Sulbactam
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Identification
- Summary
Sulbactam is an beta-lactamase inhibitor antibiotic combined with other antibiotics to treat a variety of susceptible bacterial infections.
- Brand Names
- Unasyn, Xacduro
- Generic Name
- Sulbactam
- DrugBank Accession Number
- DB09324
- Background
Sulbactam is a beta (β)-lactamase inhibitor and a derivative of the basic penicillin nucleus.6 When given in combination with β-lactam antibiotics, sulbactam produces a synergistic effect as it blocks the enzyme responsible for drug resistance by hydrolyzing β-lactams.2
- Type
- Small Molecule
- Groups
- Approved
- Structure
- 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 used in combination with other antibacterial agents. With ampicillin, it is used to treat skin and skin structure infections, intra-abdominal infections, and gynecological infections caused by susceptible bacteria.6
In combination with durlobactam, sulbactam is indicated in adults for the treatment of hospital-acquired bacterial pneumonia and ventilator-associated bacterial pneumonia (HABP/VABP), caused by susceptible isolates of Acinetobacter baumannii-calcoaceticus complex.5
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
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute bacterial rhinosinusitis Combination Product in combination with: Ampicillin (DB00415) ••• ••••• Used in combination to treat Animal bite Combination Product in combination with: Ampicillin (DB00415) ••• ••••• Used in combination to treat Bacterial infections Combination Product in combination with: Ampicillin (DB00415) •••••••••••• Used in combination to treat Bacterial infections caused by beta lactamase producing bacteria Combination Product in combination with: Amoxicillin (DB01060) •••••••••••• •••••••••• •••••• Used in combination to treat Catheter related infection Combination Product in combination with: Ampicillin (DB00415) ••• ••••• - Contraindications & Blackbox Warnings
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- Pharmacodynamics
When given together with beta-lactam antibiotics, sulbactam broadens their antibacterial spectrum by blocking the enzyme involved in their hydrolysis.2
Sulbactam alone possesses weak intrinsic antibacterial activity except against the Neisseriaceae,6 Acinetobacter spp., and Bacteroides fragilis as it can bind to the penicillin-binding proteins.3,4 Sulbactam restores the activity of beta-lactam antibiotics against a range of beta-lactamase-producing gram-positive and gram-negative bacteria.6
- Mechanism of action
Sulbactam is a competitive, irreversible bacterial beta (β)-lactamase inhibitor.4 It is reported to be more potent against class C beta-lactamases.3
Target Actions Organism ABeta-lactamase inhibitorStaphylococcus aureus - Absorption
Sulbactam is poorly absorbed after oral administration.1 Peak serum concentrations of ampicillin and sulbactam are reached following a 15-minute intravenous infusion. After the intravenous administration of 2000 mg of ampicillin plus 1000 mg sulbactam, peak sulbactam serum levels corresponded to 48 to 88 mcg/mL. After the intravenous administration of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels corresponded to 21 to 40 mcg/mL. After an intramuscular injection of 1000 mg ampicillin plus 500 mg sulbactam, peak sulbactam serum levels ranged from 6 to 24 mcg/mL.6
- Volume of distribution
The steady-state volumes of distribution range from 12.2 to 16.3 L. Sulbactam exhibits extensive distribution in extracellular fluids and tissues.2 Penetration of sulbactam into cerebrospinal fluid is enhanced in the presence of inflamed meninges.6
- Protein binding
Sulbactam is approximately 38% reversibly bound to plasma proteins.6
- Metabolism
Metabolism of sulbactam has not been characterized.1
- Route of elimination
When given in combination with ampicillin in individuals with normal renal function, approximately 75 to 85% of the drug is excreted unchanged in the urine during the first eight hours after administration.6
- Half-life
In healthy volunteers, the half-life is approximately one hour.6
- Clearance
Eenal clearance is approximately 12 L/h following infusion over 15 to 30 minutes.1
- Adverse Effects
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- Toxicity
The oral LD50 of sulbactam sodium is >4000 mg/kg in rats and >10,000 mg/kg in mice. The intravenous LD50 of sulbactam sodium is 4582 mg/kg in rats and 3604 mg/kg in mice.7
There is no information on the clinical signs and symptoms associated with a sulbactam overdose. Neurological adverse reactions, including convulsions, may occur. While sulbactam is removable by hemodialysis, there is limited clinical information regarding the use of hemodialysis to treat overdosage.5
- 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. - Food Interactions
- 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. 2011-06-08 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. 2011-01-20 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. 2009-07-03 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. 2009-07-03 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. 2008-05-14 Not applicable Turkey - 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-4lambda6-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
- Campoli-Richards DM, Brogden RN: Sulbactam/ampicillin. A review of its antibacterial activity, pharmacokinetic properties, and therapeutic use. Drugs. 1987 Jun;33(6):577-609. doi: 10.2165/00003495-198733060-00003. [Article]
- Peechakara BV, Gupta M: Ampicillin/Sulbactam. . [Article]
- Stover KR, Barber KE, Wagner JL: Allergic Reactions and Cross-Reactivity Potential with Beta-Lactamase Inhibitors. Pharmacy (Basel). 2019 Jun 28;7(3). pii: pharmacy7030077. doi: 10.3390/pharmacy7030077. [Article]
- Noguchi JK, Gill MA: Sulbactam: a beta-lactamase inhibitor. Clin Pharm. 1988 Jan;7(1):37-51. [Article]
- FDA Approved Drug Products: XACDURO (sulbactam for injection; durlobactam for injection), co-packaged for intravenous use [Link]
- DailyMed Label: UNASYN (ampicillin sodium and sulbactam sodium) intravenous and intramuscular injection, powder, for solution [Link]
- Pfizer: Unasyn (Ampicillin and Sulbactam) MSDS [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 / 7k8k / 8ebr
- FDA label
- Download (8.76 MB)
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
Explore 4,000+ rare diseases, orphan drugs & condition pairs, clinical trial why stopped data, & more. Preview package Phase Status Purpose Conditions Count Start Date Why Stopped 100+ additional columns Unlock 175K+ rows when you subscribe.View sample dataNot Available Completed Not Available Lung Abscess / Peritonitis / Pneumonia 1 somestatus stop reason just information to hide Not Available Completed Not Available Risk Factors 1 somestatus stop reason just information to hide Not Available Recruiting Prevention Antibacterial therapy / Biliary Atresia / Cholangitis 1 somestatus stop reason just information to hide Not Available Recruiting Prevention Antibiotics / Lactate / Postoperative Infections 1 somestatus stop reason just information to hide Not Available Recruiting Prevention Aortic Aneurysm and Dissection / Cardiac Valve Disease / Thoracic Aortic Aneurysm (TAA) / Thoracic Aortic Dissections 1 somestatus stop reason just information to hide
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intramuscular; Intravenous Injection, powder, for solution Intravenous Injection, powder, for suspension Intramuscular; Intravenous Injection, powder, for solution Parenteral Injection, powder, for solution Intramuscular Injection Intramuscular; Intravenous 1 gr Injection Intramuscular Injection, solution Intramuscular; Intravenous 1 g Injection, powder, for solution Parenteral Solution Conjunctival; Ophthalmic 150 mg Suspension Conjunctival; Ophthalmic Injection, powder, for solution Parenteral 547.12 MG/1062.91MG Powder 500 mg/1vial Solution Conjunctival; Ophthalmic 300 mg Suspension Oral 3.000 g Tablet, coated Oral Injection, powder, for solution Parenteral 1 g Injection, solution Intramuscular; Intravenous Injection Intramuscular; Intravenous Solution Conjunctival; Ophthalmic; Topical 300 mg Injection, solution Intramuscular Solution Conjunctival; Ophthalmic 100 mg Solution Oral Solution Parenteral 1000.000 mg Tablet Oral Powder Injection, powder, for solution Intramuscular; Intravenous 1 g Injection, powder, for solution Intramuscular; Intravenous 2 g Injection, powder, for solution Intramuscular; Intravenous 500 mg Injection, powder, lyophilized, for solution Intramuscular; Intravenous Injection, powder, for solution; injection, powder, lyophilized, for solution; kit Intravenous Injection, powder, for solution Powder, for suspension Oral Tablet, film coated - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9309245 No 2016-04-12 2033-04-02 US US9623014 No 2017-04-18 2033-04-02 US US9968593 No 2018-05-15 2035-11-17 US US10376499 No 2019-08-13 2035-11-17 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 156 https://www.fishersci.com/store/msds?partNumber=AC455350250&productDescription=SULBACTAM+25GR&vendorId=VN00032119&countryCode=US&language=en - 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 splash10-001i-0090000000-294fa7fe6b712f884149 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0590000000-de34b52fc1a9def9e8d3 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-053r-4590000000-1458fe4517fd392c8c49 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-6190000000-0668e5c19dcb76f50b86 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-01b9-9100000000-bcad6db573484195483e Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08nc-9640000000-6ded84944c6fcafe64ae Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 148.112336 predictedDarkChem Lite v0.1.0 [M-H]- 148.9225 predictedDeepCCS 1.0 (2019) [M+H]+ 148.819036 predictedDarkChem Lite v0.1.0 [M+H]+ 151.31862 predictedDeepCCS 1.0 (2019) [M+Na]+ 148.541536 predictedDarkChem Lite v0.1.0 [M+Na]+ 157.23123 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Staphylococcus aureus
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Not Available
- Specific Function
- beta-lactamase activity
- 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]
- DailyMed Label: UNASYN (ampicillin sodium and sulbactam sodium) intravenous and intramuscular injection, powder, for solution [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Secondary active transporter that functions as a Na(+)-independent organic anion (OA)/dicarboxylate antiporter where the uptake of one molecule of OA into the cell is coupled with an efflux of one molecule of intracellular dicarboxylate such as 2-oxoglutarate or glutarate (PubMed:11669456, PubMed:11907186, PubMed:14675047, PubMed:22108572, PubMed:23832370, PubMed:28534121, PubMed:9950961). Mediates the uptake of OA across the basolateral side of proximal tubule epithelial cells, thereby contributing to the renal elimination of endogenous OA from the systemic circulation into the urine (PubMed:9887087). Functions as a biopterin transporters involved in the uptake and the secretion of coenzymes tetrahydrobiopterin (BH4), dihydrobiopterin (BH2) and sepiapterin to urine, thereby determining baseline levels of blood biopterins (PubMed:28534121). Transports prostaglandin E2 (PGE2) and prostaglandin F2-alpha (PGF2-alpha) and may contribute to their renal excretion (PubMed:11907186). Also mediates the uptake of cyclic nucleotides such as cAMP and cGMP (PubMed:26377792). Involved in the transport of neuroactive tryptophan metabolites kynurenate (KYNA) and xanthurenate (XA) and may contribute to their secretion from the brain (PubMed:22108572, PubMed:23832370). May transport glutamate (PubMed:26377792). Also involved in the disposition of uremic toxins and potentially toxic xenobiotics by the renal organic anion secretory pathway, helping reduce their undesired toxicological effects on the body (PubMed:11669456, PubMed:14675047). Uremic toxins include the indoxyl sulfate (IS), hippurate/N-benzoylglycine (HA), indole acetate (IA), 3-carboxy-4- methyl-5-propyl-2-furanpropionate (CMPF) and urate (PubMed:14675047, PubMed:26377792). Xenobiotics include the mycotoxin ochratoxin (OTA) (PubMed:11669456). May also contribute to the transport of organic compounds in testes across the blood-testis-barrier (PubMed:35307651)
- Specific Function
- alpha-ketoglutarate transmembrane transporter activity
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- FDA Approved Drug Products: XACDURO (sulbactam for injection; durlobactam for injection), co-packaged for intravenous use [Link]
Drug created at November 17, 2015 17:59 / Updated at June 02, 2024 21:55