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Desoxycorticosterone Pivalate

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1 Rochem International Inc
1 DKSH
1 Nanjing Well Pharmaceutical
2 Actylis
1 BASF
1 Gangwal Chemicals
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1 Sigachi Industries
1 The Dow Chemical Company

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Synopsis

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Chemistry

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Also known as: 808-48-0, Deoxycortone pivalate, Docp, Desoxycortone pivalate, Dtma, Deoxycorticosterone pivalate

Molecular Formula

C₂₆H₃₈O₄

Molecular Weight

414.6 g/mol

InChI Key

VVOIQBFMTVCINR-WWMZEODYSA-N

FDA UNII

16665T4A2X

Desoxycorticosterone pivalate is a mineralocorticoid hormone and an analog of desoxycorticosterone. It is white, odorless, and stable in air. It is practically insoluble in water, sparingly soluble in acetone, slightly soluble in methanol, ether and vegetable oils. Federal (U.S.A.) law restricts this drug to use by or on the order of a licensed veterinarian.

1 2D Structure

Desoxycorticosterone Pivalate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[2-[(8S,9S,10R,13S,14S,17S)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate

2.1.2 InChI

InChI=1S/C26H38O4/c1-24(2,3)23(29)30-15-22(28)21-9-8-19-18-7-6-16-14-17(27)10-12-25(16,4)20(18)11-13-26(19,21)5/h14,18-21H,6-13,15H2,1-5H3/t18-,19-,20-,21+,25-,26-/m0/s1

2.1.3 InChI Key

VVOIQBFMTVCINR-WWMZEODYSA-N

2.1.4 Canonical SMILES

CC12CCC3C(C1CCC2C(=O)COC(=O)C(C)(C)C)CCC4=CC(=O)CCC34C

2.1.5 Isomeric SMILES

C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)COC(=O)C(C)(C)C)CCC4=CC(=O)CC[C@]34C

2.2 Other Identifiers

2.2.1 UNII

16665T4A2X

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Deoxycortone Pivalate

2. Desoxycoticosterone Trimethylacetate

3. Percoten Pivalate

2.3.2 Depositor-Supplied Synonyms

1. 808-48-0

2. Deoxycortone Pivalate

3. Docp

4. Desoxycortone Pivalate

5. Dtma

6. Deoxycorticosterone Pivalate

7. 11-deoxycorticosterone Pivalate

8. Deoxycortone Trimethylacetate

9. Desoxycorticosterone Trimethylacetate

10. Deoxycorticosterone Trimethylacetate

11. 11-deoxycorticosterone, Pivalate

12. Neodin-depositum

13. Cortexone M

14. Percorten M

15. 11-deoxy Corticosterone Pivalate

16. Percorten Pivalate

17. Desoxycorticosteronepivalate

18. Chebi:50782

19. Desoxycorticosterone Pivalate (usp)

20. Desoxycorticosterone Pivalate [usp]

21. 3,20-dioxopregn-4-en-21-yl 2,2-dimethylpropanoate

22. 16665t4a2x

23. Pregn-4-ene-3,20-dione, 21-(2,2-dimethyl-1-oxopropoxy)-

24. [2-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate

25. Percorten V

26. Percorten (tn)

27. Nsc 95278

28. 21-(2,2-dimethyl-1-oxopropoxy)pregn-4-ene-3,20-dione

29. Nsc-95278

30. Unii-16665t4a2x

31. 3,20-dioxopregn-4-en-21-yl Pivalate

32. Ncgc00159355-02

33. Einecs 212-366-0

34. Zycortal

35. Brn 3174879

36. Desoxycorticosterone-pivalate

37. Dsstox_cid_26036

38. Dsstox_rid_81301

39. Dsstox_gsid_46036

40. 4-08-00-02196 (beilstein Handbook Reference)

41. Schembl120007

42. Chembl1200592

43. Dtxsid8046036

44. Corticosterone, Deoxy-, Pivalate

45. Zinc4082455

46. Tox21_111599

47. Akos032428733

48. Desoxycortone Pivalate [mart.]

49. Db01134

50. Desoxycortone Pivalate [who-dd]

51. Ncgc00160511-01

52. Cas-808-48-0

53. Desoxycorticosterone Pivalate [mi]

54. Hy-107917

55. Cs-0030864

56. Desoxycorticosterone Pivalate [vandf]

57. Desoxycorticosterone Trimethyl Acetate

58. Desoxycorticosterone Pivalate [usp-rs]

59. D03699

60. 808d480

61. A839987

62. Desoxycorticosterone Pivalate [green Book]

63. Desoxycorticosterone Pivalate [orange Book]

64. Desoxycorticosterone Pivalate [usp Monograph]

65. Desoxycortone Pivalate [ema Epar Veterinary]

66. W-104224

67. Q27092729

68. [2-[(8s,9s,10r,13s,14s,17s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-17-yl]-2-oxo-ethyl] 2,2-dimethylpropanoate

2.4 Create Date

2006-11-09

3 Chemical and Physical Properties

Molecular Formula	C₂₆H₃₈O₄
Molecular Weight	414.6 g/mol
XLogP3	4.5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	414.27700969 g/mol
Monoisotopic Mass	414.27700969 g/mol
Topological Polar Surface Area	60.4 Å²
Heavy Atom Count	30
Formal Charge	0
Complexity	787
Isotope Atom Count	0
Defined Atom Stereocenter Count	6
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 Indication

Examined for treatment of adrenocortical insufficiency especially in multiple sclerosis, congenital cerebral palsy, polyarteritis nodosa, and rheumatoid arthritis. Currently only approved in treating cats and dogs for the treatment of Addison's disease.

For use as replacement therapy for mineralocorticoid deficiency in dogs with primary hypoadrenocorticism (Addison's disease).

5 Pharmacology and Biochemistry

5.1 Pharmacology

Used to treat adrenocortical insufficiency, desoxycorticosterone pivalate is a mineralocorticoid hormone and an analogue of desoxycorticosterone. It primarily acts on the metabolism of sodium, potassium and water. When the drug is given, there is decreased excretion of sodium accompanied by increased excretion of potassium; the concentration of sodium in the blood is thereby increased whereas that of potassium is decreased. There is a concomitant increase in the volume of blood and extracellular fluids, with a fall in hematocrit. It increases the rate of renal tubular absorption of sodium.

5.2 ATC Code

QH02AA03

5.3 Mechanism of Action

Desoxycorticosterone Pivalate binds to the mineralocorticoid receptor. Mineralocorticoids are a family of steroids, secreted by the adrenal cortex, necessary for the regulation of a number of metabolic processes including electrolyte regulation. Desoxycorticosterone pivalate exerts its effect through its interaction with the mineralocorticoid receptor (MR), whereby it reacts with the receptor proteins to form a steroid-receptor complex. This complex moves into the nucleus, where it binds to chromatin which results in genetic transcription of cellular DNA to messenger RNA. The steroid hormones appear to induce transcription and synthesis of specific proteins, which produce the physiological effects seen after administration.

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