TOLUDESVENLAFAXINE

Details

Stereochemistry	RACEMIC
Molecular Formula	C24H31NO3
Molecular Weight	381.5078
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CN(C)CC(C1=CC=C(OC(=O)C2=CC=C(C)C=C2)C=C1)C3(O)CCCCC3

InChI

InChIKey=QKYBZJLEMOZFFU-UHFFFAOYSA-N

InChI=1S/C24H31NO3/c1-18-7-9-20(10-8-18)23(26)28-21-13-11-19(12-14-21)22(17-25(2)3)24(27)15-5-4-6-16-24/h7-14,22,27H,4-6,15-17H2,1-3H3

HIDE SMILES / InChI

Molecular Formula	C24H31NO3
Molecular Weight	381.5078
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 183	Inhibitor 8,504		40.2 nM [Ki]
Norepinephrine transporter 197	Inhibitor 8,504		558.4 nM [Ki]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive disorder 179	Primary		Approved 8,583	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	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...

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AEs

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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

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,946 inducer 1,087 inhibitor 2,252	inhibitor 2,438	substrate 1,388 inhibitor 2,507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2A6 879 CYP2C8 1,057 CYP2C19 2,057 P-gp 1,741	P-gp 2,052 UGT1A1 479 UGT1A3 470 UGT2B4 278 UGT2B15 236 UGT2B17 237

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 2,333	inhibitor 4,027	no
CYP2A6 911	inhibitor 4,027	no
CYP2C19 2,141	inhibitor 4,027	no
CYP2C8 1,117	inhibitor 4,027	no
CYP2C9 2,497	inhibitor 4,027	no

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP3A4 1,946	substrate 4,014	minor	yes (co-administration study)
P-gp 2,052	substrate 4,014	no
CYP2D6 1,388	substrate 4,014	yes
UGT1A1 479	substrate 4,014	yes
UGT1A3 470	substrate 4,014	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
Aaron Chemicals	AR006GN3	http://www.aaronchem.com/93413-62-8
abcr GmbH	AB436252	http://www.abcr.com/shop/en/AB436252

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PubMed

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Title	Date	PubMed
Desvenlafaxine succinate: A new serotonin and norepinephrine reuptake inhibitor.	2006 Aug	16675639
Assessment of infant dose through milk in a lactating woman taking amisulpride and desvenlafaxine for treatment-resistant depression.	2010 Dec	20926994
Discovery of a potent, dual serotonin and norepinephrine reuptake inhibitor.	2013 Jun 13	24900709
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	A7CGH459FN
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TOLUDESVENLAFAXINE

Official Name

English

ANSOFAXINE

Preferred Name

English

LY-03005

Code

English

TOLUDESVENLAFAXINE [USAN]

Common Name

English

ODVP2

Code

English

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Code System

Code

Type

Description

SMS_ID

300000018837

PRIMARY

NCI_THESAURUS

C171708

PRIMARY

DRUG BANK

DB15052

PRIMARY

WIKIPEDIA

Ansofaxine

PRIMARY

PUBCHEM

15983287

PRIMARY

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Related Record

Type

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					V6Z6K3OQX4

TOLUDESVENLAFAXINE HYDROCHLORIDE ANHYDROUS

SALT/SOLVATE -> PARENT

Amount:

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					NG99554ANW

DESVENLAFAXINE

METABOLITE ACTIVE -> PRODRUG

Amount:

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					NG99554ANW

DESVENLAFAXINE

ACTIVE MOIETY

Amount:

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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