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Racephenicol

HCID 5433
NotesReactions
Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
15318-45-3
Standard SMILES
CS(=O)(=O)c1ccc(C(O)C(CO)NC(=O)C(Cl)Cl)cc1
InChIKey
OTVAEFIXJLOWRX-UHFFFAOYSA-N
Molecular formula
C12H15Cl2NO5S
Average molar mass
356.2 g/mol
Monoisotopic mass
355.0047991

Overview

See also: Thiamphenicol (related).

Names & identifiers

Preferred name
Racephenicol
IUPAC
2,2-dichloro-N-[1,3-dihydroxy-1-(4-methylsulfonylphenyl)propan-2-yl]acetamide
English name
Thiamphenicol
Molecular formula
C12H15Cl2NO5S
Molecular weight
356.22

Names & synonyms

RacefenicolRACEPHENICOLWin 5063Raceophenidol847-25-6RacefenicoloRacefenicolumWIN-5063Thiamphenicol DL-DTXSID401033713RefChem:930536DTXCID701518558
Show more names
thiophenicolD-THREO-2,2-DICHLORO-N-(BETA-HYDROXY-ALPHA-[HYDROXYMETHYL]-4-[METHYLSULFONYL]PHENETHYL)ACETAMIDENeomyson8065c.b.NSC 522822win-5063-2thiocymetinhiamphenicolSulfoxamycinTHIAMPHENICOL
283383NO13UrophenylFricolUnaseran-DDexawinThiamcolSW 50638065 C.B

Database identifiers

CAS
15318-45-3、7780-07-6
PubChem CID
5433
DTXSID
DTXSID10860157
ChEMBL
CHEMBL315338

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

Physicochemical properties

Melting point
163 · 163-166 °C
alpha
25 · D25 +12.9° (ethanol)
Density
1.3281 · 1.3281 (rough estimate)
refractive index
1.6 · 1.6000 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
50 mg/mL, · ethanol: 50 mg/mL, clear, colorless
form
powder
Boiling point
695.9 · 695.9±55.0 °C(Predicted)
pka
11.05 · 11.05±0.46(Predicted)
color
white to off-white
Water Solubility
Soluble in acetonitrile or DMF. Slightly soluble in water
Merck
14 · 14,9301
BRN
2819542 · 2819542
Major Application
clinical
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

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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.
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
22-24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
REACH Registrations
Active
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationSubstances that inhibit the growth or reproduction of BACTERIA.

Uses & manufacturing

Use ClassificationPharmaceuticals -> Antiinfectives for systemic use -> Antibiotics
Applications · 6 items

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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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
InChIKey
OTVAEFIXJLOWRX-NXEZZACHSA-N
SMILES
CS(=O)(=O)c1ccc(cc1)[C@@H](O)[C@@H](CO)NC(=O)C(Cl)Cl
CAS DataBase Reference
15318 · 15318-45-3
FDA UNII
7571 NPM · FLQ7571NPM
ATC code
1 BA02,J01BA52 · J01BA02,J01BA52
EPA Substance Registry System
Thiamphenicol (15318-45-3)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
Safety Statements
22 · 22-24/25
WGK Germany
2 · 2
RTECS
6680000 · AB6680000
HS Code
29414000 · 29414000
Storage Class
11 · 11 - Combustible Solids
Toxicity
214 mg/kg/10D · 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.
REACH Registrations
Active

UsesIt 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.

UsesAntimicrobial

Useschelating agent, antiseborrheic

UsesThiamphenicol 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.

UsesThiamphenicol 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.

Upstream & downstream products

Upstream raw materials

EthanolDichloroacetic acid methyl esterGlycine1-Methyl-4-(methylsulfonyl)-benzeneBromineHydrochloric acid1,3-Propanediol, 2-(2,2-diethoxyethyl)-,monoacetate,(R)-Peroxyacetic acidEthyl dichloroacetate

Suppliers101 total

北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
HONEST JOY HOLDINGS LIMITED[email protected]
江苏恒盛药业有限公司0512-58726293
爱斯特(成都)生物制药股份有限公司+86-28-85122536 85324413 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
上海瀚鸿科技股份有限公司021-54306202 13764082696 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
山东西亚化学有限公司13355009207 13355009207 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
湖南汇百侍生物科技有限公司0731-85526065 13308475853 · [email protected]
上海迪外化工科技有限公司021-61551100
斯百全化学(上海)有限公司021-021-021-67601398-809-809-809 15221380277 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
艾科试剂4008-755-333 18080918076 · [email protected]
上海思域化工科技有限公司86-21-34053660 · [email protected]
TOKYO CHEMICAL INDUSTRY CO., LTD.03-36680489 · [email protected]
深圳振强药物研发有限公司0755-66853366 13670046396 · [email protected]
南京杜莱生物技术有限公司025-84699383-8003;025-846993838003-8003 18013301590 · [email protected]
广州爱纯医药科技有限公司020-39119399 18927568969 · [email protected]
南京生利德生物科技有限公司025-57798810 18652991625 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
湖北鑫源顺医药化工有限公司13971561712, 13995564702, 027-50664929 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海将来实业股份有限公司021-61552785 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
四川省维克奇生物科技有限公司028-81700200 18116577057 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
上海孚一生物科技有限公司+86 (21) 61124340
凯试(上海)科技有限公司021-50135380 · [email protected]
天津阿尔塔科技有限公司022-6537-8550 15522853686 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
九鼎化学(上海)科技有限公司4009209199 · [email protected]
上海博景化工有限公司021-37199966 13681836088 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
成都润泽本土化工有限公司028-88469284 18000562381 · [email protected]
康幸生物科技(上海)有限公司021-61556450 15800904410
BOC Sciences16314854226 · [email protected]
北京华威锐科化工科技有限公司89508211 18501085097 · [email protected]
广州市齐云生物技术有限公司020-61288194 61288195 · [email protected]

Additional notes

DefinitionChEBI: Thiamphenicol is a sulfone and a monocarboxylic acid amide. It has a role as an immunosuppressive agent and an antimicrobial agent.