Thiamphenicol

Iupac Name：2,2-dichloro-N-[(1R,2R)-1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide

Molecular Weight：356.2222

Modify Date.: 2022-10-31 22:22

Introduction: Thiamphenicol 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. View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: Thiamphenicol
1.2 Synonyms: 2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propyl]acetamide 2,2-Dichloro-N-{(1S,2S)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propanyl}acetamide 8065c.b. Acetamide, 2,2-dichloro-N-(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-4-(methylsulfonyl)phenylethyl- Acetamide, 2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]- (9CI) Acetamide, 2,2-dichloro-N-[(1S,2S)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]- Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-, [R-(R*,R*)]- Dextrosulphenidol D-Thiocymetin D-Thiophenicol D-THREO-2,2-DICHLORO-N-(BETA-HYDROXY-ALPHA-[HYDROXYMETHYL]-4-[METHYLSULFONYL]PHENETHYL)ACETAMIDE d-threo-2,2-dichloro-n-(β-hydroxy-α-[hydroxymethyl]-4-[methylsulfonyl]phenethyl)acetamide D-THREO-2,2-DICHLORO-N-[BETA-HYDROXY-ALPHA-(HYDROXYMETHYL)-P-(METHYL-SULFONYL)PHENETHYL]ACETAMIDE EINECS 239-355-3 methylsulfonyl chloramphenicol MFCD00467983 Neomyson THIAMPHENICHOL thiocymetin thiophenicol win-5063-2

1.3 CAS No.: 15318-45-3

1.4 CID: 27200

1.5 EINECS(EC#): 239-355-3

1.6 Molecular Formula: C12H15Cl2NO5S (isomer)

1.7 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

1.8 InChkey: OTVAEFIXJLOWRX-NXEZZACHSA-N

1.9 Canonical Smiles: CS(=O)(=O)C1=CC=C(C=C1)C(C(CO)NC(=O)C(Cl)Cl)O

1.10 Isomers Smiles: CS(=O)(=O)C1=CC=C(C=C1)[C@H]([C@@H](CO)NC(=O)C(Cl)Cl)O

2. Properties

2.1 Density: 1.491

2.1 Melting point: 163-166?°C

2.1 Boiling point: 695.9°Cat760mmHg

2.1 Refractive index: 1.589

2.1 Flash Point: 374.7°C

2.1 Precise Quality: 355.00500

2.1 PSA: 112.08000

2.1 logP: 1.87600

2.1 Solubility: ethanol: 50?mg/mL, clear, colorless

2.2 Appearance: off-white solid

2.3 Storage: Ambient temperatures.

2.4 Color/Form: Powder

2.5 pKa: 11.05±0.46(Predicted)

2.6 Water Solubility: Slightly soluble

2.7 Stability: Stable at normal temperatures and pressures.

2.8 StorageTemp: Sealed in dry,Room Temperature

3. Use and Manufacturing

3.1 Purification Methods: Recrystallise thiamphenicol from H2O or CHCl3. The UV has max at 224, 266 and 274nm ( 13,700, 800 and 700) in 95% EtOH. The 1S,2S-isomer [1478651-7] has m 164.3-166.3o (from H2O/EtOAc/pet ether) and [] D 25 -12.6o (c 1, EtOH); and the racemate 1RS,2RS-Racefenical [847-25-6] has m 181-183o (dec) from CHCl3/EtOAc/pet ether. [Cutler et al. J Am Chem Soc 74 5475, 5482 1952, UV: Nachod & Cutler J Am Chem Soc 74 1291 1952, Suter et al. J Am Chem Soc 75 4330 1953, Cutler et al. J Am Pharm Assoc 43 687 1954, Beilstein 13 IV 2957.] Thiamphenicol Preparation Products And Raw materials Raw materials

3.2 Usage: It is 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.

4. Safety and Handling

4.1 Risk Statements: 22-24/25

4.1 Safety Statements: 22-24/25

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 2

4.1 RTECS: AB6680000

4.1 Safety: Poison by intravenous route. Moderately toxic by subcutaneous route. Mildly toxic by ingestion. Human systemic effects by an unspecified route: sleep disorders, dermatitis, nausea or vomiting. An experimental teratogen. Experimental reproductive effects. When heated to decomposition it emits very toxic fumes of SOx, NOx, and Cl?. See also CHLORAMPHENICOL.

4.2 Toxicity

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AB6680000

CHEMICAL NAME :: Acetamide, 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p- (methylsulfonyl)phene thyl)-, D-threo-(+)

CAS REGISTRY NUMBER :: 15318-45-3

LAST UPDATED :: 199806

DATA ITEMS CITED :: 16

MOLECULAR FORMULA :: C12-H15-Cl2-N-O5-S

MOLECULAR WEIGHT :: 356.24

WISWESSER LINE NOTATION :: WS1&R DYQY1QMVYGG

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Human

DOSE/DURATION :: 214 mg/kg/10D

TOXIC EFFECTS :: Behavioral - sleep Gastrointestinal - nausea or vomiting Skin and Appendages - dermatitis, other (after systemic exposure)

REFERENCE :: ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 24,944,1974

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: -,740,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 339 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >7 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >5 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 368 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,390,1969 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3724 mg/kg/4W-C

TOXIC EFFECTS :: Gastrointestinal - alteration in gastric secretion Blood - hemorrhage Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 91,137,1997

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1583 mg/kg/13W-C

TOXIC EFFECTS :: Liver - changes in liver weight Blood - pigmented or nucleated red blood cells Blood - changes in erythrocyte (RBC) count

REFERENCE :: TOLED5 Toxicology Letters. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1977- Volume(issue)/page/year: 91,137,1997 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 300 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 7,41,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 150 mg/kg

SEX/DURATION :: female 9-14 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 7,41,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 400 mg/kg

SEX/DURATION :: female 1-7 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Fertility - litter size (e.g. # fetuses per litter; measured before birth)

REFERENCE :: FESTAS Fertility and Sterility. (American Fertility Soc., 608 13th Ave. S, Birmingham, AL 35282) V.1- 1950- Volume(issue)/page/year: 21,431,1970

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

DOSE :: 400 mg/kg

SEX/DURATION :: female 10-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: TJADAB Teratology, The International Journal of Abnormal Development. (Alan R. Liss, Inc., 41 E. 11th St., New York, NY 10003) V.1- 1968- Volume(issue)/page/year: 18,93,1978

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Unreported

DOSE :: 250 mg/kg

SEX/DURATION :: female 10-11 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: NSAPCC Naunyn-Schmiedeberg's Archives of Pharmacology. (Springer Verlag, Heidelberger, Pl. 3, D-1000 Berlin 33, Fed. Rep. Ger.) V.272- 1972- Volume(issue)/page/year: 293(Suppl),R60,1976

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 2400 mg/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 7,41,1973

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 6 gm/kg

SEX/DURATION :: female 7-12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 7,41,1973

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

15318-45-3Total: 32 Synthesis Route

4302-89-0

15318-45-3 240 Suppliers

Literatures:
Davis, Franklin A.; Portonovo, Padma S.; Reddy, Rajarathnam E.; Reddy, G. Venkat; Zhou, Ping Phosphorus, Sulfur and Silicon and Related Elements, 1997 , vol. 120-121, p. 291 - 303
Yield: ~89%

5398-77-6 112 Suppliers

15318-45-3 240 Suppliers

Literatures:
Chinese Journal of Chemistry, , vol. 31, # 1 p. 149 - 153
Yield: null

3446-89-7 96 Suppliers

15318-45-3 240 Suppliers

Literatures:
Tetrahedron, , vol. 62, # 43 p. 10202 - 10207
Yield: null

View all

8. Precursor and Product

precursor:

160751-25-7

160751-27-9

108656-29-7

4302-89-0

914646-16-5

1424361-00-1

160751-26-8

3446-89-7

701935-65-1

912296-97-0

912296-98-1

38423-42-6

701935-64-0

96795-20-9

256475-83-9

23150-33-6

51458-28-7

5398-77-6

96795-22-1

96795-21-0

23150-35-8

914646-18-7

108656-28-6

108656-26-4

View all

9. Other Information

9.0 Merck: 14,9301

9.1 BRN: 2819542

9.2 Description: Thiamphenicol 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.

9.3 Uses: It is 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.

9.4 Chemical Properties: Off-White Solid

9.5 Uses: Antimicrobial

9.6 Uses: chelating agent, antiseborrheic

9.7 Uses: Thiamphenicol is an antibiotic. Thiamphenicol is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Thiamphenicol is used particul arly for the treatment of sexually transmitted infections and pelvic inflammatory disease.

9.8 Uses: Thiamphenicol is a semi-synthetic chloramphenicol prepared by total synthesis from thiophenol in which the nitro moiety of chloramphenicol is replaced by a methylsulphone, first synthesised at Sterling Winthrop in 1952. Thiamphenicol is a broad spectrum antibiotic with good activity against Gram negative and anaerobic bacteria. Thiamphenicol acts by binding to the 23S sub-unit of the 50S ribosome inhibiting protein synthesis. Thiamphenicol has been extensively studied with over 800 literature citations.

9.9 Antimicrobial activity: It is generally less active than chloramphenicol, but is equally active against Str. pyogenes, Str. pneumoniae, H. influenzae and N. meningitidis, including some strains resistant to chloramphenicol. It is more actively bactericidal against Haemophilus and Neisseria spp.

9.10 Acquired resistance: There is complete cross-resistance with chloramphenicol in those bacteria which elaborate acetyltransferase, although the affinity of the enzyme for thiamphenicol is lower. Organisms that owe their resistance to other mechanisms may be susceptible.

9.11 Clinical Use: Similar to that of chloramphenicol.

9.12 Side effects: There are no reports of irreversible bone-marrow toxicity. This has been related to the absence of the nitro group, and hence its reduction products, and differences in the biochemical effects of thiamphenicol and chloramphenicol on mammalian cells. It exerts a greater dose-dependent reversible depression of hemopoiesis and immunogenesis than chloramphenicol, and has been used for its immunosuppressive effect. Therapeutic doses (1–1.5 g) are likely to depress erythropoiesis in the elderly or others with impaired renal function.

9.13 Purification Methods: Recrystallise thiamphenicol from H2O or CHCl3. The UV has max at 224, 266 and 274nm ( 13,700, 800 and 700) in 95% EtOH. The 1S,2S-isomer [1478651-7] has m 164.3-166.3o (from H2O/EtOAc/pet ether) and [] D 25 -12.6o (c 1, EtOH); and the racemate 1RS,2RS-Racefenical [847-25-6] has m 181-183o (dec) from CHCl3/EtOAc/pet ether. [Cutler et al. J Am Chem Soc 74 5475, 5482 1952, UV: Nachod & Cutler J Am Chem Soc 74 1291 1952, Suter et al. J Am Chem Soc 75 4330 1953, Cutler et al. J Am Pharm Assoc 43 687 1954, Beilstein 13 IV 2957.]

9.14 体外研究: Thiamphenicol shows a significant post-antibiotic effect (PAE) (0.33 to 2.9h) on all pathogens studied ( S. pneumoniae , S. aureus and Escherichia coli ) and a powerful bactericidal effect against β-lactamase-positive and -negative H. influenzae . Thiamphenicol MICs for the microorganisms analyzed are: 32 mg/L ( S. aureus and E. coli ), 2 mg/L ( S. pneumoniae ) and 0.25 mg/L ( H. influenzae ). Thiamphenicol shows a good in vitro activity against difficult-to-treat multiply resistant pathogens.

9.15 体内研究: The pharmacokinetics of Thiamphenicol (30 mg/kg) after single intravenous (IV) and oral (PO) administration is investigated in Mulard ducks. After IV administration, for Thiamphenicol, the mean residence time is 2.83 hours, the general half-life is 1.96 hours, the clearance is 0.04 L/hr/kg. Pharmacokinetics after PO administration is very similar for IV administration. Thiamphenicol shows rapid absorption and bioavailability of more than 70%.

9.16 Originator: Thiophenicol,Clin Midy,France,1967

9.17 Manufacturing Process: A mixture of 50 parts by weight of racemic 2-acetylamino-1-(4- methylmercaptophenyl)-1,3-propanediol, 100 parts by weight of concentrated hydrochloric acid, and 500 parts by weight of water was warmed on a steam bath for thirty minutes. The resulting solution was cooled to about 40°C and was then made strongly alkaline by addition of 35% aqueous sodium hydroxide solution. The alkaline solution was then refrigerated. The white solid which separated from the cooled solution was collected on a filter. There was thus obtained 27 parts by weight of 2-amino-1-(4-methylmercaptophenyl)- 1,3-propanediol. This product melted at 130.7°C to 131.9°C after recrystallization from methanol.
This compound was converted to the tartrate and the optical isomers were resolved.
A mixture of 1.1 g of 2-amino-1-(4-methylmercaptophenyl)-1,3-propanediol, obtained as described above and 1.6 ml of ethyl dichloroacetate was heated on a steam bath for three hours. The resulting viscous yellow oil was dissolved in 25 ml of ethylene chloride and filtered hot with charcoal, and the filtrate was allowed to cool to about 25°C. From the filtrate there separated 0.92 g of tiny white leaflets which were collected on a filter. Recrystallization of this product, which was a dextro-rotary form of 2-dichloroacetylamino-1-(4- methylmercaptophenyl)-1,3-propanediol from nitroethane yielded the pure product, which melted at 111.6°C to 112.6°C.
7 g of the 2-dichloroacetylamino-1-(4-methylmercaptophenyl)-1,3-propanediol obtained as described above was dissolved in 30 ml of acetone. To this solution there was added dropwise with stirring 10 ml of 40% peracetic acid. The temperature during the reaction was maintained at 39°C to 45°C by cooling the reaction vessel. After stirring the mixture for two hours, it was diluted with 100 ml of water and the solution allowed to stand over the weekend in the refrigerator. The solid which separated from solution was collected on a filter, washed several times with ice water, and dried overnight at 70°C.

9.18 Therapeutic Function: Antibacterial

9.19 Usage: Thiamphenicol is used to treat chancroid in men and uncomplicated gonorrhea. It is used in studies of bacterial protein synthesis at the level of peptidyl transferase activity associated with the 23S rRNA of the 50S ribosomal subunit. It is used to study chloraniphenicol-thiamphenicol-resistance and the use of fluorinated analogs when resistance is encountered. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia.

10. Computational chemical data

Molecular Weight: 356.2222g/mol
Molecular Formula: C₁₂H₁₅Cl₂NO₅S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 355.0047991
Monoisotopic Mass: 355.0047991
Complexity: 443
Rotatable Bond Count: 6
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 112
Heavy Atom Count: 21
Defined Atom Stereocenter Count: 2
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccByOABGAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAHgYQCAAADD/h2MayAYLAAgqIAiFSEHBCAAAgCBAIiJgICIhKNiKgkRHEcAAl1gGYmAeQwKAOEAAAAAAAAAAgAAAAAAAAAAAAAAAAAA==

11. Recommended Suppliers

Global232SuppliersView all >>

Hebei Yingong New Material Technology Co.,Ltd. Diamond member

-120YR

Products:xylazine hcl,phenacetin,4-Methylpropiophenone,(2-Bromoethyl)benzene,4-Methoxybenzoyl chloride
Tel:86-311-19930599843
Email:cindy@hbyingong.com

China supply Thiamphenicol CAS 15318-45-3 with low price