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Asenapine

Asenapine

Synopsis, Chemistry

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DRUG PRODUCT COMPOSITION

TABLET;SUBLINGUAL - EQ 10MG BASE, TABLET;SUBLINGUAL - EQ 2.5MG BASE, TABLET;SUBLINGUAL - EQ 5MG BASE

TABLET;SUBLINGUAL - EQ 10MG BASE
TABLET;SUBLINGUAL - EQ 2.5MG BASE
TABLET;SUBLINGUAL - EQ 5MG BASE

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Also known as: Asenapine maleate, 85650-56-2, Asenapine (maleate), Sycrest, Asenapine maleate [usan], Org 5222

Molecular Formula

C₂₁H₂₀ClNO₅

Molecular Weight

401.8 g/mol

InChI Key

GMDCDXMAFMEDAG-CHHFXETESA-N

FDA UNII

CU9463U2E2

1 2D Structure

Asenapine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(Z)-but-2-enedioic acid;(2S,6S)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene

2.1.2 InChI

InChI=1S/C17H16ClNO.C4H4O4/c1-19-9-14-12-4-2-3-5-16(12)20-17-7-6-11(18)8-13(17)15(14)10-19;5-3(6)1-2-4(7)8/h2-8,14-15H,9-10H2,1H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t14-,15-;/m1./s1

2.1.3 InChI Key

GMDCDXMAFMEDAG-CHHFXETESA-N

2.1.4 Canonical SMILES

CN1CC2C(C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=CC(=O)O)C(=O)O

2.1.5 Isomeric SMILES

CN1C[C@H]2[C@H](C1)C3=C(C=CC(=C3)Cl)OC4=CC=CC=C24.C(=C\C(=O)O)\C(=O)O

2.2 Other Identifiers

2.2.1 UNII

CU9463U2E2

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz(2,3-6,7)oxepino(4,5-c)pyrrole

2. Asenapine

3. Asenapine Maleate

4. Org 5222

5. Org-5222

6. Secuado

7. Trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole

2.3.2 Depositor-Supplied Synonyms

1. Asenapine Maleate

2. 85650-56-2

3. Asenapine (maleate)

4. Sycrest

5. Asenapine Maleate [usan]

6. Org 5222

7. Org-5222

8. Cu9463u2e2

9. (z)-but-2-enedioic Acid;(2s,6s)-9-chloro-4-methyl-13-oxa-4-azatetracyclo[12.4.0.02,6.07,12]octadeca-1(18),7(12),8,10,14,16-hexaene

10. 1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-, Trans-, (z)-2-butenedioate (1:1)

11. Trans-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrole Maleate

12. Asenapine (as Maleate)

13. (3ars,12brs)-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenzo(2,3:6,7)oxepino(4,5-c)pyrrole (2z)-2-butenedioate (1:1)

14. 1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-, (3ar,12br)-rel-, (2z)-2-butenedioate (1:1)

15. Trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole Maleate

16. Unii-cu9463u2e2

17. Einecs 288-064-8

18. Saphris (tn)

19. Org 5222 Maleate

20. Asenapine Maleate Solution

21. (s,s)-asenapine Maleate

22. Schembl175228

23. Asenapine Maleate [mi]

24. Asenapine Maleate (jan/usan)

25. Asenapine Maleate [jan]

26. Chebi:71248

27. Asenapine Maleate [mart.]

28. Dtxsid301017360

29. Hms3884e09

30. Asenapine Maleate [who-dd]

31. Asenapine Maleate [ema Epar]

32. Asenapine Maleate, >=98% (hplc)

33. Mfcd00900588

34. S1283

35. Akos015951084

36. Asenapine Maleate [orange Book]

37. Ccg-268667

38. Cs-0859

39. Mk-8274

40. Sch-900274

41. Ac-24116

42. Hy-11100

43. Sw219879-1

44. D02995

45. 650a562

46. Q27139467

47. 65576-45-6, 135883-08-8 (maleic Acid)

48. Asenapine Maleate 1.0 Mg/ml In Methanol (as Free Base)

49. (3as,12bs)-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenz[2,3:6,7]oxepino[4,5-c]pyrrole Maleate

50. 1h-dibenz(2,3:6,7)oxepino(4,5-c)pyrrole, 5-chloro-2,3,3a,12b-tetrahydro-2-methyl-,(3ar,12br)-rel-, (2z)-2-butenedioate (1:1)

51. Trans-5-chloro-2,3,3a,12b-tetrahydro-2-methyl-1h-dibenzo[2,3;6,7]-oxepino[4,5-c]pyrrole Maleate

52. Trans-5-chloro-2-methyl-2,3,3a,12b-tetrahydro-1h-dibenzo[2,3:6,7]oxepino[4,5-c]pyrrolemaleate

2.4 Create Date

2006-07-28

3 Chemical and Physical Properties

Molecular Formula	C₂₁H₂₀ClNO₅
Molecular Weight	401.8 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	2
Exact Mass	401.1030004 g/mol
Monoisotopic Mass	401.1030004 g/mol
Topological Polar Surface Area	87.1 Å²
Heavy Atom Count	28
Formal Charge	0
Complexity	482
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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 2
Drug Name	Saphris
PubMed Health	Asenapine (By mouth)
Drug Classes	Antipsychotic
Drug Label	SAPHRIS is a psychotropic agent that is available for sublingual administration. Asenapine belongs to the class dibenzo-oxepino pyrroles. The chemical designation is (3aRS,12bRS)-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1Hdibenzo[2,3:6,7]oxepino[4,5-c...
Active Ingredient	Asenapine maleate
Dosage Form	Tablet
Route	Sublingual
Strength	eq 5mg base; eq 10mg base
Market Status	Prescription
Company	Forest Labs

2 of 2
Drug Name	Saphris
PubMed Health	Asenapine (By mouth)
Drug Classes	Antipsychotic
Drug Label	SAPHRIS is a psychotropic agent that is available for sublingual administration. Asenapine belongs to the class dibenzo-oxepino pyrroles. The chemical designation is (3aRS,12bRS)-5-Chloro-2-methyl-2,3,3a,12b-tetrahydro-1Hdibenzo[2,3:6,7]oxepino[4,5-c...
Active Ingredient	Asenapine maleate
Dosage Form	Tablet
Route	Sublingual
Strength	eq 5mg base; eq 10mg base
Market Status	Prescription
Company	Forest Labs

4.2 Drug Indication

Sycrest is indicated for the treatment of moderate to severe manic episodes associated with bipolar I disorder in adults.

Treatment of bipolar I disorder

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.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Atypical Antipsychotic [EPC]

5.3 ATC Code

N05AH05