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viomycin

viomycin structure

CAS No:
32988-50-4
Formula:
C25H43N13O10
Chemical Name:
viomycin
Synonyms:
viomycin;FLORIMYCIN;Coliomycin;Tuberactinomycin B;Vinacetin A;Vioactane;Viocin;(S)-3,6-Diamino-N-((3S,9S,12S,15S,Z)3((2R,4S)-6-amino-4-hydroxy-1,2,3,4-tetrahydropyridin-2-yl)-9,12-bis(hydroxymethyl)-2,5,8,11,14-pentaoxo-6-(ureidomethylene)-1,4,7,10,13-pentaazacyclohexadecan-15-yl)hexanamidedisulfate
Categories:
Active Pharmaceutical Ingredients > Antibiotics

Description

ChEBI: A cyclic peptide antibiotic produced by the actinomycete Streptomyces puniceus, used in the treatment of tuberculosis.

Viomycin is a cyclic peptide antibiotic produced by the actinomycete Streptomyces puniceus, used in the treatment of tuberculosis. It has a role as an antitubercular agent. It is a peptide antibiotic and a heterodetic cyclic peptide. It is a conjugate base of a viomycin(3+).|Viomycin is a tuberactinomycin antibiotic that was used to treat Mycobacterium tuberculosis until it was replaced by the less toxic capreomycin. These drugs bind RNA in bacterial ribosomes and inhibit protein synthesis. Viomycin was derived from the actinomycete Streptomyces puniceus.|Viomycin is a cyclic polypeptide isolated from Streptomyces puniceus that is used to treat tuberculosis. Viomycin acts by blocking bacterial ribosomal translocation.|A strongly basic peptide, antibiotic complex from several strains of Streptomyces. It is allergenic and toxic to kidneys and the labyrinth. Viomycin is used in tuberculosis as several different salts and in combination with other agents.

viomycin Basic Attributes

Molecular Weight：

685.696

Exact Mass：

685.32600

EC Number：

251-323-0

UNII：

YVU35998K5

DSSTox ID：

DTXSID0023741|DTXSID8046290

NCI Thesaurus Code：

C66654

Characteristics

PSA：

393

XLogP3：

-7

Density：

1.8g/cm3

Melting Point：

280 °C

Boiling Point：

695.81°C (rough estimate)

Refractive Index：

1.762

Storage Conditions：

Store at -20°C

Safety Information

Precautionary statement(s)：

P264, P270, P301+P312, P330, P501

Hazard Statements：

H302

GHS Classification：

|Warning|H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]|P264, P270, P301+P312, P330, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Drug Information

Drug Indication：

Viomycin is an essential component in the drug cocktail currently used to fight infections of Mycobacterium tuberculosis.

MeSH：

Substances that inhibit the growth or reproduction of BACTERIA. (See all compounds classified as Anti-Bacterial Agents.)|Substances obtained from various species of microorganisms that are, alone or in combination with other agents, of use in treating various forms of tuberculosis; most of these agents are merely bacteriostatic, induce resistance in the organisms, and may be toxic. (See all compounds classified as Antibiotics, Antitubercular.)|Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Mechanism of Action：

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. This inhibits protein synthesis.

MeSH Entry Terms：

Celiomycin

Computed Properties

Molecular Weight:685.7
XLogP3:-7
Hydrogen Bond Donor Count:15
Hydrogen Bond Acceptor Count:13
Rotatable Bond Count:10
Exact Mass:685.32558462
Monoisotopic Mass:685.32558462
Topological Polar Surface Area:393
Heavy Atom Count:48
Complexity:1280
Defined Atom Stereocenter Count:7
Defined Bond Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes