1CompletedTreatmentHealthy Volunteers1
1Not Yet RecruitingTreatmentHealthy Volunteers1
1RecruitingTreatmentHealthy Volunteers1
2Active Not RecruitingTreatmentUlcerative Colitis1
2CompletedTreatmentCrohn's Disease (CD)1
2, 3CompletedTreatmentRelapsing Multiple Sclerosis (RMS)1
3Active Not RecruitingTreatmentDisseminated Sclerosis1
3CompletedTreatmentDisseminated Sclerosis1
3CompletedTreatmentRelapsing Multiple Sclerosis (RMS)1
3RecruitingTreatmentCrohn's Disease (CD)4
3RecruitingTreatmentDisseminated Sclerosis1
3RecruitingTreatmentUlcerative Colitis3
Not AvailableCompletedNot AvailableHealthy Volunteers1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)134-137https://www.trc-canada.com/product-detail/?CatNum=O880000&__cf_chl_jschl_tk__=47418a3658c1bed2236975a78c4d009d9726aa64-1585324169-0-AVBdS0uIBZsziaubuiosHQ9SfMRbB8tzILtS_D8ROwXY3jfZIfe7nf68lYLXjCK3VPlPXWBy25ZsDzjuSRHMsq4i6AooTGfw__9JzT3wXrvVSSMU2EcrV7Mv40mnq3e2lIo4_w_bP6jZ3VXuonZ_xdQiH-fceyd07BbLIF4BZmVUCw323soeydBwwDrMkF8dmXn9dgJ2cvO1O9LQY8_gDfhGL3Es8UF5YZpSXPUJEPZZo2_oXA4uk-2QpHpCZeR5oZIdF_CMMX2z5--DAw52pjMVLVTwvoNQS0ux0IEnKEV-UYKTAUK2pG7eAUZl2Cjvrg
boiling point (°C)648.3±65.0https://www.chemsrc.com/en/cas/1306760-87-1_828967.html
logP3.73https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?ligandId=8709
pKa14.73±0.10https://www.chemicalbook.com/ChemicalProductProperty_EN_CB42716147.htm
Predicted Properties
PropertyValueSource
Water Solubility0.161 mg/mLALOGPS
logP2.81ALOGPS
logP3.96ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)15.6ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area104.2 Å2ChemAxon
Rotatable Bond Count7ChemAxon
Refractivity135.66 m3·mol-1ChemAxon
Polarizability45.21 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenyloxadiazoles. These are polycyclic aromatic compounds containing a benzene ring linked to a 1,2,4-oxadiazole ring through a CC or CN bond.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Azoles
Sub Class
Oxadiazoles
Direct Parent
Phenyloxadiazoles
Alternative Parents
Indanes / Phenoxy compounds / Phenol ethers / Benzonitriles / Aralkylamines / Alkyl aryl ethers / Heteroaromatic compounds / 1,2-aminoalcohols / Oxacyclic compounds / Nitriles
show 5 more
Substituents
Phenyl-1,2,4-oxadiazole / Indane / Benzonitrile / Phenol ether / Phenoxy compound / Alkyl aryl ether / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Heteroaromatic compound
show 20 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
Not Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Sphingosine-1-phosphate receptor activity
Specific Function
G-protein coupled receptor for the bioactive lysosphingolipid sphingosine 1-phosphate (S1P) that seems to be coupled to the G(i) subclass of heteromeric G proteins. Signaling leads to the activatio...
Gene Name
S1PR1
Uniprot ID
P21453
Uniprot Name
Sphingosine 1-phosphate receptor 1
Molecular Weight
42810.195 Da
References
  1. Cohen JA, Comi G, Selmaj KW, Bar-Or A, Arnold DL, Steinman L, Hartung HP, Montalban X, Kubala Havrdova E, Cree BAC, Sheffield JK, Minton N, Raghupathi K, Huang V, Kappos L: Safety and efficacy of ozanimod versus interferon beta-1a in relapsing multiple sclerosis (RADIANCE): a multicentre, randomised, 24-month, phase 3 trial. Lancet Neurol. 2019 Nov;18(11):1021-1033. doi: 10.1016/S1474-4422(19)30238-8. Epub 2019 Sep 3. [PubMed:31492652]
  2. Tran JQ, Hartung JP, Peach RJ, Boehm MF, Rosen H, Smith H, Brooks JL, Timony GA, Olson AD, Gujrathi S, Frohna PA: Results From the First-in-Human Study With Ozanimod, a Novel, Selective Sphingosine-1-Phosphate Receptor Modulator. J Clin Pharmacol. 2017 Aug;57(8):988-996. doi: 10.1002/jcph.887. Epub 2017 Apr 11. [PubMed:28398597]
  3. Tran JQ, Hartung JP, Tompkins CA, Frohna PA: Effects of High- and Low-Fat Meals on the Pharmacokinetics of Ozanimod, a Novel Sphingosine-1-Phosphate Receptor Modulator. Clin Pharmacol Drug Dev. 2018 Aug;7(6):634-640. doi: 10.1002/cpdd.409. Epub 2017 Nov 10. [PubMed:29125718]
  4. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Sphingosine-1-phosphate receptor activity
Specific Function
Receptor for the lysosphingolipid sphingosine 1-phosphate (S1P). S1P is a bioactive lysophospholipid that elicits diverse physiological effect on most types of cells and tissues. Is coupled to both...
Gene Name
S1PR5
Uniprot ID
Q9H228
Uniprot Name
Sphingosine 1-phosphate receptor 5
Molecular Weight
41774.515 Da
References
  1. Cohen JA, Comi G, Selmaj KW, Bar-Or A, Arnold DL, Steinman L, Hartung HP, Montalban X, Kubala Havrdova E, Cree BAC, Sheffield JK, Minton N, Raghupathi K, Huang V, Kappos L: Safety and efficacy of ozanimod versus interferon beta-1a in relapsing multiple sclerosis (RADIANCE): a multicentre, randomised, 24-month, phase 3 trial. Lancet Neurol. 2019 Nov;18(11):1021-1033. doi: 10.1016/S1474-4422(19)30238-8. Epub 2019 Sep 3. [PubMed:31492652]
  2. Tran JQ, Hartung JP, Peach RJ, Boehm MF, Rosen H, Smith H, Brooks JL, Timony GA, Olson AD, Gujrathi S, Frohna PA: Results From the First-in-Human Study With Ozanimod, a Novel, Selective Sphingosine-1-Phosphate Receptor Modulator. J Clin Pharmacol. 2017 Aug;57(8):988-996. doi: 10.1002/jcph.887. Epub 2017 Apr 11. [PubMed:28398597]
  3. Tran JQ, Hartung JP, Tompkins CA, Frohna PA: Effects of High- and Low-Fat Meals on the Pharmacokinetics of Ozanimod, a Novel Sphingosine-1-Phosphate Receptor Modulator. Clin Pharmacol Drug Dev. 2018 Aug;7(6):634-640. doi: 10.1002/cpdd.409. Epub 2017 Nov 10. [PubMed:29125718]
  4. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
Medium-chain-aldehyde dehydrogenase activity
Specific Function
Catalyzes the oxidation of long-chain aliphatic aldehydes to fatty acids. Active on a variety of saturated and unsaturated aliphatic aldehydes between 6 and 24 carbons in length. Responsible for co...
Gene Name
ALDH3A2
Uniprot ID
P51648
Uniprot Name
Fatty aldehyde dehydrogenase
Molecular Weight
54847.36 Da
References
  1. Tran JQ, Hartung JP, Olson AD, Mendzelevski B, Timony GA, Boehm MF, Peach RJ, Gujrathi S, Frohna PA: Cardiac Safety of Ozanimod, a Novel Sphingosine-1-Phosphate Receptor Modulator: Results of a Thorough QT/QTc Study. Clin Pharmacol Drug Dev. 2018 Mar;7(3):263-276. doi: 10.1002/cpdd.383. Epub 2017 Aug 7. [PubMed:28783871]
  2. Rasche L, Paul F: Ozanimod for the treatment of relapsing remitting multiple sclerosis. Expert Opin Pharmacother. 2018 Dec;19(18):2073-2086. doi: 10.1080/14656566.2018.1540592. Epub 2018 Nov 8. [PubMed:30407868]
  3. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
General Function
Zinc ion binding
Specific Function
Class-III ADH is remarkably ineffective in oxidizing ethanol, but it readily catalyzes the oxidation of long-chain primary alcohols and the oxidation of S-(hydroxymethyl) glutathione.
Gene Name
ADH5
Uniprot ID
P11766
Uniprot Name
Alcohol dehydrogenase class-3
Molecular Weight
39723.945 Da
References
  1. Tran JQ, Hartung JP, Olson AD, Mendzelevski B, Timony GA, Boehm MF, Peach RJ, Gujrathi S, Frohna PA: Cardiac Safety of Ozanimod, a Novel Sphingosine-1-Phosphate Receptor Modulator: Results of a Thorough QT/QTc Study. Clin Pharmacol Drug Dev. 2018 Mar;7(3):263-276. doi: 10.1002/cpdd.383. Epub 2017 Aug 7. [PubMed:28783871]
  2. Rasche L, Paul F: Ozanimod for the treatment of relapsing remitting multiple sclerosis. Expert Opin Pharmacother. 2018 Dec;19(18):2073-2086. doi: 10.1080/14656566.2018.1540592. Epub 2018 Nov 8. [PubMed:30407868]
  3. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Arylamine n-acetyltransferase activity
Specific Function
Participates in the detoxification of a plethora of hydrazine and arylamine drugs. Catalyzes the N- or O-acetylation of various arylamine and heterocyclic amine substrates and is able to bioactivat...
Gene Name
NAT2
Uniprot ID
P11245
Uniprot Name
Arylamine N-acetyltransferase 2
Molecular Weight
33542.235 Da
References
  1. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase activity
Specific Function
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Curator comments
Weak substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Tran JQ, Hartung JP, Olson AD, Mendzelevski B, Timony GA, Boehm MF, Peach RJ, Gujrathi S, Frohna PA: Cardiac Safety of Ozanimod, a Novel Sphingosine-1-Phosphate Receptor Modulator: Results of a Thorough QT/QTc Study. Clin Pharmacol Drug Dev. 2018 Mar;7(3):263-276. doi: 10.1002/cpdd.383. Epub 2017 Aug 7. [PubMed:28783871]
  2. FDA Approved Products: Zeposia (Ozanimod) oral capsules [Link]

Drug created on October 20, 2016 17:12 / Updated on March 27, 2020 17:10

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