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Thiamphenicol

Thiamphenicol structure

CAS No:
15318-45-3
Formula:
C12H15Cl2NO5S
Chemical Name:
Thiamphenicol
Synonyms:
Acetamide,2,2-dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-;Acetamide,2,2-dichloro-N-[β-hydroxy-α-(hydroxymethyl)-p-(methylsulfonyl)phenethyl]-,D-threo-(+)-;Acetamide,2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]-,[R-(R*,R*)]-;2,2-Dichloro-N-[(1R,2R)-2-hydroxy-1-(hydroxymethyl)-2-[4-(methylsulfonyl)phenyl]ethyl]acetamide;(Methylsulfonyl)chloramphenicol;8065CB;Win 5063-2;Dextrosulphenidol;D-d-threo-2-Dichloroacetamido-1-(4-methylsulfonylphenyl)-1,3-propanediol;Thiamphenicol;D-Thiocymetin;D-Thiophenicol;Thiocymetin;Thiophenicol;D-threo-(1R,2R)-1-(p-Methylsulfonylphenyl)-2-dichloroacetamido-1,3-propanediol;(+)-Thiamphenicol;NSC 522822;Tirsan;(2′R,3′R)-Thiamphenicol;90-91-5;3785-14-6;14786-51-7;32430-04-9
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

White to off-white crystalline powder or crystal. Melting point (℃) 178-180 (swirled), 164-166 (right-handed). Off-White SolidThiamphenicol 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 metabo

Thiamphenicol is a sulfone and a monocarboxylic acid amide. It has a role as an immunosuppressive agent and an antimicrobial agent.|A methylsulfonyl analog of CHLORAMPHENICOL. It is an antibiotic and immunosuppressive agent.

Thiamphenicol Basic Attributes

Molecular Weight：

356.22200

Exact Mass：

356.22

EC Number：

239-355-3

UNII：

FLQ7571NPM

NSC Number：

758396

DSSTox ID：

DTXSID5021338

ATC Code：

J01BA02|J - Antiinfectives for systemic use

HScode：

2941400000

Characteristics

PSA：

112.08000

XLogP3：

-0.3

Appearance：

off-white solid

Density：

1.55 g/cm³

Melting Point：

165.3 °C

Boiling Point：

695.9ºC at 760mmHg

Flash Point：

374.7ºC

Refractive Index：

1.589

Water Solubility：

ethanol: 50 mg/mL, clear, colorless

Collision Cross Section：

170.7 Å² [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]|179.09 Å² [M-H]-

Safety Information

Transport codes：

NONH for all modes of transport

wgk germany：

safety instructions：

S22; S24/25

RTECS Number：

AB6680000

Stability/Shelf Life：

Stable at normal temperatures and pressures.

Precautionary statement(s)：

P201, P202, P260, P261, P263, P264, P270, P271, P272, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, P501

Hazard Statements：

H315

GHS Classification：

|Warning|H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P261, P263, P264, P270, P271, P272, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P332+P313, P333+P313, P337+P313, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 8 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)

MeSH Entry Terms：

Dextrosulfenidol

Thiamphenicol Use and Manufacturing

Uses

1. Antimicrobial.
2. Chelating agent, antiseborrheic.
3. 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 particularly for the treatment of sexually transmitted infections and pelvic inflammatory disease.
4. 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.

Use Classification：

Pharmaceuticals -> Animal Drugs -> Approved in Taiwan

Food Additive Classes：

Veterinary Drug -> ANTIMICROBIAL_AGENT;

Computed Properties

Molecular Weight:356.2
XLogP3:-0.3
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:6
Exact Mass:355.0047991
Monoisotopic Mass:355.0047991
Topological Polar Surface Area:112
Heavy Atom Count:21
Complexity:443
Defined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Material

Glycine

Ethanol

Drug Function and Efficacy

This product is a congener of chloramphenicol. Its antibacterial spectrum and antibacterial effect are similar to those of chloramphenicol. It has a broad-spectrum antimicrobial effect, including aerobic Gram-negative and Gram-positive bacteria, anaerobic bacteria, Rickettsia, spirochetes and Chlamydia. It has bactericidal effects on Haemophilus influenzae, Streptococcus pneumoniae and Neisseria meningitidis; it only has antibacterial effects on anaerobic bacteria such as Staphylococcus aureus, Streptococcus pyogenes, Streptococcus viridans, Group B hemolytic Streptococcus, Escherichia coli, Klebsiella pneumoniae, Proteus mirabilis, Salmonella typhi, Salmonella paratyphi, Shigella, Bacteroides fragilis, etc. Pseudomonas aeruginosa, Acinetobacter, Enterobacter, Serratia marcescens, indole-positive Proteus, methicillin-resistant Staphylococcus and Enterococcus are usually resistant to chloramphenicol. This product is an antibacterial agent, which reversibly binds to the 50S subunit of bacterial ribosomes, inhibits the action of transpeptidase, prevents the formation of peptide chains, and thus prevents the synthesis of proteins. It is completely cross-resistant with chloramphenicol. Since thiamphenicol does not bind to glucuronic acid in the liver, it has a high antibacterial activity in vivo. This product also has a strong immunosuppressive effect, which is about 6 times stronger than chloramphenicol.

This ingredient has been used in drugs with the following functions (note: it does not mean that the ingredient itself has the following health functions)

Related Drugs

Thiamphenicol Capsules
Ingredients	Thiamphenicol
Indication	1. Antiepileptic drugs (hydantoins). Since this product can inhibit the activity of liver cell microsomal enzymes, resulting in reduced metabolism of such drugs, or replace the serum protein binding sites of such drugs, it can enhance the effect of the drugs or increase their toxicity. Therefore, when used in combination with this product or after it, the dosage of such drugs must be adjusted. 2. When used in combination with hypoglycemic drugs (such as tolbutamide), the hypoglycemic effect can be enhanced due to the replacement of protein binding sites, so the dosage of such drugs needs to be adjusted. The non-ionic binding characteristics of glipizide and glyburide make them less affected than other oral hypoglycemic drugs, but caution is still required when used in combination. 3. Long-term oral contraceptives containing estrogen, if taken at the same time as this product, can reduce the reliability of contraception and increase menstrual bleeding. 4. Since this product can have the effect of vitamin B6 antagonists or increase the renal excretion of the latter, leading to anemia or peripheral neuritis, the body's need for the former increases when vitamin B6 is used in combination with this product. 5 Chloramphenicol can antagonize the hematopoietic effect of vitamin B12, so the two should not be used together. 6 When used in combination with certain bone marrow suppressive drugs, it can enhance the bone marrow suppressive effect, such as anti-tumor drugs, colchicine, hydroxyphenylbutazone, phenylbutazone and penicillamine. When radiotherapy is performed at the same time, it can also enhance the bone marrow suppressive effect, and the dose of bone marrow suppressants or radiotherapy must be adjusted. 7 If used before or during surgery, due to the inhibitory effect of this product on liver enzymes, it can reduce the clearance of the induced anesthetic alfentanil and prolong its duration of action. 8 When liver enzyme inducers such as phenobarbital and rifampicin are used in combination with this product, their metabolism can be enhanced, resulting in a decrease in blood drug concentration. 9 Antagonism may occur when used in combination with macrolide antibiotics such as lincomycin or erythromycin, so it is not suitable for combined use.
Specifications	0.25g
Manufacturer	China Resources 39 (Beijing) Pharmaceutical Co., Ltd.

Thiamphenicol Capsules
Ingredients	The main component of this product is thiamphenicol, and its chemical name is [R-(R,R)]N-[1-(hydroxymethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl]2,2,-dichloroacetamide. Its structural formula is: Molecular formula: C12H15Cl2NO5S, molecular weight: 356.23.
Indication	1. Antiepileptic drugs (hydantoins). Since this product can inhibit the activity of liver cell microsomal enzymes, resulting in reduced metabolism of such drugs, or replace the serum protein binding sites of such drugs, it can enhance the effect of the drugs or increase their toxicity. Therefore, when used in combination with this product or after it, the dosage of such drugs must be adjusted. 2. When used in combination with hypoglycemic drugs (such as tolbutamide), the hypoglycemic effect can be enhanced due to the replacement of protein binding sites, so the dosage of such drugs needs to be adjusted. The non-ionic binding characteristics of glipizide and glyburide make them less affected than other oral hypoglycemic drugs, but caution is still required when used in combination. 3. Long-term oral contraceptives containing estrogen, if taken at the same time as this product, can reduce the reliability of contraception and increase menstrual bleeding. 4. Since this product can have the effect of vitamin B6 antagonists or increase the renal excretion of the latter, leading to anemia or peripheral neuritis, the body's need for the former increases when vitamin B6 is used in combination with this product. 5 Chloramphenicol can antagonize the hematopoietic effect of vitamin B12, so the two should not be used together. 6 When used in combination with certain bone marrow suppressive drugs, it can enhance the bone marrow suppressive effect, such as anti-tumor drugs, colchicine, hydroxyphenylbutazone, phenylbutazone and penicillamine. When radiotherapy is performed at the same time, it can also enhance the bone marrow suppressive effect, and the dose of bone marrow suppressants or radiotherapy must be adjusted. 7 If used before or during surgery, due to the inhibitory effect of this product on liver enzymes, it can reduce the clearance of the induced anesthetic alfentanil and prolong its duration of action. 8 When liver enzyme inducers such as phenobarbital and rifampicin are used in combination with this product, their metabolism can be enhanced, resulting in a decrease in blood drug concentration. 9 Antagonism may occur when used in combination with macrolide antibiotics such as lincomycin or erythromycin, so it is not suitable for combined use.
Specifications	0.25g
Manufacturer	Yichang Humanwell Pharmaceutical Co., Ltd.

Thiamphenicol Capsules
Ingredients	The main ingredient of this product is thiamphenicol. Chemical name: [R-(R,R)]N-﹛1-(hydroxymethyl)-2-hydroxy-2-[4-(methylsulfonyl)phenyl]ethyl﹜-2,2-dichloroacetamide.
Indication	1. Antiepileptic drugs (hydantoins). Since this product can inhibit the activity of liver cell microsomal enzymes, resulting in reduced metabolism of such drugs, or replace the serum protein binding sites of such drugs, it can enhance the effect of the drugs or increase their toxicity. Therefore, when used in combination with this product or after it, the dosage of such drugs must be adjusted. 2. When used in combination with hypoglycemic drugs (such as tolbutamide), the hypoglycemic effect can be enhanced due to the replacement of protein binding sites, so the dosage of such drugs needs to be adjusted. The non-ionic binding characteristics of glipizide and glyburide make them less affected than other oral hypoglycemic drugs, but caution is still required when used in combination. 3. Long-term oral contraceptives containing estrogen, if taken at the same time as this product, can reduce the reliability of contraception and increase menstrual bleeding. 4. Since this product can have the effect of vitamin B6 antagonists or increase the renal excretion of the latter, leading to anemia or peripheral neuritis, the body's need for the former increases when vitamin B6 is used in combination with this product. 5 Chloramphenicol can antagonize the hematopoietic effect of vitamin B12, so the two should not be used together. 6 When used in combination with certain bone marrow suppressive drugs, it can enhance the bone marrow suppressive effect, such as anti-tumor drugs, colchicine, hydroxyphenylbutazone, phenylbutazone and penicillamine. When radiotherapy is performed at the same time, it can also enhance the bone marrow suppressive effect, and the dose of bone marrow suppressants or radiotherapy must be adjusted. 7 If used before or during surgery, due to the inhibitory effect of this product on liver enzymes, it can reduce the clearance of the induced anesthetic alfentanil and prolong its duration of action. 8 When liver enzyme inducers such as phenobarbital and rifampicin are used in combination with this product, their metabolism can be enhanced, resulting in a decrease in blood drug concentration. 9 Antagonism may occur when used in combination with macrolide antibiotics such as lincomycin or erythromycin, so it is not suitable for combined use.
Specifications	0.25g

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Registered Holders

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China
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