SALSALATE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C14H10O5
Molecular Weight	258.2262
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

OC(=O)C1=CC=CC=C1OC(=O)C2=CC=CC=C2O

InChI

InChIKey=WVYADZUPLLSGPU-UHFFFAOYSA-N

InChI=1S/C14H10O5/c15-11-7-3-1-5-9(11)14(18)19-12-8-4-2-6-10(12)13(16)17/h1-8,15H,(H,16,17)

HIDE SMILES / InChI

Molecular Formula	C14H10O5
Molecular Weight	258.2262
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

Salsalate is a dimer of salicylic acid. Upon administration, it is metabolically hydrolyzed to salicylic acid. Salsalate is is a nonsteroidal anti-inflammatory agent for oral administration for treatment of rheumatoid arthritis, osteoarthritis and related rheumatoid disorders. In addition, salsalate is investigated for treatment of type 2 diabetes.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
prostaglandin biosynthetic process 23	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Rheumatoid arthritis 316	Palliative	Approved 8,429	DISALCID
Osteoarthritis 157	Palliative	Approved 8,429	DISALCID
Type 2 diabetes mellitus 259	Primary	Phase III 656	Unknown

C_max

Value	Dose	Analyte	Population
45 μg/mL	1500 mg single, oral	SALSALATE plasma	Homo sapiens
17 μg/mL	1500 mg single, oral	SALSALATE plasma	Homo sapiens
88 μg/mL	1500 mg single, oral	SALICYLIC ACID plasma	Homo sapiens
97 μg/mL	1500 mg single, oral	SALICYLIC ACID plasma	Homo sapiens
21.1 μg/mL	1000 mg single, oral	SALSALATE plasma	Homo sapiens
54.4 μg/mL	1000 mg single, oral	SALICYLIC ACID plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
101 μg × h/mL	1500 mg single, oral	SALSALATE plasma	Homo sapiens
50 μg × h/mL	1500 mg single, oral	SALSALATE plasma	Homo sapiens
847 μg × h/mL	1500 mg single, oral	SALICYLIC ACID plasma	Homo sapiens
1301 μg × h/mL	1500 mg single, oral	SALICYLIC ACID plasma	Homo sapiens
50 μg × h/mL	1000 mg single, oral	SALSALATE plasma	Homo sapiens
498 μg × h/mL	1000 mg single, oral	SALICYLIC ACID plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
1.2 h	1500 mg single, oral	SALSALATE plasma	Homo sapiens
2.1 h	1500 mg single, oral	SALSALATE plasma	Homo sapiens
3.8 h	1500 mg single, oral	SALICYLIC ACID plasma	Homo sapiens
8.1 h	1500 mg single, oral	SALICYLIC ACID plasma	Homo sapiens
1.1 h	1000 mg single, oral	SALSALATE plasma	Homo sapiens
3.5 h	1000 mg single, oral	SALICYLIC ACID plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
5%			SALICYLIC ACID serum	Homo sapiens

Doses

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Dose	Population	Adverse events
1.5 g 3 times / day multiple, oral Higher than recommended	unhealthy, ADULT	Disc. AE: Tinnitus, Headache... Other AEs: Tinnitus...
2 g 2 times / day multiple, oral MTD	unhealthy, ADULT	Disc. AE: Tinnitus...
1.5 g 2 times / day multiple, oral Recommended	unhealthy, ADULT	Disc. AE: Gastro-intestinal disorder NOS, Tinnitus...

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AEs

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AE	Significance	Dose	Population
Headache	14.3% Disc. AE	1.5 g 3 times / day multiple, oral Higher than recommended	unhealthy, ADULT
Tinnitus	14.3% Disc. AE	1.5 g 3 times / day multiple, oral Higher than recommended	unhealthy, ADULT
Tinnitus	85.7%	1.5 g 3 times / day multiple, oral Higher than recommended	unhealthy, ADULT
Tinnitus	37.5% Disc. AE	2 g 2 times / day multiple, oral MTD	unhealthy, ADULT
Dizziness	1.7% Disc. AE	1.5 g 2 times / day multiple, oral Recommended	unhealthy, ADULT

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587 inducer 781	inhibitor 1,767	inhibitor 1,852	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2A6 707 CYP2E1 882 BSEP 402 CYP1A2 1,524 CYP2C19 1,478 CYP19A1 60	P-gp 1,537

Drug as perpetrator

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Target	Modality	Activity
CYP1A2 1,692	inhibitor 3,277	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3,277	no [IC50 >10 uM]
CYP2C19 1,553	inhibitor 3,277	no [IC50 >10 uM]
CYP2C9 1,819	inhibitor 3,277	no [IC50 >10 uM]
CYP2D6 1,891	inhibitor 3,277	no [IC50 >10 uM]

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Drug as victim

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Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 1,537	substrate 3,367	no

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Tox targets

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Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

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PubMed

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Title	Date	PubMed
Interaction of rofecoxib and celecoxib with warfarin.	2003 Jul 1	12901032
Aspirin and NSAID sensitivity.	2004 Aug	15242723
A randomized trial of low-dose aspirin in the prevention of clinical type 2 diabetes in women.	2009 Jan	18835953
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010 Dec	21818443
An overview of salsalate as a potential antidiabetic therapy.	2010 Nov	21225023

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Patents

Sample Use Guides

In Vivo Use Guide

The usual dosage is 3000 mg daily, given in divided doses as follows: 1(two doses of two 750 mg tablets; 2) two doses of three 500 mg tablets; or 3) three doses of two 500 mg tablets.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical
Record UNII	V9MO595C9I
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

SALSALATE

Official Name

English

DISALCID

Brand Name

English

NSC-49171

Code

English

DISALICYCLIC ACID

Common Name

English

SASAPYRINE

Common Name

English

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Classification Tree

Code System

Code

Salicylic acid and derivatives

WHO-ATC

N02BA06

Salicylic acid and derivatives

WHO-VATC

QN02BA06

Mild-Moderate Pain

LIVERTOX

NBK548843

Analgesic and Antipyretic

NCI_THESAURUS

C257

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Code System

Code

Type

Description

NSC

49171

PRIMARY

LACTMED

Salsalate

PRIMARY

SMS_ID

100000086562

PRIMARY

CHEBI

9014

PRIMARY

RXCUI

36108

PRIMARY

RxNorm

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Related Record

Type

Details


					06SH0H2G8M

SALSALATE SODIUM

SALT/SOLVATE -> PARENT

Amount:


					E6HDG0QI46

COX-1

TARGET -> INHIBITOR

Amount:


					D8T754TT2I

COX-2

TARGET -> INHIBITOR

Amount:

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Related Record

Type

Details


					2JJ274J145

ASPIRIN DL-LYSINE

PARENT -> IMPURITY

Amount:


					N667F17JP1

CARBASPIRIN CALCIUM

PARENT -> IMPURITY

Amount:


					R16CO5Y76E

ASPIRIN

PARENT -> IMPURITY

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.15] PERCENT PEAK AREA (limits)

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Related Record

Type

Details


					V9MO595C9I

SALSALATE

ACTIVE MOIETY

Amount:

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Name	Property Type	Amount	Referenced Substance	Defining	Parameters	References
Biological Half-life	PHARMACOKINETIC	1 hours (average)

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator