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

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2D Structure
Also known as: Quetiapine hemifumarate, 111974-72-2, Seroquel, Ici-204636, Seroquel xr, Ici 204,636
Molecular Formula
C46H54N6O8S2
Molecular Weight
883.1  g/mol
InChI Key
ZTHJULTYCAQOIJ-WXXKFALUSA-N
FDA UNII
2S3PL1B6UJ

A dibenzothiazepine and ANTIPSYCHOTIC AGENT that targets the SEROTONIN 5-HT2 RECEPTOR; HISTAMINE H1 RECEPTOR, adrenergic alpha1 and alpha2 receptors, as well as the DOPAMINE D1 RECEPTOR and DOPAMINE D2 RECEPTOR. It is used in the treatment of SCHIZOPHRENIA; BIPOLAR DISORDER and DEPRESSIVE DISORDER.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[2-(4-benzo[b][1,4]benzothiazepin-6-ylpiperazin-1-yl)ethoxy]ethanol;(E)-but-2-enedioic acid
2.1.2 InChI
InChI=1S/2C21H25N3O2S.C4H4O4/c2*25-14-16-26-15-13-23-9-11-24(12-10-23)21-17-5-1-3-7-19(17)27-20-8-4-2-6-18(20)22-21;5-3(6)1-2-4(7)8/h2*1-8,25H,9-16H2;1-2H,(H,5,6)(H,7,8)/b;;2-1+
2.1.3 InChI Key
ZTHJULTYCAQOIJ-WXXKFALUSA-N
2.1.4 Canonical SMILES
C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C(=CC(=O)O)C(=O)O
2.1.5 Isomeric SMILES
C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C1CN(CCN1CCOCCO)C2=NC3=CC=CC=C3SC4=CC=CC=C42.C(=C/C(=O)O)\C(=O)O
2.2 Other Identifiers
2.2.1 UNII
2S3PL1B6UJ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(2-(4-dibenzo(b,f)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanol

2. Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (e)-2-butenedioate (2:1) (salt)

3. Ici 204,636

4. Ici 204636

5. Ici-204636

6. Ici204636

7. Quetiapine

8. Seroquel

2.3.2 Depositor-Supplied Synonyms

1. Quetiapine Hemifumarate

2. 111974-72-2

3. Seroquel

4. Ici-204636

5. Seroquel Xr

6. Ici 204,636

7. Quetiapine Fumarate [usan]

8. Zd5077

9. Utapine

10. Zm 204,636

11. Zm 204636

12. Quetiapine (as Fumarate)

13. Quetiapine Hemifumarate Salt

14. 2s3pl1b6uj

15. Quetiapine Fumarate (seroquel)

16. Fk947e

17. Fk-947e

18. Ici 204636

19. Zd-5077

20. Zm-204636

21. Chebi:8708

22. Fk949e

23. (2e)-but-2-enedioic Acid; Bis(2-[2-(4-{2-thia-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(15),3,5,7,9,11,13-heptaen-10-yl}piperazin-1-yl)ethoxy]ethan-1-ol)

24. 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)ethanol Fumarate (2:1) (salt)

25. Unii-2s3pl1b6uj

26. Seroquel (tn)

27. 2-(2-(4-dibenzo(b,f)(1,4)thiazepine-11-yl-1-piperazinyl)ethoxy)ethanol

28. Mfcd03423782

29. Quetiapine Fumarate Salt

30. Ethanol, 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-, (2e)-2-butenedioate (2:1)

31. D00458

32. Quetiapine Fumarate Solution

33. 2-[2-(4-dibenzo[b,f][1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]ethanol Hemifumarate

34. Dsstox_cid_24201

35. Dsstox_rid_80114

36. Dsstox_gsid_44201

37. Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (e)-2-butenedioate (2:1) (salt)

38. Schembl122596

39. Schembl390694

40. Chembl3188993

41. Dtxsid3044201

42. Quetiapine For System Suitability

43. Quetiapine Fumarate [jan]

44. Quetiapine Fumarate (jp17/usp)

45. Hms2089g04

46. Hms3713m10

47. Hms3884a10

48. Quetiapine Fumarate [vandf]

49. Bcp04154

50. Quetiapine Fumarate [mart.]

51. Quetiapine Hemifumarate [mi]

52. Tox21_302366

53. Quetiapine Fumarate [usp-rs]

54. Quetiapine Fumarate [who-dd]

55. S1763

56. Akos015855887

57. Ac-4236

58. Ccg-220464

59. Ks-1099

60. C21h25n3o2s.0.5c4h4o4

61. Ncgc00255945-01

62. Quetiapine Fumarate [orange Book]

63. As-12050

64. Quetiapine Fumarate [ep Monograph]

65. Quetiapine Fumarate [usp Monograph]

66. Cas-111974-72-2

67. Sw220283-1

68. Quetiapine Hemifumarate Salt, >=98% (hplc)

69. 974q697

70. J-002679

71. Q-201653

72. Q27108136

73. Quetiapine Fumarate 1.0 Mg/ml In Methanol (as Free Base)

74. Quetiapine Fumarate, European Pharmacopoeia (ep) Reference Standard

75. 2-[2-(4-dibenzo[b,f][1,4]thiazepin- 11-yl-1-piperazinyl)ethoxy]ethanol Hemifumarate

76. Bis(2-(2-(4-(dibenzo[b,f][1,4]thiazepin-11-yl)piperazin-1-yl)ethoxy)ethan-1-ol) Fumarate

77. Quetiapine For System Suitability, European Pharmacopoeia (ep) Reference Standard

78. Quetiapine Fumarate, Pharmaceutical Secondary Standard; Certified Reference Material

79. 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)ethanol Fumarate (2:1)

80. Ethanol, 2-(2-(4-dibenzo(b,f)(1,4)thiazepin-11-yl-1-piperazinyl)ethoxy)-, (e)-2-butenedioate (2:1)

81. Quetiapine Fumarate Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

82. Quetiapine Fumarate, United States Pharmacopeia (usp) Reference Standard, Monograph Mol Wt. 883.09 ((c21h25n3o2s)2 ?? C4h4o4)

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 883.1 g/mol
Molecular Formula C46H54N6O8S2
Hydrogen Bond Donor Count4
Hydrogen Bond Acceptor Count14
Rotatable Bond Count14
Exact Mass882.34445505 g/mol
Monoisotopic Mass882.34445505 g/mol
Topological Polar Surface Area222 Ų
Heavy Atom Count62
Formal Charge0
Complexity615
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 6  
Drug NameQuetiapine fumarate
Drug LabelQuetiapine is a psychotropic agent belonging to a chemical class, the dibenzothiazepine derivatives. The chemical designation is 2-[2-(4-dibenzo [b,f ] [1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt). It is present in tablets...
Active IngredientQuetiapine fumarate
Dosage FormTablet, extended release; Tablet
Routeoral; Oral
Strengtheq 100mg base; 200mg; eq 50mg base; 150mg; eq 150mg base; 400mg; 300mg; eq 200mg base; 50mg; eq 300mg base; eq 400mg base; eq 25mg base
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Apotex; Accord Hlthcare; Alkem Labs; Handa Pharms; Aurobindo Pharma; Torrent Pharms; Lupin; Sandoz; Sun Pharma Global; Roxane; Actavis Grp Ptc; Teva Pharms; Jubilant Generics; Dr Reddys Labs

2 of 6  
Drug NameSeroquel
PubMed HealthQuetiapine (By mouth)
Drug ClassesAntipsychotic
Drug LabelSEROQUEL (quetiapine fumarate) is a psychotropic agent belonging to a chemical class, the dibenzothiazepine derivatives. The chemical designation is 2-[2-(4-dibenzo [b,f] [1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt). It...
Active IngredientQuetiapine fumarate
Dosage FormTablet
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 200mg base; eq 300mg base; eq 400mg base; eq 25mg base
Market StatusPrescription
CompanyAstrazeneca

3 of 6  
Drug NameSeroquel xr
Drug LabelSEROQUEL XR (quetiapine fumarate) is a psychotropic agent belonging to a chemical class, the dibenzothiazepine derivatives. The chemical designation is 2-[2-(4-dibenzo [b,f ] [1,4] thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt)....
Active IngredientQuetiapine fumarate
Dosage FormTablet, extended release
Routeoral; Oral
Strength200mg; eq 50mg base; eq 150mg base; 400mg; 300mg; eq 200mg base; 50mg; eq 300mg base; eq 400mg base
Market StatusPrescription
CompanyAstrazeneca

4 of 6  
Drug NameQuetiapine fumarate
Drug LabelQuetiapine is a psychotropic agent belonging to a chemical class, the dibenzothiazepine derivatives. The chemical designation is 2-[2-(4-dibenzo [b,f ] [1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt). It is present in tablets...
Active IngredientQuetiapine fumarate
Dosage FormTablet, extended release; Tablet
Routeoral; Oral
Strengtheq 100mg base; 200mg; eq 50mg base; 150mg; eq 150mg base; 400mg; 300mg; eq 200mg base; 50mg; eq 300mg base; eq 400mg base; eq 25mg base
Market StatusTentative Approval; Prescription
CompanyMylan Pharms; Apotex; Accord Hlthcare; Alkem Labs; Handa Pharms; Aurobindo Pharma; Torrent Pharms; Lupin; Sandoz; Sun Pharma Global; Roxane; Actavis Grp Ptc; Teva Pharms; Jubilant Generics; Dr Reddys Labs

5 of 6  
Drug NameSeroquel
PubMed HealthQuetiapine (By mouth)
Drug ClassesAntipsychotic
Drug LabelSEROQUEL (quetiapine fumarate) is a psychotropic agent belonging to a chemical class, the dibenzothiazepine derivatives. The chemical designation is 2-[2-(4-dibenzo [b,f] [1,4]thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt). It...
Active IngredientQuetiapine fumarate
Dosage FormTablet
RouteOral
Strengtheq 100mg base; eq 50mg base; eq 200mg base; eq 300mg base; eq 400mg base; eq 25mg base
Market StatusPrescription
CompanyAstrazeneca

6 of 6  
Drug NameSeroquel xr
Drug LabelSEROQUEL XR (quetiapine fumarate) is a psychotropic agent belonging to a chemical class, the dibenzothiazepine derivatives. The chemical designation is 2-[2-(4-dibenzo [b,f ] [1,4] thiazepin-11-yl-1-piperazinyl)ethoxy]-ethanol fumarate (2:1) (salt)....
Active IngredientQuetiapine fumarate
Dosage FormTablet, extended release
Routeoral; Oral
Strength200mg; eq 50mg base; eq 150mg base; 400mg; 300mg; eq 200mg base; 50mg; eq 300mg base; eq 400mg base
Market StatusPrescription
CompanyAstrazeneca

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)


Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Atypical Antipsychotic [EPC]
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