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    Chemistry

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    Also known as: 82034-46-6, Lotemax, Alrex, Hgp-1, Inveltys, Cddd-5604
    Molecular Formula
    C24H31ClO7
    Molecular Weight
    466.9  g/mol
    InChI Key
    DMKSVUSAATWOCU-HROMYWEYSA-N
    FDA UNII
    YEH1EZ96K6
    Loteprednol Etabonate
    An androstadiene derivative corticosteroid that is used as an ANTI-ALLERGIC AGENT for the treatment of inflammatory and allergic eye conditions.
    1 2D Structure

    Loteprednol Etabonate

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    chloromethyl (8S,9S,10R,11S,13S,14S,17R)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthrene-17-carboxylate
    2.1.2 InChI
    InChI=1S/C24H31ClO7/c1-4-30-21(29)32-24(20(28)31-13-25)10-8-17-16-6-5-14-11-15(26)7-9-22(14,2)19(16)18(27)12-23(17,24)3/h7,9,11,16-19,27H,4-6,8,10,12-13H2,1-3H3/t16-,17-,18-,19+,22-,23-,24-/m0/s1
    2.1.3 InChI Key
    DMKSVUSAATWOCU-HROMYWEYSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)OC1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)C(=O)OCCl
    2.1.5 Isomeric SMILES
    CCOC(=O)O[C@@]1(CC[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)C(=O)OCCl
    2.2 Other Identifiers
    2.2.1 UNII
    YEH1EZ96K6
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate, Chloromethyl

    2. Alrex

    3. Cehoac

    4. Chloromethyl 17 Ethoxycarbonyloxy 11 Hydroxy 3 Oxoandrosta 1,4 Diene 17 Carboxylate

    5. Chloromethyl 17-ethoxycarbonyloxy-11-hydroxy-3-oxoandrosta-1,4-diene-17-carboxylate

    6. Etabonate, Loteprednol

    7. Lotemax

    8. Loteprednol

    2.3.2 Depositor-Supplied Synonyms

    1. 82034-46-6

    2. Lotemax

    3. Alrex

    4. Hgp-1

    5. Inveltys

    6. Cddd-5604

    7. P-5604

    8. Cddd 5604

    9. Chloromethyl (8s,9s,10r,11s,13s,14s,17r)-17-ethoxycarbonyloxy-11-hydroxy-10,13-dimethyl-3-oxo-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthrene-17-carboxylate

    10. Chebi:31784

    11. Yeh1ez96k6

    12. Kpi-121

    13. Dsstox_cid_26468

    14. Dsstox_rid_81641

    15. Dsstox_gsid_46468

    16. (11b,17a)-17-[(ethoxycarbonyl)oxy]-11-hydroxy-3-oxo-androsta-1,4-diene-17-carboxylic Acid Chloromethyl Ester

    17. Chloromethyl 17alpha-[(ethoxycarbonyl)oxy]-11beta-hydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylate

    18. Loterox

    19. Locort

    20. Lotemax (tn)

    21. Cas-82034-46-6

    22. Unii-yeh1ez96k6

    23. Hgp 1

    24. Loteprednol Etabonate [usan]

    25. Airex

    26. Loteprednol Etabonate (jan/usan)

    27. Loteprednoletabonate

    28. Ncgc00164594-01

    29. Idr-90102

    30. Idr-90103

    31. Eysuvis

    32. Loteprednol Etabonate Opphthalmic Suspension

    33. P 5604

    34. Schembl23907

    35. Mls001424221

    36. Gtpl7085

    37. Chembl1200865

    38. Dtxsid2046468

    39. Hms2051f16

    40. Hms2232j09

    41. Hms3715n06

    42. Loteprednol Etabonate [mi]

    43. Loteprednol Etabonate [usan:jan]

    44. Loteprednol Etabonate [jan]

    45. Bcp28645

    46. Zinc3920673

    47. Tox21_112219

    48. Bdbm50248301

    49. Loteprednol Etabonate [vandf]

    50. Mfcd00870765

    51. S1669

    52. Loteprednol Etabonate [mart.]

    53. Akos005145741

    54. Loteprednol Etabonate [who-dd]

    55. Tox21_112219_1

    56. Ccg-101041

    57. Cs-0900

    58. Db14596

    59. Gs-3599

    60. Nc00291

    61. Loteprednol Etabonate, >=98% (hplc)

    62. Ncgc00164594-02

    63. Chloromethyl 11beta,17-dihydroxy-3-oxoandrosta-1,4-diene-17beta-carboxylate, 17-(ethyl Carbonate)

    64. Hy-17358

    65. Smr000469178

    66. Loteprednol Etabonate [orange Book]

    67. Zylet Component Loteprednol Etabonate

    68. L0327

    69. D01689

    70. Loteprednol Etabonate Component Of Zylet

    71. Ab00698349-05

    72. Ab00698349-07

    73. Ab00698349_08

    74. 034l466

    75. Q3837481

    76. Androsta-1,4-diene-17-carboxylic Acid, 17-((ethoxycarbonyl)oxy)-11-hydroxy-3-oxo-, Chloromethyl Ester, (11.beta.,17.alpha.)-

    77. Androsta-1,4-diene-17-carboxylic Acid, 17-((ethoxycarbonyl)oxy)-11-hydroxy-3-oxo-, Chloromethyl Ester, (11beta,17alpha)-

    78. Chloromethyl (1s,2r,10s,11s,14r,15s,17s)-14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-diene-14-carboxylate

    79. Chloromethyl 11.beta.,17-dihydroxy-3-oxoandrosta-1,4-diene-17.beta.-carboxylate, 17-(ethyl Carbonate)

    2.4 Create Date
    2005-06-24
    3 Chemical and Physical Properties
    Molecular Weight 466.9 g/mol
    Molecular Formula C24H31ClO7
    XLogP33.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count7
    Exact Mass466.1758310 g/mol
    Monoisotopic Mass466.1758310 g/mol
    Topological Polar Surface Area99.1 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity882
    Isotope Atom Count0
    Defined Atom Stereocenter Count7
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameAlrex
    Drug LabelALREX (loteprednol etabonate ophthalmic suspension) contains a sterile, topical anti-inflammatory corticosteroid for ophthalmic use.Loteprednol etabonate is a white to off-white powder.Loteprednol etabonate is represented by the following structura...
    Active IngredientLoteprednol etabonate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength0.2%
    Market StatusPrescription
    CompanyBausch And Lomb

    2 of 4  
    Drug NameLotemax
    PubMed HealthLoteprednol (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelLOTEMAX (loteprednol etabonate ophthalmic suspension) contains a sterile, topical anti-inflammatory corticosteroid for ophthalmic use. Loteprednol etabonate is a white to off-white powder.Loteprednol etabonate is represented by the following struct...
    Active IngredientLoteprednol etabonate
    Dosage FormOintment; Gel; Suspension/drops
    RouteOphthalmic
    Strength0.5%
    Market StatusPrescription
    CompanyBausch And Lomb

    3 of 4  
    Drug NameAlrex
    Drug LabelALREX (loteprednol etabonate ophthalmic suspension) contains a sterile, topical anti-inflammatory corticosteroid for ophthalmic use.Loteprednol etabonate is a white to off-white powder.Loteprednol etabonate is represented by the following structura...
    Active IngredientLoteprednol etabonate
    Dosage FormSuspension/drops
    RouteOphthalmic
    Strength0.2%
    Market StatusPrescription
    CompanyBausch And Lomb

    4 of 4  
    Drug NameLotemax
    PubMed HealthLoteprednol (Into the eye)
    Drug ClassesOphthalmologic Agent
    Drug LabelLOTEMAX (loteprednol etabonate ophthalmic suspension) contains a sterile, topical anti-inflammatory corticosteroid for ophthalmic use. Loteprednol etabonate is a white to off-white powder.Loteprednol etabonate is represented by the following struct...
    Active IngredientLoteprednol etabonate
    Dosage FormOintment; Gel; Suspension/drops
    RouteOphthalmic
    Strength0.5%
    Market StatusPrescription
    CompanyBausch And Lomb

    4.2 Drug Indication

    A number of prescription loteprednol etabonate ophthalmic products are specifically indicated for the treatment of post-operative inflammation and pain following ocular surgery.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Loteprednol etabonate (LE) belongs to a unique class of corticosteroids with potent anti-inflammatory effects designed to be active at the site of action. Animal studies have shown that LE has a binding affinity to steroid receptors that is 4.3 times greater than dexamethasone. This particular class of steroids consists of bioactive molecules whose in-vivo transformation to non-toxic substances can be predicted from their chemistry and knowledge of enzymatic pathways in the body. Cortienic acid is an inactive metabolite of hydrocortisone and analogs of cortienic acid are also devoid of corticosteroid activity. Specifically, LE is an ester derivative of one of these analogs, cortienic acid etabonate. In particular, LE possesses a metabolically labile 17 beta-chloromethyl ester function which was designed in order to be hydrolyzed to an inactive carboxylic acid moiety. This inactive metabolite is more hydrophilic and is thus readily eliminated from the body. LE also exhibits good ocular permeation properties and good skin permeation properties.

    5.2 MeSH Pharmacological Classification

    Anti-Allergic Agents

    Agents that are used to treat allergic reactions. Most of these drugs act by preventing the release of inflammatory mediators or inhibiting the actions of released mediators on their target cells. (From AMA Drug Evaluations Annual, 1994, p475) (See all compounds classified as Anti-Allergic Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
    5.4 Absorption, Distribution and Excretion

    Absorption

    Loteprednol etabonate (LE) demonstrates good ocular permeation properties as it is lipid soluble, allowing the agent to penetrate into cells with relative ease. Results from the ocular administration of loteprednol in normal, healthy volunteers have shown that there are low or undetectable concentrations of either unchanged material or its metabolite. Following twice-daily unilateral topical ocular dosing of LE for 14 days in healthy subjects, the plasma concentrations of loteprednol etabonate were below the limit of quantitation (1 ng/mL) at all time points. These finds suggest that limited, if any, systemic absorption of LE occurs.

    Route of Elimination

    Following systemic administration to rats, loteprednol etabonate is eliminated primarily via the biliary/faecal route, with most of the dose eliminated in the form of the metabolite, PJ-90.

    Volume of Distribution

    The only data available regarding the volume of distribution of loteprednol etabonate (LE) is the volume of distribution the agent demonstrated when administered to dogs - a value of 3.7 L/kg. It has been shown, however, that the topical ocular administration of LE distributes preferentially into the cellular components of blood.

    Clearance

    Loteprednol etabonate was slowly hydrolyzed in liver at clearance rates of 0.21 +/- 0.04 and 2.41 +/- 0.13 ml/h/kg in the liver and plasma, respectively.

    5.5 Metabolism/Metabolites

    Loteprednol etabonate (LE) is readily and extensively metabolized to two inactive metabolites, PJ-90 (1-cortienic acid) and PJ-91 (1-cortienic acid etabonate). Metabolism occurs locally in ocular tissues, and to the extent that loteprednol etabonate reaches the systemic circulation, likely the liver and other tissues into which it distributes. In particular, studies have demonstrated that LE (chloromethyl 17alpha-ethoxycarbonyloxy-11beta-hydroxy-3-oxoandrosta-1,4-diene) is rapidly hydrolyzed at the location of its 17beta-chloromethyl ester function by paraoxonase 1 in human plasma at the site of administration at the level of the affected eye tissue to the 17beta-carboxylate PJ-91 metabolite and PJ-90 metabolite. Both metabolites are considered inactive.

    5.6 Biological Half-Life

    The terminal half-life of loteprednol etabonate as determined when administered intravenously at a dose of 5 mg/kg in the dog animal model is 2.8 hours.

    5.7 Mechanism of Action

    Corticosteroids like loteprednol etabonate inhibit the inflammatory response to a variety of inciting agents and likely delay or slow healing. They inhibit the edema, fibrin deposition, capillary dilation, leukocyte migration, capillary proliferation, fibroblast proliferation, deposition of collagen, and scar formation that are commonly associated with inflammation. While glucocorticoids are known to bind to and activate the glucocorticoid receptor, the molecular mechanisms involved in glucocorticoid/glucocorticoid receptor-dependent modulation of inflammation are not clearly established. Moreover, corticosteroids are thought to inhibit prostaglandin production through several independent mechanisms. In particular, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. The use of LE subsequently treats post-operative inflammation and pain following ocular surgery by managing the prostaglandin release, recruitment and travel of neutrophils and macrophages, and production of other inflammatory mediators that are intrinsically associated with the physical trauma of surgery.

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    27-Jan-2021
    15-Oct-2024
    KGS
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    Average Price (USD/KGS)

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    Total Quantity (KGS)

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

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

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    DOSAGE - OINTMENT;OPHTHALMIC - 0.5%

    USFDA APPLICATION NUMBER - 200738

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    DOSAGE - GEL;OPHTHALMIC - 0.38%

    USFDA APPLICATION NUMBER - 208219

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