ROSUVASTATIN CALCIUM

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C22H27FN3O6S.Ca
Molecular Weight	1001.137
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	2
Charge	0

SHOW SMILES / InChI

SMILES

[Ca++].CC(C)C1=NC(=NC(C2=CC=C(F)C=C2)=C1\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)N(C)S(C)(=O)=O.CC(C)C3=NC(=NC(C4=CC=C(F)C=C4)=C3\C=C\[C@@H](O)C[C@@H](O)CC([O-])=O)N(C)S(C)(=O)=O

InChI

InChIKey=LALFOYNTGMUKGG-BGRFNVSISA-L

InChI=1S/2C22H28FN3O6S.Ca/c2*1-13(2)20-18(10-9-16(27)11-17(28)12-19(29)30)21(14-5-7-15(23)8-6-14)25-22(24-20)26(3)33(4,31)32;/h2*5-10,13,16-17,27-28H,11-12H2,1-4H3,(H,29,30);/q;;+2/p-2/b2*10-9+;/t2*16-,17-;/m11./s1

HIDE SMILES / InChI

Molecular Formula	Ca
Molecular Weight	40.078
Charge	2
Count	MOL RATIO 1 MOL RATIO (average)

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

Molecular Formula	C22H27FN3O6S
Molecular Weight	480.53
Charge	-1
Count	MOL RATIO 2 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description

CRESTOR (rosuvastatin calcium) is an inhibitor of HMG-CoA reductase. It has been widely launched for the treatment of patients with dyslipidaemia and has also been approved in the US and EU to slow the progression of atherosclerosis.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
HMG-CoA reductase 47	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Dyslipidemia 30	Primary	Approved 8,429	CRESTOR
Hypertriglyceridemia 17	Primary	Approved 8,429	CRESTOR
Dysbetalipoproteinemia 6	Primary	Approved 8,429	CRESTOR
Hypercholesterolemia 47	Primary	Approved 8,429	CRESTOR
Atherosclerosis 74	Primary	Approved 8,429	CRESTOR

C_max

Value	Dose	Analyte	Population
10.22 ng/mL	5 mg single, oral	ROSUVASTATIN plasma	Homo sapiens
25.86 ng/mL	10 mg single, oral	ROSUVASTATIN plasma	Homo sapiens
44.99 ng/mL	20 mg single, oral	ROSUVASTATIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
75.93 ng × h/mL	5 mg single, oral	ROSUVASTATIN plasma	Homo sapiens
216.77 ng × h/mL	10 mg single, oral	ROSUVASTATIN plasma	Homo sapiens
311.35 ng × h/mL	20 mg single, oral	ROSUVASTATIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
13.01 h	5 mg single, oral	ROSUVASTATIN plasma	Homo sapiens
13.33 h	10 mg single, oral	ROSUVASTATIN plasma	Homo sapiens
15.4 h	20 mg single, oral	ROSUVASTATIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
12%			ROSUVASTATIN plasma	Homo sapiens

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	substrate 1,037	substrate 1,217	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP 450 18 P-gp 1,461 BCRP 699	CYP2C19 991 OATP1B1 406 OATP1B3 350 OATP2B1 104 BCRP 561 NTCP 17 OAT3 339	CYP 450 10

Drug as perpetrator

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Target	Modality	Activity
CYP 450 20	inducer 1,573	no
CYP 450 20	inhibitor 3,277	no
P-gp 1,650	inhibitor 3,277	no
BCRP 773	inhibitor 3,277	yes [Ki 15.4 uM]

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Drug as victim

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Target	Modality	Activity	Clinical evidence
CYP2C9 1,037	substrate 3,367	major	no (co-administration study)
CYP2D6 1,217	substrate 3,367	minor
CYP2C19 991	substrate 3,367	minor	no (co-administration study)
CYP3A4 1,737	substrate 3,367	minor	yes (co-administration study)
BCRP 561	substrate 3,367	yes

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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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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:38545	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:38545
eMolecules	877496	https://www.emolecules.com/cgi-bin/more?vid=877496
MolPort	MolPort-000-883-884	https://www.molport.com/shop/molecule-link/MolPort-000-883-884
ZINC	ZINC000001535101	http://zinc15.docking.org/substances/ZINC000001535101

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PubMed

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Title	Date	PubMed
Direct vascular and cardioprotective effects of rosuvastatin, a new HMG-CoA reductase inhibitor.	2002 Sep 18	12354446
Chronic treatment with rosuvastatin modulates nitric oxide synthase expression and reduces ischemia-reperfusion injury in rat hearts.	2005 Jun 1	15914111
Drug and bile acid transporters in rosuvastatin hepatic uptake: function, expression, and pharmacogenetics.	2006 May	16697742
Rosuvastatin protects against oxidative stress and DNA damage in vitro via upregulation of glutathione synthesis.	2008 Aug	18154958
In-vivo effects of simvastatin and rosuvastatin on global gene expression in peripheral blood leucocytes in a human inflammation model.	2008 Feb	18192897

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Patents

Sample Use Guides

In Vivo Use Guide

The dose range for CRESTOR (rosuvastatin calcium) is 5 to 40 mg orally once daily. The usual starting dose is 10-20 mg.

Route of Administration: Oral

In Vitro Use Guide

HUVECs treated with 30 mM glucose were used to simulate high-glucose conditions, and rosuvastatin concentrations ranging from 0.1 to 10 nM were used.

Substance Class	Chemical
Record UNII	83MVU38M7Q
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ROSUVASTATIN CALCIUM

Official Name

English

ROSUVASTATIN CALCIUM [JAN]

Common Name

English

ROSUVASTATIN CALCIUM [MART.]

Common Name

English

ROSUVASTATIN CALCIUM [ORANGE BOOK]

Common Name

English

ROSUVASTATIN CALCIUM SALT

Common Name

English

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Classification Tree

Code System

Code

Enzyme Inhibitor

NCI_THESAURUS

C1655

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Code System

Code

Type

Description

PUBCHEM

5282455

PRIMARY

DRUG BANK

DBSALT000154

PRIMARY

NSC

758930

PRIMARY

SMS_ID

100000091449

PRIMARY

CAS

147098-20-2

PRIMARY

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ROSUVASTATIN

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(3R,5S,6E)-7-(4-(4-FLUOROPHENYL)-2-(((2-(4-(4-FLUOROPHENYL)-6-(1-METHYLETHYL)-2-(METHYL(METHYLSULFONYL)AMINO)PYRIMIDIN-5-YL)-2-HYDROXYETHYL)SULFONYL)(METHYL)AMINO)-6-(1-METHYLETHYL)PYRIMIDIN-5-YL)-3,5-DIHYDROXYHEPT-6-ENOIC ACID

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IMPURITY -> PARENT

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IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

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Amount:

[<0.1] PERCENT PEAK AREA (limits)


					6HU79XG7AR

(3R,5S,6E)-7-(4-(4-FLUOROPHENYL)-2-(((2-HYDROXY-2-METHYLPROPYL)SULFONYL)(METHYL)AMINO)-6-(1-METHYLETHYL)PYRIMIDIN-5-YL)-3,5-DIHYDROXYHEPT-6-ENOIC ACID

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EP

Amount:

[<0.2] PERCENT PEAK AREA (limits)

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

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