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Bacampicillin-hydrochloride

Bacampicillin-hydrochloride structure

CAS No:
37661-08-8
Formula:
C21H27N3O7S.ClH
Chemical Name:
Bacampicillin-hydrochloride
Synonyms:
4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-2-amino-2-phenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester,hydrochloride (1:1),(2S,5R,6R)-;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-[2α,5α,6β(S*)]]-;4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid,6-[[(2R)-aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-,1-[(ethoxycarbonyl)oxy]ethyl ester,monohydrochloride,(2S,5R,6R)-;Bacampicillin-hydrochloride;Becampicillin hydrochloride;Penglobe;Bacampicine;Bacacil;Spectrobid;Ambacamp;Ambaxin
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

Bacampicillin hydrochloride is a penicillin antibiotic, is a prodrug of ampicillin with improved oral bioavailability.

Bacampicillin Hydrochloride is the hydrochloride salt of bacampicillin, a prodrug of ampicillin, a broad-spectrum, semisynthetic, beta-lactam aminopenicillin antibiotic with bactericidal activity. Bacampicillin is hydrolyzed in vivo by esterases to its active metabolite ampicillin. Ampicillin binds to and inactivates penicillin-binding proteins (PBP) located on the inner membrane of the bacterial cell wall. Inactivation of PBPs interferes with the cross-linkage of peptidoglycan chains necessary for bacterial cell wall strength and rigidity. This interrupts bacterial cell wall synthesis and results in the weakening of the bacterial cell wall and causes cell lysis.

Bacampicillin-hydrochloride Basic Attributes

Molecular Weight：

501.98

Exact Mass：

501.13400

EC Number：

253-580-4

DSSTox ID：

DTXSID0045466

NCI Thesaurus Code：

C65246

Characteristics

PSA：

163

XLogP3：

3.12690

Melting Point：

171-176 °C (decomp)

Boiling Point：

695.4ºC at 760 mmHg

Flash Point：

374.3ºC

Toxicity：

Intravenous-rat LD50: 176 mg/kg; peritoneal-mouse LD50; 176 mg/kg

Flammability characteristics：

Combustible; burning produces fumes of toxic nitrogen oxides, sulfur oxides and hydrogen chloride

Specific rotation：

D20 +161.5°

Collision Cross Section：

199 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|220.8 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

Transport codes：

NONH for all modes of transport

Storage features：

Ventilated, low temperature and dry; stored separately from food materials in warehouse

Toxicity

Toxicity class：

highly toxic

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

bacampicillin

Bacampicillin-hydrochloride Use and Manufacturing

Uses

Bacampicillin is a penicillin class of antibiotic. Bacampicillin is a prodrug of ampicillin (A634300) with improved oral bioavailability.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

Computed Properties

Molecular Weight:502.0
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:9
Rotatable Bond Count:10
Exact Mass:501.1336491
Monoisotopic Mass:501.1336491
Topological Polar Surface Area:163
Heavy Atom Count:33
Complexity:756
Defined Atom Stereocenter Count:4
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:2
Compound Is Canonicalized:Yes

Drug Function and Efficacy

Bacampicillin is ampicillin methyl amyl ester, which has no antibacterial activity in vitro. During in vivo absorption, it is hydrolyzed into ampicillin by nonspecific esterases in the intestinal wall to exert its antibacterial effect. Ampicillin sodium is a broad-spectrum semi-synthetic penicillin. It is effective against a variety of Gram-positive and Gram-negative bacteria and exerts its bactericidal effect by inhibiting bacterial cell wall synthesis.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Bacampicillin Hydrochloride Tablets
Ingredients	Bacampicillin hydrochloride
Indication	1. Probenecid, aspirin, indomethacin, phenylbutazone, and sulfonamides can reduce the excretion of this product in the renal tubules, thereby increasing the blood concentration of this product, prolonging the blood elimination half-life (t1/2beta;), and possibly increasing toxicity. 2. When this product is used in combination with allopurinol, the incidence of rash increases significantly, so it should be avoided. 3. This product should not be used in combination with acetaldehyde dehydrogenase inhibitors such as disulfiram. 4. When this product is used in combination with chloramphenicol for bacterial meningitis, the incidence of long-term sequelae is higher than when either is used alone. 5. This product can stimulate estrogen metabolism or reduce its enterohepatic circulation, thereby reducing the effectiveness of oral contraceptives. 6. Chloramphenicol, erythromycin, tetracyclines, sulfonamides and other antibacterial drugs can interfere with the bactericidal activity of this product, so it should not be used in combination with this product, especially in the treatment of meningitis or severe infections that urgently require bactericidal drugs. 7. This product can enhance the effect of warfarin.
Specifications	0.4g (calculated as C21H27N3O7S.HCL)
Manufacturer	Heilongjiang Fuhe Pharmaceutical Group Co., Ltd.

Bacampicillin Hydrochloride Tablets
Ingredients	The main component of this product is bacampicillin hydrochloride. Its chemical name is 1-ethoxycarbonylethoxy 6-〔D(-)-2-amino-2-phenylacetylamino〕penicillane hydrochloride.
Indication	1. Probenecid, aspirin, indomethacin, phenylbutazone, and sulfonamides can reduce the excretion of this product in the renal tubules, thereby increasing the blood concentration of this product, prolonging the blood elimination half-life (t1/2beta;), and possibly increasing toxicity. 2. When this product is used in combination with allopurinol, the incidence of rash increases significantly, so it should be avoided. 3. This product should not be used in combination with acetaldehyde dehydrogenase inhibitors such as disulfiram. 4. When this product is used in combination with chloramphenicol for bacterial meningitis, the incidence of long-term sequelae is higher than when either is used alone. 5. This product can stimulate estrogen metabolism or reduce its enterohepatic circulation, thereby reducing the effectiveness of oral contraceptives. 6. Chloramphenicol, erythromycin, tetracyclines, sulfonamides and other antibacterial drugs can interfere with the bactericidal activity of this product, so it should not be used in combination with this product, especially in the treatment of meningitis or severe infections that urgently require bactericidal drugs. 7. This product can enhance the effect of warfarin.
Specifications	400mg/tablet
Manufacturer	Simcere Pharmaceutical Co., Ltd.

Registered Holders

FRESENIUS KABI IPSUM S.R.L.

European Union
Active
ASTRA LAKEMEDEL AB

United States
Inactive
Kyongbo Pharmaceutical Co., Ltd.

European Union
Inactive

See More Registered Holders

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Guide of Bacampicillin-hydrochloride

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Drug Function and Efficacy
Related Drugs
Registered Holders
Latest News
Learn More Other Chemicals

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