DESVENLAFAXINE FUMARATE MONOHYDRATE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H25NO2.C4H4O4.H2O
Molecular Weight	397.4626
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure of DESVENLAFAXINE FUMARATE MONOHYDRATE

SMILES

O.OC(=O)\C=C\C(O)=O.CN(C)CC(C1=CC=C(O)C=C1)C2(O)CCCCC2

InChI

InChIKey=YETWCSLOYUZBLK-JITBQSAISA-N

InChI=1S/C16H25NO2.C4H4O4.H2O/c1-17(2)12-15(13-6-8-14(18)9-7-13)16(19)10-4-3-5-11-16;5-3(6)1-2-4(7)8;/h6-9,15,18-19H,3-5,10-12H2,1-2H3;1-2H,(H,5,6)(H,7,8);1H2/b;2-1+;

HIDE SMILES / InChI

Molecular Formula	C4H4O4
Molecular Weight	116.0722
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Molecular Formula	C16H25NO2
Molecular Weight	263.3752
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

Desvenlafaxine is a dual serotonin and norepinephrine reuptake inhibitor in vitro and in vivo that demonstrates good brain-to-plasma ratios. Desvenlafaxine has demonstrated antidepressant effects in preclinical studies. Pfizer is developing an oral, extended-release formulation of desvenlafaxine for the treatment of major depressive disorder. Desvenlafaxine has been registered and is available on the market for the treatment of major depressive disorder in adults.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Serotonin transporter 178	Inhibitor 8,297		40.2 nM [Ki]
Norepinephrine transporter 191	Inhibitor 8,297		558.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 173	Primary		Approved 8,429	PRISTIQ

C_max

Value	Dose	Co-administered	Analyte	Population
39.6 ng/mL	75 mg single, oral		DESVENLAFAXINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
591 ng × h/mL	75 mg single, oral		DESVENLAFAXINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
10.9 h	75 mg single, oral		DESVENLAFAXINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
70%	75 mg single, oral		DESVENLAFAXINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
750 mg single, oral MTD	healthy, 23.95 n = 11	Other AEs: Vomiting...
900 mg single, oral Highest studied dose	healthy, 27.5 ± 9.0 n = 6	DLT: Vomiting... Other AEs: Nausea...
600 mg 1 times / day multiple, oral Highest studied dose	healthy, 32.9 ± 4.7 n = 9	DLT: Orthostatic hypotension...
3500 mg single, oral Overdose	healthy, 33 n = 1	Disc. AE: Serotonin syndrome...
450 mg 1 times / day multiple, oral MTD	healthy, 34.9 ± 7.4 n = 9	Other AEs: Nausea...

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AEs

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AE	Significance	Dose	Population
Vomiting	27%	750 mg single, oral MTD	healthy, 23.95 n = 11
Vomiting	67% DLT	900 mg single, oral Highest studied dose	healthy, 27.5 ± 9.0 n = 6
Nausea	severe, 33%	900 mg single, oral Highest studied dose	healthy, 27.5 ± 9.0 n = 6
Orthostatic hypotension	67% DLT	600 mg 1 times / day multiple, oral Highest studied dose	healthy, 32.9 ± 4.7 n = 9
Serotonin syndrome	Disc. AE	3500 mg single, oral Overdose	healthy, 33 n = 1

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737 inducer 781 inhibitor 1,587	inhibitor 1,767	substrate 1,217 inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C8 911 CYP2C19 1,478 P-gp 1,461	P-gp 1,537 UGT1A1 418 UGT1A3 422 UGT2B4 249 UGT2B15 203 UGT2B17 213

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no
CYP2A6 739	inhibitor 3,277	no
CYP2C19 1,553	inhibitor 3,277	no
CYP2C8 965	inhibitor 3,277	no
CYP2C9 1,819	inhibitor 3,277	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,737	substrate 3,367	minor	yes (co-administration study)
P-gp 1,537	substrate 3,367	no
CYP2D6 1,217	substrate 3,367	yes
UGT1A1 418	substrate 3,367	yes
UGT1A3 422	substrate 3,367	yes

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
001 Chemical	NO11197	https://www.001chemical.com/chem/93413-62-8
3B Scientific (Wuhan) Corp	3B3-032554	http://www.3bsc.com/index/pro_info.php?id=53818
AA Blocks	AA006FVB	http://www.aablocks.com/goods/Goods/detail?id=AA006FVB
AEchem Scientific Corp., USA	AE1-014851	http://www.aechemsc.com/info_products/AE1-014851.php
AHH Chemical co.,ltd	MT-49703	http://www.ahhchemical.com/product/MT-49703.html

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PubMed

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Title	Date	PubMed
Desvenlafaxine succinate identifies novel antagonist binding determinants in the human norepinephrine transporter.	2007 Nov	17673606
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

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Patents

Sample Use Guides

In Vivo Use Guide

Recommended dose: 50 mg once daily with or without food.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	R5JHD7L72A
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DESVENLAFAXINE FUMARATE MONOHYDRATE

Common Name

English

O-DESMETHYLVENLAFAXINE FUMARATE MONOHYDRATE

Common Name

English

PHENOL, 4-(2-(DIMETHYLAMINO)-1-(1-HYDROXYCYCLOHEXYL)ETHYL)-, (2E)-2-BUTENEDIOATE (1:1) (SALT), MONOHYDRATE

Common Name

English

DESVENLAFAXINE FUMARATE MONOHYDRATE [MI]

Common Name

English

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Code System

Code

Type

Description

CAS

313471-75-9

PRIMARY

PUBCHEM

44178220

PRIMARY

MERCK INDEX

m4207

PRIMARY

Merck Index

RXCUI

1487366

PRIMARY

RxNorm

DRUG BANK

DBSALT001893

PRIMARY

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Related Record

Type

Details


					NG99554ANW

DESVENLAFAXINE

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					PKC68M4LCM

DESVENLAFAXINE BENZYL ETHER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)


					DYW3W9739Y

N,O-DIDESMETHYLVENLAFAXINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)

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Related Record

Type

Details


					NG99554ANW

DESVENLAFAXINE

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator