This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Sultamicillin is a mutual prodrug of ampicillin and sulbactam useful in the treatment of infections caused by beta-lactamase-producing bacteria.

Generic Name
Sultamicillin
DrugBank Accession Number
DB12127
Background

Sultamicillin has been used in trials studying the prevention and treatment of Ventilator Associated Pneumonia and Chronic Obstructive Pulmonary Disease (COPD).

Type
Small Molecule
Groups
Approved, Investigational
Structure
Weight
Average: 594.65
Monoisotopic: 594.14542091
Chemical Formula
C25H30N4O9S2
Synonyms
  • Sultamicilina
  • Sultamicillin
  • Sultamicillinum
External IDs
  • CP 49952
  • CP-49,952
  • CP-49952
  • VD 1827
  • VD-1827

Pharmacology

Indication

Not Available

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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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.
DrugInteraction
AcemetacinAcemetacin may decrease the excretion rate of Sultamicillin which could result in a higher serum level.
AcenocoumarolSultamicillin may increase the anticoagulant activities of Acenocoumarol.
AmikacinThe serum concentration of Amikacin can be decreased when it is combined with Sultamicillin.
AtracuriumThe therapeutic efficacy of Atracurium can be increased when used in combination with Sultamicillin.
Atracurium besylateThe therapeutic efficacy of Atracurium besylate can be increased when used in combination with Sultamicillin.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Sultamicillin.
CapreomycinThe serum concentration of Capreomycin can be decreased when it is combined with Sultamicillin.
CinoxacinThe serum concentration of Cinoxacin can be increased when it is combined with Sultamicillin.
CiprofloxacinThe serum concentration of Ciprofloxacin can be increased when it is combined with Sultamicillin.
CisatracuriumThe therapeutic efficacy of Cisatracurium can be increased when used in combination with Sultamicillin.
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sultamicillin hydrochlorideSUI1Z5PXSN76203-99-1JLBADLWTHWGGNE-CGAOXQFVSA-N
Sultamicillin tosilate46940LU8EO83105-70-8FFCSPKNZHGIDQM-CGAOXQFVSA-N
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
SULTAMAT 250 MG 40 ML SUSPANSIYONSultamicillin (250 mg/5ml)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag
SULTAMAT 250 MG 70 ML SUSPANSIYONSultamicillin (250 mg/5ml)SuspensionOralATABAY KİMYA SAN. VE TİC. A.Ş.2020-08-14Not applicableTurkey flag

Categories

ATC Codes
J01CR50 — Combinations of penicillinsJ01CR04 — Sultamicillin
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as penicillins. These are organic compounds containing the penicillin core structure, which is structurally characterized by a penam ring bearing two methyl groups at position 2, and an amide group at position 6 [starting from the sulfur atom at position 1].
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Lactams
Sub Class
Beta lactams
Direct Parent
Penicillins
Alternative Parents
Alpha amino acid esters / N-acyl-alpha amino acids and derivatives / Alpha amino acid amides / Phenylacetamides / Acylals / Aralkylamines / Dicarboxylic acids and derivatives / Thiazolidines / Tertiary carboxylic acid amides / Sulfones
show 11 more
Substituents
Acetal / Acylal / Alpha-amino acid amide / Alpha-amino acid ester / Alpha-amino acid or derivatives / Amine / Amino acid or derivatives / Aralkylamine / Aromatic heteropolycyclic compound / Azacycle
show 27 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
penicillanic acid ester (CHEBI:51770)
Affected organisms
Not Available

Chemical Identifiers

UNII
65DT0ML581
CAS number
76497-13-7
InChI Key
OPYGFNJSCUDTBT-PMLPCWDUSA-N
InChI
InChI=1S/C25H30N4O9S2/c1-24(2)17(29-20(32)16(21(29)39-24)27-19(31)15(26)12-8-6-5-7-9-12)22(33)37-11-38-23(34)18-25(3,4)40(35,36)14-10-13(30)28(14)18/h5-9,14-18,21H,10-11,26H2,1-4H3,(H,27,31)/t14-,15-,16-,17+,18+,21-/m1/s1
IUPAC Name
[(2S,5R,6R)-6-[(2R)-2-amino-2-phenylacetamido]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carbonyloxy]methyl (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4lambda6-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
SMILES
[H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)[C@H](N)C1=CC=CC=C1)C(=O)OCOC(=O)[C@@H]1N2C(=O)C[C@@]2([H])S(=O)(=O)C1(C)C

References

General References
  1. AIFA Product Information: Unasyn (sultamicillin) for oral use [Link]
PubChem Compound
444022
PubChem Substance
347828426
ChemSpider
392048
ChEBI
51770
ChEMBL
CHEMBL506110
ZINC
ZINC000042834847
Wikipedia
Sultamicillin

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentChronic Obstructive Pulmonary Disease (COPD)1
4WithdrawnPreventionVentilator Associated Bacterial Pneumonia1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
SuspensionOral
Powder, for solutionOral20 g
Powder, for suspensionOral
Tablet, coatedOral
Powder; suspensionOral
TabletOral
Powder, for suspensionOral250 mg/5mL
InjectionIntramuscular; Intravenous250 mg/5ml
Powder, for suspensionOral5 g
Tablet, film coatedOral750 mg
TabletOral375 mg
TabletOral750 mg
SuspensionOral5 g
TabletOral375 g
Powder, for solutionOral5 g
Powder, for suspensionOral250 MG
Tablet, film coatedOral375 mg
Tablet, coatedOral375 mg
Tablet, coatedOral750 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.283 mg/mLALOGPS
logP1.55ALOGPS
logP-0.4ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.71ChemAxon
pKa (Strongest Basic)7.23ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area182.48 Å2ChemAxon
Rotatable Bond Count9ChemAxon
Refractivity138.12 m3·mol-1ChemAxon
Polarizability58.76 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created at October 20, 2016 21:24 / Updated at May 21, 2021 10:22