Thiamphenicol
Basic information
- CAS
15318-45-3- Standard SMILES
CS(=O)(=O)c1ccc([C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl)cc1- InChIKey
OTVAEFIXJLOWRX-NXEZZACHSA-N- Molecular formula
- C12H15Cl2NO5S
- Average molar mass
- 356.2 g/mol
- Monoisotopic mass
- 355.0047991
Overview
Thiamphenicol is a monocarboxylic acid amide and a sulfone. It has a role as an antimicrobial agent and an immunosuppressive agent.
Names & identifiers
- Preferred name
- Thiamphenicol
- IUPAC
- 2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
- English name
- Thiamphenicol
- Molecular formula
- C12H15Cl2NO5S
- Molecular weight
- 356.22
Names & synonyms
thiamphenicol15318-45-3ThiophenicolThiocymetinDextrosulphenidolNeomysonUrfamycineIgralin(+)-ThiamphenicolThiamphenicolumTiamfenicoloTiamfenicol
Show more names
D-THREO-2,2-DICHLORO-N-(BETA-HYDROXY-ALPHA-[HYDROXYMETHYL]-4-[METHYLSULFONYL]PHENETHYL)ACETAMIDE8065c.b.NSC 522822hiamphenicolSulfoxamycin
ArmaiWIN-5063-2DescocinMacphenicolMasatirinUrfamicinaEfnicolHyrazin
Database identifiers
- CAS
15318-45-3、847-25-6- PubChem CID
- 27200
- DTXSID
DTXSID5021338- ChEMBL
CHEMBL1236282- ChEBI
CHEBI:32215- UNII
- 283383NO13、FLQ7571NPM
- EC Number
- 239-355-3
- Nikkaji
- J9.286J
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 112 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 443
Experimental & physicochemical properties
Chemical ClassesOther Uses -> Pharmaceuticals
Drugs
Pharmaceuticals -> Antibiotics (Amphenicols)
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Antibiotics
LogP0.15
Solubility>53.4 [ug/mL] (The mean of the results at pH 7.4)
Animal DrugsPharmaceuticals -> Animal Drugs -> Approved in Taiwan
Collision Cross Section
174.56 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
170.7 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
179.09 Ų [M-H]-
Physicochemical properties
- Melting point
- 163 · 163-166 °C
- alpha
- 25 · D25 +12.9° (ethanol)
- Density
- 1.3281 · 1.3281 (rough estimate)
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
This chemical does not meet GHS hazard criteria for 96.8% (60 of 62) of all reports.
Not Classified
Aggregated GHS information provided per 62 reports by companies from 3 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
REACH registered substance: Thiamphenicol (EC: 239-355-3)
Acetamide, 2,2-dichloro-N-(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-4-(methylsulfonyl)phenylethyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazards SummaryOccupational asthma confirmed in three pharmaceutical workers; [Malo]
Hazard Classes and CategoriesNot Classified
Toxicology
Adverse EffectsAsthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents.
Safety data
- wgk
- 2
- rtecs
- AB6680000
- hs_code
- 29414000
- Toxicity
- human,TDLo,unreported,214mg/kg/10D (214mg/kg),BEHAVIORAL: SLEEPGASTROINTESTINAL: NAUSEA OR VOMITINGSKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE",Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 944, 1974.
Chemistry & industry
Pharmacology
ATC Code
J01BA02
J - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
QJ - Antiinfectives for systemic use
MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.
Uses & manufacturing
UsesAn antibiotic (analog of chloramphenicol); [ChemIDplus]
Use Classification
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Veterinary Drug -> ANTIMICROBIAL_AGENT -> JECFA Functional Classes
Pharmaceuticals -> Animal Drugs -> Approved in Taiwan
Applications
DescriptionThiamphenicol is a broad-spectrum antibiotic chloramphenicol, which is more effective to the gram-negative bacteria than the gram-positive bacteria. At room temperature, it is a white to off-white crystalline powder or crystal, which can be quickly and completely absorped by oral adminstration, as well as it is excreted mainly in the prototype from the urine for metabolism. It is clinically applied for the treatment of respiratory, urinary tract, liver and gallbladder, typhoid and other intestinal surgery, gynecology and ENT infections. Especially in the mild infections it is more effective. It has the similar chemical structure with the chloramphenicol. Its methyl sulfone substituted the nitro of chloramphenicol, which reduced its toxicity, and in vivo its antibacterial activity is 2.5-5 times stronger than chloramphenicol. For gram-positive bacteria, such as streptococcus pneumoniae and hemolytic streptococcus, it has very strong antibacterial effect, while for gram-negative bacteria, such as Neisseria gonorrhoeae, meningococcus, lung Bacteroides, E. coli, Vibrio cholerae, Shigella and influenza bacillus, it also has strong antibacterial effect. For anaerobic bacteria, Rickettsia and amoeba, it has antibacterial effect in some extent. It has the same antimicrobial mechanism with chloramphenicol, which mainly inhibits the synthesis of bacterial protein. This drug is absorped quickly by oral administration, which reaches peak blood concentration within two hours. Its half-life is 5 hours, that is more longer than chloramphenicol. The bacteria have complete cross resistance to it and chloramphenicol, while the bacteria have some cross-resistance phenomenon to it and tetracycline. Thiamphenicol also has strong immunosuppressive effects, which is an excellent immunosuppressant. Its mechanism of action have significantly different with other immunosuppressive agents. The immunosuppressive effect is several times higher than the chloramphenicol. It can be as the effective extender for transplantation reaction and surgically allogeneic transplantation.
Related reactions
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Compound notes
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