Please Wait
Applying Filters...
Menu
Xls
2D Structure
Also known as: Dermatop, 73771-04-7, Hoe 777, Hoe-777, Dermatop e emollient, S-770777
Molecular Formula
C27H36O8
Molecular Weight
488.6  g/mol
InChI Key
FNPXMHRZILFCKX-KAJVQRHHSA-N
FDA UNII
V901LV1K7D

Prednicarbate is a synthetic non-halogenated double-ester derivative of the corticosteroid prednisolone with anti-inflammatory, antipruritic and vasoconstrictive properties. Following skin permeation, prednicarbate enters cells and binds to and activates specific nuclear receptors, resulting in an altered gene expression and inhibition of pro-inflammatory cytokine production by increasing the expression of lipocortins. These block phospholipase A-dependent release of arachidonic acid thereby inhibiting prostaglandin synthesis. This agent also decreases the number of circulating lymphocytes by suppression of the production of vasodilators such as prostacyclin and nitric oxide.
Prednicarbate is a Corticosteroid. The mechanism of action of prednicarbate is as a Corticosteroid Hormone Receptor Agonist.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(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]phenanthren-17-yl]-2-oxoethyl] propanoate
2.1.2 InChI
InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3/t18-,19-,20-,23+,25-,26-,27-/m0/s1
2.1.3 InChI Key
FNPXMHRZILFCKX-KAJVQRHHSA-N
2.1.4 Canonical SMILES
CCC(=O)OCC(=O)C1(CCC2C1(CC(C3C2CCC4=CC(=O)C=CC34C)O)C)OC(=O)OCC
2.1.5 Isomeric SMILES
CCC(=O)OCC(=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)OC(=O)OCC
2.2 Other Identifiers
2.2.1 UNII
V901LV1K7D
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Batmen

2. Dermatop

3. Hoe 777

4. Hoe-777

5. Peitel

6. Prednisolone-17-ethylcarbonate-21-propionate

2.3.2 Depositor-Supplied Synonyms

1. Dermatop

2. 73771-04-7

3. Hoe 777

4. Hoe-777

5. Dermatop E Emollient

6. S-770777

7. Mls002154121

8. V901lv1k7d

9. Las189961

10. S 77 0777

11. S-77 0777

12. Las-189961

13. Nsc-760042

14. Peitel

15. Las-41003 Component Prednicarbate

16. Unii-v901lv1k7d

17. S-77-0777

18. Prednicarbato

19. Prednicarbatum

20. [2-[(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]phenanthren-17-yl]-2-oxoethyl] Propanoate

21. Dermatop (tn)

22. Prednicarbate (usp/inn)

23. Prednicarbatum [inn-latin]

24. Prednicarbat

25. Prednicarbato [inn-spanish]

26. Ncgc00016926-01

27. Einecs 277-590-3

28. Prednicarbate [usan:usp:inn:ban]

29. Cas-73771-04-7

30. Prestwick0_001044

31. Prestwick1_001044

32. Prestwick2_001044

33. Prestwick3_001044

34. Prednicarbate [mi]

35. Prednicarbate [inn]

36. Schembl3941

37. Dsstox_cid_25502

38. Dsstox_rid_80919

39. Prednicarbate [usan]

40. Dsstox_gsid_45502

41. Bspbio_000968

42. Prednicarbate [vandf]

43. Prednicarbate [mart.]

44. S 770777

45. Spbio_002904

46. Prednicarbate [usp-rs]

47. Prednicarbate [who-dd]

48. Bpbio1_001066

49. Gtpl7605

50. Chembl1200386

51. Dtxsid9045502

52. Chebi:135791

53. Hms1571a10

54. Hms2098a10

55. Hms2230o11

56. Hms3715a10

57. Prednicarbate [orange Book]

58. Hy-b1365

59. Zinc3938652

60. Prednicarbate [ep Monograph]

61. Tox21_110687

62. Prednicarbate [usp Monograph]

63. Akos025402043

64. Prednicarbate For System Suitability A

65. Ac-3521

66. Ccg-221044

67. Db01130

68. Nsc 760042

69. 11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17-(ethyl Carbonate) 21-propionate

70. Ncgc00179357-01

71. Ncgc00179357-05

72. Pregna-1,4-diene-3,20-dione, 17-((ethoxycarbonyl)oxy)-11-hydroxy-21-(1-oxopropoxy)-, (11beta)-

73. Smr001233428

74. Ab00514017

75. Cs-0013106

76. D05601

77. 771p047

78. Sr-01000841201

79. Q-101379

80. Q4376623

81. Sr-01000841201-2

82. Brd-k46137903-001-03-3

83. 11.beta.,17,21-trihydroxypregna-1,4-diene-3,20-dione 17-(ethyl Carbonate) 21-propionate

84. Pregna-1,4-diene-3,20-dione, 17-((ethoxycarbonyl)oxy)-11-hydroxy-21-(1-oxopropoxy)-, (11.beta.)-

2.4 Create Date
2006-06-05
3 Chemical and Physical Properties
Molecular Weight 488.6 g/mol
Molecular Formula C27H36O8
XLogP34.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count8
Rotatable Bond Count9
Exact Mass488.24101810 g/mol
Monoisotopic Mass488.24101810 g/mol
Topological Polar Surface Area116 Ų
Heavy Atom Count35
Formal Charge0
Complexity982
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 6  
Drug NameDermatop
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormOintment
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

2 of 6  
Drug NameDermatop e emollient
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormCream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

3 of 6  
Drug NamePrednicarbate
Active IngredientPrednicarbate
Dosage FormOintment; Cream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyFougera Pharms

4 of 6  
Drug NameDermatop
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormOintment
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

5 of 6  
Drug NameDermatop e emollient
PubMed HealthPrednicarbate (Topical application route)
Drug ClassesAdrenal Glucocorticoid, Corticosteroid, Intermediate
Drug LabelDERMATOP Ointment (prednicarbate ointment) 0.1% contains the non-halogenated prednisolone derivative prednicarbate. The topical corticosteroids constitute a class of primarily synthetic steroids used topically as anti-inflammatory and anti-pruritic...
Active IngredientPrednicarbate
Dosage FormCream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyValeant Bermuda

6 of 6  
Drug NamePrednicarbate
Active IngredientPrednicarbate
Dosage FormOintment; Cream
RouteTopical
Strength0.1%
Market StatusPrescription
CompanyFougera Pharms

4.2 Drug Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of messenger RNA (mRNA) and subsequent protein synthesis of various inhibitory enzymes responsible for the anti-inflammatory effects of topical corticosteroids. These anti-inflammatory effects include inhibition of early processes such as edema, fibrin deposition, capillary dilatation, movement of phagocytes into the area, and phagocytic activities. Later processes, such as capillary production, collagen deposition, and keloid formation also are inhibited by corticosteroids.


5.2 MeSH Pharmacological Classification

Anti-Inflammatory Agents

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)


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
PREDNICARBATE
5.3.2 FDA UNII
V901LV1K7D
5.3.3 Pharmacological Classes
Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]
5.4 ATC Code

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC18 - Prednicarbate


5.5 Absorption, Distribution and Excretion

Absorption

Absorbed systemically across the stratum corneum.


5.6 Metabolism/Metabolites

Primarily in skin


5.7 Mechanism of Action

In common with other topical corticosteroids, prednicarbate has anti-inflammatory, antipruritic, and vasoconstrictive properties. In general, the mechanism of the anti-inflammatory activity of topical steroids is unclear. However, 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.