VIOMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H43N13O10
Molecular Weight	685.69
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]1(C[C@H](O)NC(N)=N1)[C@]2([H])NC(=O)\C(NC(=O)[C@H](CO)NC(=O)[C@H](CO)NC(=O)[C@H](CNC2=O)NC(=O)C[C@@H](N)CCCN)=C\NC(N)=O

InChI

InChIKey=GXFAIFRPOKBQRV-GHXCTMGLSA-N

InChI=1S/C25H43N13O10/c26-3-1-2-10(27)4-16(41)32-12-6-30-23(47)18(11-5-17(42)37-24(28)36-11)38-20(44)13(7-31-25(29)48)33-21(45)14(8-39)35-22(46)15(9-40)34-19(12)43/h7,10-12,14-15,17-18,39-40,42H,1-6,8-9,26-27H2,(H,30,47)(H,32,41)(H,33,45)(H,34,43)(H,35,46)(H,38,44)(H3,28,36,37)(H3,29,31,48)/b13-7-/t10-,11+,12-,14-,15-,17-,18-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C25H43N13O10
Molecular Weight	685.69
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	2
Optical Activity	UNSPECIFIED

Description
Sources: https://www.drugbank.ca/drugs/DB06827 | https://www.ncbi.nlm.nih.gov/pubmed/26755601
Curator's Comment: Description was created based on several sources, including https://books.google.ru/books?id=JxElBQAAQBAJ&pg=PA421&lpg=PA421&dq=VIOMYCIN retrieved from Antibiotics: Origin, Nature and Properties Tadeusz Korzybski,Zuzanna Kowszyk-Gindifer,Wlodzimierz Kurylowicz, p. 421

Viomycin is a basic peptide antibiotic, which is among the most effective agents against multidrug-resistant tuberculosis. The tuberactinomycins, such as Viomycin, target bacterial ribosomes, binding RNA and disrupting bacterial protein biosynthesis. Specifically, viomycin binds to a site on the ribosome which lies at the interface between helix 44 of the small ribosomal subunit and helix 69 of the large ribosomal subunit. The structures of this complexes suggest that the viomycin inhibits translocation by stabilizing the tRNA in the A site in the pretranslocation state.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
70S ribosome 16 Target ID: CHEMBL2363965 Sources: https://www.ncbi.nlm.nih.gov/pubmed/22779429 \| https://www.ncbi.nlm.nih.gov/pubmed/26755601 \| https://www.ncbi.nlm.nih.gov/pubmed/12936980 \| https://www.drugbank.ca/drugs/DB06827 \| https://www.ncbi.nlm.nih.gov/pubmed/20154709	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Tuberculosis 83 Sources: https://www.drugbank.ca/drugs/DB06827 http://www.rightdiagnosis.com/medical/viomycin.htm https://www.ncbi.nlm.nih.gov/pubmed/13287785	Curative		Approved 8429	VIOCIN SULFATE Approved Use Viomycin is used to fight infections of Mycobacterium tuberculosis.

C_max

Value	Dose	Co-administered	Analyte	Population
50 μg/mL REVIEW https://pubmed.ncbi.nlm.nih.gov/6391781/	1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered:		VIOMYCIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
15 mg/kg 1 times / day multiple, intravenous Dose: 15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 15 mg/kg, 1 times / day Co-administed with:: pyrazinamide Sources: https://pubmed.ncbi.nlm.nih.gov/4340029	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: tubersulosis Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4340029	Other AEs: Hypomagnesemia, Hypocalcemia... Other AEs: Hypomagnesemia Hypocalcemia Hypokalemia Sources: https://pubmed.ncbi.nlm.nih.gov/4340029
75 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 75 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 75 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513	unhealthy Health Status: unhealthy Condition: tubersulosis Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513	Other AEs: Hypocalcemia, Hypokalemia... Other AEs: Hypocalcemia Hypokalemia Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513

AEs

AE	Dose	Population
Hypocalcemia	15 mg/kg 1 times / day multiple, intravenous Dose: 15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 15 mg/kg, 1 times / day Co-administed with:: pyrazinamide Sources: https://pubmed.ncbi.nlm.nih.gov/4340029	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: tubersulosis Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4340029
Hypokalemia	15 mg/kg 1 times / day multiple, intravenous Dose: 15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 15 mg/kg, 1 times / day Co-administed with:: pyrazinamide Sources: https://pubmed.ncbi.nlm.nih.gov/4340029	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: tubersulosis Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4340029
Hypomagnesemia	15 mg/kg 1 times / day multiple, intravenous Dose: 15 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 15 mg/kg, 1 times / day Co-administed with:: pyrazinamide Sources: https://pubmed.ncbi.nlm.nih.gov/4340029	unhealthy, 58 years n = 1 Health Status: unhealthy Condition: tubersulosis Age Group: 58 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4340029
Hypocalcemia	75 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 75 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 75 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513	unhealthy Health Status: unhealthy Condition: tubersulosis Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513
Hypokalemia	75 mg/kg 1 times / day multiple, intravenous Highest studied dose Dose: 75 mg/kg, 1 times / day Route: intravenous Route: multiple Dose: 75 mg/kg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513	unhealthy Health Status: unhealthy Condition: tubersulosis Sources: https://pubmed.ncbi.nlm.nih.gov/4340029 https://pubmed.ncbi.nlm.nih.gov/13148513

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:15782	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:15782
ZINC	ZINC000049799668	http://zinc15.docking.org/substances/ZINC000049799668

PubMed

Title	Date	PubMed
Chemical studies on tuberactinomycin. 3. The chemical structure of viomycin (tuberactinomycin B).	1972 Jul	4350196
Hypocalcemia, hypomagnesemia and hypokalemia during chemotherapy of pulmonary tuberculosis.	1972 May	4340029
In vitro and in vivo susceptibility of atypical mycobacteria to various drugs.	1981 Sep-Oct	7339820
Antibacterial activity of palmitoyltuberactinamine N and di-beta-lysylcapreomycin IIA.	1983 Dec	6198315
Small molecules that selectively block RNA binding of HIV-1 Rev protein inhibit Rev function and viral production.	1993 Sep 24	8402886
Use of genomics and combinatorial chemistry in the development of new antimycobacterial drugs.	2000 Feb 1	10609550

Patents

Sample Use Guides

In Vivo Use Guide

Pulmunary tuberculosis: 30-75 mg/kg, intramuscularly, 14-182 days

Route of Administration: Intramuscular

In Vitro Use Guide

Viomycin at a concentration of 10 uM inhibits E. coli ribosomes to the extent of about 70% as measured in the poly (U) system, and to about 85% in a natural mRNA (R17) system.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:15:38 GMT 2023` Edited by `admin` on `Fri Dec 15 16:15:38 GMT 2023`
Record UNII	YVU35998K5
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

VIOMYCIN

Official Name

English

CELIOMYCIN

Common Name

English

FLORIMYCIN

Common Name

English

viomycin [INN]

Common Name

English

Viomycin [WHO-DD]

Common Name

English

VINACETIN A

Common Name

English

GLYCINE, 3-AMINO-N-((3S)-3,6-DIAMINO-1-OXOHEXYL)-L-ALANYL-L-SERYL-L-SERYL-(2Z)-3-((AMINOCARBONYL)AMINO)-2,3-DIDEHYDROALANYL-2-((4R,6S)-2-AMINO-1,4,5,6-TETRAHYDRO-6-HYDROXY-4-PYRIMIDINYL)-, (5->13)-LACTAM, (2S)-

Common Name

English

VIOACTANE

Common Name

English

TUBERACTINOMYCIN B

Common Name

English

TUBERACTINOMYCIN B [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C280