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Chemistry

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Also known as: Doxepin, (e)-doxepin, Trans-doxepin, 1668-19-5, Doxepin, (e)-, Doxepinum [inn-latin]
Molecular Formula
C19H21NO
Molecular Weight
279.4  g/mol
InChI Key
ODQWQRRAPPTVAG-GZTJUZNOSA-N
FDA UNII
851NLB57HQ

Doxepin
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

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
2.1.2 InChI
InChI=1S/C19H21NO/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/b17-11+
2.1.3 InChI Key
ODQWQRRAPPTVAG-GZTJUZNOSA-N
2.1.4 Canonical SMILES
CN(C)CCC=C1C2=CC=CC=C2COC3=CC=CC=C31
2.1.5 Isomeric SMILES
CN(C)CC/C=C/1\C2=CC=CC=C2COC3=CC=CC=C31
2.2 Other Identifiers
2.2.1 UNII
851NLB57HQ
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

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

13. Doxepin Rph

14. Doxepin-rph

15. Espadox

16. Hydrochloride, Doxepin

17. Mareen

18. Novo Doxepin

19. Novo-doxepin

20. Prudoxin

21. Quitaxon

22. Sinquan

23. Xepin

24. Zonalon

2.3.2 Depositor-Supplied Synonyms

1. Doxepin

2. (e)-doxepin

3. Trans-doxepin

4. 1668-19-5

5. Doxepin, (e)-

6. Doxepinum [inn-latin]

7. Doxepina [inn-spanish]

8. Sinequan (tn)

9. 3607-34-9

10. 851nlb57hq

11. Doxepin [usan]

12. Doxepina

13. Doxepinum

14. 11-(3-dimethylaminopropylidene)-6,11-dihydrodibenz(b,e)oxipin

15. Deptran

16. 1-propanamine, 3-dibenz(b,e)oxepin-11(6h)-ylidene-n,n-dimethyl-

17. Mf 10

18. (3e)-3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n,n-dimethylpropan-1-amine

19. Doxepin (inn)

20. [11c]doxepin

21. 3-(dibenzo[b,e]oxepin-11(6h)-ylidene)-n,n-dimethylpropan-1-amine

22. [11c]-doxepin

23. Ccris 9176

24. (3e)-3-(6h-benzo[c][1]benzoxepin-11-ylidene)-n,n-dimethylpropan-1-amine

25. Hsdb 3069

26. Doxepin [inn:ban]

27. Ncgc00015344-03

28. Unii-5asj6huz7d

29. Cas-1229-29-4

30. Unii-851nlb57hq

31. Methyllactate

32. 11-(3-(dimethylamino)propylidene)-6h-dibenz(b,e)oxepine

33. 11-(3-dimethylamino-propyliden)-6,11-dihydro-dibenz(b,e)oxipin

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

35. E-doxepin

36. Tocris-0508

37. P-3693a

38. Prestwick2_000263

39. Prestwick3_000263

40. Doxepin, E-isomer

41. Lopac-d-4526

42. 5asj6huz7d

43. Chembl860

44. Doxepin [usan:inn:ban]

45. Lopac0_000339

46. Bspbio_000106

47. Schembl116895

48. Bpbio1_000118

49. Gtpl1225

50. Gtpl3958

51. Zinc1331

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

53. Hy-b0725a

54. Dtxsid90859605

55. (3e)-3-dibenzo(b,e)oxepin-11(6h)-ylidene-n,n-dimethylpropan-1-amine

56. Bdbm112780

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

58. Ccg-204434

59. Sdccgsbi-0050327.p002

60. Ncgc00015344-01

61. Ncgc00015344-02

62. Ncgc00015344-04

63. Ncgc00015344-12

64. Ncgc00024623-01

65. Ncgc00162127-01

66. Us8629135, Sw-07

67. Cs-0013584

68. C06971

69. D07875

70. L000699

71. Brd-k36616567-003-01-5

72. Brd-k54462405-003-03-3

73. Brd-k54462405-003-16-5

74. Q27077103

75. 1-propanamine, 3-dibenz(b,e)oxepin-11(6h)-ylidene-n,n-dimethyl-, (3e)-

76. 5eh

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 279.4 g/mol
Molecular Formula C19H21NO
XLogP34.3
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count3
Exact Mass279.162314293 g/mol
Monoisotopic Mass279.162314293 g/mol
Topological Polar Surface Area12.5 Ų
Heavy Atom Count21
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 Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameZonalon
PubMed HealthDoxepin
Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
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

2 of 2  
Drug NameZonalon
PubMed HealthDoxepin
Drug ClassesAntianxiety, Antidepressant, Antiulcer, Dermatological Agent, Sleep Aid
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

4.2 Therapeutic Uses

Adrenergic Uptake Inhibitors; Anti-Anxiety Agents; Antidepressive Agents, Tricyclic; Antipruritics

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


A DIBENZOXEPIN DERIVATIVE THAT IS A PSYCHOTHERAPEUTIC AGENT WITH ANTIANXIETY & ANTIDEPRESSANT PROPERTIES. ...RECOMMENDED FOR MGMNT OF ANXIETY &/OR DEPRESSIVE STATES ASSOCIATED WITH PSYCHONEUROSIS, PSYCHOSIS, ALCOHOLISM, & ORG DISEASE. /HYDROCHLORIDE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1030


VET: FOR RELIEF OF PRURITIS IN DERMATOSES IN DOGS. MILD TRANQUILIZING EFFECT IS NOTED AFTER PROLONGED THERAPY OR ON DOSES ABOVE THOSE RECOMMENDED.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 189


Doxepin is indicated for the short-term (up to 8 days) topical treatment of moderate pruritus in adult patients with eczematous dermatitis, e.g., atopic dermatitis and lichen simplex chronicus. /Included in US product labeling; Doxepin, topical/

USP Convention. USPDI - Drug Information for the Health Care Professional. 17th ed. Volume I. Rockville, MD: Convention, Inc., 1997. (Plus Updates)., p. 1280


For more Therapeutic Uses (Complete) data for DOXEPIN (9 total), please visit the HSDB record page.


4.3 Drug Warning

DOXEPIN HYDROCHLORIDE IS CONTRAINDICATED IN PT WITH GLAUCOMA OR TENDENCY TO URINARY RETENTION. ...SHOULD NOT BE ADMIN TO PT EITHER ON MAO INHIBITORS OR WHO HAVE BEEN...WITHIN THE PRIOR 2 WK. ...MAY...POTENTIATE DEPRESSANT EFFECT OF ALCOHOL. USE...IN PREGNANT PT OR...CHILDREN UNDER 12...NOT RECOMMENDED. /HYDROCHLORIDE/

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 1030


ABOUT 2-3 WK MUST PASS BEFORE THERAPEUTIC EFFECTS...ARE EVIDENT. FOR THIS REASON, TRICYCLIC ANTIDEPRESSANTS SHOULD NEVER BE PRESCRIBED ON AN "AS-NEEDED" BASIS. ...SLOW ONSET OF EFFECTS MAY RELATE TO CHANGES IN METAB OF BIOGENIC AMINES THAT OCCUR... /IMIPRAMINE/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 175


...GENERAL USE FOR HYPNOSIS IS NOT RECOMMENDED. IN ADEQUATE DOSES THEY CAUSE HANGOVER & ARE NOT AS EFFECTIVE AS A CONVENTIONAL HYPNOTIC. /TRICYCLIC ANTIDEPRESSANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 175


OCCASIONAL PT WILL SHOW PHYSICAL DEPENDENCE ON TRICYCLIC ANTIDEPRESSANTS, WITH MALAISE, CHILLS, CORYZA, & MUSCLE ACHING FOLLOWING ABRUPT DISCONTINUATION OF HIGH DOSES... /IMIPRAMINE/

Hardman, J.G., L.E. Limbird, P.B. Molinoff, R.W. Ruddon, A.G. Goodman (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 9th ed. New York, NY: McGraw-Hill, 1996., p. 441


For more Drug Warnings (Complete) data for DOXEPIN (25 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

4 OR 5. 4= VERY TOXIC: PROBABLE ORAL LETHAL DOSE (HUMAN) IS 50-500 MG/KG, BETWEEN 1 TEASPOON & 1 OUNCE FOR 70 KG PERSON (150 LB). 5= EXTREMELY TOXIC, PROBABLE ORAL LETHAL DOSE (HUMAN) IS 5-50 MG/KG, BETWEEN 7 DROPS & 1 TEASPOON FOR 70 KG PERSON (150 LB).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-229


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


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.)


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]
5.3 ATC Code

D - Dermatologicals

D04 - Antipruritics, incl. antihistamines, anesthetics, etc.

D04A - Antipruritics, incl. antihistamines, anesthetics, etc.

D04AX - Other antipruritics

D04AX01 - Doxepin


N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AA - Non-selective monoamine reuptake inhibitors

N06AA12 - Doxepin


5.4 Absorption, Distribution and Excretion

/DOXEPIN HAS/...A PECULIAR AFFINITY FOR UVEAL MELANIN...ALSO...BOUND BY OCULAR MELANIN BOTH IN VIVO & IN VITRO.

Grant, W. M. Toxicology of the Eye. 2nd ed. Springfield, Illinois: Charles C. Thomas, 1974., p. 427


AFTER HUMAN ORAL DOSE 75 MG DOXEPIN-HCL, EST 1ST-PASS METAB RANGED FROM 55-87% OF ORAL DOSE ASSUMING COMPLETE ABSORPTION.

ZIEGLER ET AL; CLIN PHARMACOL THER 23 (5) 573-9 (1978)


The pharmacokinetics of doxepin have not been extensively studied, but the drug is well absorbed from the GI tract in animals. Peak plasma concentrations occur within 2 hours after oral administration of the drug.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1807


Limited data indicate that doxepin and its active N-demethylated metabolite are distributed into milk in concentrations reportedly ranging from about 30-140% and 10-115%, respectively, of those in maternal serum and that substantial concentrations of the active metabolite have been detected in the serum and urine of nursing infants whose mothers were receiving 75-150 mg daily.

McEvoy, G.K. (ed.). American Hospital Formulary Service-Drug Information 19 98. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1998 (Plus Supplements)., p. 1807


5.5 Metabolism/Metabolites

AFTER ORAL DOSING OF DOXEPIN-HCL TO HUMANS, METABOLITE DESMETHYLDOXEPIN WAS PRODUCED.

ZIEGLER ET AL; CLIN PHARMACOL THER 23 (5) 573-9 (1978)


Doxepin has known human metabolites that include Doxepin N-glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.6 Biological Half-Life

AFTER ORAL 75 MG DOXEPIN-HCL TO HUMANS, PEAK PLASMA CONCN 8.8-45.8 NG/ML, REACHED WITHIN 4 HR. DISAPPEARANCE OF DOXEPIN WAS BIPHASIC & FOLLOWED 1ST-ORDER KINETICS. MEAN DOXEPIN T/2 WAS 16.8 HR. MEAN APPARENT VOL OF DISTRIBUTION WAS 20.2 L/KG.

ZIEGLER ET AL; CLIN PHARMACOL THER 23 (5) 573-9 (1978)


5.7 Mechanism of Action

ACTION OF TRICYCLIC ANTIDEPRESSANTS ON CATECHOLAMINES & INDOLEAMINES IN BRAIN...BLOCK RE-UPTAKE OF NOREPINEPHRINE BY ADRENERGIC NERVE TERMINALS. /TRICYCLIC ANTIDEPRESSANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 176


API Reference Price

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12-Jan-2021
23-Oct-2024
KGS
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