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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
    08-Aug-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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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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