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Calcium atorvastatin

HCID 9851656
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Basic information

CAS
134523-03-8
Standard SMILES
CC(C)c1c(C(=O)Nc2ccccc2)c(-c2ccccc2)c(-c2ccc(F)cc2)n1CC[C@@H](O)C[C@@H](O)CC(=O)O.[Ca]
InChIKey
BWFCZHDTTAYGNN-CNZCJKERSA-N
Molecular formula
C33H35CaFN2O5
Average molar mass
598.7 g/mol
Monoisotopic mass
598.2155912

Names & identifiers

Preferred name
Calcium atorvastatin
English name
Atorvastatin calcium
Molecular formula
C33H37CaFN2O5
Molecular weight
600.74

Names & synonyms

Calcium atorvastatinSCHEMBL30617046BWFCZHDTTAYGNN-CNZCJKERSA-NAtorvastatin CalciuM TrihydrateAtorvastatin CalciuM APIAtrovastatin calciumATORVASTATIN CAATORVASTATIN CALCIUM SALTAtorvastatin calciuM salt trihydrate[r-(r*, r*)]-7-[2-(4-fluorophenyl)-5-(1-methylethyl)-3-phenyl-4-(phenylaminocarbonyl)-1h-pyrrol-1-yl]-3,5-dihydroxy-heptanoic acid calcium saltAtorvastation CalciuMAtorvastatin Ca Hydrate
Show more names
Atorvastatin Calcium RS

Database identifiers

CAS
134523-03-8
PubChem CID
9851656

Properties

Computed structural properties

Topological polar surface area
112 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
6
Rotatable bonds
12
Heavy atoms
42
Formal charge
0
Complexity
822

Physicochemical properties

Melting point
176 · 176-178°C
storage temp.
2 · Keep in dark place,Inert atmosphere,2-8°C
solubility
10 mg/mL · DMSO: ≥10mg/mL
form
white powder
color
White to Off-White
BCS Class
2 · 2
Major Application
pharmaceutical
InChIKey
FQCKMBLVYCEXJB-MNSAWQCASA-L
SMILES
C(C1=C(N(CC[C@@H](O)C[C@@H](O)CC(=O)O)C(C2C=CC(F)=CC=2)=C1C1C=CC=CC=1)C(C)C)(=O)NC1C=CC=CC=1.[Ca] |&1:6,9,r|
CAS DataBase Reference
134523 · 134523-03-8(CAS DataBase Reference)
NCI Dictionary of Cancer Terms
atorvastatin calcium; Lipitor
FDA UNII
0 GEJ5QCSO · C0GEJ5QCSO
NCI Drug Dictionary
atorvastatin calcium
EPA Substance Registry System
1 H-Pyrrole-1-heptanoic · 1H-Pyrrole-1-heptanoic acid, 2-(4-fluorophenyl)-.beta.,delta.-dihydroxy-5-(1-methylethyl)-3-phenyl-4-[(phenylamino)carbonyl]-, calcium salt (2:1),(.beta.R,.delta.R)- (134523-03-8)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Safety data

wgk
3
risk_code
20/21/22-36/37/38-39/23/24/25-23/24/25-11
Signal word
Warning
Symbol(GHS)
GHS07,GHS08,GHS09
hazard_code
Xn,T,F
safety_code
26-36-45-36/37-16-7
Storage Class
11 - Combustible Solids
target organs
Liver
Hazard statements
H411-H351-H361f-H372-H319
Hazard Classifications
Aquatic Chronic 2STOT RE 2
Precautionary statements
P201-P202-P281-P308+P313-P405-P501-P260-P264-P270-P314-P501-P264-P280-P305+P351+P338-P337+P313P

Chemistry & industry

Applications · 4 items

DescriptionAtorvastatin calcium (Lipitor®) was launched in Canada, the Netherlands, the UK and the US as an orally-active hypocholesterolemic agent. It was the first pharmaceutical product ever to attain over one billion dollars in sales in its first year. It can be synthesized by a number of routes but the most efficient involves the Paal-Knorr reaction of an acetonide protected dihydroxy amino ester and a diaryl phenylacetamide diketone. Lipitor is a liver selective, reversible competitive inhibitor of HMG-CoA reductase, the rate limiting step in cholesterol biosynthesis. Lipitor monotherapy resulted in a reduction of LDL cholesterol by up to 60%. Lipitor is about 2-4 times more potent, on a dosage basis, than Simvastatin. The superior properties of Lipitor can be attributed to its greater uptake and longer duration of action in the liver. In addition to its effects on cholesterol, Lipitor is also effective in lowering triglycerides. While the mechanism is not clear, two theories proposed are: a) the decrease in cholesterol causes a concomitant increase in hepatic LDL-receptor activity (mostly B and E type) which results in a decrease in triglycerides through an increase in binding of triglycerides to VLDL and LDL, and b) the decreased level of cholesterol impairs VLDL transport of triglycerides.

UsesAtorvastatin Calcium Salt Trihydrate is a compound used as standard in the method development and validation for simultaneous determination of Atorvastatin calcium (A791750) and Ezetimibe (E975000) in tablets using UV spectrophotometric, HPLC and HPTLC methods.

UsesA selective, competitive HMG-CoA reductase inhibitor. The only drug in its class specfically indicated for lowering both elevated LDL-cholesterol and triglycerides in patients with hypercholesterolemia

UsesThe primary uses of atorvastatin is for the treatment of dyslipidemia and the prevention of cardiovascular disease.

Upstream & downstream products

Upstream raw materials

n-ButyllithiumMagnesiumSodium borohydride

Related reactions

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Compound notes

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UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07,GHS08,GHS09
Signal word
Warning
Hazard statements
411 · H411-H351-H361f-H372-H319
Precautionary statements
201 · P201-P202-P281-P308+P313-P405-P501-P260-P264-P270-P314-P501-P264-P280-P305+P351+P338-P337+P313P
target organs
Liver
Hazard Codes
Xn,T,F
Risk Statements
20 · 20/21/22-36/37/38-39/23/24/25-23/24/25-11
Safety Statements
26 · 26-36-45-36/37-16-7
WGK Germany
3 · 3
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
2 STOT · Aquatic Chronic 2STOT RE 2
Triethylborane
(S)-(-)-2-Acetoxy-1,1,2-triphenylethanol

Downstream products

Atorvastatin AcetonideAtorvastatin Ethyl Ester

Additional notes

DefinitionChEBI: Atorvastatin calcium is an organic calcium salt composed of calcium cations and atorvastatin anions in a 1:2 ratio. It contains an atorvastatin(1-).