CAS 92623-85-3|F 2207|Toledomin|milnacipran|Ixel|(1R,2S)-2-(aminomethyl)-N,N-diethyl-1-phenylcyclopropane-1-carboxamide|milnacipran|Midalcipran|(-)-milnacipran|Milnacipran|Milnacipranum [latin]

General Information

Structure

Molecular Formula

C₁₅H₂₂N₂O

Molecular Mass

246.34798

Exact Mass

246.17321333

Charge

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

InChIKey

GJJFMKBJSRMPLA-HIFRSBDPSA-N

Canonic Smiles

NC[C@H]1C[C@@]1(c1ccccc1)C(=O)N(CC)CC

Isomeric Smiles

O=C(N(CC)CC)[C@]1([C@H](C1)CN)c1ccccc1

Calculated Properties

JChem

H Acceptors

H Donor

LogD (pH = 5.5)

-1.5899252

LogD (pH = 7.4)

-0.91125065

Log P

1.4217067

Molar Refractivity

73.8095

Polarizability

28.916954

Polar Surface Area

46.33

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

1.72

LOG S

-2.3

Solubility (Water)

1.23e+00 g/l

Data Source

Academic Data

Data Source

Names and Identifiers

Synonyms

F 2207milnacipranMilnacipran(-)-milnacipranMilnacipranum [latin]Midalcipran

Brand Name

ToledominIxel

IUPAC Traditional name

milnacipran

IUPAC name

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

Names and Identifiers

Registration numbers

PubChem CID

CAS Number

PubChem SID

KEGG ID

DrugBank ID

Medline Plus

CHEMBL

ATC CODE

Wikipedia Title

Unique Ingredient Identifier

G56VK1HF36

Chemspider ID

59245

Registration numbers

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

Click here to submit data

Molecule Details

Wikipedia

Milnacipran

DrugBank

DB04896

Drug Groups

approved; investigational

Description

Milnacipran is an antidepressant of the serotonin-norepinephrine reuptake inhibitor class. Milnacipran has been approved and sold in Austria since September 1998 under the brand name Ixel. Cypress Bioscience bought the exclusive rights for approval and marketing of the drug for any purpose in the US and Canada in 2003 from the manufacturer Pierre Fabre; the approval procedure in both countries is ongoing.

Indication

Milnacipran is used to treat moderate to severe clinical depression and chronic pain.

Affected Organisms

Humans and other mammals

Biotransformation

Only traces of active metabolites are found. Cytochrome P450 enzymes play no role in the metabolism of Milnacipran.

Absorption

Milnacipran is well absorbed following oral administration with an absolute bioavailability of 85%. Meals have no effect on absorption.

Half Life

8 hours

Elimination

It is excreted predominantly unchanged in urine (55%) and has a terminal elimination half-life of about 6 to 8 hours. The main route of elimination of bepotastine besilate is urinary excretion (with approximately 75-90% excreted unchanged in urine).

Distribution

* 400 L

References

• Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. [Pubmed]

• Sato S, Yamakawa Y, Terashima Y, Ohta H, Asada T: Efficacy of milnacipran on cognitive dysfunction with post-stroke depression: preliminary open-label study. Psychiatry Clin Neurosci. 2006 Oct;60(5):584-9. [Pubmed]

• Simon LS: Is milnacipran effective in treating pain in patients with fibromyalgia? Nat Clin Pract Rheumatol. 2006 Mar;2(3):126-7. [Pubmed]

• Soya A, Terao T, Nakajima M, Kojima H, Okamoto T, Inoue Y, Iwakawa M, Shinkai K, Yoshimura R, Ueta Y, Nakamura J: Effects of repeated milnacipran administration on brain serotonergic and noradrenergic functions in healthy volunteers. Psychopharmacology (Berl). 2006 Sep;187(4):526-7. Epub 2006 Jul 8. [Pubmed]

• King T, Rao S, Vanderah T, Chen Q, Vardanyan A, Porreca F: Differential blockade of nerve injury-induced shift in weight bearing and thermal and tactile hypersensitivity by milnacipran. J Pain. 2006 Jul;7(7):513-20. [Pubmed]

• Moojen VK, Martins MR, Reinke A, Feier G, Agostinho FR, Cechin EM, Quevedo J: Effects of milnacipran in animal models of anxiety and memory. Neurochem Res. 2006 Apr;31(4):571-7. Epub 2006 May 9. [Pubmed]

• Moret C, Charveron M, Finberg JP, Couzinier JP, Briley M: Biochemical profile of midalcipran (F 2207), 1-phenyl-1-diethyl-aminocarbonyl-2-aminomethyl-cyclopropane (Z) hydrochloride, a potential fourth generation antidepressant drug. Neuropharmacology. 1985 Dec;24(12):1211-9. [Pubmed]

• Briley M, Prost JF, Moret C: Preclinical pharmacology of milnacipran. Int Clin Psychopharmacol. 1996 Sep;11 Suppl 4:9-14. [Pubmed]

• Puozzo C, Panconi E, Deprez D: Pharmacology and pharmacokinetics of milnacipran. Int Clin Psychopharmacol. 2002 Jun;17 Suppl 1:S25-35. [Pubmed]

• Leinonen E, Lepola U, Koponen H, Mehtonen OP, Rimon R: Long-term efficacy and safety of milnacipran compared to clomipramine in patients with major depression. Acta Psychiatr Scand. 1997 Dec;96(6):497-504. [Pubmed]

• Papakostas GI, Fava M: A meta-analysis of clinical trials comparing milnacipran, a serotonin--norepinephrine reuptake inhibitor, with a selective serotonin reuptake inhibitor for the treatment of major depressive disorder. Eur Neuropsychopharmacol. 2007 Jan;17(1):32-6. Epub 2006 Jun 8. [Pubmed]

• Kako Y, Niwa Y, Toyomaki A, Yamanaka H, Kitagawa N, Denda K, Koyama T: A case of adult attention-deficit/hyperactivity disorder alleviated by milnacipran. Prog Neuropsychopharmacol Biol Psychiatry. 2007 Apr 13;31(3):772-5. Epub 2007 Jan 12. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Molecule Details

References

PubChem Literature

From Data Sources

• Simon LS: Is milnacipran effective in treating pain in patients with fibromyalgia? Nat Clin Pract Rheumatol. 2006 Mar;2(3):126-7. Pubmed

• Puozzo C, Panconi E, Deprez D: Pharmacology and pharmacokinetics of milnacipran. Int Clin Psychopharmacol. 2002 Jun;17 Suppl 1:S25-35. Pubmed

• Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. Pubmed

• Briley M, Prost JF, Moret C: Preclinical pharmacology of milnacipran. Int Clin Psychopharmacol. 1996 Sep;11 Suppl 4:9-14. Pubmed

References

Bioactivity

PubChem BioAssay

Bioactivity

Navigation

General Information

Calculated Properties

• RDKit

• JChem

• ALOGPS 2.1

Data Source

• Academic Data

Names and Identifiers

• Synonyms

• Brand Name

• IUPAC Traditional name

• IUPAC name

Names and Identifiers

Registration numbers

• PubChem CID

• CAS Number

• PubChem SID

• KEGG ID

• DrugBank ID

• Medline Plus

• CHEMBL

• ATC CODE

• Wikipedia Title

• Unique Ingredient Identifier

• Chemspider ID

Registration numbers

Properties

• Pharmacology Properties

Related Proteins

Molecular Spectra

Molecule Details

• Wikipedia

• DrugBank

Molecule Details

References

• PubChem Literature

• From Data Sources

Bioactivity

• PubChem BioAssay

CAS Number

PubChem SID

Medline Plus

Wikipedia Title

Unique Ingredient Identifier

G56VK1HF36

From Data Sources

• Simon LS: Is milnacipran effective in treating pain in patients with fibromyalgia? Nat Clin Pract Rheumatol. 2006 Mar;2(3):126-7. Pubmed

• Puozzo C, Panconi E, Deprez D: Pharmacology and pharmacokinetics of milnacipran. Int Clin Psychopharmacol. 2002 Jun;17 Suppl 1:S25-35. Pubmed

• Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. Pubmed

• Briley M, Prost JF, Moret C: Preclinical pharmacology of milnacipran. Int Clin Psychopharmacol. 1996 Sep;11 Suppl 4:9-14. Pubmed

Pharmacology Properties

DrugBank

DB04896

Drug Groups

approved; investigational

Description

Indication

Milnacipran is used to treat moderate to severe clinical depression and chronic pain.

Affected Organisms

Humans and other mammals

Biotransformation

Only traces of active metabolites are found. Cytochrome P450 enzymes play no role in the metabolism of Milnacipran.

Absorption

Milnacipran is well absorbed following oral administration with an absolute bioavailability of 85%. Meals have no effect on absorption.

Half Life

8 hours

Elimination

Distribution

* 400 L

References

• Leo RJ, Brooks VL: Clinical potential of milnacipran, a serotonin and norepinephrine reuptake inhibitor, in pain. Curr Opin Investig Drugs. 2006 Jul;7(7):637-42. [Pubmed]

• Simon LS: Is milnacipran effective in treating pain in patients with fibromyalgia? Nat Clin Pract Rheumatol. 2006 Mar;2(3):126-7. [Pubmed]

• Briley M, Prost JF, Moret C: Preclinical pharmacology of milnacipran. Int Clin Psychopharmacol. 1996 Sep;11 Suppl 4:9-14. [Pubmed]

• Puozzo C, Panconi E, Deprez D: Pharmacology and pharmacokinetics of milnacipran. Int Clin Psychopharmacol. 2002 Jun;17 Suppl 1:S25-35. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

Synonyms

F 2207milnacipranMilnacipran(-)-milnacipranMilnacipranum [latin]Midalcipran

Brand Name

ToledominIxel

IUPAC Traditional name

milnacipran

IUPAC name

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

Molecule

ID:4398