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Synopsis

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Chemistry

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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

Doxepin Hydrochloride

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 Formula	C₁₉H₂₂ClNO
Molecular Weight	315.8 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	3
Exact Mass	315.1389920 g/mol
Monoisotopic Mass	315.1389920 g/mol
Topological Polar Surface Area	12.5 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	363
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 6
Drug Name	Doxepin hydrochloride
PubMed Health	Doxepin
Drug Classes	Antianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug Label	Doxepin 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 Ingredient	Doxepin hydrochloride
Dosage Form	Tablet; Concentrate; Capsule
Route	oral; Oral
Strength	eq 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 Status	Tentative Approval; Prescription
Company	Wockhardt; Mylan Pharms; Silarx; Actavis Elizabeth; Teva Pharms; Zydus Pharms Usa; Par Pharm; Mylan

2 of 6
Drug Name	Silenor
PubMed Health	Doxepin
Drug Classes	Antianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug Label	Silenor (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 Ingredient	Doxepin hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 6mg base; eq 3mg base
Market Status	Prescription
Company	Pernix Theraps

3 of 6
Drug Name	Zonalon
Drug Label	Zonalon (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 Ingredient	Doxepin hydrochloride
Dosage Form	Cream
Route	Topical
Strength	5%
Market Status	Prescription
Company	Fougera Pharms

4 of 6
Drug Name	Doxepin hydrochloride
PubMed Health	Doxepin
Drug Classes	Antianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug Label	Doxepin 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 Ingredient	Doxepin hydrochloride
Dosage Form	Tablet; Concentrate; Capsule
Route	oral; Oral
Strength	eq 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 Status	Tentative Approval; Prescription
Company	Wockhardt; Mylan Pharms; Silarx; Actavis Elizabeth; Teva Pharms; Zydus Pharms Usa; Par Pharm; Mylan

5 of 6
Drug Name	Silenor
PubMed Health	Doxepin
Drug Classes	Antianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
Drug Label	Silenor (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 Ingredient	Doxepin hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 6mg base; eq 3mg base
Market Status	Prescription
Company	Pernix Theraps

6 of 6
Drug Name	Zonalon
Drug Label	Zonalon (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 Ingredient	Doxepin hydrochloride
Dosage Form	Cream
Route	Topical
Strength	5%
Market Status	Prescription
Company	Fougera 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]

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

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

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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