Cas no 37661-08-8 (Bacampicillin hydrochloride)

Bacampicillin hydrochloride is a prodrug of ampicillin, designed to enhance oral bioavailability through improved absorption in the gastrointestinal tract. As a semisynthetic beta-lactam antibiotic, it is hydrolyzed in vivo to release active ampicillin, providing broad-spectrum antibacterial activity against Gram-positive and Gram-negative organisms. The hydrochloride salt form ensures stability and solubility, facilitating formulation. Key advantages include higher plasma concentrations compared to ampicillin alone, reduced dosing frequency, and minimized gastrointestinal irritation. Its esterified structure allows for efficient transport across biological membranes, making it particularly useful in treating respiratory, urinary, and soft tissue infections. Suitable for clinical and research applications, it maintains the efficacy of ampicillin with optimized pharmacokinetics.
Bacampicillin hydrochloride structure
Bacampicillin hydrochloride structure
Product Name:Bacampicillin hydrochloride
CAS No:37661-08-8
MF:C21H28ClN3O7S
MW:501.980923652649
MDL:MFCD11215256
CID:306338
PubChem ID:441398
Update Time:2025-07-04

Bacampicillin hydrochloride Chemical and Physical Properties

Names and Identifiers

    • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester, hydrochloride (1:1), (2S,5R,6R)-
    • Bacampicillin Hydrochloride
    • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3...
    • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylicacid, 6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarb
    • Bacampicillin (hydrochloride)
    • BACAMPICILLIN HYDROCHLORIDE USP STANDARD
    • ambacamp
    • ambaxin
    • bacacil
    • Bacampicillin HCl
    • Bacampicine
    • bapc
    • becampicillin
    • penglobe
    • Pengood
    • Spectrobid
    • UNII-PM034U953T
    • Bacampicillin hydrochloride (JP17/USAN)
    • D00927
    • 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydrochloride
    • IWVTXAGTHUECPN-ANBBSHPLSA-N
    • BACAMPICILLIN HYDROCHLORIDE [VANDF]
    • 4-THIA-1-AZABICYCLO(3.2.0)HEPTANE-2-CARBOXYLIC ACID, 6-((AMINOPHENYLACETYL)AMINO)-3,3-DIMETHYL-7-OXO-, 1-((ETHOXYCARBONYL)OXY)ETHYL ESTER, MONOHYDROCHLORIDE, (2S-(2.ALPHA.,5.ALPHA.,6.BETA.(S*)))-
    • CHEMBL1200965
    • NSC 758228
    • 1-Ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate;hydron;chloride
    • 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenyl-acetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
    • BACAMPICILLIN HYDROCHLORIDE (EP MONOGRAPH)
    • CHEBI:2969
    • (2S,5R,6R)-6-[(R)-(2-Amino-2-phenylacetamido)]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid ester with ethyl 1-hydroxyethyl carbonate, monohydrochloride
    • MLS002153801
    • HY-B1149A
    • AKOS016014246
    • SCHEMBL124593
    • MS-29322
    • Spectrobid (TN)
    • Velbacil
    • BACAMPICILLIN HYDROCHLORIDE [MART.]
    • CCG-220416
    • Bacampicillin-hydrochloride
    • BACAMPICILLIN HYDROCHLORIDE [JAN]
    • Becampicillin hydrochloride
    • 1-((Ethoxycarbonyl)oxy)ethyl (2S-(2alpha,5alpha,6beta(S*)))-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate monohydrochloride
    • PM034U953T
    • DTXSID0045466
    • Bacampicillin hydrochloride [USAN:USP:JAN]
    • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl ester, monohydrochloride, (2S-(2alpha,5alpha,6beta(S*)))-
    • BACAMPICILLIN HYDROCHLORIDE [USP IMPURITY]
    • BACAMPICILLIN HYDROCHLORIDE (USP IMPURITY)
    • SMR001233177
    • F85245
    • 37661-08-8 (HCl)
    • Prestwick_776
    • BACAMPICILLIN HYDROCHLORIDE [ORANGE BOOK]
    • CS-4754
    • (2S,5R,6R)-6-((R)-(2-Amino-2-phenylacetamido))-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid ester with ethyl 1-hydroxyethyl carbonate, monohydrochloride
    • (2S,5R,6R)-6-[[(2R)-2-amino-1-oxo-2-phenylethyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 1-ethoxycarbonyloxyethyl ester hydrochloride
    • BACAMPICILLIN HYDROCHLORIDE (MART.)
    • 1-((ethoxycarbonyl)oxy)ethyl 6beta-((2R)-2-amino-2-phenylacetamido)-2,2-dimethylpenam-3alpha-carboxylate hydrochloride
    • NSC-758228
    • Bacampicillin hydrochoride
    • Q27105902
    • BACAMPICILLIN HYDROCHLORIDE [EP MONOGRAPH]
    • 4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-((aminophenylacetyl)amino)-3,3-dimethyl-7-oxo-, 1-((ethoxycarbonyl)oxy)ethyl ester, hydrochloride
    • CAS-37661-08-8
    • Tox21_110640_1
    • DTXCID8025466
    • BACAMPICILLIN HYDROCHLORIDE [USAN]
    • C08123
    • BACAMPICILLIN HYDROCHLORIDE [MI]
    • EINECS 253-580-4
    • A823813
    • SureCN721373
    • HMS1569C14
    • BACAMPICILLIN HYDROCHLORIDE [WHO-DD]
    • 1-Ethoxycarbonyloxyethyl (2S,5R,6R)-6-((2R)-2-amino-2-phenylacetylamino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate monohydrochloride
    • 1-ethoxycarbonyloxyethyl (2S,5R,6R)-6-[[(2R)-2-azanyl-2-phenyl-ethanoyl]amino]-3,3-dimethyl-7-oxidanylidene-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
    • NCGC00016837-01
    • Bacampicillin hydrochloride (USAN:USP:JAN)
    • NCGC00179582-03
    • Tox21_110640
    • 37661-08-8
    • BACAMPICILLINHYDROCHLORIDE
    • DA-61469
    • Bacampicillin hydrochloride; (1RS)-1-[(Ethoxycarbonyl)oxy]ethyl (2S,5R,6R)-6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride
    • Bacampicillin hydrochloride
    • MDL： MFCD11215256
    • Inchi： 1S/C21H27N3O7S.ClH/c1-5-29-20(28)31-11(2)30-19(27)15-21(3,4)32-18-14(17(26)24(15)18)23-16(25)13(22)12-9-7-6-8-10-12;/h6-11,13-15,18H,5,22H2,1-4H3,(H,23,25);1H/t11?,13-,14-,15+,18-;/m1./s1
    • InChI Key： IWVTXAGTHUECPN-ANBBSHPLSA-N
    • SMILES： Cl.S1C(C)(C)[C@H](C(=O)OC(C)OC(=O)OCC)N2C([C@H]([C@@H]12)NC([C@@H](C1C=CC=CC=1)N)=O)=O

Computed Properties

  • Exact Mass: 501.13400
  • Monoisotopic Mass: 501.134
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 2
  • Hydrogen Bond Acceptor Count: 10
  • Heavy Atom Count: 33
  • Rotatable Bond Count: 11
  • Complexity: 756
  • Covalently-Bonded Unit Count: 2
  • Defined Atom Stereocenter Count: 4
  • Undefined Atom Stereocenter Count : 1
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Topological Polar Surface Area: 163A^2

Experimental Properties

  • Melting Point: 171-176° (dec)
  • Boiling Point: 695.4°C at 760 mmHg
  • Flash Point: 374.3°C
  • PSA: 162.56000
  • LogP: 3.12690
  • Specific Rotation: D20 +161.5°

Bacampicillin hydrochloride Security Information

  • Toxicity：LD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga)
  • Storage Condition：Powder -20°C 3 years ? 4°C 2 years In solvent -80°C 6 months ? -20°C 1 month

Bacampicillin hydrochloride Pricemore >>

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Bacampicillin hydrochloride Related Literature

Related Categories

Additional information on Bacampicillin hydrochloride

Introduction to Bacampicillin Hydrochloride (CAS No. 37661-08-8) and Its Emerging Applications in Modern Medicine

Bacampicillin hydrochloride, with the chemical identifier CAS No. 37661-08-8, is a semisynthetic penicillin derivative that has garnered significant attention in the field of pharmaceutical chemistry and microbiology. As a member of the beta-lactam class of antibiotics, it exhibits potent activity against a broad spectrum of Gram-positive and Gram-negative bacteria, making it a valuable compound in the armamentarium of modern antimicrobial therapy. The unique structural features of Bacampicillin hydrochloride, particularly its extended side chain, contribute to its enhanced stability and efficacy compared to earlier generations of penicillins.

The development of Bacampicillin hydrochloride was driven by the need for more effective and durable antibiotics to combat increasingly resistant bacterial strains. Its mechanism of action involves inhibiting bacterial cell wall synthesis by binding to penicillin-binding proteins (PBPs), thereby disrupting the integrity of the bacterial cell wall and leading to cell lysis. This mechanism has been further refined through structural modifications that improve pharmacokinetic properties, such as bioavailability and tissue penetration.

Recent advancements in medicinal chemistry have highlighted the potential of Bacampicillin hydrochloride as a lead compound for novel therapeutic strategies. For instance, studies have demonstrated its efficacy in treating multidrug-resistant infections, where traditional antibiotics have failed. The compound’s ability to maintain activity against beta-lactamase-producing bacteria has made it a promising candidate for combination therapies, particularly when paired with beta-lactamase inhibitors.

One of the most compelling aspects of Bacampicillin hydrochloride is its potential in veterinary medicine. Research indicates that it exhibits favorable pharmacokinetic profiles in animal models, suggesting its suitability for treating bacterial infections in livestock and companion animals. This has opened up new avenues for agricultural applications, where efficient infection control is critical for maintaining animal health and productivity.

The pharmacological profile of Bacampicillin hydrochloride has also been explored in clinical trials for human infections. Its extended half-life allows for less frequent dosing, improving patient compliance and convenience. Additionally, its low toxicity profile makes it an attractive option for long-term treatment regimens without significant adverse effects.

In recent years, the use of computational modeling and high-throughput screening has accelerated the discovery of new derivatives of Bacampicillin hydrochloride. These approaches have identified modified analogs with enhanced antibacterial activity and reduced resistance development. Such innovations are crucial in addressing the global challenge of antibiotic resistance, where novel compounds are needed to stay ahead of evolving bacterial defenses.

The synthesis of Bacampicillin hydrochloride involves multi-step organic reactions, starting from commercially available precursors such as 6-amino-penicillanic acid. The process typically includes steps like side chain attachment, salt formation, and purification to obtain high-purity material suitable for pharmaceutical use. Advances in synthetic methodologies have improved yield and efficiency, making large-scale production more feasible.

Regulatory considerations play a critical role in the approval and commercialization of Bacampicillin hydrochloride. Rigorous testing is required to demonstrate safety and efficacy across various populations, including pediatrics and geriatrics. Regulatory agencies such as the FDA and EMA have stringent guidelines that must be met before a drug can be marketed widely.

The environmental impact of antibiotic use is another area where Bacampicillin hydrochloride has been scrutinized. Efforts are underway to develop environmentally sustainable production methods that minimize waste and reduce ecological footprints. Green chemistry principles are being applied to optimize synthetic routes, ensuring that pharmaceutical manufacturing aligns with environmental stewardship goals.

The future prospects for Bacampicillin hydrochloride are bright, with ongoing research exploring its potential in novel therapeutic applications beyond traditional antimicrobial uses. For example, its structural framework may inspire new classes of bioactive molecules with applications in anti-inflammatory or immunomodulatory therapies.

In conclusion, Bacampicillin hydrochloride (CAS No. 37661-08-8) represents a significant advancement in antibiotic development, offering enhanced efficacy against resistant bacteria while maintaining a favorable safety profile. Its versatility across human and veterinary medicine underscores its importance as a cornerstone compound in modern therapeutics.

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