PENTISOMICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H37N5O7
Molecular Weight	447.5264
Optical Activity	UNSPECIFIED
Defined Stereocenters	11 / 11
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]3(O[C@@H]1[C@@H](N)C[C@@H](N)[C@H](O[C@@]2([H])OC[C@](C)(O)[C@H](NC)[C@H]2O)[C@@H]1O)OC(CN)=CC[C@H]3N

InChI

InChIKey=URWAJWIAIPFPJE-VHLNBGGKSA-N

InChI=1S/C19H37N5O7/c1-19(27)7-28-18(13(26)16(19)24-2)31-15-11(23)5-10(22)14(12(15)25)30-17-9(21)4-3-8(6-20)29-17/h3,9-18,24-27H,4-7,20-23H2,1-2H3/t9-,10+,11-,12-,13-,14-,15+,16-,17-,18-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C19H37N5O7
Molecular Weight	447.5264
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	11 / 11
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/697346
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/3839236 | https://www.ncbi.nlm.nih.gov/pubmed/4073862 | https://www.ncbi.nlm.nih.gov/pubmed/3571044

Pentisomicin (Sch 21420) is semisynthetic aminoglycosides with marked antibacterial activity. Like many new aminoglycosides prepared by chemical modification or mutational biosynthesis, Pentisomicin was designed either to enhance potency of the parent compound and/or resist enzymatic inactivation. The activity of Pentisomicin was comparable to gentamicin, sisomicin, netilmicin, and tobramycin but greater than amikacin or kanamycin against S. aureus and most genera of Enterobacteriaceae.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus 67 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/697346	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Human pharmacology of 5-epi-sisomicin (Sch 22591) following intramuscular administration.	1987 Feb	3571044

Patents

Sample Use Guides

In Vivo Use Guide

5-epi-sisomicin (Pentisomicin) was given as a single 1 mg/kg intramuscular injection to six adult male volunteers.

Route of Administration: Intramuscular

In Vitro Use Guide

Agar dilution susceptibility tests were performed with N. gonorrhoeae. Serial twofold agar dilution tests were performed with GC agar base (BBL) plus 1% Kellogg defined supplement. A standardized suspension of cells was prepared from an overnight culture on chocolate agar so that inoculation of each test plate with 0.01 ml (calibrated loop) yielded ca. 10^4 CFU/cm2. The MIC was defined as the lowest concentration of Pentisomicin preventing all growth after 24 h of incubation at 37C in 10% C02 in air.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 17:52:59 GMT 2023` Edited by `admin` on `Sat Dec 16 17:52:59 GMT 2023`
Record UNII	L5BS6WSR0E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PENTISOMICIN

Official Name

English

pentisomicin [INN]

Common Name

English

SCH-22591

Code

English

PENTISOMICIN [USAN]

Common Name

English

SCH 22591

Code

English

Code System Code Type Description

PUBCHEM

65453