AZILSARTAN MEPIXETIL SODIUM

Details

Stereochemistry	RACEMIC
Molecular Formula	C36H33N6O8.Na
Molecular Weight	700.6724
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of AZILSARTAN MEPIXETIL SODIUM

SMILES

[Na+].CCOC1=NC2=C(N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)[N-]5)C(=CC=C2)C(=O)OC(C)OC(=O)OCC6=NC(C)=C(C)N=C6C

InChI

InChIKey=HQKSMPMMUHZJDA-UHFFFAOYSA-M

InChI=1S/C36H34N6O8.Na/c1-6-46-34-39-29-13-9-12-28(33(43)48-23(5)49-36(45)47-19-30-22(4)37-20(2)21(3)38-30)31(29)42(34)18-24-14-16-25(17-15-24)26-10-7-8-11-27(26)32-40-35(44)50-41-32;/h7-17,23H,6,18-19H2,1-5H3,(H,40,41,44);/q;+1/p-1

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Description

TAK-536 (generic name: azilsartan) is an angiotensin II type 1 receptor blocker, discovered by Takeda and its mechanism of action is to lower blood pressure by inhibiting action of a vasopressor hormone Angiotensin II. Angiotensin II type 1 receptor antagonists have become an important drug class in the treatment of hypertension and heart failure. TAK-536 is in phase III clinical trial for treatment hypertension. This drug also known as active metabolite of the prodrug azilsartan medoxomil (also known as azilsartan kamedoxomil), but in some countries azilsartan rather than its prodrug is used for oral treatment.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Type-1 angiotensin II receptor 41	Antagonist 2,849		0.62 nM [IC50]
Type-1 angiotensin II receptor 41	Antagonist 2,849

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575	Primary		Approved 8,583	EDARBI
Hypertension 575	Primary		Phase III 665	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
831.3 ng/mL	10 mg single, oral		AZILSARTAN plasma	Homo sapiens
141.3 ng/mL	10 mg single, oral		AZILSARTAN METABOLITE M-I plasma	Homo sapiens
179.3 ng/mL	10 mg single, oral		AZILSARTAN METABOLITE M-II plasma	Homo sapiens
888.3 ng/mL	5 mg single, oral		AZILSARTAN plasma	Homo sapiens
191.3 ng/mL	5 mg single, oral		AZILSARTAN METABOLITE M-I plasma	Homo sapiens
227.7 ng/mL	5 mg single, oral		AZILSARTAN METABOLITE M-II plasma	Homo sapiens
5355.71 ng/mL	80 mg single, oral	Chlorthalidone	AZILSARTAN plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
6871.7 ng*h/mL	10 mg single, oral		AZILSARTAN plasma	Homo sapiens
1420.5 ng*h/mL	10 mg single, oral		AZILSARTAN METABOLITE M-I plasma	Homo sapiens
3526 ng*h/mL	10 mg single, oral		AZILSARTAN METABOLITE M-II plasma	Homo sapiens
6350.3 ng*h/mL	5 mg single, oral		AZILSARTAN plasma	Homo sapiens
1592.7 ng*h/mL	5 mg single, oral		AZILSARTAN METABOLITE M-I plasma	Homo sapiens
1986.5 ng*h/mL	5 mg single, oral		AZILSARTAN METABOLITE M-II plasma	Homo sapiens
46688.2 ng × h/mL	80 mg single, oral	Chlorthalidone	AZILSARTAN plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
12.1 h	80 mg single, oral	Chlorthalidone	AZILSARTAN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1%	80 mg 1 times / day unknown, oral		AZILSARTAN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
80 mg 1 times / day multiple, oral Recommended	unhealthy, 50.4+/-10.2	Disc. AE: Dizziness, Fatigue...
320 mg 1 times / day multiple, oral Overdose	healthy
80 mg 1 times / day multiple, oral Recommended	unhealthy	Disc. AE: Hypotension orthostatic...

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AEs

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AE	Significance	Dose	Population
Fatigue	2.79% Disc. AE	80 mg 1 times / day multiple, oral Recommended	unhealthy, 50.4+/-10.2
Dizziness	3.35% Disc. AE	80 mg 1 times / day multiple, oral Recommended	unhealthy, 50.4+/-10.2
Hypotension orthostatic	0.4% Disc. AE	80 mg 1 times / day multiple, oral Recommended	unhealthy

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2,252 substrate 1,946 inducer 1,087	inhibitor 2,438 substrate 1,193	inhibitor 2,507 substrate 1,388	inhibitor 2,217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2,153 CYP2B6 926 CYP2C8 1,057 CYP2C19 2,057 CYP2E1 1,060 CYP1A1 132 CYP2A6 879 P-gp 1,741	CYP2C8 810 CYP1A1 389 CYP1A2 1,197 CYP2A6 626 CYP2B6 776 CYP2C19 1,119 CYP2E1 729 CYP4A11 137 P-gp 2,052

Drug as perpetrator

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Target	Modality	Activity
CYP1A1 272	inhibitor 4,027	no [IC50 >100 uM]
CYP2A6 911	inhibitor 4,027	no [IC50 >100 uM]
CYP2B6 1,160	inhibitor 4,027	no [IC50 >100 uM]
CYP2C19 2,141	inhibitor 4,027	no [IC50 >100 uM]
CYP2E1 1,146	inhibitor 4,027	no [IC50 >100 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
P-gp 2,052	substrate 4,014	inconclusive
CYP2C9 1,193	substrate 4,014	major	yes (co-administration study)
CYP1A1 389	substrate 4,014	yes
CYP1A2 1,197	substrate 4,014	yes
CYP2A6 626	substrate 4,014	yes

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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
ChEBI	CHEBI:68850	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:68850
ChemicalBook	CB21090899	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB21090899
eMolecules	36762351	https://www.emolecules.com/cgi-bin/more?vid=36762351
eMolecules	36905408	https://www.emolecules.com/cgi-bin/more?vid=36905408
MolPort	MolPort-023-219-167	https://www.molport.com/shop/molecule-link/MolPort-023-219-167

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PubMed

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Title	Date	PubMed
TAK-536, a new AT1 receptor blocker, improves glucose intolerance and adipocyte differentiation.	2007 May	17485025
Differential pharmacology and benefit/risk of azilsartan compared to other sartans.	2012	22399858

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Patents

Sample Use Guides

In Vivo Use Guide

The recommended dose in adults is 80 mg taken orally once daily. Consider a starting dose of 40 mg for patients who are treated with high doses of diuretics.

Route of Administration: Oral

In Vitro Use Guide

Unknown

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Name

Type

Language

QR-01019NA

Preferred Name

English

AZILSARTAN MEPIXETIL SODIUM

Common Name

English

1H-BENZIMIDAZOLE-7-CARBOXYLIC ACID, 1-((2'-(2,5-DIHYDRO-5-OXO-1,2,4-OXADIAZOL-3-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-2-ETHOXY-, 1-((((3,5,6-TRIMETHYL-2-PYRAZINYL)METHOXY)CARBONYL)OXY)ETHYL ESTER, SODIUM SALT (1:1)

Systematic Name

English

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Code System

Code

Type

Description

PUBCHEM

162625108

PRIMARY

CAS

2153458-34-3

PRIMARY

FDA UNII

UV3DFZ5794

PRIMARY

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PARENT (SALT/SOLVATE)


					C2GK4G74Y7

AZILSARTAN MEPIXETIL

SUBSTANCE RECORD


					UV3DFZ5794

AZILSARTAN MEPIXETIL SODIUM

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

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