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Amcinonide

Amcinonide

Synopsis, Chemistry

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Also known as: 51022-69-6, Cyclocort, Amcinonidum, Cl-34699, Triamcinolonacetatcyclopentanonid, Cl 34699

Molecular Formula

C₂₈H₃₅FO₇

Molecular Weight

502.6 g/mol

InChI Key

ILKJAFIWWBXGDU-MOGDOJJUSA-N

FDA UNII

423W026MA9

Amcinonide is a synthetic glucocorticoid receptor agonist that mimics the metabolic, anti-inflammatory, and immunosuppressive activity of the natural glucocorticoids. Amcinonide interacts with specific corticosteroid receptors and was internalized, which leads to binding of DNA and modification of gene expression. This results in synthesis of anti-inflammatory mediators while inhibiting synthesis of inflammatory mediators. Consequently, an overall reduction in chronic inflammation and autoimmune reactions are achieved.

Amcinonide is a Corticosteroid. The mechanism of action of amcinonide is as a Corticosteroid Hormone Receptor Agonist.

1 2D Structure

Amcinonide

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-[(1S,2S,4R,8S,9S,11S,12R,13S)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] acetate

2.1.2 InChI

InChI=1S/C28H35FO7/c1-16(30)34-15-22(33)28-23(35-26(36-28)9-4-5-10-26)13-20-19-7-6-17-12-18(31)8-11-24(17,2)27(19,29)21(32)14-25(20,28)3/h8,11-12,19-21,23,32H,4-7,9-10,13-15H2,1-3H3/t19-,20-,21-,23+,24-,25-,27-,28+/m0/s1

2.1.3 InChI Key

ILKJAFIWWBXGDU-MOGDOJJUSA-N

2.1.4 Canonical SMILES

CC(=O)OCC(=O)C12C(CC3C1(CC(C4(C3CCC5=CC(=O)C=CC54C)F)O)C)OC6(O2)CCCC6

2.1.5 Isomeric SMILES

CC(=O)OCC(=O)[C@@]12[C@@H](C[C@@H]3[C@@]1(C[C@@H]([C@]4([C@H]3CCC5=CC(=O)C=C[C@@]54C)F)O)C)OC6(O2)CCCC6

2.2 Other Identifiers

2.2.1 UNII

423W026MA9

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Amciderm

2. Amcininide

3. Cl 34,699

4. Cyclocort

5. Cyclort

6. Penticort

7. Triamcinolone 16,17-cyclopentylidenedioxy-21-acetate

2.3.2 Depositor-Supplied Synonyms

1. 51022-69-6

2. Cyclocort

3. Amcinonidum

4. Cl-34699

5. Triamcinolonacetatcyclopentanonid

6. Cl 34699

7. Visderm

8. Mls000028656

9. Mls001333715

10. Chebi:31199

11. 423w026ma9

12. Nsc-758620

13. Amcinonido

14. Smr000058920

15. [2-[(1s,2s,4r,8s,9s,11s,12r,13s)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] Acetate

16. [2-[(4r,8s,9s,11s,12r,13s)-12-fluoro-11-hydroxy-9,13-dimethyl-16-oxospiro[5,7-dioxapentacyclo[10.8.0.02,9.04,8.013,18]icosa-14,17-diene-6,1'-cyclopentane]-8-yl]-2-oxoethyl] Acetate

17. Amcinonida

18. Amcinonidum [inn-latin]

19. Amcinonido [inn-spanish]

20. Cyclocort (tn)

21. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxy-, (11.beta.,16.alpha.)-

22. Amcinonide (jan/usp/inn)

23. Unii-423w026ma9

24. Ncgc00095071-01

25. (11?,16?)-21-(acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxypregna-1,4-diene-3,20-dione

26. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-16,17-(cyclopentylidenebis(oxy))-9-fluoro-11-hydroxy-, (11.beta.,16.alpha.)-

27. Einecs 256-915-2

28. Amcinonide [usan:usp:inn:ban:jan]

29. Amcinonide [mi]

30. Amcinonide [inn]

31. Amcinonide [jan]

32. Opera_id_1472

33. Amcinonide [usan]

34. Amcinonide [vandf]

35. Amcinonide [mart.]

36. Schembl4720

37. 1,4-pregnadiene-2,20-dione-16,17-cyclopentylidenedioxy-9-fluoro-11,21-dihydroxy-21-acetate

38. Amcinonide [usp-rs]

39. Amcinonide [who-dd]

40. Dsstox_cid_25905

41. Dsstox_rid_81217

42. Dsstox_gsid_45905

43. 19alpha-fluor-11beta,21-dihydroxy-16alpha,17alpha-(tetramethylen)methylendioxy-1,4-pregnadien-3,20-dion 21-acetat

44. 9-fluoro-11beta,16alpha,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Cyclopentanone, 21-acetate

45. Mls001146959

46. Mls002695893

47. Amcinonide, Analytical Standard

48. Gtpl7060

49. Amcinonide [orange Book]

50. Chembl1200732

51. Dtxsid6045905

52. Amcinonide [usp Monograph]

53. Hms2235k23

54. Hms3715d11

55. 9-fluoro-11.beta.,16.alpha.,17,21-tetrahydroxypregna-1,4-diene-3,20-dione Cyclic 16,17-acetal With Cyclopentanone, 21-acetate

56. Amy38534

57. Hy-b1197

58. Zinc3977777

59. Tox21_111411

60. S5671

61. Akos015961167

62. Amcinonide 100 Microg/ml In Methanol

63. Ccg-221135

64. Cs-4805

65. Db00288

66. Nsc 758620

67. Ncgc00021193-03

68. 16alpha,17alpha-(cyclopentane-1,1-diyldioxy)-9-fluoro-11beta-hydroxy-3,20-dioxopregna-1,4-dien-21-yl Acetate

69. Ac-13190

70. Pregna-1,4-diene-3,20-dione, 21-(acetyloxy)-16,17-(cyclopentylidenebis(oxy))-9-fluoro-11-hydroxy-, (11beta,16alpha)-

71. Cas-51022-69-6

72. D01387

73. Sr-01000003161

74. Q4742041

75. Sr-01000003161-2

76. Brd-k13960744-001-09-7

77. Amcinonide, United States Pharmacopeia (usp) Reference Standard

78. 5,6-dimethoxy-2-methyl-3-[2-(4-phenyl-1-piperazinyl)ethyl]-1h-indolehydrochloride

79. 2-((6a's,6b'r,7's,8a's,8b's,11a'r,12a's,12b's)-6b'-fluoro-7'-hydroxy-6a',8a'-dimethyl-4'-oxo-2',4',6a',6b',7',8',8a',8b',11a',12',12a',12b'-dodecahydro-1'h-spiro[cyclopentane-1,10'-naphtho[2',1':4,5]indeno[1,2-d][1,3]dioxole]-8b'-yl)-2-oxoethyl Acetate

80. 2-[(1's,2's,4'r,8's,9's,11's,12'r,13's)-12'-fluoro-11'-hydroxy-9',13'-dimethyl-16'-oxo-5',7'-dioxaspiro[cyclopentane-1,6'-pentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosane]-14',17'-dien-8'-yl]-2-oxoethyl Acetate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₈H₃₅FO₇
Molecular Weight	502.6 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	8
Rotatable Bond Count	4
Exact Mass	502.23668161 g/mol
Monoisotopic Mass	502.23668161 g/mol
Topological Polar Surface Area	99.1 Å²
Heavy Atom Count	36
Formal Charge	0
Complexity	1090
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	Amcinonide
PubMed Health	Amcinonide (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Strong
Drug Label	The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents.Each gram of Amcinonide Ointment USP, 0.1% contains 1 mg of the active steroid amcinonide in a specially formulated base...
Active Ingredient	Amcinonide
Dosage Form	Lotion; Ointment; Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Fougera Pharms; Taro Pharm Inds

2 of 2
Drug Name	Amcinonide
PubMed Health	Amcinonide (Topical application route)
Drug Classes	Adrenal Glucocorticoid, Corticosteroid, Strong
Drug Label	The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents.Each gram of Amcinonide Ointment USP, 0.1% contains 1 mg of the active steroid amcinonide in a specially formulated base...
Active Ingredient	Amcinonide
Dosage Form	Lotion; Ointment; Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Fougera Pharms; Taro Pharm Inds

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

Amcinonide is a topical corticosteroid. The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. Amcinonide reduces or inhibits the actions of chemicals in the body that cause inflammation, redness, and swelling. The mechanism of anti-inflammatory activity of the topical corticosteroids is unclear. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man. When in an ointment form, amcinonide also helps the skin maintain moisture.

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

AMCINONIDE

5.3.2 FDA UNII

423W026MA9

5.3.3 Pharmacological Classes

Corticosteroid [EPC]; Corticosteroid Hormone Receptor Agonists [MoA]

5.4 ATC Code

D07AC11

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

D - Dermatologicals

D07 - Corticosteroids, dermatological preparations

D07A - Corticosteroids, plain

D07AC - Corticosteroids, potent (group iii)

D07AC11 - Amcinonide

5.5 Absorption, Distribution and Excretion

Absorption

Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.

Route of Elimination

Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.

5.6 Metabolism/Metabolites

Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.

5.7 Mechanism of Action

The mechanism of the anti-inflammatory activity of the topical steroids, in general, 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. Amcinonide has affinity for the glucocorticoid receptor. It has weak affinity for the progesterone receptor, and virtually no affinity for the mineralocorticoid, estrogen, or androgen receptors.