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    Doxepin Hydrochloride

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

    FINISHED DOSAGE FORMULATIONS

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    $ API Ref.Price (USD/KG) : 226Xls

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    2D Structure
    Also known as: 1229-29-4, Doxepin hcl, (e)-doxepin hydrochloride, 4698-39-9, Curatin, Novoxapin
    Molecular Formula
    C19H22ClNO
    Molecular Weight
    315.8  g/mol
    InChI Key
    MHNSPTUQQIYJOT-SJDTYFKWSA-N
    FDA UNII
    CU61C5RH24
    A dibenzoxepin tricyclic compound. It displays a range of pharmacological actions including maintaining adrenergic innervation. Its mechanism of action is not fully understood, but it appears to block reuptake of monoaminergic neurotransmitters into presynaptic terminals. It also possesses anticholinergic activity and modulates antagonism of histamine H(1)- and H(2)-receptors.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3E)-3-(6H-benzo[c][1]benzoxepin-11-ylidene)-N,N-dimethylpropan-1-amine;hydrochloride
    2.1.2 InChI
    InChI=1S/C19H21NO.ClH/c1-20(2)13-7-11-17-16-9-4-3-8-15(16)14-21-19-12-6-5-10-18(17)19;/h3-6,8-12H,7,13-14H2,1-2H3;1H/b17-11+;
    2.1.3 InChI Key
    MHNSPTUQQIYJOT-SJDTYFKWSA-N
    2.1.4 Canonical SMILES
    CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31.Cl
    2.1.5 Isomeric SMILES
    CN(C)CC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31.Cl
    2.2 Other Identifiers
    2.2.1 UNII
    CU61C5RH24
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Apo Doxepin

    2. Apo-doxepin

    3. Apodoxepin

    4. Aponal

    5. Deptran

    6. Desidox

    7. Doneurin

    8. Doxepia

    9. Doxepin

    10. Doxepin Beta

    11. Doxepin Hydrochloride, Cis-trans Isomer Mixture (approximately 1:5)

    12. Doxepin Rph

    13. Doxepin-rph

    14. Espadox

    15. Hydrochloride, Doxepin

    16. Mareen

    17. Novo Doxepin

    18. Novo-doxepin

    19. Prudoxin

    20. Quitaxon

    21. Sinequan

    22. Sinquan

    23. Xepin

    24. Zonalon

    2.3.2 Depositor-Supplied Synonyms

    1. 1229-29-4

    2. Doxepin Hcl

    3. (e)-doxepin Hydrochloride

    4. 4698-39-9

    5. Curatin

    6. Novoxapin

    7. Silenor

    8. Sinequan

    9. Adapin

    10. Aponal

    11. Toruan

    12. Doxepine Hydrochloride

    13. Novoxapin Hydrochloride

    14. Doxepin (hydrochloride)

    15. Mls000069794

    16. Cu61c5rh24

    17. Mf 10 Hcl

    18. Smr000058230

    19. Sinequan (tn)

    20. Nsc-108160

    21. Dsstox_cid_25145

    22. Dsstox_rid_80701

    23. Dsstox_gsid_45145

    24. Quitaxon

    25. Sinequin

    26. P-3693a

    27. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethylpropan-1-amine;hydrochloride

    28. 3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n,n-dimethylpropan-1-amine Hydrochloride

    29. Sr-01000075551

    30. Ncgc00015344-03

    31. Einecs 214-966-8

    32. Cas-1229-29-4

    33. Trans-doxepin Hydrochloride

    34. Unii-3u9a0fe9n5

    35. Unii-cu61c5rh24

    36. Doxepin Hydrochloride (e)-isomer

    37. (e)-3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n,n-dimethylpropan-1-amine Hydrochloride

    38. Doxepin Hydrochloride [usan:usp]

    39. Prestwick_187

    40. Zonalon (tn)

    41. (e)-doxepin Hcl

    42. Mfcd00079135

    43. Opera_id_675

    44. 1-propanamine, 3-dibenz(b,e)oxepin-11(6h)ylidene-n,n-dimethyl-, Hydrochloride

    45. 11-(3-(dimethylamino)propylidene)-6,11-dihydrodibenz(b,e)oxepin Hydrochloride

    46. N,n-dimethyldibenz(b,e)oxepin-delta(sup 11(6h),gamma)-propylamine Hydrochloride

    47. Doxepin Hydrochloride (usp)

    48. Schembl60287

    49. Mls001148235

    50. Mls002207250

    51. Mls002222181

    52. Mls002548858

    53. Doxepin For System Suitability

    54. E-doxepin Hydrochloride

    55. 3u9a0fe9n5

    56. Chebi:4711

    57. Chembl1200462

    58. Dtxsid8045145

    59. Hms1568f08

    60. Hy-b0725

    61. Doxepin Hydrochloride, (e)-

    62. Tox21_110130

    63. Tox21_500339

    64. S3120

    65. Akos015895087

    66. Dibenz(b,e)oxepin-delta11(6h),gamma-propylamine, N,n-dimethyl-, Hydrochloride

    67. Tox21_110130_1

    68. Ccg-220263

    69. Ccg-221643

    70. Ks-5094

    71. Lp00339

    72. Nc00447

    73. Dibenz(b,e)oxepin-delta(sup 11(6h),gamma)-propylamine, N,n-dimethyl-, Hydrochloride

    74. Ncgc00024623-04

    75. Ncgc00093778-01

    76. Ncgc00093778-02

    77. Ncgc00261024-01

    78. Bd166235

    79. Eu-0100339

    80. D 4526

    81. D00814

    82. 229d294

    83. A804993

    84. Q-201044

    85. Sr-01000075551-1

    86. Sr-01000075551-5

    87. Q27275787

    88. Doxepin Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

    89. Doxepin Hydrochloride, European Pharmacopoeia (ep) Reference Standard

    90. Doxepin Hydrochloride, United States Pharmacopeia (usp) Reference Standard

    91. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethyl-1-propanamine Hydrochloride

    92. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethyl-propan-1-amine Hydrochloride

    93. Doxepin For System Suitability, European Pharmacopoeia (ep) Reference Standard

    94. Doxepin Hydrochloride, ~85% E-isomer Basis, >=98% (gc), 15% Z-isomer Basis, Powder

    95. 1-propanamine, 3-dibenz(b,e)oxepin-11(6h)-ylidene-n,n-dimethyl-, Hydrochloride (1:1), (3e)-

    96. 1-propanamine, 3-dibenz(b,e)oxepin-11-(6h)-ylidene-n,n-dimethyl-dimethyl-, Hydrochloride, (e)-

    2.4 Create Date
    2006-04-14
    3 Chemical and Physical Properties
    Molecular Weight 315.8 g/mol
    Molecular Formula C19H22ClNO
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count3
    Exact Mass315.1389920 g/mol
    Monoisotopic Mass315.1389920 g/mol
    Topological Polar Surface Area12.5 Ų
    Heavy Atom Count22
    Formal Charge0
    Complexity363
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count2
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameDoxepin hydrochloride
    PubMed HealthDoxepin
    Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
    Drug LabelDoxepin hydrochloride is one of a class of psychotherapeutic agents known as dibenzoxepin tricyclic compounds. The molecular formula of the compound is C19H21NOHCl having a molecular weight of 316. It is a white crystalline solid readily soluble in w...
    Active IngredientDoxepin hydrochloride
    Dosage FormTablet; Concentrate; Capsule
    Routeoral; Oral
    Strengtheq 100mg base; eq 50mg base; 6mg; eq 6mg base; eq 150mg base; eq 10mg base; eq 10mg base/ml; eq 25mg base; 3mg; eq 3mg base; eq 75mg base
    Market StatusTentative Approval; Prescription
    CompanyWockhardt; Mylan Pharms; Silarx; Actavis Elizabeth; Teva Pharms; Zydus Pharms Usa; Par Pharm; Mylan

    2 of 6  
    Drug NameSilenor
    PubMed HealthDoxepin
    Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
    Drug LabelSilenor (doxepin) is available in 3 mg and 6 mg strength tablets for oral administration. Each tablet contains 3.39 mg or 6.78 mg doxepin hydrochloride, equivalent to 3 mg and 6mg of doxepin, respectively.Chemically, doxepin hydrochloride is an (E) a...
    Active IngredientDoxepin hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 6mg base; eq 3mg base
    Market StatusPrescription
    CompanyPernix Theraps

    3 of 6  
    Drug NameZonalon
    Drug LabelZonalon (doxepin hydrochloride) Cream, 5% is a topical cream. Each gram contains: 50 mg of doxepin hydrochloride (equivalent to 44.3 mg of doxepin).Doxepin hydrochloride is one of a class of agents known as dibenzoxepin tricyclic antidepressant com...
    Active IngredientDoxepin hydrochloride
    Dosage FormCream
    RouteTopical
    Strength5%
    Market StatusPrescription
    CompanyFougera Pharms

    4 of 6  
    Drug NameDoxepin hydrochloride
    PubMed HealthDoxepin
    Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
    Drug LabelDoxepin hydrochloride is one of a class of psychotherapeutic agents known as dibenzoxepin tricyclic compounds. The molecular formula of the compound is C19H21NOHCl having a molecular weight of 316. It is a white crystalline solid readily soluble in w...
    Active IngredientDoxepin hydrochloride
    Dosage FormTablet; Concentrate; Capsule
    Routeoral; Oral
    Strengtheq 100mg base; eq 50mg base; 6mg; eq 6mg base; eq 150mg base; eq 10mg base; eq 10mg base/ml; eq 25mg base; 3mg; eq 3mg base; eq 75mg base
    Market StatusTentative Approval; Prescription
    CompanyWockhardt; Mylan Pharms; Silarx; Actavis Elizabeth; Teva Pharms; Zydus Pharms Usa; Par Pharm; Mylan

    5 of 6  
    Drug NameSilenor
    PubMed HealthDoxepin
    Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
    Drug LabelSilenor (doxepin) is available in 3 mg and 6 mg strength tablets for oral administration. Each tablet contains 3.39 mg or 6.78 mg doxepin hydrochloride, equivalent to 3 mg and 6mg of doxepin, respectively.Chemically, doxepin hydrochloride is an (E) a...
    Active IngredientDoxepin hydrochloride
    Dosage FormTablet
    RouteOral
    Strengtheq 6mg base; eq 3mg base
    Market StatusPrescription
    CompanyPernix Theraps

    6 of 6  
    Drug NameZonalon
    Drug LabelZonalon (doxepin hydrochloride) Cream, 5% is a topical cream. Each gram contains: 50 mg of doxepin hydrochloride (equivalent to 44.3 mg of doxepin).Doxepin hydrochloride is one of a class of agents known as dibenzoxepin tricyclic antidepressant com...
    Active IngredientDoxepin hydrochloride
    Dosage FormCream
    RouteTopical
    Strength5%
    Market StatusPrescription
    CompanyFougera Pharms

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Histamine Antagonists

    Drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists. Classical antihistaminics block the histamine H1 receptors only. (See all compounds classified as Histamine Antagonists.)

    Antidepressive Agents, Tricyclic

    Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system. (See all compounds classified as Antidepressive Agents, Tricyclic.)

    Sleep Aids, Pharmaceutical

    Drugs used to induce SLEEP, prevent SLEEPLESSNESS, or treat SLEEP INITIATION AND MAINTENANCE DISORDERS. (See all compounds classified as Sleep Aids, Pharmaceutical.)

    5.2 FDA Pharmacological Classification
    5.2.1 Pharmacological Classes
    Tricyclic Antidepressant [EPC]