Brand Name(s) in US
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CARBENICILLIN

Brand Name(s) in US
Product Name
CARBENICILLIN
CAS No.
4697-36-3
Chemical Name
CARBENICILLIN
Synonyms
Pyocianil;onamic acid;ARBENICILLIN;CARBENICILLIN;Carboxybenzylpenicillin;CARBENICILLIN USP/EP/BP;Lactic Acid Impurity 53;CARBENICILLIN READY MADE;Carbenicillinum natricum;(α-Carboxybenzyl)penicillin
CBNumber
CB0243304
Molecular Formula
C17H18N2O6S
Formula Weight
378.4
MOL File
4697-36-3.mol
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CARBENICILLIN Property

Boiling point:
737.8±60.0 °C(Predicted)
Density 
1.53±0.1 g/cm3(Predicted)
storage temp. 
−20°C
solubility 
Soluble in DMSO
form 
Powder
pka
pKa 2.22±0.05(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain);3.25±0.02 (Uncertain)
CAS DataBase Reference
4697-36-3
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Safety

Hazard Codes 
Xn
Risk Statements 
10-42/43
Safety Statements 
36/37-45-22
RIDADR 
UN 1170 3/PG 3
WGK Germany 
2
Hazardous Substances Data
4697-36-3(Hazardous Substances Data)
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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.

P272Contaminated work clothing should not be allowed out of the workplace.

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

P285In case of inadequate ventilation wear respiratory protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P304+P341IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.

P321Specific treatment (see … on this label).

P333+P313IF SKIN irritation or rash occurs: Get medical advice/attention.

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

P363Wash contaminated clothing before reuse.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

ChemScene
Product number
CS-2745
Product name
Carbenicillin
Packaging
250mg
Price
$50
Updated
2021/12/16
ApexBio Technology
Product number
B3412
Product name
Carbenicillin
Packaging
250mg
Price
$87
Updated
2021/12/16
ApexBio Technology
Product number
B3412
Product name
Carbenicillin
Packaging
1g
Price
$110
Updated
2021/12/16
ApexBio Technology
Product number
B3412
Product name
Carbenicillin
Packaging
5g
Price
$403
Updated
2021/12/16
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CARBENICILLIN Chemical Properties,Usage,Production

Brand Name(s) in US

Carbenicillin: Geopen, Pyopen
Carbenicillin indanyl sodium: Geocillin

Originator

Pyopen,Beecham,Switz.,1968

Uses

Antibacterial.

Definition

ChEBI: A penicillin antibiotic having a 6beta-2-carboxy-2-phenylacetamido side-chain.

Indications

Carbenicillin has a broad spectrum of antibacterial use with respect to Gram-negative and Gram-positive microorganisms. However, using this drug for infections caused by Grampositive microorganisms is pointless. It is used for diseases such as urinary tract infections, septicemia, endocarditis, meningitis, osteomelitis, peritonitis, purulent otitis, infected wounds, infected burns, and so on that are caused by Gram-negative microorganisms which are sensitive to such antibiotics. Synonyms of this drug are carindapen, pyopen, geopen, gripenin, and others.

Manufacturing Process

The required monobenzyl phenylmalonate, MP 68°C, was prepared by treating a mixture of phenylmalonic acid (18 g) and benzyl alcohol (13 g) in carbon tetrachloride (80 ml) with dry hydrogen chloride.
Monobenzyl phenylmalonate (13.3 g) in dry benzene (100 ml) was refluxed with thionyl chloride (6.45 g) for 90 minutes, then concentrated in vacuo. The residual oil was dissolved in dry acetone (50 ml) and added to a stirred, ice-cooled solution of 6-aminopenicillanic acid (9.7 g) in N sodium bicarbonate solution (135 ml), water (150 ml), and acetone (300 ml). The mixture was stirred for 30 minutes at 0°C and then for 90 minutes at room temperature, then concentrated under reduced pressure to remove acetone. The aqueous solution was brought to pH 2 with dilute hydrochloric acid and extracted with ether (3 x 100 ml). The ether solution was washed with water and then itself extracted with sufficient N sodium bicarbonate solution to give an aqueous phase of pH 7.5. The aqueous layer was separated and evaporated at low temperature and pressure to leave the impure sodium salt of alpha- (benzyloxycarbonyl) benzylpenicillin.
This crude product (15.8 g) in water (360 ml) was added to a prehydrogenated suspension of 10% palladium on charcoal (4 g) in water (400 ml), and hydrogenation was continued for 30 minutes. The catalyst was removed and the filtrate was adjusted to pH 7.5 with sodium bicarbonate, then evaporated at low temperature and pressure. The residue was purified by chromatography on a column of cellulose powder, eluting first with butanol/ethanol/water mixture and then with acetone/isopropanol/water. The main fraction was evaporated at low temperature and pressure to give a 32% yield of the sodium salt of alpha-carboxybenzylpenicillin as a white powder. The product was estimated by monometric assay with penicillinase to be 58% pure.

brand name

Geopen (Roerig); Pyopen (GlaxoSmithKline).

Therapeutic Function

Antibacterial

Antimicrobial activity

α-Carboxybenzylpenicillin; the first antipseudomonal penicillin to be developed. A semisynthetic carboxypenicillin supplied as the disodium salt for parenteral administration. The two esterified prodrug formulations, carindacillin (carbenicillin indanyl sodium) and carfecillin (carbenicillin carboxyphenyl ester) are no longer available.
It is the least active of the group 5 agents, even against Ps. aeruginosa (MIC 64 mg/L) with notably reduced activity against Gram-positive cocci. It is labile to many plasmidmediated β-lactamases, but is comparatively stable to class C chromosomal β-lactamases (pp. 228–230). Synergy is demonstrable with aminoglycosides against Ps. aeruginosa and other Gram-negative bacteria.
It is not orally absorbed, except in esterified form. A 1 g intramuscular injection achieves a plasma peak concentration of 20–30 mg/L after 0.5–1.5 h. The half-life is around 1 h. Plasma protein binding is 50–60%.
The drug is distributed in the extracellular fluid, providing concentrations up to 60% of those of the plasma. In patients with cystic fibrosis sputum concentrations may not reach inhibitory levels for Ps. aeruginosa. It does not cross the normal meninges but levels of up to 50% of those of the plasma can be found in patients with meningitis. Around 80% of the dose appears as unchanged drug in the urine, producing very high levels (2–4 g/L). It is more rapidly disposed of in patients with cystic fibrosis. Hypersensitivity reactions may occur, but these are less frequent and severe than those associated with benzylpenicillin. High blood levels sometimes cause a coagulation defect that has occasionally progressed to life-threatening bleeding in patients with impaired excretion while receiving 500 mg/kg per day or more. Reversible abnormalities of liver function apparently occur more commonly than with other antipseudomonal penicillins. Since large doses of the drug have to be used, convulsions can occur (as with other penicillins; p. 203) and, being administered as the disodium salt, electrolyte disturbances can result. It was formerly used for treatment of serious infections, especially those involving Ps. aeruginosa. It has extremely limited availability.

Biological Activity

carbenicillin is broad-spectrum semisynthetic penicillin derivative used parenterally.

Synthesis

Carbenicillin, [2S-(2|á,5|á,6|?)]-3,3-dimethyl-7-oxo-6-(2-carboxy-2- phenylacetamido)-4-thia-1-azabicyclo[3.2.0]-heptan-2-carboxylic acid (32.1.1.32), is synthesized by direct acylation of 6-APA in the presence of sodium bicarbonate by phenylmalonic acid monobenzyl ester chloride, which forms the benzyl ester of carbenicillin (32.1.1.31), the hydrogenolysis of which using palladium on carbon or calcium carbonate as catalyst gives the desired product (32.1.1.32).

CARBENICILLIN Preparation Products And Raw materials

Raw materials

Preparation Products

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CARBENICILLIN Suppliers

Beijing Ouhe Technology Co., Ltd
Tel
010-82967028 13552068683
Fax
+86-10-82967029
Email
2355560935@qq.com
Country
China
ProdList
12390
Advantage
60
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
Guangzhou Isun Pharmaceutical Co., Ltd
Tel
020-39119399 18927568969
Fax
020-39119999
Email
isunpharm@qq.com
Country
China
ProdList
4674
Advantage
55
Shanghai Synchem Pharma Co., ltd
Tel
21-619849051-1 18521059765
Email
synchempharma@aliyun.com
Country
China
ProdList
6463
Advantage
55
ShangHai Biochempartner Co.,Ltd
Tel
177-54423994 17754423994
Fax
QQ:2853530913
Email
2853530910@QQ.com
Country
China
ProdList
8012
Advantage
62
Amadis Chemical Company Limited
Tel
571-89925085
Fax
0086-571-89925065
Email
sales@amadischem.com
Country
China
ProdList
131957
Advantage
58
Musechem
Tel
+1-800-259-7612
Fax
+1-800-259-7612
Email
info@musechem.com
Country
United States
ProdList
4660
Advantage
60
Fan De(Beijing) Biotechnology Co., Ltd.
Tel
15911056312
Email
liming@bio-fount.com
Country
China
ProdList
9729
Advantage
58
Hangzhou Synstar pharmaceutical Technology CO.,Ltd
Tel
0571-85361029
Fax
0571-85361029
Email
synstar518@163.com
Country
China
ProdList
1990
Advantage
58
BOC Sciences
Tel
16314854226; +16314854226
Email
inquiry@bocsci.com
Country
United States
ProdList
19741
Advantage
58
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View Lastest Price from CARBENICILLIN manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
Carbenicillin 4697-36-3
Price
US $1.00-22.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
100000KG
Release date
2024-08-07
Zhuozhou Wenxi import and Export Co., Ltd
Product
Carbenicillin 4697-36-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-10
Zhuozhou Wenxi import and Export Co., Ltd
Product
Carbenicillin 4697-36-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-07-09

4697-36-3, CARBENICILLINRelated Search:


  • ALPHA-CARBOXYBENZYLPENICILLIN
  • CARBENICILLIN READY MADE
  • CARBENICILLIN
  • (α-Carboxybenzyl)penicillin
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxyphenylacetyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxyphenylacetyl)amino]-3,3-dimethyl-7-oxo-, [2S-(2α,5α,6β)]-
  • 6-(α-Carboxyphenylacetamido)penicillanic acid
  • Carboxybenzylpenicillin
  • Carboxybenzylpenicillin acid
  • Malonamic acid, N-(2-carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]hept-6-yl)-2-phenyl- (7CI, 8CI)
  • Pyocianil
  • Carbenicillinum natricum
  • onamic acid
  • Carbenicillin (base and/or unspecified salts)
  • N-[(2S,5R,6R)-2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptan-6-yl]-2-phenylmalonamidic acid
  • 6-(alpha-Carboxyphenylacetamido)penicillanic acid
  • 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(2-carboxy-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-, (2S,5R,6R)-
  • CARBENICILLIN USP/EP/BP
  • Lactic Acid Impurity 53
  • ARBENICILLIN
  • 4697-36-3
  • C17H18N2O6S
  • carbenicillin sky