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    Chemistry

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    Also known as: 1306760-87-1, Rpc1063, Rpc-1063, Ozanimod (rpc1063), (s)-5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1h-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile, Z80293urpv
    Molecular Formula
    C23H24N4O3
    Molecular Weight
    404.5  g/mol
    InChI Key
    XRVDGNKRPOAQTN-FQEVSTJZSA-N
    FDA UNII
    Z80293URPV
    Ozanimod Hydrochloride
    Ozanimod is an orally bioavailable sphingosine-1-phosphate (S1P) receptors 1 (S1PR1, S1P1) and 5 (S1PR5, S1P5) modulator, with potential anti-inflammatory and immunomodulating activities. Upon oral administration, ozanimod selectively targets and binds to S1PR1 on lymphocytes and induces S1PR1 internalization and degradation. This results in the sequestration of lymphocytes in lymph nodes. By preventing egress of lymphocytes, ozanimod reduces both the amount of circulating peripheral lymphocytes and the infiltration of lymphocytes into target tissues. This prevents a lymphocyte-mediated immune response and may reduce inflammation. S1PR1, a G-protein coupled receptor, plays a key role in lymphocyte migration from lymphoid tissues. Modulation of S1PR5 by ozanimod may be neuroprotective.
    1 2D Structure

    Ozanimod Hydrochloride

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-[3-[(1S)-1-(2-hydroxyethylamino)-2,3-dihydro-1H-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-propan-2-yloxybenzonitrile
    2.1.2 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
    2.1.3 InChI Key
    XRVDGNKRPOAQTN-FQEVSTJZSA-N
    2.1.4 Canonical SMILES
    CC(C)OC1=C(C=C(C=C1)C2=NC(=NO2)C3=C4CCC(C4=CC=C3)NCCO)C#N
    2.1.5 Isomeric SMILES
    CC(C)OC1=C(C=C(C=C1)C2=NC(=NO2)C3=C4CC[C@@H](C4=CC=C3)NCCO)C#N
    2.2 Other Identifiers
    2.2.1 UNII
    Z80293URPV
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Rpc1063

    2.3.2 Depositor-Supplied Synonyms

    1. 1306760-87-1

    2. Rpc1063

    3. Rpc-1063

    4. Ozanimod (rpc1063)

    5. (s)-5-(3-(1-((2-hydroxyethyl)amino)-2,3-dihydro-1h-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-isopropoxybenzonitrile

    6. Z80293urpv

    7. Zeposia

    8. Unii-z80293urpv

    9. Benzonitrile, 5-(3-((1s)-2,3-dihydro-1-((2-hydroxyethyl)amino)-1h-inden-4-yl)-1,2,4-oxadiazol-5-yl)-2-(1-methylethoxy)-

    10. Ozanimod [inn]

    11. 5-[3-[(1~{s})-1-(2-hydroxyethylamino)-2,3-dihydro-1~{h}-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-propan-2-yloxy-benzenecarbonitrile

    12. Benzonitrile, 5-[3-[(1s)-2,3-dihydro-1-[(2-hydroxyethyl)amino]-1h-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-(1-methylethoxy)-

    13. Ozanimod [usan:inn]

    14. 5-[3-[(1s)-1-(2-hydroxyethylamino)-2,3-dihydro-1h-inden-4-yl]-1,2,4-oxadiazol-5-yl]-2-propan-2-yloxybenzonitrile

    15. Rpc 1063

    16. Ozanimod [usan]

    17. Ozanimod; Rpc1063

    18. Ozanimod (usan/inn)

    19. Ozanimod [mi]

    20. Ozanimod [who-dd]

    21. Gtpl8709

    22. Schembl2195490

    23. Chembl3707247

    24. Amy3373

    25. Dtxsid501026488

    26. Bcp16513

    27. Ex-a1316

    28. Rpc1063:rpc-1063

    29. Bdbm50507186

    30. Mfcd28386168

    31. S7952

    32. Akos026674086

    33. Zinc116109867

    34. Ccg-268695

    35. Cs-5070

    36. Db12612

    37. Ac-29883

    38. As-75063

    39. Hy-12288

    40. J3.612.016i

    41. D10968

    42. P14657

    43. Q21098986

    44. 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

    45. Jeu

    2.4 Create Date
    2011-06-13
    3 Chemical and Physical Properties
    Molecular Weight 404.5 g/mol
    Molecular Formula C23H24N4O3
    XLogP33.1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count7
    Exact Mass404.18484064 g/mol
    Monoisotopic Mass404.18484064 g/mol
    Topological Polar Surface Area104 Ų
    Heavy Atom Count30
    Formal Charge0
    Complexity609
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug 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.

    FDA Label

    Multiple sclerosis

    - Zeposia is indicated for the treatment of adult patients with relapsing remitting multiple sclerosis (RRMS) with active disease as defined by clinical or imaging features.

    Ulcerative colitis

    - Zeposia is indicated for the treatment of adult patients with moderately to severely active ulcerative colitis (UC) who have had an inadequate response, lost response, or were intolerant to either conventional therapy or a biologic agent.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Ozanimod reduces circulating lymphocytes that cause the neuroinflammation associated with MS, reducing debilitating symptoms and, possibly, disease progression. During clinical trials, ozanimod reduced MS-associated brain volume loss in several regions. Ozanimod causes the sequestration of peripheral lymphocytes, reducing circulating lymphocytes in the gastrointestinal tract.

    5.2 MeSH Pharmacological Classification

    Sphingosine 1 Phosphate Receptor Modulators

    Agents that affect the function of G-protein coupled SPHINGOSINE 1-PHOSPHATE RECEPTORS. Their binding to the receptors blocks lymphocyte migration and are often used as IMMUNOSUPPRESSANTS. (See all compounds classified as Sphingosine 1 Phosphate Receptor Modulators.)

    5.3 ATC Code

    L04AA38

    L - Antineoplastic and immunomodulating agents

    L04 - Immunosuppressants

    L04A - Immunosuppressants

    L04AA - Selective immunosuppressants

    L04AA38 - Ozanimod

    5.4 Absorption, Distribution and Excretion

    Absorption

    Ozanimod is absorbed in the gastrointestinal tract after oral administration. The Cmax of ozanimod is 0.244 ng/mL and is achieved at 6 to 8 hours after administration, reaching steady-state at about 102 hours after administration. The AUC is 4.46 ng*h/mL. Its delayed absorption reduces effects that may occur after the first dose, such as heart rate changes. The peak plasma concentration of ozanimod is low due to a high volume of distribution.

    Route of Elimination

    The kidneys are not a major source of elimination for ozanimod. After a 0.92 mg dose of radiolabeled ozanimod was administered, about 26% of the labeled drug was accounted for in the urine and 37 % in the feces, mainly in the form of inactive metabolites.

    Volume of Distribution

    The average volume of distribution of ozanimod is 5590L. Another reference mentions a volume of distribution ranging from 73-101 L/kg. This drug crosses the blood-brain barrier.

    Clearance

    The mean apparent oral clearance of ozanimod, according to prescribing information, is 192 L/h. Another reference indicates an oral clearance of 233 L/h.

    5.5 Metabolism/Metabolites

    Ozanimod has two major active metabolites CC112273 and CC1084037 and minor active metabolites such as RP101988, RP101075, and RP101509, which target the S1P1 and S1P5 receptors. The enzymes involved in the metabolism of ozanimod include ALDH/ADH, NAT-2, Monoamine Oxidase B, and AKR 1C1/1C2. After metabolism, ozanimod (6%), CC112273 (73%), and CC1084037 (15%) are accounted for in the circulation.

    5.6 Biological Half-Life

    The half-life of ozanimod ranges from 17-21 hours.

    5.7 Mechanism of Action

    Sphingosine1phosphate (S1P) is an important phospholipid that binds to various Gproteincoupled receptor subtypes, which can be identified as S1P15R. S1P and the receptors it binds to perform regular functions in the immune, cardiovascular, pulmonary, and nervous system. S1P can be expressed ubiquitously, playing an important role in regulating inflammation. 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 is a selective modulator of S1P receptors and binds to S1P1R and S1P5R subtypes. The mechanism of action of ozanimod is not fully understood, but this drug likely reduces the migration of lymphocytes that usually aggravate the inflammation associated with MS.

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    OZANIMOD HYDROCHLORIDE

    NDC Package Code : 52076-6266

    Start Marketing Date : 2020-12-11

    End Marketing Date : 2024-12-31

    Dosage Form (Strength) : POWDER (1kg/kg)

    Marketing Category : BULK INGREDIENT

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    03

    CARBOGEN AMCIS AG

    Switzerland
    Cosmoprof India
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    CARBOGEN AMCIS AG

    Switzerland
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    OZANIMOD HYDROCHLORIDE

    NDC Package Code : 58567-110

    Start Marketing Date : 2024-02-01

    End Marketing Date : 2025-12-31

    Dosage Form (Strength) : POWDER (1kg/kg)

    Marketing Category : BULK INGREDIENT

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    04

    Maithri Drugs Private Limited

    India
    Cosmoprof India
    Not Confirmed
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    Maithri Drugs Private Limited

    India
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    OZANIMOD HYDROCHLORIDE

    NDC Package Code : 70600-033

    Start Marketing Date : 2022-03-24

    End Marketing Date : 2024-12-31

    Dosage Form (Strength) : POWDER (1kg/kg)

    Marketing Category : BULK INGREDIENT

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    05

    Patheon API Manufacturing, Inc.

    U.S.A
    Cosmoprof India
    Not Confirmed
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    Patheon API Manufacturing, Inc.

    U.S.A
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    Cosmoprof India
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    OZANIMOD HYDROCHLORIDE

    NDC Package Code : 64274-9000

    Start Marketing Date : 2020-03-25

    End Marketing Date : 2024-12-31

    Dosage Form (Strength) : POWDER (1kg/kg)

    Marketing Category : BULK INGREDIENT

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    06

    Teva Czech Industries s.r.o.

    Israel
    Cosmoprof India
    Not Confirmed
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    Teva Czech Industries s.r.o.

    Israel
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    Cosmoprof India
    Not Confirmed
    • fda
    • EDQM
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    OZANIMOD HYDROCHLORIDE

    NDC Package Code : 47848-061

    Start Marketing Date : 2023-09-25

    End Marketing Date : 2024-12-31

    Dosage Form (Strength) : POWDER (1kg/kg)

    Marketing Category : BULK INGREDIENT

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    API Reference Price

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    [{"dataSource":"API Export","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1717525800,"product":"OZANIMOD HYDROCHLORIDE","address":"5\/502, GARDEN ESTATE,","city":"THANE, MAHARASHTRA.","supplier":"AMTEC HEALTHCARE PVT LTD","supplierCountry":"INDIA","foreign_port":"KUALA LUMPUR - INT\\'L","customer":"SUNSHINE WORLDWIDE BUSINESS LIMITED","customerCountry":"MALAYSIA","quantity":"0.37","actualQuantity":"370","unit":"GMS","unitRateFc":"21689.5","totalValueFC":"95246.2","currency":"INR","unitRateINR":21489.450000000001,"date":"05-Jun-2024","totalValueINR":"7951096.5","totalValueInUsd":"95246.2","indian_port":"Bombay Air","hs_no":"29339990","bill_no":"1446834","productDescription":"API","marketType":"LESS REGULATED MARKET","country":"MALAYSIA","selfForZScoreResived":"Pharma Grade","supplierPort":"Bombay Air","supplierAddress":"5\/502, GARDEN ESTATE,, THANE, MAHARASHTRA.","customerAddress":""}]
    05-Jun-2024
    05-Jun-2024
    KGS
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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