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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H18Cl2N2O6S.ClH
Molecular Weight 449.734
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THIAMPHENICOL AMINOACETATE HYDROCHLORIDE

SMILES

Cl.CS(=O)(=O)C1=CC=C(C=C1)[C@@H](O)[C@@H](COC(=O)CN)NC(=O)C(Cl)Cl

InChI

InChIKey=DKXJDBJNAXSJDH-MHDYBILJSA-N
InChI=1S/C14H18Cl2N2O6S.ClH/c1-25(22,23)9-4-2-8(3-5-9)12(20)10(7-24-11(19)6-17)18-14(21)13(15)16;/h2-5,10,12-13,20H,6-7,17H2,1H3,(H,18,21);1H/t10-,12-;/m1./s1

HIDE SMILES / InChI
Molecular Formula C14H18Cl2N2O6S
Molecular Weight 413.274
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15224555 and https://www.drugs.com/international/urfamycin.html

Thiamphenicol aminoacetate 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. It is used in many countries as a veterinary antibiotic, but is available in China, Morocco and Italy for use in humans. Thiamphenicol aminoacetate is reported as an ingredient of Urfamycin in Ecuador, Indonesia, Italy, Taiwan, Thailand, Turkey, Japan. It is indicated for the treatment of GUT, hepatobiliary, respiratory tract, enteric tract infections, typhoid, paratyphoid fever and salmonellosis, brucellosis.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Neisseria gonorrhoeae growth
2
Target ID: Neisseria gonorrhoeae growth
Inhibitor
8504
Moraxella catarrhalis growth
2
Target ID: Moraxella catarrhalis growth
Inhibitor
8504
Streptococcus pneumoniae growth
20
Target ID: Streptococcus pneumoniae growth
Inhibitor
8504
Haemophilus influenzae growth
4
Target ID: Haemophilus influenzae growth
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8583
Urfamycin

Approved Use

GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.
Curative
Approved
8583
Urfamycin

Approved Use

GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.
Curative
Approved
8583
Urfamycin

Approved Use

GUT, hepatobiliary, resp tract, enteric tract infections, typhoid, paratyphoid fever & salmonellosis, brucellosis.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
26.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
38.1 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
66.1 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
30.4 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
53.2 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
78.5 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
18.58 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
29.56 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
849.1 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
1305.2 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
2315.9 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
4509 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
7506.5 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
12613.3 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
234.1 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4114.2 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
THIAMPHENICOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
17.6 min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg single, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
16.8 min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1000 mg single, intravenous
dose: 1000 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
16.8 min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
1500 mg single, intravenous
dose: 1500 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
20.7 min
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/24597465/
500 mg 2 times / day multiple, intravenous
dose: 500 mg
route of administration: Intravenous
experiment type: MULTIPLE
co-administered:
THIAMPHENICOL AMINOACETATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
80%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/7394975/
THIAMPHENICOL unknown
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
2 g single, intraperineal
Highest studied dose
Dose: 2 g
Route: intraperineal
Route: single
Dose: 2 g
Sources:
https://pubmed.ncbi.nlm.nih.gov/7394975/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/7394975/
Sources:
https://pubmed.ncbi.nlm.nih.gov/7394975/
631 mg 2 times / day multiple, respiratory
Studied dose
Dose: 631 mg, 2 times / day
Route: respiratory
Route: multiple
Dose: 631 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
Disc. AE: Asthma, Nausea...
AEs leading to
discontinuation/dose reduction:
Asthma (1.1%)
Nausea (3.4%)
Vomiting (3.4%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
AEs

AEs

AESignificanceDosePopulation
Asthma 1.1%
Disc. AE
631 mg 2 times / day multiple, respiratory
Studied dose
Dose: 631 mg, 2 times / day
Route: respiratory
Route: multiple
Dose: 631 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
Nausea 3.4%
Disc. AE
631 mg 2 times / day multiple, respiratory
Studied dose
Dose: 631 mg, 2 times / day
Route: respiratory
Route: multiple
Dose: 631 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
Vomiting 3.4%
Disc. AE
631 mg 2 times / day multiple, respiratory
Studied dose
Dose: 631 mg, 2 times / day
Route: respiratory
Route: multiple
Dose: 631 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/12120883/
PubMed

PubMed

TitleDatePubMed
Comparative in vitro activity of thiamphenicol-glycinate and thiamphenicol-glycinate-acetylcysteinate and other antimicrobials against respiratory pathogens.
2001
[Re-evaluation of single-dose treatment with thiamphenicol and spectinomycin of uncomplicated male gonococcal urethritis].
1987
Patents

Patents

US2013137099
2

Sample Use Guides

In Vivo Use Guide
Adult 500 mg 8 hrly. Childn 20-30 mg/kg/day. Gonorrhea 2.5 g/day for 1-2 days.
Route of Administration: Oral
In Vitro Use Guide
THIAMPHENICOL AMINOACETATE inhibited M. catarrhalis with MIC90 0.5 ug/ml
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:46:23 GMT 2025
Edited
by admin
on Mon Mar 31 17:46:23 GMT 2025
Record UNII
88VGC22BWE
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLYCINE, (2R,3R)-2-((2,2-DICHLOROACETYL)AMINO)-3-HYDROXY-3-(4-(METHYLSULFONYL)PHENYL)PROPYL ESTER, HYDROCHLORIDE (1:1)
Preferred Name English
THIAMPHENICOL AMINOACETATE HYDROCHLORIDE
JAN   WHO-DD  
Common Name English
THIAMPHENICOL GLYCINATE HYDROCHLORIDE
Common Name English
Thiamphenicol aminoacetate hydrochloride [WHO-DD]
Common Name English
THIAMPHENICOL AMINOACETATE HYDROCHLORIDE [JAN]
Common Name English
Code System Code Type Description
SMS_ID
100000079926
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
EVMPD
SUB04802MIG
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
ChEMBL
CHEMBL1236282
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
FDA UNII
88VGC22BWE
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
EPA CompTox
DTXSID6023650
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
ECHA (EC/EINECS)
220-033-6
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
PUBCHEM
197006
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
CAS
2611-61-2
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
EVMPD
SUB16147MIG
Created by admin on Mon Mar 31 17:46:23 GMT 2025 , Edited by admin on Mon Mar 31 17:46:23 GMT 2025
PRIMARY
NIH
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