Identification
- Summary
Thiamphenicol is a semisynthetic derivative of chloramphenicol with a broad spectrum of antibacterial activity.
- Generic Name
- Thiamphenicol
- DrugBank Accession Number
- DB08621
- Background
Not Available
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Thiamphenicol (DB08621)
- Weight
- Average: 356.222
Monoisotopic: 355.004798699 - Chemical Formula
- C12H15Cl2NO5S
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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 Treatment of Gram-negative bacteria infection •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UDr hemagglutinin structural subunit Not Available Escherichia coli - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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 softwareAcenocoumarol The risk or severity of bleeding can be increased when Thiamphenicol is combined with Acenocoumarol. Ambroxol The risk or severity of methemoglobinemia can be increased when Thiamphenicol is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Thiamphenicol is combined with Articaine. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Thiamphenicol. Benzocaine The risk or severity of methemoglobinemia can be increased when Thiamphenicol is combined with Benzocaine. - Food Interactions
- Not Available
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.
Categories
- ATC Codes
- J01BA02 — Thiamphenicol
- J01BA — Amphenicols
- J01B — AMPHENICOLS
- J01 — ANTIBACTERIALS FOR SYSTEMIC USE
- J — ANTIINFECTIVES FOR SYSTEMIC USE
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzenesulfonyl compounds. These are aromatic compounds containing a benzenesulfonyl group, which consists of a monocyclic benzene moiety that carries a sulfonyl group.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonyl compounds
- Direct Parent
- Benzenesulfonyl compounds
- Alternative Parents
- Sulfones / Secondary carboxylic acid amides / Secondary alcohols / Primary alcohols / Organopnictogen compounds / Organonitrogen compounds / Organochlorides / Organic oxides / Hydrocarbon derivatives / Carbonyl compounds show 2 more
- Substituents
- Alcohol / Alkyl chloride / Alkyl halide / Aromatic alcohol / Aromatic homomonocyclic compound / Benzenesulfonyl group / Carbonyl group / Carboxamide group / Carboxylic acid derivative / Hydrocarbon derivative show 14 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- sulfone, monocarboxylic acid amide (CHEBI:32215)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- FLQ7571NPM
- CAS number
- 15318-45-3
- InChI Key
- OTVAEFIXJLOWRX-NXEZZACHSA-N
- InChI
- InChI=1S/C12H15Cl2NO5S/c1-21(19,20)8-4-2-7(3-5-8)10(17)9(6-16)15-12(18)11(13)14/h2-5,9-11,16-17H,6H2,1H3,(H,15,18)/t9-,10-/m1/s1
- IUPAC Name
- 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methanesulfonylphenyl)propan-2-yl]acetamide
- SMILES
- [H][C@](CO)(NC(=O)C(Cl)Cl)[C@]([H])(O)C1=CC=C(C=C1)S(C)(=O)=O
References
- Synthesis Reference
Franco Pozzi, Claudia Tortora, Angelo Carenzi, "Pharmaceutical preparation containing thiamphenicol for veterinary use." U.S. Patent US4912138, issued January, 1979.
US4912138- General References
- Not Available
- External Links
- KEGG Compound
- C12853
- PubChem Compound
- 27200
- PubChem Substance
- 99445092
- ChemSpider
- 25315
- BindingDB
- 58925
- 10463
- ChEBI
- 32215
- ChEMBL
- CHEMBL1236282
- ZINC
- ZINC000000538440
- PDBe Ligand
- TH8
- Wikipedia
- Thiamphenicol
- PDB Entries
- 2jkj
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 1 Completed Basic Science Healthy Subjects (HS) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Suppository Granule, for solution Oral 2.5 mg Injection, powder, for solution 250 MG/2ML Powder, for solution 250 MG/4ML Powder, for solution 250 MG/2.5ML Powder, for solution 500 MG/5ML Powder, for solution 500 MG/4ML Tablet 250 MG Tablet 500 MG Injection Intramuscular; Intravenous Syrup Capsule Oral 500 MG Suspension Suspension; syrup Tablet Powder Injection, powder, lyophilized, for solution Intramuscular; Intravenous 750 mg Injection Intramuscular; Intravenous 750 mg Suspension 60 ml Capsule Oral Capsule Oral 250 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 2.27 mg/mL ALOGPS logP 0.33 ALOGPS logP -0.22 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 8.75 Chemaxon pKa (Strongest Basic) -2.8 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 103.7 Å2 Chemaxon Rotatable Bond Count 6 Chemaxon Refractivity 79.88 m3·mol-1 Chemaxon Polarizability 32.29 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.931 Blood Brain Barrier + 0.9383 Caco-2 permeable - 0.61 P-glycoprotein substrate Non-substrate 0.7574 P-glycoprotein inhibitor I Non-inhibitor 0.9489 P-glycoprotein inhibitor II Non-inhibitor 0.9432 Renal organic cation transporter Non-inhibitor 0.9236 CYP450 2C9 substrate Non-substrate 0.5856 CYP450 2D6 substrate Non-substrate 0.8164 CYP450 3A4 substrate Non-substrate 0.5896 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.831 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8529 Ames test Non AMES toxic 0.7181 Carcinogenicity Non-carcinogens 0.6535 Biodegradation Ready biodegradable 0.706 Rat acute toxicity 2.2718 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9972 hERG inhibition (predictor II) Non-inhibitor 0.9289
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 175.21062 predictedDeepCCS 1.0 (2019) [M+H]+ 177.56862 predictedDeepCCS 1.0 (2019) [M+Na]+ 184.25081 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Escherichia coli
- Pharmacological action
- Unknown
- General Function
- Not Available
- Specific Function
- Hemagglutinins of uropathogenic E.coli mediate adherence to the upper urinary tract. These adhesins bind to the Dr blood group antigen and also agglutinate human erythrocytes in the presence of D-m...
- Gene Name
- draA
- Uniprot ID
- P24093
- Uniprot Name
- Dr hemagglutinin structural subunit
- Molecular Weight
- 17058.095 Da
References
- Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Drug created at September 15, 2010 21:33 / Updated at June 19, 2021 00:27