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    Quetiapine Fumarate

    ACTIVE PHARMA INGREDIENTS

    DEVELOPMENTS

    INTERMEDIATES

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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]