U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of TROSPECTOMYCIN

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

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.
1987

Sample Use Guides

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 Sat Dec 16 16:04:45 GMT 2023
Edited
by admin
on Sat Dec 16 16:04:45 GMT 2023
Record UNII
5S94MC2FRG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TROSPECTOMYCIN
INN   MI   VANDF  
INN  
Official Name English
(2R,4AR,5AR,6S,7S,8R,9S,9AR,10AS)-2-BUTYLDECAHYDRO-4A,7,9-TRIHYDROXY-6,8-BIS(METHYLAMINO)-4H-PYRANO(2,3-B)(1,4)BENZODIOXIN-4-ONE
Common Name English
4H-PYRANO(2,3-B)(1,4)BENZODIOXIN-4-ONE, 2-BUTYLDECAHYDRO-4A,7,9-TRIHYDROXY-6,8-BIS(METHYLAMINO)-, (2R-(2.ALPHA.,4A.BETA.,5A.BETA.,6.BETA.,7.BETA.,8.BETA.,9.ALPHA.,9A.ALPHA.,10A.BETA.))-
Common Name English
TROSPECTINOMYCIN
Common Name English
trospectomycin [INN]
Common Name English
U-63366
Common Name English
TROSPECTOMYCIN [VANDF]
Common Name English
TROSPECTOMYCIN [MI]
Common Name English
U-63,366
Code English
Classification Tree Code System Code
NCI_THESAURUS C2363
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
Code System Code Type Description
DRUG CENTRAL
3846
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
EVMPD
SUB11348MIG
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
ChEMBL
CHEMBL1614655
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
PUBCHEM
55886
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
FDA UNII
5S94MC2FRG
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
NCI_THESAURUS
C152769
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
CAS
88669-04-9
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
SMS_ID
100000076981
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
INN
5730
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
MERCK INDEX
m981
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY Merck Index
EPA CompTox
DTXSID20869010
Created by admin on Sat Dec 16 16:04:46 GMT 2023 , Edited by admin on Sat Dec 16 16:04:46 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY