CAS 15318-45-3|Thiamphenicol

Introduction：Basic information about CAS 15318-45-3|Thiamphenicol, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Thiamphenicol BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Articles47
8. Synonyms

Common Name	Thiamphenicol
CAS Number	15318-45-3	Molecular Weight	356.222
Density	1.5±0.1 g/cm3	Boiling Point	695.9±55.0 °C at 760 mmHg
Molecular Formula	C₁₂H₁₅Cl₂NO₅S	Melting Point	163-166ºC
MSDS	ChineseUSA	Flash Point	374.7±31.5 °C

Names

Name	thiamphenicol
Synonym	More Synonyms

Thiamphenicol BiologicalActivity

Description	Thiamphenicol is an antimicrobial antibiotic and a methyl-sulfonyl analogue of chloramphenicol.Target: AntibacterialThiamphenicol (also known as thiophenicol and dextrosulphenidol) is an antibiotic. It is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Like chloramphenicol, it is insoluble in water, but highly soluble in lipids. It is used in many countries as a veterinary antibiotic, but is available in China, Morocco and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia. Thiamphenicol is a derivative of chloramphenicol characterized by a spectrum comparable to that of the parent compound against multiresistant pathogens but showing satisfactory tolerability. Thiamphenicol showed a significant PAE (0.33 to 2.9h) on all pathogens studied and a powerful bactericidal effect against beta-lactamase-positive and -negative H. influenzae. These results indicate a good in vitro activity of thiamphenicol against difficult-to-treat multiply resistant pathogens [1, 2].
Related Catalog	Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection
References	[1]. http://en.wikipedia.org/wiki/Thiamphenicol [2]. Marchese, A., et al., In vitro activity of thiamphenicol against multiresistant Streptococcus pneumoniae, Haemophilus influenzae and Staphylococcus aureus in Italy. J Chemother, 2002. 14(6): p. 554-61.

Description

Thiamphenicol is an antimicrobial antibiotic and a methyl-sulfonyl analogue of chloramphenicol.Target: AntibacterialThiamphenicol (also known as thiophenicol and dextrosulphenidol) is an antibiotic. It is the methyl-sulfonyl analogue of chloramphenicol and has a similar spectrum of activity, but is 2.5 to 5 times as potent. Like chloramphenicol, it is insoluble in water, but highly soluble in lipids. It is used in many countries as a veterinary antibiotic, but is available in China, Morocco and Italy for use in humans. Its main advantage over chloramphenicol is that it has never been associated with aplastic anaemia. Thiamphenicol is a derivative of chloramphenicol characterized by a spectrum comparable to that of the parent compound against multiresistant pathogens but showing satisfactory tolerability. Thiamphenicol showed a significant PAE (0.33 to 2.9h) on all pathogens studied and a powerful bactericidal effect against beta-lactamase-positive and -negative H. influenzae. These results indicate a good in vitro activity of thiamphenicol against difficult-to-treat multiply resistant pathogens [1, 2].

Related Catalog

Signaling Pathways >>Anti-infection >>BacterialResearch Areas >>Infection

References

[1]. http://en.wikipedia.org/wiki/Thiamphenicol

[2]. Marchese, A., et al., In vitro activity of thiamphenicol against multiresistant Streptococcus pneumoniae, Haemophilus influenzae and Staphylococcus aureus in Italy. J Chemother, 2002. 14(6): p. 554-61.

Chemical & Physical Properties

Density	1.5±0.1 g/cm3
Boiling Point	695.9±55.0 °C at 760 mmHg
Melting Point	163-166ºC
Molecular Formula	C₁₂H₁₅Cl₂NO₅S
Molecular Weight	356.222
Flash Point	374.7±31.5 °C
Exact Mass	355.004791
PSA	112.08000
LogP	-0.27
Vapour Pressure	0.0±2.3 mmHg at 25°C
Index of Refraction	1.583
InChIKey	OTVAEFIXJLOWRX-NXEZZACHSA-N
SMILES	CS(=O)(=O)c1ccc(C(O)C(CO)NC(=O)C(Cl)Cl)cc1

Toxicological Information

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

Safety Information

Personal Protective Equipment	Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes	Xn
Safety Phrases	22-24/25
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	AB6680000
HS Code	2941400000

Customs

HS Code	2924299090
Summary	2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles47

Cheminformatics analysis of assertions mined from literature that describe drug-induced liver injury in different species.

Chem. Res. Toxicol. 23 , 171-83, (2010)

Drug-induced liver injury is one of the main causes of drug attrition. The ability to predict the liver effects of drug candidates from their chemical structures is critical to help guide experimental...

Multiresidue method for the determination of pharmacologically active substances in egg and honey using a continuous solid-phase extraction system and gas chromatography-mass spectrometry.

Food Chem. 178 , 63-9, (2015)

A sensitive, selective, efficient gas chromatography-mass spectrometry method for the simultaneous determination of 22 pharmacologically active substances (antibacterials, nonsteroidal antiinflammator...

Fast extraction of amphenicols residues from raw milk using novel fabric phase sorptive extraction followed by high-performance liquid chromatography-diode array detection.

Anal. Chim. Acta 855 , 41-50, (2014)

A simple, sensitive, reliable, and fast analytical method was developed for the simultaneous determination of amphenicols residues in raw milk by combining fabric phase sorptive extraction (FPSE) and ...

Synonyms

2,2-Dichloro-N-[(1R,2R)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propyl]acetamide

8065c.b.

thiophenicol

D-Thiocymetin

EINECS 239-355-3

MFCD00467983

thiocymetin

D-Thiophenicol

win-5063-2

Acetamide, 2,2-dichloro-N-[(1S,2S)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-

2,2-Dichloro-N-{(1S,2S)-1,3-dihydroxy-1-[4-(methylsulfonyl)phenyl]-2-propanyl}acetamide

Neomyson

ThiaMphenicol

Dextrosulphenidol

THIAMPHENICHOL

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