Cas no 7177-50-6 (Nafcillin sodium monohydrate)

Nafcillin sodium monohydrate is a semisynthetic penicillinase-resistant penicillin antibiotic, commonly used to treat infections caused by susceptible strains of staphylococci. Its monohydrate form enhances stability and solubility, making it suitable for both intravenous and intramuscular administration. The compound exhibits potent activity against beta-lactamase-producing staphylococci, offering a reliable option for combating resistant bacterial infections. Its narrow spectrum of activity minimizes disruption to normal flora, reducing the risk of secondary infections. The sodium salt formulation ensures improved bioavailability and consistent pharmacokinetics. Nafcillin sodium monohydrate is particularly valued in clinical settings for its efficacy in treating serious infections such as endocarditis, osteomyelitis, and septicemia. Proper storage and handling are essential to maintain its integrity.
Nafcillin sodium monohydrate structure
Nafcillin sodium monohydrate structure
Product Name:Nafcillin sodium monohydrate
CAS No:7177-50-6
MF:C21H23N2NaO6S
MW:454.471895456314
MDL:MFCD01941128
CID:47273
PubChem ID:23704143
Update Time:2025-06-13

Nafcillin sodium monohydrate Chemical and Physical Properties

Names and Identifiers

    • Nafcillin sodium salt monohydrate
    • Sodium (2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
    • Nafcillin (sodium monohydrate)
    • Nafcillin sodium
    • NAFCILLIN SODIUM SALT
    • Sodium Nafcillin Monohydrate
    • Nafcillin monohydrate sodium salt
    • Nafcillin sodium monohydrate
    • NAFCILLINSODIUMSTERILE
    • Unipen (tn)
    • Nafcil
    • Nafcillin sodium hydrate
    • Wy 3277
    • 49G3001BCK
    • DSSTox_RID_80967
    • DSSTox_CID_25570
    • DSSTox_GSID_45570
    • Nafcillin natrium-1-wasser
    • SMR000653476
    • Nafcillin sodium (USP)
    • Naphthicillin
    • nafcillin-sodium
    • Nafcillin sodium [USAN:USP]
    • Monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1
    • BCP17430
    • NAFCILLIN SODIUM [MART.]
    • DTXCID5025570
    • HMS2233C12
    • DTXSID7045570
    • D82069
    • Nallpen
    • Tox21_110767_1
    • CHEMBL1568276
    • Monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate monohydrate
    • CL 8491
    • NAFCILLIN SODIUM MONOHYDRATE [VANDF]
    • HMS3714J07
    • NSC-757108
    • NAFCILLIN SODIUM SALT MONOHYDRATE [MI]
    • NAFCILLIN SODIUM [ORANGE BOOK]
    • 6-(2-Ethoxy-1-naphthamido)penicillin monohydrate
    • Tox21_110767
    • CCG-220843
    • Nafcillin sodium microg/mL in Acetonitrile
    • Q27122988
    • AC-8800
    • HMS1570J07
    • NCGC00017070-01
    • (2S,5R,6R)-6-[[(2-Ethoxy-1-naphthalenyl)carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid sodium salt
    • NAFCILLIN SODIUM [USP-RS]
    • HMS2097J07
    • Nafcillin sodium [USAN]
    • 4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2-ETHOXY-1-NAPHTHALENYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, MONOSODIUM SALT, MONOHYDRATE, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.))
    • monohydrate of sodium salt of 6-(2-ethoxy-1-naphthamido)penicillanic acid
    • NAFCILLIN SODIUM [VANDF]
    • NCGC00273482-01
    • CAS-7177-50-6
    • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, monohydrate, (2S-(2alpha,5alpha,6beta))-
    • 985-16-0 (anhydrous)
    • HY-B0555A
    • Unipen
    • Monosodium (2S,5R,6R)-6-(2-ethoxy-1-naphthamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate monohydrate
    • MFCD01941128
    • NAFCILLIN SODIUM [USP MONOGRAPH]
    • Nafcillin sodium salt anhydrous
    • sodium (2S,5R,6R)-6-{[(2-ethoxynaphthalen-1-yl)carbonyl]amino}-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrate
    • NAFCILLIN SODIUM MONOHYDRATE [WHO-DD]
    • sodium 6beta-[(2-ethoxy-1-naphthoyl)amino]-2,2-dimethylpenam-3alpha-carboxylate hydrate
    • 7177-50-6
    • UNII-49G3001BCK
    • AKOS025402388
    • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((2-ethoxy-1-naphthalenyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, monosodium salt, monohydrate, (2S-(2alpha,5alpha,6beta))
    • D00928
    • 147-52-4 (free acid)
    • 4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-(((2-ETHOXY-1-NAPHTHALENYL)CARBONYL)AMINO)-3,3-DIMETHYL-7-OXO-, MONOSODIUM SALT, MONOHYDRATE, (2S,5R,6R)-
    • s4042
    • Nafcillin sodium monohydrate 100 microg/mL in Acetonitrile
    • SCHEMBL65687
    • NAFCILLIN SODIUM MONOHYDRATE [MART.]
    • CHEBI:51919
    • CCG-269279
    • sodium;(2S,5R,6R)-6-[(2-ethoxynaphthalene-1-carbonyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrate
    • MLS002222166
    • Nafcillin sodium salt monohydrat
    • WY-3277
    • MLS001077264
    • NSC 757108
    • 1ST5640A
    • DA-75972
    • MDL: MFCD01941128
    • Inchi: 1S/C21H22N2O5S.Na.H2O/c1-4-28-13-10-9-11-7-5-6-8-12(11)14(13)17(24)22-15-18(25)23-16(20(26)27)21(2,3)29-19(15)23;;/h5-10,15-16,19H,4H2,1-3H3,(H,22,24)(H,26,27);;1H2/q;+1;/p-1/t15-,16+,19-;;/m1../s1
    • InChI Key: OCXSDHJRMYFTMA-KMFBOIRUSA-M
    • SMILES: S1C(C)(C)[C@H](C(=O)[O-])N2C([C@H]([C@@H]12)NC(C1=C(C=CC2C=CC=CC1=2)OCC)=O)=O.[Na+].O

Computed Properties

  • Exact Mass: 454.11700
  • Monoisotopic Mass: 436.107
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 7
  • Heavy Atom Count: 31
  • Rotatable Bond Count: 5
  • Complexity: 705
  • Covalently-Bonded Unit Count: 3
  • Defined Atom Stereocenter Count: 3
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • XLogP3: Not available
  • Topological Polar Surface Area: 125

Experimental Properties

  • Color/Form: Not available
  • Density: 1.4200
  • Melting Point: Not available
  • Boiling Point: 714.1°C at 760 mmHg
  • Flash Point: 385.7 °C
  • Solubility: H2O: soluble50mg/mL
  • PSA: 133.30000
  • LogP: 1.41360
  • Solubility: Not available
  • Vapor Pressure: Not available

Nafcillin sodium monohydrate Security Information

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Nafcillin sodium monohydrate Related Literature

Additional information on Nafcillin sodium monohydrate

Introduction to Nafcillin Sodium Monohydrate (CAS No. 7177-50-6)

Nafcillin Sodium Monohydrate, with the chemical name 6-(3-amino-4-hydroxyphenyl)-1,4-dimethyl-4-oxo-1,4-thiazetidin-3-carboxylic acid sodium salt monohydrate, is a well-established antibiotic belonging to the penicillin class. Its CAS number, 7177-50-6, uniquely identifies it in the chemical and pharmaceutical industries. This compound has been widely utilized in the treatment of bacterial infections, particularly those caused by penicillinase-producing staphylococci. The monohydrate form indicates that the compound crystallizes with one molecule of water, which can influence its solubility and stability.

The development of Nafcillin Sodium Monohydrate was a significant milestone in antibiotic therapy, especially during the latter half of the 20th century. Its ability to resist degradation by beta-lactamase enzymes produced by certain bacteria made it a crucial weapon against resistant strains. Over the years, extensive research has been conducted to optimize its pharmacokinetic properties and explore novel therapeutic applications.

In recent years, advancements in microbiology and pharmacology have led to a deeper understanding of how Nafcillin Sodium Monohydrate interacts with bacterial cell walls. Studies have revealed that its mechanism of action involves inhibiting the synthesis of peptidoglycan, a critical component of bacterial cell walls, thereby leading to cell lysis and death. This mechanism has been further refined through structural modifications aimed at enhancing efficacy and reducing side effects.

One of the most compelling aspects of Nafcillin Sodium Monohydrate is its role in treating methicillin-resistant Staphylococcus aureus (MRSA) infections. While MRSA has become increasingly resistant to many antibiotics, Nafcillin Sodium Monohydrate remains effective against susceptible strains. Recent clinical trials have demonstrated its efficacy when used in combination with other antibiotics, providing a promising strategy for managing multidrug-resistant infections.

The pharmacokinetic profile of Nafcillin Sodium Monohydrate has been extensively studied to ensure optimal dosing regimens. Its relatively short half-life necessitates frequent administration, which can be challenging for patients. However, novel formulations such as extended-release versions are being developed to improve patient compliance and convenience. These formulations aim to maintain therapeutic levels in the bloodstream for longer periods, reducing the frequency of dosing while maintaining efficacy.

From a chemical perspective, the structure of Nafcillin Sodium Monohydrate (CAS No. 7177-50-6) is characterized by a beta-lactam ring fused with a thiazetidine ring. This unique structural motif contributes to its potent antibacterial activity. The sodium salt form enhances solubility, making it more suitable for intravenous administration. The monohydrate designation indicates the presence of one water molecule in its crystal lattice, which can affect its physical properties such as melting point and solubility.

Recent research has also explored the potential applications of Nafcillin Sodium Monohydrate in veterinary medicine. Its effectiveness against Gram-positive bacteria makes it a viable option for treating infections in livestock and companion animals. Studies have shown that it can be used to manage infections caused by Staphylococcus aureus and other resistant pathogens in animals, contributing to improved animal health and welfare.

The safety profile of Nafcillin Sodium Monohydrate has been well-documented through decades of clinical use. Common side effects include mild gastrointestinal disturbances such as nausea and diarrhea. More serious adverse effects are rare but may include allergic reactions ranging from mild rashes to anaphylaxis. Patients with a history of penicillin allergy should use this medication with caution under medical supervision.

Manufacturing processes for Nafcillin Sodium Monohydrate have evolved significantly over time to ensure high purity and consistency. Modern synthetic routes involve multi-step organic reactions starting from readily available precursors such as phenylacetic acid derivatives. Advances in biocatalysis have also enabled more efficient production methods, reducing environmental impact while maintaining high yields.

The future prospects for Nafcillin Sodium Monohydrate are promising, particularly in light of rising antibiotic resistance rates worldwide. Ongoing research aims to develop new derivatives with enhanced properties such as broader spectrum activity or improved pharmacokinetics. Additionally, combination therapies involving Nafcillin Sodium Monohydrate with other antibiotics or non-pharmacological agents are being explored to combat resistant strains more effectively.

In conclusion,Nafcillin Sodium Monohydrate (CAS No. 7177-50-6) remains a cornerstone in antibiotic therapy despite challenges posed by increasing bacterial resistance. Its unique structure, potent activity against resistant pathogens, and well-established safety profile make it an invaluable tool in modern medicine. Continued research and development efforts will further enhance its therapeutic potential and ensure its relevance in addressing global health challenges.

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Amadis Chemical Company Limited
(CAS:7177-50-6)Nafcillin sodium monohydrate
A1204833
Purity:99%/99%/99%
Quantity:5g/10g/25g
Price ($):191.0/318.0/665.0
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Tiancheng Chemical (Jiangsu) Co., Ltd
(CAS:7177-50-6)Nafcillin sodium salt monohydrate
LE12842
Purity:99%
Quantity:25KG,200KG,1000KG
Price ($):Inquiry
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