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Chemistry

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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

Prednicarbate

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 Formula	C₂₇H₃₆O₈
Molecular Weight	488.6 g/mol
XLogP3	4.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	9
Exact Mass	488.24101810 g/mol
Monoisotopic Mass	488.24101810 g/mol
Topological Polar Surface Area	116 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	982
Isotope Atom Count	0
Defined Atom Stereocenter Count	7
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 6
Drug Name	Dermatop
PubMed Health	Prednicarbate (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Intermediate
Drug Label	DERMATOP 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 Ingredient	Prednicarbate
Dosage Form	Ointment
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Valeant Bermuda

2 of 6
Drug Name	Dermatop e emollient
PubMed Health	Prednicarbate (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Intermediate
Drug Label	DERMATOP 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 Ingredient	Prednicarbate
Dosage Form	Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Valeant Bermuda

3 of 6
Drug Name	Prednicarbate
Active Ingredient	Prednicarbate
Dosage Form	Ointment; Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Fougera Pharms

4 of 6
Drug Name	Dermatop
PubMed Health	Prednicarbate (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Intermediate
Drug Label	DERMATOP 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 Ingredient	Prednicarbate
Dosage Form	Ointment
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Valeant Bermuda

5 of 6
Drug Name	Dermatop e emollient
PubMed Health	Prednicarbate (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Intermediate
Drug Label	DERMATOP 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 Ingredient	Prednicarbate
Dosage Form	Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Valeant Bermuda

6 of 6
Drug Name	Prednicarbate
Active Ingredient	Prednicarbate
Dosage Form	Ointment; Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Fougera 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.

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DOSAGE - OINTMENT;TOPICAL - 0.1% **Federal Re...DOSAGE - OINTMENT;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 19568

DOSAGE - CREAM;TOPICAL - 0.1% **Federal Regis...DOSAGE - CREAM;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20279

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FINISHED DOSAGE FORMULATIONS

29 FDF Dossiers

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21 Europe

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DRUG PRODUCT COMPOSITIONS

OINTMENT;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

CREAM;TOPICAL - 0.1% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

RELATED EXCIPIENT COMPANIES

1 Minakem

1 DKSH

1 Pharm-RX Chemical

1 Faran Shimi Pharmaceutical

1 Gangwal Healthcare

3 Nanjing Well Pharmaceutical

1 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

8 BASF

1 Finar

5 Microlex e.U

1 Pluviaendo

1 Prachin Chemical

1 Seppic

1 Shanghai Shenmei Pharmaceutical Technology Co., Ltd

1 Valens Pharmachem

1 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

14 Topical

8 Lubricants & Glidants

5 Fillers, Diluents & Binders

4 Thickeners and Stabilizers

4 Emulsifying Agents

3 Solubilizers

2 Film Formers & Plasticizers

2 API Stability Enhancers

1 Controlled & Modified Release

1 Parenteral

1 Co-Processed Excipients

1 Direct Compression

1 Surfactant & Foaming Agents

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1 US Medicaid Prescriptions

21 Finished Drug Prices

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1 APIs

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2 EDQM

4 USP

4 Others

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OINTMENT;TOPICAL - 0.1% Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons

CREAM;TOPICAL - 0.1% Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons