Cas no 148553-51-9 ((R)-Pregabalin)

(R)-Pregabalin is the biologically active enantiomer of pregabalin, a gamma-aminobutyric acid (GABA) analog. It exhibits high binding affinity for the α2-δ subunit of voltage-gated calcium channels in the central nervous system, modulating neurotransmitter release. This compound is particularly valued for its stereoselective pharmacological activity, offering enhanced efficacy compared to the racemic mixture. (R)-Pregabalin is widely utilized in research and pharmaceutical development due to its well-characterized mechanism of action, consistent purity, and reproducibility. Its applications include studies in neuropathic pain, epilepsy, and anxiety disorders, where its enantiomeric purity ensures precise experimental outcomes. The compound is typically supplied with rigorous analytical validation to meet research and industrial standards.
(R)-Pregabalin structure
(R)-Pregabalin structure
Product Name:(R)-Pregabalin
CAS No:148553-51-9
MF:C8H17NO2
MW:159.2260825634
MDL:MFCD08277235
CID:223972
PubChem ID:125889
Update Time:2025-05-19

(R)-Pregabalin Chemical and Physical Properties

Names and Identifiers

    • Hexanoic acid,3-(aminomethyl)-5-methyl-, (3R)-
    • (R)-Pregabalin
    • 3-isobutyl-GABA
    • ent-Pregabalin
    • HMS1922H16
    • (3R)-3-(Aminomethyl)-5-methylhexanoic acid
    • EOS-60963
    • PD 144550
    • Pregabalin R-Isomer
    • Pregabalin IMpurity V
    • (R)-3-(AMinoMethyl)-5-Methylhexanoic acid
    • Pregabalin Related Compound A Minimum Pack
    • EX-A4191
    • SPECTRUM1505816
    • SBI-0206875.P001
    • CHEMBL167003
    • Pregabalin, (R)-
    • Hexanoic acid, 3-(aminomethyl)-5-methyl-, (3R)-
    • PD-144550
    • Pregabalin(Renantiomer)
    • NCGC00178709-01
    • CCG-40213
    • UNII-81R7ZI0HBG
    • SCHEMBL263450
    • AKOS027425242
    • DTXSID90276292
    • Pregabalin (R enantiomer)
    • HMS2093F10
    • Pharmakon1600-01505816
    • NSC759256
    • BSPBio_002316
    • 148553-51-9
    • 81R7ZI0HBG
    • MDL: MFCD08277235
    • Inchi: 1S/C8H17NO2/c1-6(2)3-7(5-9)4-8(10)11/h6-7H,3-5,9H2,1-2H3,(H,10,11)/t7-/m1/s1
    • InChI Key: AYXYPKUFHZROOJ-SSDOTTSWSA-N
    • SMILES: OC(C[C@H](CN)CC(C)C)=O

Computed Properties

  • Exact Mass: 159.12600
  • Monoisotopic Mass: 159.125928785g/mol
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 3
  • Heavy Atom Count: 11
  • Rotatable Bond Count: 5
  • Complexity: 123
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 1
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • XLogP3: -1.6
  • Topological Polar Surface Area: 63.3?2

Experimental Properties

  • PSA: 63.32000
  • LogP: 1.78240

(R)-Pregabalin Security Information

  • Hazardous Material transportation number:NONH for all modes of transport
  • Storage Condition:2-8°C

(R)-Pregabalin Pricemore >>

Related Categories No. Product Name Cas No. Purity Specification Price update time Inquiry
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O32856-1G
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Advanced ChemBlocks
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Additional information on (R)-Pregabalin

Introduction to (R)-Pregabalin and Its Significance in Modern Medicine

Chemical compounds play a pivotal role in the advancement of pharmaceuticals, particularly in the realm of neurology and pain management. One such compound, (R)-Pregabalin, with the CAS number 148553-51-9, has emerged as a cornerstone in therapeutic interventions. This enantiomer, specifically the (R)-configuration of pregabalin, is widely recognized for its efficacy in treating various neurological disorders and chronic pain conditions.

The molecular structure of (R)-Pregabalin is characterized by its unique stereochemistry, which significantly influences its pharmacological properties. As a derivative of gabapentin, it shares a similar chemical backbone but exhibits enhanced selectivity and potency. The CAS number 148553-51-9 serves as a unique identifier for this specific compound, ensuring precise classification and regulatory compliance in pharmaceutical manufacturing and distribution.

In recent years, (R)-Pregabalin has been extensively studied for its mechanisms of action, particularly its interaction with voltage-gated calcium channels in central nervous system neurons. This interaction modulates neurotransmitter release, thereby alleviating symptoms associated with neuropathic pain and seizures. The compound's ability to bind preferentially to these channels makes it a highly effective therapeutic agent.

Recent clinical trials have highlighted the efficacy of (R)-Pregabalin in managing postherpetic neuralgia, diabetic neuropathy, fibromyalgia, and partial-onset seizures. These studies have demonstrated not only its superior pain relief capabilities but also its improved tolerability compared to older anticonvulsant medications. The (R)-enantiomer's specificity reduces the incidence of side effects, making it a preferred choice for long-term treatment regimens.

The pharmacokinetic profile of (R)-Pregabalin is another area of significant interest. It is rapidly absorbed after oral administration and has a relatively short half-life, necessitating twice-daily dosing regimens for optimal therapeutic effect. This characteristic ensures consistent plasma levels, minimizing inter-individual variability in response. Additionally, its low protein binding allows for easier distribution throughout the body, enhancing its overall efficacy.

Advances in synthetic chemistry have enabled more efficient production methods for (R)-Pregabalin, ensuring high purity and yield. These innovations have not only reduced production costs but also improved accessibility for patients worldwide. The development of chiral resolution techniques has been particularly crucial in isolating the (R)-enantiomer from racemic mixtures, ensuring that formulations are standardized and predictable in their clinical outcomes.

The role of (R)-Pregabalin extends beyond traditional pain management into emerging therapeutic areas. Preliminary research suggests potential benefits in managing mood disorders and sleep disturbances associated with chronic pain syndromes. Its ability to modulate central nervous system activity may offer novel treatment strategies for conditions previously resistant to conventional therapies.

Regulatory agencies worldwide have recognized the significance of (R)-Pregabalin through approvals in numerous indications. Its inclusion in clinical guidelines underscores its established role in modern medicine. As research continues to uncover new applications and refine existing knowledge, the therapeutic landscape for neurological and pain conditions is likely to evolve further with this compound at the forefront.

In conclusion, (R)-Pregabalin, identified by the CAS number 148553-51-9, represents a significant advancement in pharmaceutical intervention for neurological and chronic pain disorders. Its unique stereochemistry, favorable pharmacokinetic profile, and robust clinical evidence position it as a cornerstone therapy in contemporary medical practice. Ongoing research promises to expand its applications further, reinforcing its importance in addressing complex neurological challenges.

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