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    Technical details about DSSTox_CID_3036, learn more about the structure, uses, toxicity, action, side effects and more

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    DSSTox_CID_3036

    APIs // Active Pharmaceutical Ingredients

    INTERMEDIATES

    DOSSIERs // Finished Dosage Forms

    PharmaCompass

    Phyton is a World Leader in Plant Cell Fermentation Technology and Commercial Manufacturing.

    Athena Pharmaceutiques is a Partner of Choice for Drug Delivery & Life Cycle Management.

    2D Structure
    Also known as: 54350-48-0, Tegison, Ethyl etrinoate, Retinoid, Etretinato, Ro 10-9359
    Molecular Formula
    C23H30O3
    Molecular Weight
    354.5  g/mol
    InChI Key
    HQMNCQVAMBCHCO-DJRRULDNSA-N
    FDA UNII
    65M2UDR9AG
    An oral retinoid used in the treatment of keratotic genodermatosis, lichen planus, and psoriasis. Beneficial effects have also been claimed in the prophylaxis of epithelial neoplasia. The compound may be teratogenic.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    ethyl (2E,4E,6E,8E)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate
    2.1.2 InChI
    InChI=1S/C23H30O3/c1-8-26-23(24)14-17(3)11-9-10-16(2)12-13-21-18(4)15-22(25-7)20(6)19(21)5/h9-15H,8H2,1-7H3/b11-9+,13-12+,16-10+,17-14+
    2.1.3 InChI Key
    HQMNCQVAMBCHCO-DJRRULDNSA-N
    2.1.4 Canonical SMILES
    CCOC(=O)C=C(C)C=CC=C(C)C=CC1=C(C(=C(C=C1C)OC)C)C
    2.1.5 Isomeric SMILES
    CCOC(=O)/C=C(\C)/C=C/C=C(\C)/C=C/C1=C(C(=C(C=C1C)OC)C)C
    2.2 Other Identifiers
    2.2.1 UNII
    65M2UDR9AG
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. B10 9359

    2. B10-9359

    3. B109359

    4. Ethyl Etrinoate

    5. Etrinoate, Ethyl

    6. Ro 10 9359

    7. Ro 10-9359

    8. Ro 109359

    9. Ro-10-9359

    10. Ro109359

    11. Tigason

    12. Tigazon

    2.3.2 Depositor-Supplied Synonyms

    1. 54350-48-0

    2. Tegison

    3. Ethyl Etrinoate

    4. Retinoid

    5. Etretinato

    6. Ro 10-9359

    7. Etretinatum

    8. Tigason

    9. Ro-109359

    10. Chebi:4913

    11. Ro-10-9359

    12. Ethyl (2e,4e,6e,8e)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate

    13. Nsc-297936

    14. 65m2udr9ag

    15. Acitretin Related Compound B

    16. Ethyl (all-e)-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

    17. Ethyl All-trans-9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

    18. 3,7-dimethyl-9-(4-methoxy-2,3,6-trimethylphenyl)-2,4,6,8-nonanetetraenoic Acid Ethyl Ester

    19. Ncgc00167500-01

    20. Dsstox_cid_3036

    21. 2,4,6,8-nonatetraenoic Acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-, Ethyl Ester, (all-e-)

    22. Dsstox_rid_76843

    23. Dsstox_gsid_23036

    24. Etretinatum [inn-latin]

    25. Etretinato [inn-spanish]

    26. (2e,4e,6e,8e)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoic Acid Ethyl Ester

    27. Cas-54350-48-0

    28. Ccris 3615

    29. Hsdb 7185

    30. Sr-05000001511

    31. Einecs 259-119-3

    32. Unii-65m2udr9ag

    33. Nsc 297936

    34. Etretinate [usan:inn:ban:jan]

    35. 2,4,6,8-nonatetraenoic Acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, Ethyl Ester, (all-e)-

    36. Etretinate [mi]

    37. Etretinate [inn]

    38. Etretinate [jan]

    39. Tegison (tn)

    40. Etretinate [hsdb]

    41. Etretinate [usan]

    42. Etretinate [vandf]

    43. Chembl464

    44. Etretinate [mart.]

    45. Schembl3123

    46. Etretinate [who-dd]

    47. Etretinate (jan/usan/inn)

    48. Gtpl7599

    49. Dtxsid0023036

    50. Etretinate [orange Book]

    51. Chebi:94591

    52. 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoic Acid Ethyl Ester

    53. Hms2090g06

    54. Hms3713f22

    55. Hy-b0797

    56. Zinc3830820

    57. Tox21_112501

    58. Bdbm50248000

    59. Lmpr01090046

    60. Mfcd00866624

    61. Nsc297936

    62. S4699

    63. Akos015889992

    64. Tox21_112501_1

    65. Ac-6823

    66. Ccg-220590

    67. Cs-3926

    68. Ncgc00167500-02

    69. Ro-13-7837

    70. 2,4,6,8-nonanetetraenoic Acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, Ethyl Ester, All-trans-

    71. 2,4,6,8-nonatetraenoic Acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, Ethyl Ester, (2e,4e,6e,8e)-

    72. As-77381

    73. Etretinate 100 Microg/ml In Acetonitrile

    74. Acitretin Impurity B [ep Impurity]

    75. E1293

    76. Acitretin Related Compound B [usp-rs]

    77. A16356

    78. D00316

    79. Ab01275503-01

    80. 350e480

    81. A830117

    82. Isopropyl-pyridin-4-yl-aminedihydrochloride

    83. Q554297

    84. Acitretin Related Compound B [usp Impurity]

    85. Sr-05000001511-1

    86. Sr-05000001511-2

    87. W-105640

    88. Brd-k36248164-001-01-8

    89. Ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoate

    90. Ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate

    91. (2e,4e,6e,8e)-ethyl 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethylnona-2,4,6,8-tetraenoate

    92. 2,6,8-nonatetraenoic Acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, Ethyl Ester, (all E)-

    93. 2,6,8-nonatetraenoic Acid, 9-(4-methoxy-2,3,6-trimethylphenyl)-3,7-dimethyl-, Ethyl Ester, (all-e)-

    94. Ethyl (2e,4e,6e,8e)-3,7-dimethyl-9-[2,3,6-trimethyl-4-(methyloxy)phenyl]nona-2,4,6,8-tetraenoate

    95. Ethyl (2e,4e,6e,8e)-9-(4-methoxy-2,3,6-trimethyl-phenyl)-3,7-dimethyl-nona-2,4,6,8-tetraenoate;etretinate

    2.4 Create Date
    2005-03-26
    3 Chemical and Physical Properties
    Molecular Weight 354.5 g/mol
    Molecular Formula C23H30O3
    XLogP36.8
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count8
    Exact Mass354.21949481 g/mol
    Monoisotopic Mass354.21949481 g/mol
    Topological Polar Surface Area35.5 Ų
    Heavy Atom Count26
    Formal Charge0
    Complexity568
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count4
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Therapeutic Uses

    Antipsoriatic

    O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 689

    Etretinate is indicated for the treatment of severe recalcitrant psoriasis, including the erythrodermic and generalized pustular types, in patients who are unresponsive to or intolerant of the standard therapies. /Included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1330

    Etretinate is used for the treatment of severe, intractable oral lichen planus. /NOT included in use product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1330

    Etretinate is also used in correcting severe intractable forms of keratinization disorders, such as: dermatoses, ichthyosiform; erythroderma, congenital ichthyosiform; ichthyosis, lamellar, and other ichthyoses; keratosis follicularis (Darier's disease); keratosis palmaris et plantaris; pityriasis rubra pilaris (PRP); pustulosis, palmoplanter. /NOT included in US product labeling/

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1330

    4.2 Drug Warning

    Pregnancy risk category: X /CONTRAINDICATED IN PREGNANCY. Studies in animals or humans, or investigational or post-marketing reports, have demonstrated positive evidence of fetal abnormalities or risk which clearly outweights any possible benefit to the patient./

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    Etretinate is contraindicated during pregnancy, since it has caused major human fetal abnormalities, including meningomyelocele; meningoencephalocoele; multiple synostoses; facial dysmorphia; syndactyly; absence of terminal phalanges; malformations of hip, ankle, and forearm; abnormalities of the heart and thymus; low set ears; high palate; decreased cranial volume; and alterations of the skull and cervical vertebrae.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    ... It has not been determined how long pregnancy should be avoided after discontinuation of treatment; patients have been followed for a long as 2 years after treatment was discontinued, and fetal abnormalities associated with etretinate have occurred during this 2 year period. Therefore, etretinate should not be used in women who plan to have children in the future.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    In women of childbearing potential, etretinate should not be used until the possibility of pregnancy is ruled out. In addition, etretinate should not be used in women who, while undergoing treatment and for an indefinite period of time thereafter, are deemed unreliable in their use of contraception or who may not use reliable contraception.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    For more Drug Warnings (Complete) data for ETRETINATE (13 total), please visit the HSDB record page.

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Keratolytic Agents

    Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. (See all compounds classified as Keratolytic Agents.)

    5.2 ATC Code

    D - Dermatologicals

    D05 - Antipsoriatics

    D05B - Antipsoriatics for systemic use

    D05BB - Retinoids for treatment of psoriasis

    D05BB01 - Etretinate

    5.3 Absorption, Distribution and Excretion

    Concentrations of etretinate and its active metabolite in epidermal specimens obtained after 1 to 36 months of therapy were a function of location; subcutis much greater than serum greater than epidermis greater than dermis.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    Etretinate accumulates in high concentrations in adipose tissue, especially in the liver and in subcutaneous fat. Liver concentrations of etretinate in patients who had received therapy for six months were generally higher than accompanying plasma concentrations and tended to be higher still in livers with a higher degree of fatty infiltration.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    Studies in normal volunteers indicate that the absorption of etretinate is greater in patients consuming whole milk or a high-fat diet than in patients in a fasting state.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    Etretinate is absorbed in the small intestine.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

    For more Absorption, Distribution and Excretion (Complete) data for ETRETINATE (8 total), please visit the HSDB record page.

    5.4 Metabolism/Metabolites

    The aromatic retinoid acitretin is the primary active metabolite of etretinate, and in this study the ethyl esterification of acitretin to etretinate using [(14)C]acitretin and human liver microsomes /was investigated/. ... This study demonstrated that in the presence of ethanol the ethyl esterification of acitretin to etretinate proceeds via formation of acitretinoyl-CoA. Predicting clearance of acitretin in vivo via this unique metabolic pathway will be a challenge, as the intracellular concentration of ethanol could never be predicted with any degree of accuracy in humans.

    PMID:10874125 Knights KM et al; Biochem Pharmacol 60 (4): 507-16 (2000)

    5.5 Biological Half-Life

    In one study, the apparent terminal half life of etretinate after 6 months of therapy was approximately 120 days.

    Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 1331

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