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Chemistry

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Also known as: Calcipotriene, Dovonex, Daivonex, Sorilux, 112965-21-6, Calciptriol
Molecular Formula
C27H40O3
Molecular Weight
412.6  g/mol
InChI Key
LWQQLNNNIPYSNX-UROSTWAQSA-N
FDA UNII
143NQ3779B

Calcipotriol
Calcipotriene is a synthetic vitamin D derivative usually formulated for topical dermatological use, antipsoriatic Calcipotriene (calcipotriol) competes equally with active 1,25-hydroxy-2D3 (the natural form of vitamin D) for 1,25-hydroxy-2D3 receptors in regulating cell proliferation and differentiation. It induces differentiation and suppresses proliferation of keratinocytes, reversing abnormal keratinocyte changes in psoriasis, and leads to normalization of epidermal growth. (NCI04)
Calcipotriene is a Vitamin D Analog.
1 2D Structure

Calcipotriol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,3S,5Z)-5-[(2E)-2-[(1R,3aS,7aR)-1-[(E,2R,5S)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol
2.1.2 InChI
InChI=1S/C27H40O3/c1-17(6-13-25(29)20-8-9-20)23-11-12-24-19(5-4-14-27(23,24)3)7-10-21-15-22(28)16-26(30)18(21)2/h6-7,10,13,17,20,22-26,28-30H,2,4-5,8-9,11-12,14-16H2,1,3H3/b13-6+,19-7+,21-10-/t17-,22-,23-,24+,25-,26+,27-/m1/s1
2.1.3 InChI Key
LWQQLNNNIPYSNX-UROSTWAQSA-N
2.1.4 Canonical SMILES
CC(C=CC(C1CC1)O)C2CCC3C2(CCCC3=CC=C4CC(CC(C4=C)O)O)C
2.1.5 Isomeric SMILES
C[C@H](/C=C/[C@H](C1CC1)O)[C@H]2CC[C@@H]\3[C@@]2(CCC/C3=C\C=C/4\C[C@H](C[C@@H](C4=C)O)O)C
2.2 Other Identifiers
2.2.1 UNII
143NQ3779B
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,24(oh)2-22-ene-24-cyclopropyl D3

2. Calcipotriene

3. Daivonex

4. Dovonex

5. Heximar Win Care

6. Mc 903

7. Mc-903

8. Pri-2205

9. Psorcutan

10. Sorilux

2.3.2 Depositor-Supplied Synonyms

1. Calcipotriene

2. Dovonex

3. Daivonex

4. Sorilux

5. 112965-21-6

6. Calciptriol

7. Psorcutan

8. Calcipotriol Hydrate

9. Mc 903

10. Calcitrene

11. Mc-903

12. Calcipotriene [usan]

13. Calcipotriol [inn]

14. Calcipotriol Anhydrous

15. Chebi:50749

16. Dovonex (tn)

17. 112828-00-9

18. Pri-2201

19. Calcipotriol (jan)

20. 143nq3779b

21. (1r,3s,5z)-5-[(2e)-2-[(1r,3as,7ar)-1-[(e,2r,5s)-5-cyclopropyl-5-hydroxypent-3-en-2-yl]-7a-methyl-2,3,3a,5,6,7-hexahydro-1h-inden-4-ylidene]ethylidene]-4-methylidenecyclohexane-1,3-diol

22. Ncgc00167465-01

23. Calcipotriol [jan]

24. Dsstox_cid_26648

25. Dsstox_rid_81793

26. Dsstox_gsid_46648

27. Divonex

28. (22e)-(24s)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrovitamin D3 / (22e)-(24s)-1alpha,24-dihydroxy-26,27-cyclo-22,23-didehydrocholecalciferol / Calcipotriol

29. (5z,7e,22e)-(1s,3r,24s)-26,27-cyclo-9,10-seco-5,7,10(19),22-cholestatetraene-1,3,24-triol

30. Smr000466353

31. Cas-112965-21-6

32. Sr-01000762910

33. Ccris 7700

34. Unii-143nq3779b

35. Pri 2201

36. Calcipotriene (usp)

37. Bms-181161

38. Calcipotrienemc 903

39. Calcipotriene [mi]

40. Epitope Id:114242

41. Schembl2853

42. Calcipotriene [vandf]

43. Calcipotriol [mart.]

44. Mls000759467

45. Mls001424130

46. Calcipotriol [who-dd]

47. Calcipotriene [usp-rs]

48. Gtpl2778

49. Chembl1200666

50. Dtxsid0046648

51. Amy2864

52. 1s19

53. Hms2051n11

54. Hms2089j08

55. Hms3269p03

56. Hms3413d04

57. Hms3677d04

58. Hms3713k08

59. Mc903

60. Calcipotriene [orange Book]

61. Calcipotriol [ep Monograph]

62. Ex-a4430

63. Zinc3921872

64. Tox21_112469

65. Bdbm50369964

66. Calcipotriene [usp Monograph]

67. Lmst03020106

68. S3739

69. Akos015855239

70. Tox21_112469_1

71. Ccg-100949

72. Cs-0387

73. Db02300

74. Nc00199

75. Stf-115469

76. Ncgc00167465-02

77. (5z,7e,22e,24s)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1alpha,3beta,24-triol

78. As-56390

79. Cpd000466353

80. Hy-10001

81. D01125

82. U-0267

83. Ab00698343-05

84. 828c009

85. Q155683

86. Sr-01000762910-3

87. Sr-01000762910-4

88. (1?,3?,5z,7e,22e,24s)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol

89. (1s,3r,5z,7e,14beta,17alpha,22e,24s)-26,27-cyclo-9,10-secocholesta-5,7,10,22-tetraene-1,3,24-triol

90. (5z,7e,22e,24s)-24-cyclopropyl-9,10-secochola-5,7,10(19),22-tetraene-1.alpha.,3.beta.,24-triol

91. (5z,7e,24s)-26,27-cyclo-9,10-secocholesta-5,7,10(19),22-tetraene-1alpha,3beta,24-triol

92. 9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1.alpha.,3.beta.,5z,7e,22e,24s)-

93. 9,10-secochola-5,7,10(19),22-tetraene-1,3,24-triol, 24-cyclopropyl-, (1alpha,3beta,5z,7e,22e,24s)-

2.4 Create Date
2005-11-29
3 Chemical and Physical Properties
Molecular Weight 412.6 g/mol
Molecular Formula C27H40O3
XLogP34.3
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass412.29774513 g/mol
Monoisotopic Mass412.29774513 g/mol
Topological Polar Surface Area60.7 Ų
Heavy Atom Count30
Formal Charge0
Complexity743
Isotope Atom Count0
Defined Atom Stereocenter Count7
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count3
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameCalcipotriene
PubMed HealthCalcipotriene (On the skin)
Drug ClassesAntipsoriatic
Drug LabelDovonex (calcipotriene solution) Scalp Solution, 0.005% is a colorless topical solution containing calcipotriene monohydrate, a synthetic vitamin D3 derivative, for topical dermatologic use.Chemically, calcipotriene monohydrate is (5Z,7E,22E,24S)...
Active IngredientCalcipotriene
Dosage FormOintment; Cream; Solution
RouteTopical
Strength0.005%
Market StatusPrescription
CompanyGlenmark Generics; Fougera Pharms; Tolmar; G And W Labs

2 of 6  
Drug NameDovonex
PubMed HealthCalcipotriene (On the skin)
Drug ClassesAntipsoriatic
Drug LabelDovonex (calcipotriene solution) Scalp Solution, 0.005% is a colorless topical solution containing calcipotriene monohydrate, a synthetic vitamin D3 derivative, for topical dermatologic use.Chemically, calcipotriene monohydrate is (5Z,7E,22E,24S)...
Active IngredientCalcipotriene
Dosage FormCream
RouteTopical
Strength0.005%
Market StatusPrescription
CompanyLeo Pharma As

3 of 6  
Drug NameSorilux
PubMed HealthCalcipotriene (On the skin)
Drug ClassesAntipsoriatic
Drug LabelSORILUX Foam contains the compound calcipotriene, a synthetic vitamin D3 analog.Chemically, calcipotriene is (5Z,7E,22E,24S)-24-cyclopropyl-9,10-secochola-5,7,10(19), 22-tetraene-1,3,24-triol. The structural formula is represented below:Molecular...
Active IngredientCalcipotriene
Dosage FormAerosol, foam
RouteTopical
Strength0.005%
Market StatusPrescription
CompanyStiefel Labs

4 of 6  
Drug NameCalcipotriene
PubMed HealthCalcipotriene (On the skin)
Drug ClassesAntipsoriatic
Drug LabelDovonex (calcipotriene solution) Scalp Solution, 0.005% is a colorless topical solution containing calcipotriene monohydrate, a synthetic vitamin D3 derivative, for topical dermatologic use.Chemically, calcipotriene monohydrate is (5Z,7E,22E,24S)...
Active IngredientCalcipotriene
Dosage FormOintment; Cream; Solution
RouteTopical
Strength0.005%
Market StatusPrescription
CompanyGlenmark Generics; Fougera Pharms; Tolmar; G And W Labs

5 of 6  
Drug NameDovonex
PubMed HealthCalcipotriene (On the skin)
Drug ClassesAntipsoriatic
Drug LabelDovonex (calcipotriene solution) Scalp Solution, 0.005% is a colorless topical solution containing calcipotriene monohydrate, a synthetic vitamin D3 derivative, for topical dermatologic use.Chemically, calcipotriene monohydrate is (5Z,7E,22E,24S)...
Active IngredientCalcipotriene
Dosage FormCream
RouteTopical
Strength0.005%
Market StatusPrescription
CompanyLeo Pharma As

6 of 6  
Drug NameSorilux
PubMed HealthCalcipotriene (On the skin)
Drug ClassesAntipsoriatic
Drug LabelSORILUX Foam contains the compound calcipotriene, a synthetic vitamin D3 analog.Chemically, calcipotriene is (5Z,7E,22E,24S)-24-cyclopropyl-9,10-secochola-5,7,10(19), 22-tetraene-1,3,24-triol. The structural formula is represented below:Molecular...
Active IngredientCalcipotriene
Dosage FormAerosol, foam
RouteTopical
Strength0.005%
Market StatusPrescription
CompanyStiefel Labs

4.2 Drug Indication

For the treatment of moderate plaque psoriasis in adults.


Treatment of psoriasis


5 Pharmacology and Biochemistry
5.1 Pharmacology

Calcipotriene is a synthetic analog of vitamin D. In humans, the natural supply of vitamin D depends mainly on exposure to the ultraviolet rays of the sun for conversion of 7-dehydrocholesterol to vitamin D3 (cholecalciferol) in the skin.


5.2 MeSH Pharmacological Classification

Dermatologic Agents

Drugs used to treat or prevent skin disorders or for the routine care of skin. (See all compounds classified as Dermatologic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
CALCIPOTRIENE
5.3.2 FDA UNII
143NQ3779B
5.3.3 Pharmacological Classes
Vitamin D [CS]; Vitamin D Analog [EPC]
5.4 ATC Code

D05AX52

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

D05 - Antipsoriatics

D05A - Antipsoriatics for topical use

D05AX - Other antipsoriatics for topical use

D05AX02 - Calcipotriol


5.5 Absorption, Distribution and Excretion

Absorption

Clinical studies with radiolabeled ointment indicate that approximately 6% (+3%, SD) of the applied dose of calcipotriene is absorbed systemically when the ointment is applied topically to psoriasis plaques or 5% (+2.6%, SO) when applied to normal skin.


Route of Elimination

The active form of the vitamin, 1,25-dihydroxy vitamin D3 (calcitriol), is known to be recycled via the liver and excreted in the bile. There is evidence that maternal 1,25-dihydroxy vitamin D3 (calcitriol) may enter the fetal circulation, but it is not known whether it is excreted in human milk.


5.6 Metabolism/Metabolites

Hepatic. Calcipotriene metabolism following systemic uptake is rapid, and occurs via a similar pathway to the natural hormone. The primary metabolites are much less potent than the parent compound.


5.7 Mechanism of Action

The precise mechanism of calcipotriol in remitting psoriasis is not well-understood, however, it has been shown to have comparable affinity with calcitriol for the Vitamin D receptor while being less than 1% the activity in regulating calcium metabolism. The Vitamin D receptor (VDR) belongs to the steroid/thyroid receptor superfamily, and is found on the cells of many different tissues including the thyroid, bone, kindney, and T cells of the immune system. T cells are known to play a role in psoriasis and are believed to undergo modulation of gene expression with binding of calcipotriol to the VDR. This modulation is thought to affect gene products related to cell differentiation and proliferation.


API Reference Price

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11-Jan-2021
18-Aug-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CREAM;TOPICAL - 0.005%

USFDA APPLICATION NUMBER - 20554

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DOSAGE - SOLUTION;TOPICAL - 0.005% **Federal ...DOSAGE - SOLUTION;TOPICAL - 0.005% **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20611

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DOSAGE - OINTMENT;TOPICAL - 0.064%;0.005%

USFDA APPLICATION NUMBER - 21852

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DOSAGE - SUSPENSION;TOPICAL - 0.064%;0.005%

USFDA APPLICATION NUMBER - 22185

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DOSAGE - AEROSOL, FOAM;TOPICAL - 0.005%

USFDA APPLICATION NUMBER - 22563

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Solubilizers

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Emulsifying Agents

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Parenteral

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Film Formers & Plasticizers

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Lubricants & Glidants

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Thickeners and Stabilizers

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Controlled & Modified Release

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Granulation

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Direct Compression

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Surfactant & Foaming Agents

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Coating Systems & Additives

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