DESVENLAFAXINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C16H25NO2
Molecular Weight	263.3752
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN(C)CC(C1=CC=C(O)C=C1)C2(O)CCCCC2

InChI

InChIKey=KYYIDSXMWOZKMP-UHFFFAOYSA-N

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

HIDE SMILES / InChI

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	( + / - )

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

Show entries

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

Showing 1 to 5 of 8 entries

Previous1 2Next

AEs

Show entries

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

Showing 1 to 5 of 36 entries

Previous1 2 3 4 5…8Next

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

Show entries

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

Showing 1 to 5 of 9 entries

Previous1 2Next

Drug as victim

Show entries

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

Showing 1 to 5 of 8 entries

Previous1 2Next

Sourcing

Sourcing

Show entries

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
Aaron Chemicals	AR006GN3	http://www.aaronchem.com/93413-62-8
abcr GmbH	AB436252	http://www.abcr.com/shop/en/AB436252

Showing 1 to 5 of 64 entries

Previous1 2 3 4 5…13Next

PubMed

Show entries

Title	Date	PubMed
Discovery of a potent, dual serotonin and norepinephrine reuptake inhibitor.	2013 Jun 13	24900709
Syndrome of inappropriate antidiuretic hormone secretion associated with desvenlafaxine.	2014 Apr	24234943
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.	2015 May 18	25811541

Showing 1 to 3 of 3 entries

Previous1Next

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	NG99554ANW
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

DESVENLAFAXINE

Official Name

English

DESVENLAFAXINE [USP-RS]

Common Name

English

desvenlafaxine [INN]

Common Name

English

NEWVEN

Common Name

English

MDD-XR

Common Name

English

Showing 1 to 5 of 12 entries

Previous1 2 3Next

Show entries

Classification Tree

Code System

Code

Antidepressant

LIVERTOX

286

Established Pharmacologic Class

NDF-RT

N0000175749

Other antidepressants

WHO-ATC

N06AX23

Norepinephrine Transporter Interactions

NDF-RT

N0000000102

Agent Affecting Nervous System

NCI_THESAURUS

C265

Showing 1 to 5 of 7 entries

Previous1 2Next

Show entries

Code System

Code

Type

Description

NCI_THESAURUS

C61703

PRIMARY

RS_ITEM_NUM

1175751

PRIMARY

WIKIPEDIA

DESVENLAFAXINE

PRIMARY

MESH

C086816

PRIMARY

CHEBI

83527

PRIMARY

Showing 1 to 5 of 23 entries

Previous1 2 3 4 5Next

Show entries

Related Record

Type

Details


					6D53G0FD0Z

PLASMA PROTEIN FRACTION (HUMAN)

BINDER->LIGAND

Amount:

30 % (average)


					NG99554ANW

DESVENLAFAXINE

EXCRETED UNCHANGED

Interaction Type:

AMOUNT EXCRETED

Qualification:

URINE

Amount:

45 % (average)


					HY5T9WKI4O

O-DESMETHYLVENLAFAXINE, (-)-

ENANTIOMER -> RACEMATE

Amount:


					ZB22ENF0XR

DESVENLAFAXINE SUCCINATE

SALT/SOLVATE -> PARENT

Amount:


					H9E1T0BI90

DESVENLAFAXINE SUCCINATE ANHYDROUS

SALT/SOLVATE -> PARENT

Amount:

Showing 1 to 5 of 11 entries

Previous1 2 3Next

Show entries

Related Record

Type

Details


					GRZ5RCB1QG

VENLAFAXINE

PARENT -> METABOLITE ACTIVE

Interaction Type:

MAJOR

Amount:


					DYW3W9739Y

N,O-DIDESMETHYLVENLAFAXINE

METABOLITE INACTIVE -> PARENT

Comments:

<5% (NODV and NODV-glucuronide); Unit: percent of amount administered

Interaction Type:

IN-VIVO

Qualification:

URINE

Amount:

RELATIONSHIP_AMOUNT 5 (average)


					68PDXVEFMN

DESVENLAFAXINE-O-GLUCURONIDE

METABOLITE INACTIVE -> PARENT

Comments:

Unit: percent of amount administered

Interaction Type:

IN-VIVO

Qualification:

URINE

Amount:

RELATIONSHIP_AMOUNT 19 (average)


					1H23L3816Q

N,O-DIDESMETHYLVENLAFAXINE-GLUCURONIDE

METABOLITE INACTIVE -> PARENT

Comments:

<5% (NODV and NODV-glucuronide combined); Unit: percent of amount administered

Interaction Type:

IN-VIVO

Qualification:

URINE

Amount:

RELATIONSHIP_AMOUNT 5 (average)


					A7CGH459FN

TOLUDESVENLAFAXINE

PRODRUG -> METABOLITE ACTIVE

Amount:

Showing 1 to 5 of 5 entries

Previous1Next

Show entries

Related Record

Type

Details


					GRZ5RCB1QG

VENLAFAXINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)


					84ZK5B3ZT6

RAC DEHYDRO-O-DESMETHYL VENLAFAXINE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.15] PERCENT PEAK AREA (limits)

Showing 1 to 2 of 2 entries

Previous1Next

Show entries

Related Record

Type

Details


					NG99554ANW

DESVENLAFAXINE

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Name	Property Type	Amount	Parameters
Volume of Distribution	PHARMACOKINETIC	3.4 Liters/Kilogram (average)	STEADY-STATE INTRAVENOUS ADMINISTRATION

Tmax	PHARMACOKINETIC	7.5 hours (average)	ORAL ADMINISTRATION

ORAL BIOAVAILABILITY	PHARMACOKINETIC	80 % (average)

Biological Half-life	PHARMACOKINETIC	11 hours (average)	ORAL ADMINISTRATION

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