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Prestwick3_001020

Prestwick3_001020

Synopsis, Chemistry

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Also known as: Vexol, 49697-38-3, Rimexolon, Org-6216, Org 6216, Mls002154105

Molecular Formula

C₂₄H₃₄O₃

Molecular Weight

370.5 g/mol

InChI Key

QTTRZHGPGKRAFB-OOKHYKNYSA-N

FDA UNII

O7M2E4264D

Rimexolone is a derivative of prednisolone, a synthetic glucocorticoid with anti-inflammatory and immunosuppressive property. Upon binding to the cytosolic glucocorticoid receptor and cell entry, rimexolone activates specific glucocorticoid response elements, resulting in altered gene expression. These include induction of synthesis of anti-inflammatory protein IkappaB-alpha and inhibition of synthesis of nuclear factor kappaB (NFkappa B). As a result, pro-inflammatory cytokine production such as interleukin-1 (IL-1), IL-2 and IL-6 is down-regulated and cytotoxic T-lymphocyte activation inhibited. Therefore, an overall reduction in chronic inflammation and autoimmune reactions may be achieved.

Rimexolone is a Corticosteroid. The mechanism of action of rimexolone is as a Corticosteroid Hormone Receptor Agonist.

1 2D Structure

Prestwick3_001020

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(8S,9S,10R,11S,13S,14S,16R,17S)-11-hydroxy-10,13,16,17-tetramethyl-17-propanoyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one

2.1.2 InChI

InChI=1S/C24H34O3/c1-6-20(27)24(5)14(2)11-18-17-8-7-15-12-16(25)9-10-22(15,3)21(17)19(26)13-23(18,24)4/h9-10,12,14,17-19,21,26H,6-8,11,13H2,1-5H3/t14-,17+,18+,19+,21-,22+,23+,24-/m1/s1

2.1.3 InChI Key

QTTRZHGPGKRAFB-OOKHYKNYSA-N

2.1.4 Canonical SMILES

CCC(=O)C1(C(CC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)C)C

2.1.5 Isomeric SMILES

CCC(=O)[C@]1([C@@H](C[C@@H]2[C@@]1(C[C@@H]([C@H]3[C@H]2CCC4=CC(=O)C=C[C@]34C)O)C)C)C

2.2 Other Identifiers

2.2.1 UNII

O7M2E4264D

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 11 Beta-hydroxy-16 Alpha,17 Alpha,21-trimethylpregna-1,4-diene-3,20-dione

2. Org 6216

3. Org-6216

4. Rimexel

5. Vexol

2.3.2 Depositor-Supplied Synonyms

1. Vexol

2. 49697-38-3

3. Rimexolon

4. Org-6216

5. Org 6216

6. Mls002154105

7. Rimexel

8. O7m2e4264d

9. Trimexolone

10. Rimexolona

11. Rimexolonum

12. Rimexolonum [inn-latin]

13. Rimexolona [inn-spanish]

14. Unii-o7m2e4264d

15. Rimexolone [usan:usp:inn:ban]

16. Vexol (tn)

17. Al 02178

18. Rimexolone [mi]

19. Rimexolone (usp/inn)

20. Rimexolone [inn]

21. Prestwick0_001020

22. Prestwick1_001020

23. Prestwick2_001020

24. Prestwick3_001020

25. Rimexolone [usan]

26. Rimexolone [vandf]

27. Rimexolone [mart.]

28. Rimexolone [usp-rs]

29. Rimexolone [who-dd]

30. Bspbio_001179

31. Schembl445300

32. Spbio_003050

33. Bpbio1_001297

34. Gtpl7099

35. Chembl1200617

36. Rimexolone [orange Book]

37. Rimexolone [usp Impurity]

38. Chebi:135566

39. Hms1571k21

40. Hms2098k21

41. Hms2235b18

42. Hms3715k21

43. Rimexolone [usp Monograph]

44. Hy-b1754

45. Zinc3945984

46. 11beta-hydroxy-16alpha,17,21-trimethyl-1,4-pregnadien-3,20-dion

47. Bdbm50103606

48. 11beta-hydroxy-16alpha,17alpha-dimethyl-17-propionylandrosta-1,4-dien-3-one

49. Al-2178

50. Ccg-221020

51. Db00896

52. Ncgc00179273-01

53. (8s,9s,10r,11s,13s,14s,16r,17s)-11-hydroxy-10,13,16,17-tetramethyl-17-propanoyl-7,8,9,11,12,14,15,16-octahydro-6h-cyclopenta[a]phenanthren-3-one

54. Smr001233413

55. Ab00514006

56. Cs-0013781

57. D05729

58. 697r383

59. Sr-01000841221

60. Q7334443

61. Sr-01000841221-2

62. Brd-k31627533-001-03-8

63. 11.beta.-hydroxy-16.alpha.,17.alpha.-dimethyl-17-propionylandrosta-1,4-dien-3-one

64. (11beta, 16alpha, 17beta)-11-hydroxy-16,17-dimethyl-17-(1-oxopropyl)androstra-1,4-dien-3-one

65. (11beta,16alpha,17beta)-11-hydroxy-16,17-dimethyl-17-(1-oxopropyl)androsta-1,4-dien-3-one

66. Androsta-1,4-dien-3-one, 11-hydroxy-16,17-dimethyl-17-(1-oxopropyl)-, (11.beta.,16,alpha.,17.beta.)-

67. Androsta-1,4-dien-3-one, 11-hydroxy-16,17-dimethyl-17-(1-oxopropyl)-, (11beta,16alpha,17beta)-

2.4 Create Date

2005-12-16

3 Chemical and Physical Properties

Molecular Formula	C₂₄H₃₄O₃
Molecular Weight	370.5 g/mol
XLogP3	3.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	2
Exact Mass	370.25079494 g/mol
Monoisotopic Mass	370.25079494 g/mol
Topological Polar Surface Area	54.4 Å²
Heavy Atom Count	27
Formal Charge	0
Complexity	749
Isotope Atom Count	0
Defined Atom Stereocenter Count	8
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Vexol
PubMed Health	Rimexolone (Into the eye)
Drug Classes	Ophthalmologic Agent
Drug Label	VEXOL 1% Ophthalmic Suspension is a sterile, multi-dose topical ophthalmic suspension containing the corticosteroid, rimexolone. Rimexolone is a white, water-insoluble powder with an empirical formula of C24H34O3 and a molecular weight of 370.53. I...
Active Ingredient	Rimexolone
Dosage Form	Suspension/drops
Route	Ophthalmic
Strength	1%
Market Status	Prescription
Company	Alcon

2 of 2
Drug Name	Vexol
PubMed Health	Rimexolone (Into the eye)
Drug Classes	Ophthalmologic Agent
Drug Label	VEXOL 1% Ophthalmic Suspension is a sterile, multi-dose topical ophthalmic suspension containing the corticosteroid, rimexolone. Rimexolone is a white, water-insoluble powder with an empirical formula of C24H34O3 and a molecular weight of 370.53. I...
Active Ingredient	Rimexolone
Dosage Form	Suspension/drops
Route	Ophthalmic
Strength	1%
Market Status	Prescription
Company	Alcon

4.2 Drug Indication

For the treatment of postoperative inflammation following ocular surgery and in the treatment of anterior uveitis.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Rimexolone is a glucocorticoid corticosteroid for systemic use. Corticosteroids suppress the inflammatory response to a variety of inciting agents of a mechanical, chemical, or immunological nature. They inhibit edema, cellular infiltration, capillary dilatation, fibroblastic proliferation, deposition of collagen and scar formation associated with inflammation.

5.2 MeSH Pharmacological Classification

Glucocorticoids

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

RIMEXOLONE

5.3.2 FDA UNII

O7M2E4264D

5.3.3 Pharmacological Classes

Mechanisms of Action [MoA] - Corticosteroid Hormone Receptor Agonists

5.4 ATC Code

H - Systemic hormonal preparations, excl. sex hormones and insulins

H02 - Corticosteroids for systemic use

H02A - Corticosteroids for systemic use, plain

H02AB - Glucocorticoids

H02AB12 - Rimexolone

S - Sensory organs

S01 - Ophthalmologicals

S01B - Antiinflammatory agents

S01BA - Corticosteroids, plain

S01BA13 - Rimexolone

5.5 Absorption, Distribution and Excretion

Absorption

Systemically absorbed.

Route of Elimination

Following IV administration of radio-labelled rimexolone to rats, greater than 80% of the dose is excreted via the feces as rimexolone and metabolites.

5.6 Metabolism/Metabolites

Undergoes extensive metabolism. Following intravenous administration of radiolabeled rimexolone in rats, more than 80% of the dose was excreted in the feces as rimexolone and metabolites. Metabolites have been shown to be either less active than rimexolone or inactive in human glucocorticoid receptor binding assays.

5.7 Biological Half-Life

The serum half-life of rimexolone could not be reliably estimated due to the large number of samples below the quantitation limit of the assay (80 pg/mL). However, based on the time required to reach steady-state, the half-life appears to be short (1-2 hours).

5.8 Mechanism of Action

Rimexolone is a glucocorticoid receptor agonist. The antiinflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition of arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. By binding to the glucocorticoid receptor, this drug ultimately leads to changes in genetic transcription involving the lipocortins and prostaglandins.