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Prestwick3_001119

Prestwick3_001119

Synopsis, Chemistry

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Also known as: 34097-16-0, Clocortolone 21-pivalate, Cloderm, Sh 863, Qbl8izh14x, Purantix

Molecular Formula

C₂₇H₃₆ClFO₅

Molecular Weight

495.0 g/mol

InChI Key

SXYZQZLHAIHKKY-GSTUPEFVSA-N

FDA UNII

QBL8IZH14X

Clocortolone Pivalate is a glucocorticoid receptor agonist with metabolic, anti-inflammatory, and immunosuppressive activity. Clocortolone pivalate exerts its effect by interacting with specific intracellular receptors and subsequently binds to DNA to modify gene expression. This results in an induction of the synthesis of certain anti-inflammatory proteins while inhibiting the synthesis of certain inflammatory mediators. Consequently, an overall reduction in chronic inflammation and autoimmune reactions are accomplished.

1 2D Structure

Prestwick3_001119

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-[(6S,8S,9R,10S,11S,13S,14S,16R,17S)-9-chloro-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate

2.1.2 InChI

InChI=1S/C27H36ClFO5/c1-14-9-16-17-11-19(29)18-10-15(30)7-8-26(18,6)27(17,28)21(32)12-25(16,5)22(14)20(31)13-34-23(33)24(2,3)4/h7-8,10,14,16-17,19,21-22,32H,9,11-13H2,1-6H3/t14-,16+,17+,19+,21+,22-,25+,26+,27+/m1/s1

2.1.3 InChI Key

SXYZQZLHAIHKKY-GSTUPEFVSA-N

2.1.4 Canonical SMILES

CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1C(=O)COC(=O)C(C)(C)C)C)O)Cl)C)F

2.1.5 Isomeric SMILES

C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@H]1C(=O)COC(=O)C(C)(C)C)C)O)Cl)C)F

2.2 Other Identifiers

2.2.1 UNII

QBL8IZH14X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Cl 68

2. Clocortolone Trimethylacetate

3. Cloderm

4. Purantix

2.3.2 Depositor-Supplied Synonyms

1. 34097-16-0

2. Clocortolone 21-pivalate

3. Cloderm

4. Sh 863

5. Qbl8izh14x

6. Purantix

7. Clocortolone Pivalate (200 Mg)

8. Mls002154165

9. [2-[(6s,8s,9r,10s,11s,13s,14s,16r,17s)-9-chloro-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6h-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate

10. Chebi:59583

11. Sh-863

12. 9-chloro-6alpha-fluoro-11beta,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-pivalate

13. Cilder

14. Cl 68

15. 9-chloro-6alpha-fluoro-11beta-hydroxy-16alpha-methyl-3,20-dioxopregna-1,4-dien-21-yl 2,2-dimethylpropanoate

16. Unii-qbl8izh14x

17. Clocortolone Pivalate [usan]

18. Clocortolone Pivalate [usan:usp]

19. Ncgc00016824-01

20. Pregna-1,4-diene-3,20-dione, 9-chloro-21-(2,2-dimethyl-1-oxopropoxy)-6-fluoro-11-hydroxy-16-methyl-, (6.alpha.,11.beta.,16.alpha.)-

21. Clocortolone-pivalate

22. Cloderm (tn)

23. Einecs 251-826-5

24. Cas-34097-16-0

25. Prestwick0_001119

26. Prestwick1_001119

27. Prestwick2_001119

28. Prestwick3_001119

29. Schembl5120

30. Dsstox_cid_25460

31. Dsstox_rid_80891

32. Clocortolone Pivalate (usp)

33. Dsstox_gsid_45460

34. Bspbio_001258

35. Spbio_003119

36. Bpbio1_001383

37. Chembl1200975

38. Dtxsid0045460

39. Hms1571o20

40. Hms2098o20

41. Hms2236m06

42. Hms3715o20

43. 9-chloro-6.alpha.-fluoro-11.beta.,21-dihydroxy-16.alpha.-methylpregna-1,4-diene-3,20-dione 21-pivalate

44. Zinc4212603

45. Tox21_110632

46. Clocortolone Pivalate [vandf]

47. Clocortolone Pivalate [mart.]

48. Clocortolone Pivalate [usp-rs]

49. Clocortolone Pivalate [who-dd]

50. Ccg-221119

51. Clocortolone 21-pivalate [mi]

52. Ncgc00179239-01

53. Ncgc00179239-05

54. Smr001233464

55. Clocortolone Pivalate [orange Book]

56. Ab00514058

57. Clocortolone Pivalate [usp Monograph]

58. D02287

59. Sr-01000838872

60. Sr-01000838872-2

61. Brd-k38003476-001-03-4

62. Q39045318

63. (6alpha,11beta,16alpha)-9-chloro-21-(2,2-dimethyl-1-oxopropoxy)-6-fluoro-11-hydroxy-16-methypregna-1,4-diene-3,20-dione

64. 9-chloro-6

65. A-fluoro-11

66. A,21-dihydroxy-16

67. A-methylpregna-1,4-diene-3,20-dione 21-pivalate Pound Clocortolone Pivalate)

68. 9alpha-chloro-6alpha-fluoro-11beta,21-dihydroxy-16alpha-methylpregna-1,4-diene-3,20-dione 21-pivalate

69. Pregna-1,4-diene-3,20-dione, 9-chloro-21-(2,2-dimethyl-1-oxopropoxy)-6-fluoro-11-hydroxy-16-methyl-, (6alpha,11beta,16alpha)-

2.4 Create Date

2005-10-11

3 Chemical and Physical Properties

Molecular Formula	C₂₇H₃₆ClFO₅
Molecular Weight	495.0 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	494.2235301 g/mol
Monoisotopic Mass	494.2235301 g/mol
Topological Polar Surface Area	80.7 Å²
Heavy Atom Count	34
Formal Charge	0
Complexity	982
Isotope Atom Count	0
Defined Atom Stereocenter Count	9
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	Cloderm
PubMed Health	Clocortolone Pivalate (On the skin)
Drug Classes	Corticosteroid, Weak
Drug Label	Cloderm Cream 0.1% contains the medium potency topical corticosteroid, clocortolone pivalate, in a specially formulated water-washable emollient cream base consisting of purified water, white petrolatum, mineral oil, stearyl alcohol, polyoxyl 40 stea...
Active Ingredient	Clocortolone pivalate
Dosage Form	Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Promius Pharma

2 of 2
Drug Name	Cloderm
PubMed Health	Clocortolone Pivalate (On the skin)
Drug Classes	Corticosteroid, Weak
Drug Label	Cloderm Cream 0.1% contains the medium potency topical corticosteroid, clocortolone pivalate, in a specially formulated water-washable emollient cream base consisting of purified water, white petrolatum, mineral oil, stearyl alcohol, polyoxyl 40 stea...
Active Ingredient	Clocortolone pivalate
Dosage Form	Cream
Route	Topical
Strength	0.1%
Market Status	Prescription
Company	Promius Pharma

5 Pharmacology and Biochemistry

5.1 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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

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