Sulbactam
Identification
- Summary
Sulbactam is an beta-lactamase inhibitor antibiotic combined with other antibiotics to treat a variety of susceptible bacterial infections.
- Brand Names
- Unasyn
- Generic Name
- Sulbactam
- DrugBank Accession Number
- DB09324
- Background
Sulbactam is a β-lactamase inhibitor given in combination with β-lactam antibiotics to inhibit β-lactamase, an enzyme produced by bacteria that destroys antibiotic activity.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Sulbactam (DB09324)
- Weight
- Average: 233.242
Monoisotopic: 233.035793157 - Chemical Formula
- C8H11NO5S
- Synonyms
- (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid 4,4-dioxide
- (2S,5R)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid 4,4-dioxide
- Penicillanic acid 1,1-dioxide
- Penicillanic acid sulfone
- Sulbactam
- Sulbactamum
- External IDs
- CP 45899
- CP-45899
- CP45899
Pharmacology
- Indication
Sulbactam is currently available in combination products with ampicillin. Within this formulation it is indicated for the treatment of infections due to susceptible strains of the designated microorganisms in the conditions listed below. Skin and Skin Structure Infections caused by beta-lactamase producing strains of Staphylococcus aureus, Escherichia coli, Klebsiella spp. (including K. pneumoniae), Proteus mirabilis, Bacteroides fragilis, Enterobacter spp., and Acinetobacter calcoaceticus. Intra-Abdominal Infections caused by beta-lactamase producing strains of Escherichia coli, Klebsiella spp. (including K. pneumoniae), Bacteroides spp. (including B. fragilis), and Enterobacter spp. Gynecological Infections caused by beta-lactamase producing strains of Escherichia coli, and Bacteroides spp. (including B. fragilis).
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
- Animal bite
- Bacterial Infections
- Bacterial Infections caused by Beta lactamase producing bacteria
- Bacterial Sinusitis
- Bites, Human
- Catheter Related Infections
- Community Acquired Pneumonia (CAP)
- Gynaecological infection
- Infective Endocarditis (IE)
- Intraabdominal Infections
- Nosocomial Pneumonia
- Postoperative Infections
- Postoperative Wound Infection
- Skin and Subcutaneous Tissue Bacterial Infections
- Complicated Bacterial Infections caused by Beta lactamase producing bacteria
- Moderate Bacterial Infections
- Severe Bacterial Infections
- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- Pharmacodynamics
Not Available
- Mechanism of action
Sulbactam is an irreversible inhibitor of β-lactamase; by binding and inhibiting β-lactamase produced by bacterial cells, sulbactam is thereby able to prevent it from reducing antibiotic activity. Although sulbactam alone possesses little useful antibacterial activity, except against the Neisseriaceae, whole organism studies have shown that sulbactam restores ampicillin activity against beta-lactamase producing strains. In particular, sulbactam has good inhibitory activity against the clinically important plasmid mediated beta-lactamases most frequently responsible for transferred drug resistance. The presence of sulbactam in formulations with ampicillin effectively extends the antibacterial spectrum of ampicillin to include many bacteria normally resistant to it and to other beta-lactam antibacterials. Thus, products with ampicillin + sulbactam possess the properties of a broad-spectrum antibacterial and a beta-lactamase inhibitor.
Target Actions Organism ABeta-lactamase inhibitorStaphylococcus aureus - Absorption
Peak serum concentrations are reached almost immediately following a 15-minute intravenous infusion of sulbactam + ampicillin. Mean peak serum levels for sulbactam range from 48 to 88 mcg/mL following intravenous administration of 2000 mg of ampicillin plus 1000 mg sulbactam. After an intramuscular injection of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels ranging from 6 to 24 mcg/mL are attained.
- Volume of distribution
Penetration of both ampicillin and sulbactam into cerebrospinal fluid in the presence of inflamed meninges has been demonstrated after IV administration.
- Protein binding
Approximately 38% reversibly bound to human serum protein.
- Metabolism
- Not Available
- Route of elimination
Approximately 75 to 85% of both ampicillin and sulbactam are excreted unchanged in the urine during the first 8 hours after administration.
- Half-life
~1 hr
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Abacavir may decrease the excretion rate of Sulbactam which could result in a higher serum level. Aceclofenac Aceclofenac may decrease the excretion rate of Sulbactam which could result in a higher serum level. Acemetacin Acemetacin may decrease the excretion rate of Sulbactam which could result in a higher serum level. Acetaminophen Acetaminophen may decrease the excretion rate of Sulbactam which could result in a higher serum level. Acetazolamide Acetazolamide may increase the excretion rate of Sulbactam which could result in a lower serum level and potentially a reduction in efficacy. Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Sulbactam which could result in a higher serum level. Aclidinium Aclidinium may decrease the excretion rate of Sulbactam which could result in a higher serum level. Acrivastine Sulbactam may decrease the excretion rate of Acrivastine which could result in a higher serum level. Acyclovir Acyclovir may decrease the excretion rate of Sulbactam which could result in a higher serum level. Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Sulbactam which could result in a higher serum level. 
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- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Sulbactam benzathine 49MU89FVBV 83031-43-0 YSEPFTSCLHUBNH-HFKSPEPWSA-N Sulbactam sodium DKQ4T82YE6 69388-84-7 NKZMPZCWBSWAOX-IBTYICNHSA-M - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ALFASID 1 G IM/IV ENJEKSIYON ICIN TOZ ICEREN FLAKON, 1 ADET Sulbactam (500 mg) + Ampicillin (1000 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey 
ALFASID 1 GR IM ENJ. ICIN TOZ ICEREN FLAKON, 1 ADET Sulbactam (500 mg) + Ampicillin (1000 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 250 MG IM ENJ.ICIN TOZ ICEREN FLAKON, 1 ADET Sulbactam (125 mg) + Ampicillin sodium (250 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 250 MG IM/IV ENJ.ICIN TOZ ICEREN FLAKON, 1 ADET Sulbactam (125 mg) + Ampicillin sodium (250 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 500 MG IM ENJ.ICIN TOZ ICEREN FLAKON Sulbactam (500 mg) + Ampicillin (1000 mg) Injection, powder, for solution Intramuscular YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey ALFASID 500 MG IM/IV ENJ.ICIN TOZ ICEREN FLAKON Sulbactam (500 mg) + Ampicillin (1000 mg) Injection, powder, for solution Intramuscular; Intravenous YAVUZ İLAÇ ECZA DEPOSU MEDİKAL ÜRÜNLER SAN.VE TİC. A.Ş. 2020-08-14 Not applicable Turkey AMPICILINA + SULBACTAM 1.5 G POLVO ESTÉRIL PARA INYECCIÓN Sulbactam sodium (0.5 g) + Ampicillin sodium (1 g) Injection, powder, for solution Intravenous NORTH CHINA PHARMACEUTICAL CO LTD 2015-04-16 2021-10-01 Colombia 
AMPICILINA + SULBACTAM 1.5 G POLVO PARASOLUCIÓN INYECTABLE Sulbactam sodium (0.5 g) + Ampicillin sodium (1 g) Injection, powder, for solution Intramuscular; Intravenous PHARMAYECT S.A. 2008-06-25 Not applicable Colombia AMPICILINA Y SULBACTAM 1.5 G. Sulbactam (0.5 g) + Ampicillin sodium (1 g) Injection, powder, for solution Intramuscular; Intravenous FARMALOGICA S.A. 2006-11-10 2020-04-07 Colombia Ampicillin and Sulbactam Sulbactam sodium (1 g/20mL) + Ampicillin sodium (2 g/20mL) Injection, powder, for solution Intramuscular; Intravenous WG Critical Care, LLC 2005-11-30 Not applicable US 
- Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Ampicillin and Sulbactam Sulbactam sodium (1 g/1) + Ampicillin sodium (2 g/1) Injection, powder, for suspension Intramuscular; Intravenous Cardinal Health 2011-05-20 2014-02-28 US
Categories
- ATC Codes
- J01CG01 — Sulbactam
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as alpha amino acids and derivatives. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon), or a derivative thereof.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Amino acids, peptides, and analogues
- Direct Parent
- Alpha amino acids and derivatives
- Alternative Parents
- Penams / Thiazolidines / Tertiary carboxylic acid amides / Sulfones / Azetidines / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds / Organonitrogen compounds show 3 more
- Substituents
- Aliphatic heteropolycyclic compound / Alpha-amino acid or derivatives / Azacycle / Azetidine / Beta-lactam / Carbonyl group / Carboxamide group / Carboxylic acid / Hydrocarbon derivative / Lactam show 12 more
- Molecular Framework
- Aliphatic heteropolycyclic compounds
- External Descriptors
- penicillanic acids (CHEBI:9321)
- Affected organisms
- Streptococcus pyogenes
- Streptococcus pneumoniae
- Staphylococcus saprophyticus
- Haemophilus influenzae
- Neisseria gonorrhoeae
- Escherichia coli
- Staphylococcus aureus
- Enterococcus faecalis
- Moraxella catarrhalis
- Staphylococcus epidermidis
- Proteus vulgaris
- Klebsiella
- Proteus mirabilis
- Providencia stuartii
- Streptococcus viridans
- Providencia rettgeri
- Morganella morganii
- Bacteroides
- Bacteroides fragilis
- Peptococcus
- Peptostreptococcus
- Clostridium
Chemical Identifiers
- UNII
- S4TF6I2330
- CAS number
- 68373-14-8
- InChI Key
- FKENQMMABCRJMK-RITPCOANSA-N
- InChI
- InChI=1S/C8H11NO5S/c1-8(2)6(7(11)12)9-4(10)3-5(9)15(8,13)14/h5-6H,3H2,1-2H3,(H,11,12)/t5-,6+/m1/s1
- IUPAC Name
- (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ⁶-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid
- SMILES
- [H][C@@]12CC(=O)N1[C@@]([H])(C(O)=O)C(C)(C)S2(=O)=O
References
- General References
- Totir MA, Helfand MS, Carey MP, Sheri A, Buynak JD, Bonomo RA, Carey PR: Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 beta-lactamase. Biochemistry. 2007 Aug 7;46(31):8980-7. Epub 2007 Jul 13. [Article]
- Helfand MS, Totir MA, Carey MP, Hujer AM, Bonomo RA, Carey PR: Following the reactions of mechanism-based inhibitors with beta-lactamase by Raman crystallography. Biochemistry. 2003 Nov 25;42(46):13386-92. [Article]
- INVIMA Product Authorization: Sulamp Duo (amoxicillin/sulbactam) coated tablets for oral use [Link]
- MiVademecum Colombia: Minovelt (ceftriaxone/sulbactam) product information [Link]
- External Links
- KEGG Drug
- D02223
- KEGG Compound
- C07770
- PubChem Compound
- 130313
- PubChem Substance
- 310265206
- ChemSpider
- 115306
- BindingDB
- 50021954
- 10167
- ChEBI
- 9321
- ChEMBL
- CHEMBL403
- ZINC
- ZINC000000897244
- PDBe Ligand
- 0RN
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Sulbactam
- PDB Entries
- 4fh2
- FDA label
- Download (8.76 MB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Other Acinetobacter Infections 1 4 Completed Prevention Breast Cancer 1 4 Completed Prevention Surgical Site Infections 1 4 Completed Treatment Gonorrhea 1 4 Completed Treatment Infection 1 4 Completed Treatment Intraabdominal Infections 2 4 Completed Treatment Pneumonia 1 4 Completed Treatment Recurrent Upper and Lower Respiratory Tract Infections (RTIs) / Urinary Tract Infection 1 4 Completed Treatment Recurrent Upper and Lower Respiratory Tract Infections (RTIs) / Urinary Tract Infections in Children 1 4 Completed Treatment Skin Diseases, Bacterial 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Intravenous Injection, powder, for suspension Intramuscular; Intravenous Injection, powder, for solution Parenteral Injection, solution Intramuscular; Intravenous Injection Intramuscular; Intravenous Injection Intramuscular; Intravenous Injection Intramuscular Injection, powder, for solution Suspension Conjunctival; Ophthalmic Injection, powder, for solution Parenteral Solution Conjunctival; Ophthalmic 150 mg Injection, solution Intramuscular Injection, powder, for solution Parenteral 547.12 MG/1062.91MG Powder 500 mg/1vial Tablet, coated Oral Solution Conjunctival; Ophthalmic; Topical 300 mg Solution Conjunctival; Ophthalmic 300 mg Solution Conjunctival; Ophthalmic 100 mg Powder Injection, powder, lyophilized, for solution Intramuscular; Intravenous Powder, for suspension Oral Tablet, film coated - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 48.5 mg/mL ALOGPS logP -0.92 ALOGPS logP -0.89 ChemAxon logS -0.68 ALOGPS pKa (Strongest Acidic) 3.09 ChemAxon pKa (Strongest Basic) -3.8 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 5 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 91.75 Å2 ChemAxon Rotatable Bond Count 1 ChemAxon Refractivity 48.21 m3·mol-1 ChemAxon Polarizability 20.63 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Beta-lactamase activity
- Specific Function
- Not Available
- Gene Name
- blaZ
- Uniprot ID
- P00807
- Uniprot Name
- Beta-lactamase
- Molecular Weight
- 31348.98 Da
References
- Totir MA, Helfand MS, Carey MP, Sheri A, Buynak JD, Bonomo RA, Carey PR: Sulbactam forms only minimal amounts of irreversible acrylate-enzyme with SHV-1 beta-lactamase. Biochemistry. 2007 Aug 7;46(31):8980-7. Epub 2007 Jul 13. [Article]
- Helfand MS, Totir MA, Carey MP, Hujer AM, Bonomo RA, Carey PR: Following the reactions of mechanism-based inhibitors with beta-lactamase by Raman crystallography. Biochemistry. 2003 Nov 25;42(46):13386-92. [Article]
Drug created on November 17, 2015 17:59 / Updated on May 07, 2021 21:41