DEXTROMILNACIPRAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C15H22N2O
Molecular Weight	246.348
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

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

InChI

InChIKey=GJJFMKBJSRMPLA-HIFRSBDPSA-N

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

HIDE SMILES / InChI

Molecular Formula	C15H22N2O
Molecular Weight	246.348
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Dextromilnacipran (1R, 2S/F2696) is an enantiomer of milnacipran, a serotonin/norepinephrine (5-HT/NE) reuptake inhibitor. Dextromilnacipran is pharmacologically less active as compared with racemic mixture and levomilnacipran (1S, 2R/F2695).

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Serotonin transporter 183	Inhibitor 8,504	290.0 nM [Ki]
Serotonin transporter 183	Inhibitor 8,504	16.9 nM [Ki]
Norepinephrine transporter 197	Inhibitor 8,504	139.0 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Fibromyalgia 90	Primary		Approved 8,583	SAVELLA
Unknown 2,596

C_max

Value	Dose	Co-administered	Analyte	Population
132 ng/mL	50 mg single, oral		MILNACIPRAN plasma	Homo sapiens
150 ng/mL	50 mg single, oral		MILNACIPRAN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
1316.9 ng × h/mL	50 mg single, oral		MILNACIPRAN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
7 h	50 mg single, oral	MILNACIPRAN plasma	Homo sapiens
8 h	50 mg single, oral	MILNACIPRAN plasma	Homo sapiens
6 h	50 mg single, oral	MILNACIPRAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
87%	50 mg single, oral		MILNACIPRAN plasma	Homo sapiens
87%	50 mg single, oral		MILNACIPRAN plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946	inhibitor 2,438 inducer 440	inhibitor 2,507 substrate 1,388	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2A6 879 CYP2C19 2,057 CYP2E1 1,060	P-gp 2,052 CYP2C19 1,119 CYP1A2 1,197	CYP1A2 832 CYP2B6 669 CYP2C8 198 CYP2C19 329 CYP3A4/5 133

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 2,333	inducer 1,966	no
CYP1A2 2,333	inhibitor 4,027	no
CYP2A6 911	inhibitor 4,027	no
CYP2B6 1,160	inducer 1,966	no
CYP2C19 2,141	inducer 1,966	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
P-gp 2,052	substrate 4,014	no
CYP2C19 1,119	substrate 4,014	no	no (co-administration study)
CYP1A2 1,197	substrate 4,014	no	unlikely (co-administration study)
CYP2D6 1,388	substrate 4,014	no	unlikely (co-administration study)
CYP3A4 1,946	substrate 4,014	no	unlikely (co-administration study)

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2,263	inhibitor 2,237

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B2-6287	http://www.3bsc.com/index/pro_info.php?id=116365
Acorn PharmaTech	ACN-035533	http://www.acornpharmatech.com/
AK Scientific, Inc. (AKSCI)	R211	http://www.aksci.com/item_detail.php?cat=R211
Ambinter	Amb22801750	http://www.ambinter.com/reference/22801750
BioCrick	BCC4194	http://www.biocrick.com/Milnacipran-BCC4194.html

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PubMed

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Title	Date	PubMed
Elevation of blood pressure induced by high-dose milnacipran.	2002 Dec	12457380
Remarkable effect of milnacipran in the treatment of Japanese major depressive patients.	2002 Jun	12404688
Clinical utility of milnacipran in comparison with other antidepressants.	2002 Jun	12369610
Japanese experience with dual-action antidepressants.	2002 Jun	12369609
Pharmacology and pharmacokinetics of milnacipran.	2002 Jun	12369608

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose of Savella (Milnacipran) is 100 mg/day (50 mg twice daily). Based on efficacy and tolerability dosing may be titrated according to the following schedule: Day 1: 12.5 mg once Days 2-3: 25 mg/day (12.5 mg twice daily) Days 4-7: 50 mg/day (25 mg twice daily) After Day 7: 100 mg/day (50 mg twice daily) Based on individual patient response, the dose may be increased to 200 mg/day (100 mg twice daily). Doses above 200 mg/day have not been studied.

Route of Administration: Oral

In Vitro Use Guide

Milnacipran inhibits norepinephrine and serotonin reuptake in rat hypothalamic synaptosomes with IC50 values of 30 and 150 nM, respectively

Substance Class	Chemical
Record UNII	ES1O38J3C4
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

F-2696

Preferred Name

English

DEXTROMILNACIPRAN

Common Name

English

F2696

Code

English

(1R,2S)-MILNACIPRAN

Common Name

English

CYCLOPROPANECARBOXAMIDE, 2-(AMINOMETHYL)-N,N-DIETHYL-1-PHENYL-, (1R-CIS)-

Systematic Name

English

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Code System

Code

Type

Description

FDA UNII

ES1O38J3C4

PRIMARY

DRUG BANK

DB08918

PRIMARY

CAS

96847-55-1

PRIMARY

EPA CompTox

DTXSID601025164

PRIMARY

PUBCHEM

65833

PRIMARY

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Related Record

Type

Details


					G56VK1HF36

MILNACIPRAN

RACEMATE -> ENANTIOMER


					UGM0326TXX

LEVOMILNACIPRAN

ENANTIOMER -> ENANTIOMER

Amount:

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Related Record

Type

Details


					9TK9IO76V9

MILNACIPRAN CARBAMOYL O-GLUCURONIDE, D-

METABOLITE -> PARENT

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator