Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C17H30N2O7 |
Molecular Weight | 374.4293 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12O[C@H](CCCC)CC(=O)[C@]1(O)O[C@]3([H])[C@@H](NC)[C@@H](O)[C@@H](NC)[C@H](O)[C@@]3([H])O2
InChI
InChIKey=KHAUBYTYGDOYRU-IRXASZMISA-N
InChI=1S/C17H30N2O7/c1-4-5-6-8-7-9(20)17(23)16(24-8)25-15-13(22)10(18-2)12(21)11(19-3)14(15)26-17/h8,10-16,18-19,21-23H,4-7H2,1-3H3/t8-,10-,11+,12+,13+,14-,15-,16+,17+/m1/s1
Molecular Formula | C17H30N2O7 |
Molecular Weight | 374.4293 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 9 / 9 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Trospectomycin is an aminocyclitol antibiotic similar in structure to spectinomycin. The drug was originally developed by Pharmacia & Upjohn. It is a 6'-propyl analogue of spectinomycin, and lacks the aminosugars in glycosidic linkage which are thought to be responsible for the ototoxicity and nephrotoxicity associated with the aminoglycosides. The mechanism of action of trospectomycin is
similar to that of its parent compound, spectinomycin: it binds to the bacterial 30S
ribosome and inhibits protein synthesis. The transport mechanism for its delivery to its
target site does not appear to be oxygen dependent, and this explains the in-vitro
activity of trospectomycin against anaerobic organisms. Trospectomycin has activity
against a broad spectrum of pathogenic organisms including Streptococcus, Haemophilus, Gardnerella, Neisseria, Peptococcus, Peptostreptococcus, Bacteroides, Mobiluncus,
Chlamydia, Mycoplasma and Ureaplasma spp. Results of in-vivo testing suggest potential utility in a variety of clinical conditions including non-gonococcal urethritis,
chlamydial cervicitis, gonorrhoea, pelvic inflammatory disease, pneumonia, anaerobic
infections and meningitis. Trospectomycin progressed to late stage clinical trials for treatment of pelvic inflammatory disease (chlamydia) before being abandoned for commercial reasons as the third generation cephalosporins and second generation macrolides in development and use were judged superior at the time.
Originator
Approval Year
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1981727
Following a 5 mg/kg iv dose to four rats, approximately 70% of the dose was recovered within 24 hr primarily in urine as unchanged drug, and the remainder was eliminated with a terminal phase half-life in blood and tissues of 3 days.
Route of Administration:
Intravenous
The MIC90 for Enterococcus faecalis was 4 mg/l and that for E. faecium was 8 mg/l. Trospectomycin is quite active against Gram-positive cocci (MIC 90 = 4 - 8 mg/l), Gram-negative rods (MIC 90 = 8 - 16 mg/l), Gram-positive rods (MIC 90 = 4 mg/l) and Mobiluncus spp. (MIC 90 = 0.5 mg/l).
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 16:04:45 GMT 2023
by
admin
on
Sat Dec 16 16:04:45 GMT 2023
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Record UNII |
5S94MC2FRG
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C2363
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3846
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SUB11348MIG
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CHEMBL1614655
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55886
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5S94MC2FRG
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C152769
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88669-04-9
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100000076981
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5730
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m981
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DTXSID20869010
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