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2D Structure
Also known as: 175131-60-9, Milnacipran hydrochloride, (1s-cis)-milnacipran hydrochloride, Fetzima, F 2695 hydrochloride, 101152-94-7
Molecular Formula
C15H23ClN2O
Molecular Weight
282.81  g/mol
InChI Key
XNCDYJFPRPDERF-NQQJLSKUSA-N
FDA UNII
371U2ZK31U

The (1S,2R)-isomer of milnacipran that is used for the treatment of MAJOR DEPRESSIVE DISORDER.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide;hydrochloride
2.1.2 InChI
InChI=1S/C15H22N2O.ClH/c1-3-17(4-2)14(18)15(10-13(15)11-16)12-8-6-5-7-9-12;/h5-9,13H,3-4,10-11,16H2,1-2H3;1H/t13-,15+;/m0./s1
2.1.3 InChI Key
XNCDYJFPRPDERF-NQQJLSKUSA-N
2.1.4 Canonical SMILES
CCN(CC)C(=O)C1(CC1CN)C2=CC=CC=C2.Cl
2.1.5 Isomeric SMILES
CCN(CC)C(=O)[C@]1(C[C@H]1CN)C2=CC=CC=C2.Cl
2.2 Other Identifiers
2.2.1 UNII
371U2ZK31U
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Fetzima

2. Levomilnacipran

2.3.2 Depositor-Supplied Synonyms

1. 175131-60-9

2. Milnacipran Hydrochloride

3. (1s-cis)-milnacipran Hydrochloride

4. Fetzima

5. F 2695 Hydrochloride

6. 101152-94-7

7. Milnacipran ((1s-cis) Hydrochloride)

8. Milnacipran (1s-cis) Hydrochloride

9. Levomilnacipran Hcl

10. F2695 Hydrochloride

11. Levomilnacipran Hydrochloride [usan]

12. F-2695 Hydrochloride

13. 371u2zk31u

14. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide;hydrochloride

15. (1s-cis)-milnacipran Hcl

16. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanecarboxamide Hydrochloride

17. Levomilnacipran Hydrochloride (usan)

18. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-, Hydrochloride (1:1), (1s,2r)-

19. Midalcipran Hydrochloride

20. Rac-milnacipran Hydrochloride

21. Joncia

22. Unii-371u2zk31u

23. L-milnacipran Hcl

24. (1s,2r)-milnacipran Hydrochloride

25. Fetzima (tn)

26. Tn-912

27. Schembl1148742

28. Chembl2105732

29. Hy-b0168b

30. Milnacipran Hydrochloride Solution

31. Dtxsid801026201

32. Amy10333

33. Mfcd18433402

34. S5693

35. Akos025311514

36. Ccg-231710

37. Cs-4972

38. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide Hydrochloride

39. As-12868

40. M2133

41. Milnacipran Hydrochloride, (1s,2r)-

42. Levomilnacipran Hydrochloride [who-dd]

43. A14391

44. C13985

45. C73344

46. D10133

47. F-2207

48. 152m947

49. A899431

50. Levomilnacipran Hydrochloride [orange Book]

51. Q27256611

52. Milnacipran Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 282.81 g/mol
Molecular Formula C15H23ClN2O
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass282.1498911 g/mol
Monoisotopic Mass282.1498911 g/mol
Topological Polar Surface Area46.3 Ų
Heavy Atom Count19
Formal Charge0
Complexity295
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameFetzima
PubMed HealthLevomilnacipran (By mouth)
Drug ClassesAntidepressant
Active IngredientLevomilnacipran hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strengtheq 40mg base; eq 80mg base; eq 120mg base; eq 20mg base
Market StatusPrescription
CompanyForest Labs

2 of 2  
Drug NameFetzima
PubMed HealthLevomilnacipran (By mouth)
Drug ClassesAntidepressant
Active IngredientLevomilnacipran hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strengtheq 40mg base; eq 80mg base; eq 120mg base; eq 20mg base
Market StatusPrescription
CompanyForest Labs

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

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.)


Serotonin and Noradrenaline Reuptake Inhibitors

Drugs that selectively block or suppress the plasma membrane transport of SEROTONIN and NORADRENALINE into axon terminals and are used as ANTIDEPRESSIVE AGENTS. (See all compounds classified as Serotonin and Noradrenaline Reuptake Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]