Basic information
- CAS
4800-94-6- Standard SMILES
CC1(C)S[C@@H]2[C@H](NC(=O)C(C(=O)[O-])c3ccccc3)C(=O)N2[C@H]1C(=O)[O-].[Na+].[Na+]- InChIKey
RTYJTGSCYUUYAL-YCAHSCEMSA-L- Molecular formula
- C17H16N2Na2O6S
- Average molar mass
- 422.4 g/mol
- Monoisotopic mass
- 422.05244597
Overview
Carbenicillin disodium is an organic sodium salt. It contains a carbenicillin(2-).
Names & identifiers
- Preferred name
- Carbenicillin Disodium
- IUPAC
- disodium;(2S,5R,6R)-6-[(2-carboxylato-2-phenylacetyl)amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
- English name
- Carbenicillin disodium
- Molecular formula
- C17H19N2NaO6S
- Molecular weight
- 402.4
Names & synonyms
Carbenicillin disodium4800-94-6Carbenicillin disodium saltcarbenicillin sodiumPyocianilHyoperSodium carbenicillinDisodium carbenicillinalpha-Carboxybenzylpenicillin disodium saltBRL-2064NSC-111071CP-15-639-2
Show more names
geopenpyopenCARBENICILINpiopenpyopeneCarbapengripenincarbecin
alpha-Carboxybenzylpenicillin sodium saltDisodium alpha-carboxybenzylpenicillinDTXSID60458209TS4B3H261CP 15639-2N-(2-Carboxy-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)-hept-6-yl)-2-phenylmalonamic acid disodium saltDTXCID4025820CHEBI:34609
Database identifiers
- CAS
4800-94-6- PubChem CID
- 20933
- DTXSID
DTXSID6045820- ChEMBL
CHEMBL606260- ChEBI
Properties
Computed structural properties
- Topological polar surface area
- 155 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 7
- Rotatable bonds
- 3
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 634
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 190 °C · >190°C (dec.)
- alpha
- 175 · +175~+190°(D/20℃)(c=4,H2O)(calculated on the dehydrous basis)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 2 O: · H2O: 50 mg/mL
- form
- powder
- color
- white to off-white
- PH
- 5.5 · 5.5~7.5 (10g/l, 25℃)
- Water Solubility
- Soluble in water.
- Merck
- 13 · 13,1801
- BRN
- 5722128 · 5722128
- Major Application
- pharmaceutical (small molecule)
- InChIKey
- HUKAYYNGXWHSGG-MRDJHEKFNA-N
- SMILES
- C([C@H]1C(S[C@]2([H])[C@H](NC(=O)C(C3C=CC=CC=3)C(=O)O)C(=O)N12)(C)C)(=O)O.[NaH] |&1:1,4,6,r|
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (99.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 225 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationCarbenicillin sodium: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - 4-Thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid, 6-[(carboxyphenylacetyl)amino]-3,3-dimethyl-7-oxo-, disodium salt,[2S-(2.alpha.,5.alpha.,6.beta.)]-: Human health tier I assessment
Hazard Classes and CategoriesSkin Sens. 1 (99.6%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Carbenicillin disodium
vLess-DILI-concern
3
Warnings & precautions
DOI:10.1016/j.drudis.2016.02.015
Safety data
- F
- 3-8-10
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 2
Chemistry & industry
Pharmacology
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Applications
DescriptionCarbenicillin is a broad-spectrum carboxypenicillin antibiotic. It is active against Gram-negative and certain Gram-positive bacteria, including S. pyogenes, S. epidermidis, P. mirabilis, P. vulgaris, E. coli, and P. aeruginosa (MICs = 0.19, 1.56, 1.56, 3.12, 3.12, and 50 μg/ml, respectively). It is also active against penicillinase-producing and non-producing strains of S. aureus (MICs = 1.56 and 12.5 μg/ml, respectively). Carbenicillin is protective against systemic S. pyogenes, P. vulgaris, E. coli, and S. aureus infection in a mouse model of systemic lethal infection with 50% protective dose (PD50) values of 7.8, 224, 19.3, and 34 mg/kg, respectively. It also decreases viable colony counts in the kidney in a rat model of P. vulgaris or E. coli urinary tract infection when administered at a dose of 100 mg/kg. Formulations containing carbenicillin have previously been used in the treatment of upper and lower urinary tract infections and prostatitis.
UsesCarbenicillin disodium salt is a water-soluble antibiotic which is effective against gram-negative bacteria.Carbenicillin disodium salt is widely utilized as an antibiotic which is used to control bacterial cell-wall synthesis by inactivating transpeptidases on the inner surface of the bacterial cell membrane. It has been involved in the study of the role of penicillin-sensitive transpeptidases in cell wall biosynthesis.
UsesSemi-synthetic antibiotic related to Penicillin (P223500). Antibacterial.
General DescriptionCarbenicillin was synthesized by Brain et al. of Beecham Research Laboratories in 1965. It was the first synthetic penicillin to show activity against Pseudomonas aeruginosa. Although its activity against the microorganism is not strong (MIC = 25 – 100 μg/mL), it is widely used against P. aeruginosa infections because of its low toxicity and the lack of other antibiotics suitable for use against this microorganism. Carbenicillin is mainly used clinically to treat urinary tract and respiratory tract infections and sepsis caused by Proteus, Escherichia coli, Klebsiella, and Pseudomonas aeruginosa.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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