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Chemistry

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Also known as: 96847-54-0, (1s,2r)-milnacipran, (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide, F 2695, Milnacipran, (1s,2r)-, Ugm0326txx
Molecular Formula
C15H22N2O
Molecular Weight
246.35  g/mol
InChI Key
GJJFMKBJSRMPLA-DZGCQCFKSA-N
FDA UNII
UGM0326TXX

Levomilnacipran
The (1S,2R)-isomer of milnacipran that is used for the treatment of MAJOR DEPRESSIVE DISORDER.
Levomilnacipran is a Serotonin and Norepinephrine Reuptake Inhibitor. The mechanism of action of levomilnacipran is as a Norepinephrine Uptake Inhibitor, and Serotonin Uptake Inhibitor.
1 2D Structure

Levomilnacipran

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1S,2R)-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+/m0/s1
2.1.3 InChI Key
GJJFMKBJSRMPLA-DZGCQCFKSA-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
UGM0326TXX
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Fetzima

2. Levomilnacipran Hydrochloride

2.3.2 Depositor-Supplied Synonyms

1. 96847-54-0

2. (1s,2r)-milnacipran

3. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropane-1-carboxamide

4. F 2695

5. Milnacipran, (1s,2r)-

6. Ugm0326txx

7. Chembl99946

8. F-2695

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

10. (1s,2r)-2-(aminomethyl)-n,n-diethyl-1-phenylcyclopropanecarboxamide

11. Unii-ugm0326txx

12. Levomilnacipran [usan:inn]

13. Milnacipram

14. (+)-milnacipran

15. Starbld0000863

16. Levomilnacipran (usan/inn)

17. Levomilnacipran [inn]

18. Zinc506

19. Levomilnacipran [usan]

20. Levomilnacipran [vandf]

21. Gtpl7435

22. Schembl1414867

23. Levomilnacipran [who-dd]

24. Chebi:136040

25. Dtxsid701025167

26. Bdbm50032379

27. Db08918

28. F2-695

29. D10072

30. Q6535779

31. (1s,2r)-2-aminomethyl-1-phenyl-cyclopropanecarboxylic Acid Diethylamide

2.4 Create Date
2006-07-28
3 Chemical and Physical Properties
Molecular Weight 246.35 g/mol
Molecular Formula C15H22N2O
XLogP31.4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass246.173213330 g/mol
Monoisotopic Mass246.173213330 g/mol
Topological Polar Surface Area46.3 Ų
Heavy Atom Count18
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 Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameFetzima
PubMed HealthLevomilnacipran (By mouth)
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)
Active IngredientLevomilnacipran hydrochloride
Dosage FormCapsule, extended release
RouteOral
Strengtheq 40mg base; eq 80mg base; eq 120mg base; eq 20mg base
Market StatusPrescription
CompanyForest Labs

4.2 Drug Indication

Levomilnacipran is a serotonin and norepinephrine reuptake inhibitor and is indicated for the treatment of major depressive disorder (MDD).


FDA Label


Treatment of stroke


5 Pharmacology and Biochemistry
5.1 Pharmacology

Levomilnacipran binds with high affinity to human serotonin (5-HT) and norepinephrine (NE) transporters (Ki = 11 and 91 nM, respectively). It potently inhibits 5-HT and NE reuptake (IC50 = 16 - 19 and 11 nM, respectively). Levomilnacipran does not bind to any other receptors, ion channels, or transporters, including serotonergic (5HT1-7), - and adrenergic, muscarinic, or histaminergic receptors and Ca2+, Na+, K+ or Cl- channels to a significant degree. Levomilnacipran did not inhibit monoamine oxidase (MAO). Furthermore, levomilnacipran does not prolong the QTc interval to a clinically relevant extent.


5.2 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.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
LEVOMILNACIPRAN
5.3.2 FDA UNII
UGM0326TXX
5.3.3 Pharmacological Classes
Serotonin Uptake Inhibitors [MoA]; Serotonin and Norepinephrine Reuptake Inhibitor [EPC]; Norepinephrine Uptake Inhibitors [MoA]
5.4 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AX - Other antidepressants

N06AX28 - Levomilnacipran


5.5 Absorption, Distribution and Excretion

Absorption

The relative bioavailability after administration of the extended-release capsule was 92% when compared to oral solution. Food does not affect the concentration of levomilnacipran. After daily dosing of levomilnacipran (extended-release capsule) the mean Cmax is 341 ng/mL, and the mean steady-state AUC value is 5196 ngh/mL. The Tmax is 6 - 8 hours after oral administration. Interconversion of stereoisomers does not occur in humans.


Route of Elimination

Levomilnacipran and its metabolites are eliminated primarily by renal excretion. 58% of the dose is excreted in urine as unchanged levomilnacipran. N-desethyl levomilnacipran is the major metabolite excreted in the urine and accounted for approximately 18% of the dose. Other identifiable metabolites excreted in the urine are levomilnacipran glucuronide (4%), desethyl-levomilnacipran glucuronide (3%), p-hydroxy levomilnacipran glucuronide (1%), and p-hydroxylevomilnacipran (1%). The metabolites are inactive.


Volume of Distribution

387 - 473 L [apparent volume of distribution]


Clearance

21 - 29 L/h [mean apparent total clearance]


5.6 Metabolism/Metabolites

Hepatic. Levomilnacipran undergoes desethylation to form desethyl levomilnacipran and hydroxylation to form p-hydroxy-levomilnacipran. Desethylation is facilitated primarily by CYP3A4 and by CYP2C8, 2C19, 2D6, and 2J2 to a lesser extent. Both metabolites undergo further conjugation with glucuronide to form conjugates.


5.7 Biological Half-Life

12 hours


5.8 Mechanism of Action

The exact mechanism of the antidepressant action of levomilnacipran is unknown but is thought to be related to the potentiation of serotonin and norephinephrine in the central nervous system through inhibition of reuptake at serotonin and norepinephrine transporters.


API Reference Price

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03-Dec-2021
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ABOUT THIS PAGE

Levomilnacipran Manufacturers

A Levomilnacipran manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Levomilnacipran, including repackagers and relabelers. The FDA regulates Levomilnacipran manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Levomilnacipran API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Levomilnacipran manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Levomilnacipran Suppliers

A Levomilnacipran supplier is an individual or a company that provides Levomilnacipran active pharmaceutical ingredient (API) or Levomilnacipran finished formulations upon request. The Levomilnacipran suppliers may include Levomilnacipran API manufacturers, exporters, distributors and traders.

click here to find a list of Levomilnacipran suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Levomilnacipran USDMF

A Levomilnacipran DMF (Drug Master File) is a document detailing the whole manufacturing process of Levomilnacipran active pharmaceutical ingredient (API) in detail. Different forms of Levomilnacipran DMFs exist exist since differing nations have different regulations, such as Levomilnacipran USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Levomilnacipran DMF submitted to regulatory agencies in the US is known as a USDMF. Levomilnacipran USDMF includes data on Levomilnacipran's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Levomilnacipran USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Levomilnacipran suppliers with USDMF on PharmaCompass.

Levomilnacipran GMP

Levomilnacipran Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Levomilnacipran GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Levomilnacipran GMP manufacturer or Levomilnacipran GMP API supplier for your needs.

Levomilnacipran CoA

A Levomilnacipran CoA (Certificate of Analysis) is a formal document that attests to Levomilnacipran's compliance with Levomilnacipran specifications and serves as a tool for batch-level quality control.

Levomilnacipran CoA mostly includes findings from lab analyses of a specific batch. For each Levomilnacipran CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Levomilnacipran may be tested according to a variety of international standards, such as European Pharmacopoeia (Levomilnacipran EP), Levomilnacipran JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Levomilnacipran USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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