Cas no 250737-12-3 (6'-epipravastatin)

6'-Epipravastatin is a stereoisomer of pravastatin, a well-known HMG-CoA reductase inhibitor used for cholesterol management. This compound shares structural similarities with pravastatin but exhibits distinct pharmacokinetic and metabolic properties due to its epimeric configuration at the 6' position. It is of interest in pharmaceutical research for its potential to modulate lipid metabolism with possible variations in efficacy, bioavailability, or tissue selectivity compared to pravastatin. Studies suggest it may offer alternative metabolic pathways or reduced drug-drug interactions, making it a candidate for further investigation in statin therapy optimization. Its synthesis and characterization are critical for understanding structure-activity relationships in statin derivatives.
6'-epipravastatin structure
6'-epipravastatin structure
Product Name:6'-epipravastatin
CAS No:250737-12-3
MF:C23H36O7
MW:424.52774810791
CID:1886156
PubChem ID:10071008
Update Time:2025-10-29

6'-epipravastatin Chemical and Physical Properties

Names and Identifiers

    • 6'-epipravastatin
    • N-(3-ACETYLTHIO-2-METHYLPROPANOYL)GLYCINE TERT-BUTYL ESTER-D5
    • (3R,5R)-3,5-Dihydroxy-7-[(1S,2S,6R,8S,8aR)-6-hydroxy-2-methyl-8-[[(2S)-2-methylbutanoyl]oxy]-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]heptanoic acid
    • PRAVASTATIN SODIUM IMPURITY, 6'-EPIPRAVASTATIN-[USP IMPURITY]
    • 6-Epi-pravastatin
    • Q27287878
    • (3R,5R)-3,5-Dihydroxy-7-((1S,2S,6R,8S,8aR)-6-hydroxy-2-methyl-8-(((2S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid
    • (3R,5R)-3,5-Dihydroxy-7-((1S,2S,6R,8S,8aR)-6-hydroxy-2-methyl-8-(((S)-2-methylbutanoyl)oxy)-1,2,6,7,8,8a-hexahydronaphthalen-1-yl)heptanoic acid
    • PRAVASTATIN SODIUM IMPURITY, 6'-EPIPRAVASTATIN- [USP IMPURITY]
    • Pravastatin sodium specified impurity A [EP]
    • 1-NAPHTHALENEHEPTANOIC ACID, 1,2,6,7,8,8A-HEXAHYDRO-.BETA.,.DELTA.,6-TRIHYDROXY-2-METHYL-8-((2S)-2-METHYL-1-OXOBUTOXY)-, (.BETA.R,.DELTA.R,1S,2S,6R,8S,8AR)-
    • PRAVASTATIN SODIUM IMPURITY A (EP IMPURITY)
    • (3R,5R)-7-[(1S,2S,6R,8S,8aR)-6-hydroxy-2-methyl-8-[(2S)-2-methylbutanoyl]oxy-1,2,6,7,8,8a-hexahydronaphthalen-1-yl]-3,5-dihydroxyheptanoic acid
    • R76ZW7E32P
    • PRAVASTATIN SODIUM IMPURITY, 6'-EPIPRAVASTATIN-(USP IMPURITY)
    • 1-Naphthaleneheptanoic acid, 1,2,6,7,8,8a-hexahydro-beta,delta,6-trihydroxy-2-methyl-8-((2S)-2-methyl-1-oxobutoxy)-, (betaR,deltaR,1S,2S,6R,8S,8aR)-
    • Pravastatin sodium specified impurity A
    • 250737-12-3
    • PRAVASTATIN SODIUM IMPURITY A [EP IMPURITY]
    • SCHEMBL14430866
    • UNII-R76ZW7E32P
    • CHEMBL3544781
    • Pravastatin sodium impurity, 6'-epipravastatin-(USP)
    • Pravastatin sodium impurity, 6'-epipravastatin-[USP]
    • Pravastatin sodium impurity, 6'-epipravastatin- [USP]
    • Inchi: 1S/C23H36O7/c1-4-13(2)23(29)30-20-11-17(25)9-15-6-5-14(3)19(22(15)20)8-7-16(24)10-18(26)12-21(27)28/h5-6,9,13-14,16-20,22,24-26H,4,7-8,10-12H2,1-3H3,(H,27,28)/t13-,14-,16+,17-,18+,19-,20-,22-/m0/s1
    • InChI Key: TUZYXOIXSAXUGO-PZSHMICQSA-N
    • SMILES: O(C([C@@H](C)CC)=O)[C@H]1C[C@H](C=C2C=C[C@H](C)[C@H](CC[C@H](C[C@H](CC(=O)O)O)O)[C@@H]12)O

Computed Properties

  • Exact Mass: 424.24610348Da
  • Monoisotopic Mass: 424.24610348Da
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 4
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 30
  • Rotatable Bond Count: 11
  • Complexity: 656
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 8
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: 1.6
  • Topological Polar Surface Area: 124?2

6'-epipravastatin Pricemore >>

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Additional information on 6'-epipravastatin

Comprehensive Overview of 6'-Epipravastatin (CAS No. 250737-12-3): Properties, Applications, and Research Insights

6'-Epipravastatin (CAS No. 250737-12-3) is a stereoisomer of the well-known cholesterol-lowering drug pravastatin, which belongs to the class of HMG-CoA reductase inhibitors. This compound has garnered significant attention in pharmaceutical research due to its unique structural properties and potential therapeutic applications. With the growing global focus on cardiovascular health and metabolic disorders, understanding the role of 6'-epipravastatin in drug development and its mechanism of action has become a topic of interest for researchers and healthcare professionals alike.

The chemical structure of 6'-epipravastatin differs from pravastatin by the epimerization at the 6'-position, which may influence its pharmacokinetic and pharmacodynamic properties. Recent studies have explored whether this structural modification enhances its bioavailability, tissue selectivity, or metabolic stability compared to its parent compound. These investigations align with the current trend in drug discovery to optimize existing therapeutics through structural analogs and isomer engineering.

In the context of personalized medicine, researchers are examining how 6'-epipravastatin might offer advantages for specific patient populations. For instance, its potential reduced side effects or improved hepatic targeting could address limitations observed with conventional statins. This aligns with frequently searched queries such as "alternatives to pravastatin" and "next-generation statins with fewer side effects", reflecting patient concerns about statin-associated muscle pain or liver toxicity.

The synthesis of 6'-epipravastatin involves sophisticated stereoselective methods, often employing biocatalysis or asymmetric synthesis techniques. These processes are crucial for ensuring the compound's chiral purity, a critical quality attribute given the stringent regulatory requirements for pharmaceutical intermediates. The compound's role as a reference standard in analytical testing further underscores its importance in quality control laboratories.

Emerging research directions include investigating 6'-epipravastatin's potential pleiotropic effects beyond cholesterol reduction, such as anti-inflammatory properties or endothelial function improvement. These studies respond to growing scientific interest in statins' multifaceted mechanisms, a topic frequently explored in recent literature and conference presentations. The compound's structure-activity relationship continues to be a subject of computational modeling and molecular docking studies.

From a commercial perspective, 6'-epipravastatin represents an important pharmaceutical intermediate in the development of improved statin formulations. Its market relevance connects to broader industry trends toward patent-extended drugs and value-added generics. Analytical methods for 6'-epipravastatin quantification, including HPLC and LC-MS techniques, have been refined to support these applications.

Environmental and green chemistry considerations are increasingly applied to 6'-epipravastatin production processes, addressing concerns about sustainable pharmaceutical manufacturing. This reflects the industry's response to regulatory pressures and consumer demand for eco-friendly drug production methods. The compound's degradation pathways and environmental fate are also subjects of ongoing investigation.

In conclusion, 6'-epipravastatin (CAS No. 250737-12-3) represents a fascinating case study in medicinal chemistry innovation, combining aspects of stereochemistry, drug optimization, and therapeutic advancement. Its continued study contributes valuable insights to the evolving landscape of cardiovascular therapeutics and precision medicine approaches. As research progresses, this compound may yield important discoveries that address current challenges in lipid management and preventive cardiology.

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