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Atorvastatin

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Identification
Molecular formula
C33H35FN2O5
CAS number
134523-03-8
IUPAC name
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
State
State

Atorvastatin is typically a solid at room temperature. It is used primarily in tablet form as a pharmaceutical product for the treatment of high cholesterol.

Melting point (Celsius)
159.00
Melting point (Kelvin)
432.15
Boiling point (Celsius)
217.00
Boiling point (Kelvin)
490.15
General information
Molecular weight
558.64g/mol
Molar mass
558.6440g/mol
Density
1.2000g/cm3
Appearence

Atorvastatin is a white to off-white crystalline powder. It is often found in its salt form, particularly atorvastatin calcium, which enhances its solubility and handling in pharmaceutical preparations.

Comment on solubility

Solubility Characteristics

The compound (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid has a complex structure that significantly influences its solubility properties. When examining solubility, it's important to consider several factors:

  • Functional Groups: The presence of hydroxyl (-OH) groups typically enhances solubility in polar solvents via hydrogen bonding.
  • Hydrophobic Regions: The large hydrocarbon backbone may hinder solubility in water, indicating potential solubility in organic solvents.
  • Steric Effects: The spatial arrangement of the substituents might further complicate interactions with solvent molecules.

As a result, it is expected that this compound exhibits:

  1. A limited solubility in water due to its hydrophobic characteristics.
  2. Relatively better solubility in organic solvents such as ethanol or methanol, where the polar and non-polar regions can interact more favorably.

In summary, the solubility of (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid is likely to be significantly influenced by both its polar and non-polar regions, making it crucial to consider the solvent choice in experimental applications. Understanding these characteristics ensures the compound is effectively utilized in its respective fields.

Interesting facts

Exploring the Intricacies of a Unique Compound

The compound known as (4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid represents an intriguing blend of structural complexity and biological significance. This compound, with its multifaceted stereochemistry, is a prime example of how natural products can manifest in intricate forms, leading to diverse applications.

Key Features of the Compound

  • Natural Origin: This compound is often classified as a steroid or a related molecule, showcasing its potential natural origins and biological roles, particularly in hormone synthesis.
  • Structural Complexity: With numerous chiral centers and a unique tetradecahydro structure, it exemplifies the rich tapestry of organic compounds found in nature.
  • Biological Interactions: The presence of hydroxy groups suggests possible interactions with biological systems, potentially influencing various cellular pathways.
  • Pharmacological Potential: Given its structure, this compound may offer bases for developing pharmaceuticals, especially in the realms of endocrinology and oncology.

Chemistry students and professionals alike are fascinated by such compounds for their potential to unlock new avenues in research and medicine. As one renowned chemist once stated, "Nature has perfected the art of chemistry over billions of years; our task is merely to follow her lead."

This compound serves not only as a subject of study but also as an inspiration, exemplifying the beauty and complexity of chemical structures in the natural world. Its journey from theory to application can yield profound insights into human health and disease.

Synonyms
URSODEOXYCHOLIC ACID
ursodiol
128-13-2
Actigall
UDCA
Ursodesoxycholic acid
Urso Forte
Deursil
3alpha,7beta-Dihydroxy-5beta-cholan-24-oic acid
Acido ursodeoxicolico
Urso 250
Ursonorm
Acidum ursodeoxycholicum
(3alpha,5beta,7beta)-3,7-dihydroxycholan-24-oic acid
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
CHEBI:9907
acide ursodeoxycholique
DTXSID6023731
724L30Y2QR
NSC-683769
Ursacholic Acid
Deoxyursocholic Acid
Cholan-24-oic acid, 3,7-dihydroxy-, (3alpha,5beta,7beta)-
Cholan-24-oic acid, 3,7-dihydroxy-, (3-alpha,5-beta,7-beta)-
3 alpha,7 beta Dihydroxy 5 beta cholan 24 oic Acid
Acid, Ursacholic
Acid, Deoxyursocholic
Acid, Ursodeoxycholic
Ursodeoxycholate, Sodium
3 alpha,7 beta-Dihydroxy-5 beta-cholan-24-oic Acid
Cholurso
Usodiol
NSC657950
NSC683769
(4R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta(a)phenanthren-17-yl)pentanoic acid
Ursodiol 200 mg
Ursodiol 400 mg
Reltone 200 mg
Reltone 400 mg
URUSA
acido ursodesossicolico
acidum ursodesoxycholicum
RefChem:56193
DTXCID003731
Ursodeoxycholic Acid (Ursodiol)
A05AA02
204-879-3
ursodeoxycholate
Ursofalk
Ursolvan
UrSO
Delursan
Destolit
Ursochol
Cholit-ursan
Litursol
Solutrat
Ursobilin
Ursodamor
Arsacol
Lyeton
Ursacol
Urso DS
Ursosan
3-alpha,7-beta-Dioxycholanic acid
Ursocholic acid, deoxy-
Ursodeoxycholicacid
3-alpha,7-beta-Dihydroxycholanic acid
MFCD00003680
3-alpha,7-beta-Dihydroxy-5-beta-cholanoic acid
NSC 683769
Peptarom
Ursodeoxycholic acid [INN]
CHEMBL1551
MLS000028461
Ursodiol [USAN]
Antigall
SMR000058403
Urosiol
Cholan-24-oic acid, 3,7-dihydroxy-, (3.alpha.,5.beta.,7.beta.)-
7-beta-Hydroxylithocholic acid
Ursodexycholic Acid
Acido ursodeossicolico [Italian]
Acido ursodeossicolico
Acido ursodeoxicolico [INN-Spanish]
Acidum ursodeoxycholicum [INN-Latin]
Acide ursodesoxycholique
Acide ursodesoxycholique [INN-French]
7beta-Hydroxylithocholic acid
Actigall (TN)
Ursodiol (USP)
CCRIS 5502
Urso (TN)
SR-01000737091
Ursodiol [USAN:USP]
IU5
EINECS 204-879-3
NSC 657950
5beta-Cholanic Acid-3alpha,7beta-diol
BRN 3219888
Ursodexycholate
Paptarom
Udiliv
Ursodesoxycholic acid (UDCA)
Desol
Urdes
UNII-724L30Y2QR
Urosdesoxycholate
5beta-Cholan-24-oic acid-3alpha,7beta-diol
17-beta-(1-Methyl-3-carboxypropyl)etiocholane-3-alpha,7-beta-diol
Ursodeoxycholoc acid
Urosdesoxycholic acid
3alpha,7beta-Dihydroxy-5beta-cholanic acid
URSODIOL [MI]
Ursodiol (Actigal Urso)
URSODIOL [VANDF]
Prestwick0_000958
Prestwick1_000958
Prestwick2_000958
Prestwick3_000958
U0030
7A-Hydroxylithocholic acid
URSODIOL [USP-RS]
EC 204-879-3
SCHEMBL27200
BSPBio_000956
4-10-00-01604 (Beilstein Handbook Reference)
cid_31401
MLS001066373
MLS002548885
SPBio_003105
Ursodeoxycholic acid, >=99%
URSODIOL [ORANGE BOOK]
BPBio1_001052
GTPL7104
7.beta.-Hydroxylithocholic acid
5-beta-Cholan-24-oic acid, 3-alpha,7-beta-dihydroxy-
URSODIOL [USP MONOGRAPH]
BDBM53721
(3alpha,5beta,7beta,8xi)-3,7-dihydroxycholan-24-oic acid
GLXC-06706
HMS1570P18
HMS2097P18
HMS2233L14
HMS3259A13
HMS3714P18
Ursodeoxycholic acid (JP18/INN)
URSODEOXYCHOLIC ACID [JAN]
3alpha,7beta-dihydroxycholanic acid
MSK10386
3a,7b-dihydroxy-5b-cholan-24-oate
HB4645
LMST04010033
s1643
URSODEOXYCHOLIC ACID [MART.]
URSODEOXYCHOLIC ACID [WHO-DD]
5A-Cholan-24-oic acid-3A,7A-diol
AKOS015955898
CCG-220958
CS-1932
DB01586
FU09676
KS-5243
NC00487
SMP2_000012
3.alpha.,7.beta.-Dihydroxycholanic acid
3A,7A-Dihydroxy-5A-holan-24-oic acid
3a,7b-dihydroxy-5b-cholan-24-oic acid
NCGC00179363-01
NCGC00179363-12
(R)-4-((3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)pentanoic acid
AC-18919
CAS#128-13-2
CPD000058403
HY-13771
NCI60_028904
URSODEOXYCHOLIC ACID [EP IMPURITY]
URSODEOXYCHOLIC ACID [EP MONOGRAPH]
AB00513977
NS00003715
(3a,5b,7b)-3,7-dihydroxy-cholan-24-oate
3alpha, 7beta-dihydroxy-5beta-cholanoic acid
C07880
D00734
EN300-373707
(3a,5b,7b)-3,7-dihydroxy-cholan-24-oic acid
AB00513977-09
AB00513977_10
F095820
Q241374
3.alpha.,7.beta.-Dihydroxy-5.beta.-cholanic acid
SR-01000737091-3
SR-01000737091-4
BRD-K15697815-001-15-4
BRD-K15697815-001-16-2
UDCA;Ursodiol;3a,7b-Dihydroxy-5b-cholan-24-oic acid
3.alpha.,7.beta.-Dihydroxy-5.beta.-cholan-24-oic acid
Z2588039022
3.ALPHA.,7.BETA.-DIHYDROXY-5B-CHOLAN-24-OIC ACID
5.beta.-Cholan-24-oic acid, 3.alpha.,7.beta.-dihydroxy-
Ursodiol, United States Pharmacopeia (USP) Reference Standard
Ursodeoxycholic acid, British Pharmacopoeia (BP) Reference Standard
Ursodeoxycholic acid, European Pharmacopoeia (EP) Reference Standard
17.beta.-(1-Methyl-3-carboxypropyl)etiocholane-3.alpha.,7.beta.-diol
3,7-Dihydroxycholan-24-oic acid-, (3.alpha.,5.beta.,7.beta.)- #
Ursodeoxycholic acid, 500 mug/mL in methanol, certified reference material
Ursodiol, Pharmaceutical Secondary Standard; Certified Reference Material
Ursodeoxycholic acid for system suitability, European Pharmacopoeia (EP) Reference Standard
(4R)-4-[(1R,3aS,3bR,4S,5aS,7R,9aS,9bS,11aR)-4,7-dihydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]pentanoic acid
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-10,13-dimethyl-3,7-bis(oxidanyl)-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoic acid
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]pentanoicacid
(4R)-4-[(3R,5S,7S,8R,9S,10S,13R,14S,17R)-3,7-dihydroxy-10,13-dimethyl-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl]valeric acid
108609-27-4