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Milnacipran

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Also known as: 92623-85-3, Dextromilnacipran, Levomilnacipran, 96847-55-1, Milnacipranum [latin], Toledomin

Molecular Formula

C₁₅H₂₂N₂O

Molecular Weight

246.35 g/mol

InChI Key

GJJFMKBJSRMPLA-HIFRSBDPSA-N

FDA UNII

G56VK1HF36

A cyclopropanecarboxamide serotonin and norepinephrine reuptake inhibitor (SNRI) that is used in the treatment of FIBROMYALGIA.

Milnacipran is a Serotonin and Norepinephrine Reuptake Inhibitor. The mechanism of action of milnacipran is as a Norepinephrine Uptake Inhibitor, and Serotonin Uptake Inhibitor.

1 2D Structure

Milnacipran

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide

2.1.2 InChI

InChI=1S/C15H22N2O/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/t13-,15+/m1/s1

2.1.3 InChI Key

GJJFMKBJSRMPLA-HIFRSBDPSA-N

2.1.4 Canonical SMILES

CCN(CC)C(=O)C1(CC1CN)C2=CC=CC=C2

2.1.5 Isomeric SMILES

CCN(CC)C(=O)[C@@]1(C[C@@H]1CN)C2=CC=CC=C2

2.2 Other Identifiers

2.2.1 UNII

G56VK1HF36

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1 Phenyl 1 Diethylaminocarbonyl 2 Aminomethylcyclopropane Hcl

2. 1-phenyl-1-diethylaminocarbonyl-2-aminomethylcyclopropane Hcl

3. F 2207

4. F-2207

5. F2207

6. Ixel

7. Midalcipran

8. Milnacipran Hydrochloride

9. Savella

2.3.2 Depositor-Supplied Synonyms

1. 92623-85-3

2. Dextromilnacipran

3. Levomilnacipran

4. 96847-55-1

5. Milnacipranum [latin]

6. Toledomin

7. Milnacipran [inn]

8. Ixel

9. (1r,2s)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide

10. Es1o38j3c4

11. G56vk1hf36

12. F2696

13. Milnacipran (inn)

14. (+-)-milnacipran

15. (1r,2s)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanecarboxamide

16. Impulsor

17. F2207

18. Milnacipranum

19. Milnace

20. (1r,2s)-2-(aminomethyl)-n,n-diethyl-1-phenyl-cyclopropane-1-carboxamide

21. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-,(1r,2s)-rel-

22. (-)-milnacipran

23. Milnacipran [inn:ban]

24. Unii-es1o38j3c4

25. Unii-g56vk1hf36

26. (?)-milnacipran

27. Milnacipran [mi]

28. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-, Cis-(+-)-

29. Milnacipran [vandf]

30. Schembl8099

31. Milnacipran [who-dd]

32. (1r,2s)-milnacipran

33. Milnacipran [ema Epar]

34. Chembl252923

35. Dtxsid3048287

36. Bdbm86420

37. Chebi:94468

38. Zinc14037

39. Dtxsid601025164

40. Hy-b0168

41. (+-)-cis-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanecarboxamide

42. Ncgc00165825-01

43. Hy-14794

44. Milnacipran Pierre Fabre Medicament

45. Cas_92623-85-3

46. Cs-0003566

47. C16729

48. D08222

49. F-2696

50. Ab00640027_06

51. 623m853

52. Q421058

53. (1rs,2sr)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanecarboxamide

54. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-, (1r,2s)-

55. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-, (1r,2s)-rel-

56. Cyclopropanecarboxamide, 2-(aminomethyl)-n,n-diethyl-1-phenyl-, (1r-cis)-

57. F0f

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₂N₂O
Molecular Weight	246.35 g/mol
XLogP3	1.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	5
Exact Mass	246.173213330 g/mol
Monoisotopic Mass	246.173213330 g/mol
Topological Polar Surface Area	46.3 Å²
Heavy Atom Count	18
Formal Charge	0
Complexity	295
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Savella
PubMed Health	Milnacipran (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	Milnacipran hydrochloride is a selective norepinephrine and serotonin reuptake inhibitor; it inhibits norepinephrine uptake with greater potency than serotonin. It is a racemic mixture with the chemical name: ()-[1R(S),2S(R)]-2-(aminomethyl)-N,N-di...
Active Ingredient	Milnacipran hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	25mg; 100mg; 50mg; 12.5mg
Market Status	Prescription
Company	Cypress Bioscience

2 of 2
Drug Name	Savella
PubMed Health	Milnacipran (By mouth)
Drug Classes	Central Nervous System Agent
Drug Label	Milnacipran hydrochloride is a selective norepinephrine and serotonin reuptake inhibitor; it inhibits norepinephrine uptake with greater potency than serotonin. It is a racemic mixture with the chemical name: ()-[1R(S),2S(R)]-2-(aminomethyl)-N,N-di...
Active Ingredient	Milnacipran hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	25mg; 100mg; 50mg; 12.5mg
Market Status	Prescription
Company	Cypress Bioscience

4.2 Drug Indication

Treatment of stroke

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Analgesics, Non-Narcotic

A subclass of analgesic agents that typically do not bind to OPIOID RECEPTORS and are not addictive. Many non-narcotic analgesics are offered as NONPRESCRIPTION DRUGS. (See all compounds classified as Analgesics, Non-Narcotic.)

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 Active Moiety

MILNACIPRAN

5.2.2 FDA UNII

G56VK1HF36

5.2.3 Pharmacological Classes

Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]

5.3 ATC Code

N06AX17

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX17 - Milnacipran

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX28 - Levomilnacipran