ChemicalBook > CAS DataBase List > BACAMPICILLIN HYDROCHLORIDE

BACAMPICILLIN HYDROCHLORIDE

Product Name: BACAMPICILLIN HYDROCHLORIDE
CAS No.: 37661-08-8
Chemical Name: BACAMPICILLIN HYDROCHLORIDE
Synonyms: bapc;bacacil;ambaxin;Pengood;ambacamp;penglobe;Spectrobid;Bacampicine;becampicillin;Bacampicillin HCl
CBNumber: CB3762112
Molecular Formula: C21H28ClN3O7S
Formula Weight: 501.98
MOL File: 37661-08-8.mol

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BACAMPICILLIN HYDROCHLORIDE Property

Melting point:: 171-176° (dec)
alpha: D20 +161.5°
storage temp.: Store at -20°C
solubility: Soluble in water, freely soluble in ethanol (96 per cent), soluble in methylene chloride.
form: Solid
color: Crystals from Me2CO pet ether

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Safety

Toxicity: LD50 in mice (mg/kg): 8529 orally; 176 i.p.; 9475 s.c.; 184 i.v. (Edanaga)

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H317May cause an allergic skin reaction

H334May cause allergy or asthma symptoms or breathing difficulties if inhaled

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P284Wear respiratory protection.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P342+P311IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: B0070000
Product name: Bacampicillin hydrochloride
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: 120 mg
Price: $236
Updated: 2025/07/31

Sigma-Aldrich

Product number: B0070000
Product name: Bacampicillin hydrochloride
Purity: European Pharmacopoeia (EP) Reference Standard
Packaging: b0070000
Price: $220
Updated: 2024/03/01

TRC

Product number: B101500
Product name: Bacampicillin hydrochloride
Packaging: 25mg
Price: $185
Updated: 2021/12/16

TRC

Product number: B101500
Product name: Bacampicillin hydrochloride
Packaging: 50mg
Price: $370
Updated: 2021/12/16

ChemScene

Product number: CS-4754
Product name: Bacampicillin hydrochloride
Purity: 99.61%
Packaging: 10mg
Price: $90
Updated: 2021/12/16

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BACAMPICILLIN HYDROCHLORIDE Chemical Properties,Usage,Production

Description

Bacampicillin was synthesized by Ekstrom¨ et al. of Astra Lakemedel in 1975. It is ¨ more stable against acid than ampicillin and more rapidly absorbed orally; its absorption is less affected by a patient’s most recent meal than is the case for ampicillin. Bacampicillin is hydrolyzed by intestinal esterase after oral administration and then behaves the same as ampicillin. In double-blind comparison studies, bacampicillin was shown to be as effective as ampicillin when administered at half the dose.

Chemical Properties

White or almost white powder or granules, hygroscopic.

Originator

Penglobe,Astra,W. Germany,1977

Uses

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

Definition

ChEBI: The hydrochloride salt of bacampicillin.

Manufacturing Process

1'-Ethoxycarbonyloxyethyl 6-(D-α-azidophenylacetamido)penicillinate (98 g) was prepared from sodium 6-(D-α-azidophenylacetamido)penicillinate (397 g, 1 mol), α-chlorodiethylcarbonate (458 g, 3 mols) and sodium bicarbonate (504 g, 6 mols). The product showed strong IR absorption at 2090 cm-1 and 1780-1750 cm-1 showing the presence of azido group and β-lactam and ester carbonyls.
It was dissolved in ethyl acetate (700 ml) and hydrogenated at ambient conditions over a palladium (5%)on carbon catalyst (18 g). The catalyst was removed by filtration and washed with ethyl acetate. The combined filtrates were extracted with water at pH 2.5 by addition of dilute hydrochloric acid. Lyophilization of the aqueous phase gave the hydrochloride of 1'- ethoxycarbonyloxyethyl 6-(D-α-aminophenylacetarnido)penicillinate (94 g), MP 171°-176°C.

brand name

Spectrobid (Pfizer).

Therapeutic Function

Antibacterial

Clinical Use

Bacampicillin hydrochloride (Spectrobid) is the hydrochloridesalt of the 1-ethoxycarbonyloxyethyl ester of ampicillin.It is a prodrug of ampicillin with no antibacterial activity.After oral absorption, bacampicillin is hydrolyzed rapidly byesterases in the plasma to form ampicillin.
Oral absorption of bacampicillin is more rapid and completethan that of ampicillin and less affected by food.Plasma levels of ampicillin from oral bacampicillin exceedthose of oral ampicillin or amoxicillin for the first 2.5 hoursbut thereafter are the same as for ampicillin and amoxicillin.49 Effective plasma levels are sustained for 12 hours,allowing twice-a-day dosing.

Safety Profile

Poison by intraperitoneal andintravenous routes. Mildly toxic by ingestion andsubcutaneous routes. When heated to decomposition itemits very toxic fumes of NOx, SOx, and HCl.

BACAMPICILLIN HYDROCHLORIDE Preparation Products And Raw materials

Raw materials

Preparation Products

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BACAMPICILLIN HYDROCHLORIDE Suppliers

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37661-08-8, BACAMPICILLIN HYDROCHLORIDERelated Search:

D-2-Phenylglycine (4S)-2-(((R)-2-Amino-2-phenylacetamido)(carboxy)-methyl)-5,5-dimethylthiazolidine-4-carboxylic AMpicillin EP IMpurity C Arbidol HCl METHICILLIN SODIUM*) USP(CRM STANDARD) PIVAMPICILLIN AMPICILINE BACAMPICILLIN (S)-Bacampicillin hydrochloride BACAMPICILLIN HYDROCHLORIDE EPB(CRM STANDARD) (R)-Bacampicillin hydrochloride

ambacamp

ambaxin

bacacil

bapc

becampicillin

o)-3,3-dimethyl-7-oxo-,1-((ethoxycarbonyl)oxy)ethylester,hydrochloride

penglobe

BACAMPICILLIN HYDROCHLORIDE

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)-

Bacampicine

Spectrobid

BECAMPICILLINHYDROCHLORIDE

Pengood

Bacampicilline Hydrochloride

Bacampicillin Hydrochloride (200 mg)

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

Bacampicillin HCl

BACAMPICILLIN HYDROCHLORIDE USP STANDARD

BACAMPICILLIN HYDROCHLORIDE EP STANDARD

IWVTXAGTHUECPN-ANBBSHPLSA-N

Bacampicillin hydrochloride CRS

(2S,5R,6R)-1-((ethoxycarbonyl)oxy)ethyl 6-((R)-2-amino-2-phenylacetamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate hydrochloride

BACAMPICILLIN HYDROCHLORIDE USP/EP/BP

Bacampicillin Hydrochloride (1047300)

37661-08-8

C21H28ClN3O7S

C21H27N3O7SHCl