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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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SDNF","customerAddress":"208, OKHLA INDUSTRIAL ESTATE,,PHAS"}]
27-Jan-2021
05-Aug-2024
KGS
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Average Price (USD/KGS)

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

API Imports and Exports

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(USD/KGS)
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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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