GENETICIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H40N4O10
Molecular Weight	496.5524
Optical Activity	UNSPECIFIED
Defined Stereocenters	15 / 15
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)O[C@]([H])([C@@H](C)O)[C@@H](O)[C@H](O)[C@H]3N

InChI

InChIKey=BRZYSWJRSDMWLG-DJWUNRQOSA-N

InChI=1S/C20H40N4O10/c1-6(25)14-11(27)10(26)9(23)18(32-14)33-15-7(21)4-8(22)16(12(15)28)34-19-13(29)17(24-3)20(2,30)5-31-19/h6-19,24-30H,4-5,21-23H2,1-3H3/t6-,7+,8-,9-,10-,11+,12+,13-,14-,15-,16+,17-,18-,19-,20+/m1/s1

HIDE SMILES / InChI

Molecular Formula	C20H40N4O10
Molecular Weight	496.5524
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	15 / 15
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6159822
Curator's Comment: description was created based on several sources, including: http://www.invivogen.com/g418 | http://www.g418-evopure.com/Technical.html

Geneticin (G-418) is produced by Micromonospora phodorangea. The antibiotic has brad spectrum antibacterial activity similar to gentamicins and other previously described aminoglycosides but of particular interest because of its high activity against protozoa, amoebae, tapeworm and pinworm infections in mice. G418 blocks polypeptide synthesis by inhibiting the elongation step in both prokaryotic and eukaryotic cells. G418 is commonly used in laboratory research to select genetically engineered cells.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Elongation step of polypeptide synthesis 1 Target ID: Elongation step of polypeptide synthesis Sources: http://www.invivogen.com/g418 \| https://www.ncbi.nlm.nih.gov/pubmed/6193810	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Proximal spinal muscular atrophy 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19150990	Primary	Basic research	Unknown Approved Use Unknown
Vaginal trichomoniasis 9 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1155922	Curative	Preclinical	Unknown Approved Use Unknown
Salmonellosis 5 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15825308	Curative	Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Paromomycin and geneticin inhibit intracellular Cryptosporidium parvum without trafficking through the host cell cytoplasm: implications for drug delivery.	1998 Aug	9673275
Inhibition of HIV type 1 production by hygromycin B.	1998 Jul 1	9671217
Aminoglycoside pretreatment partially restores the function of truncated V(2) vasopressin receptors found in patients with nephrogenic diabetes insipidus.	2002 Nov	12414899
Classification and rescue of ROMK mutations underlying hyperprostaglandin E syndrome/antenatal Bartter syndrome.	2003 Sep	12911542
Cytochrome c release and endoplasmic reticulum stress are involved in caspase-dependent apoptosis induced by G418.	2004 Jul	15241557
Aminoglycoside-mediated rescue of a disease-causing nonsense mutation in the V2 vasopressin receptor gene in vitro and in vivo.	2004 May 1	14998935
Correction of ATM gene function by aminoglycoside-induced read-through of premature termination codons.	2004 Nov 2	15498871
Aminoglycosides decrease glutathione peroxidase-1 activity by interfering with selenocysteine incorporation.	2006 Feb 10	16354666
Intracellular readthrough of nonsense mutations by aminoglycosides in coagulation factor VII.	2006 Jun	16706976
Restoration of W1282X CFTR activity by enhanced expression.	2007 Sep	17541014
G418-mediated ribosomal read-through of a nonsense mutation causing autosomal recessive proximal renal tubular acidosis.	2008 Sep	18614622
Translational readthrough by the aminoglycoside geneticin (G418) modulates SMN stability in vitro and improves motor function in SMA mice in vivo.	2009 Apr 1	19150990
Stop codon read-through of a methylmalonic aciduria mutation.	2009 Aug	19427250
ATP-binding cassette transporters as pitfalls in selection of transgenic cells.	2010 Apr 15	20018165

Patents

Sample Use Guides

In Vivo Use Guide

4 mg/kg to neonatal mice from postnatal day (PND) 5–13.

Route of Administration: Intraperitoneal

In Vitro Use Guide

All of the Saccharomyces sp. strains, including the brewing strains, were found to be susceptible to G418 in the concentration range of 150 to 500 ug/ml. Of the three Schwanniomyces species investigated, only Schwanniomyces castellii (strain 1402) was found to be resistant to G418 at concentrations up to 1 mg/ml.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:07:23 GMT 2023` Edited by `admin` on `Fri Dec 15 15:07:23 GMT 2023`
Record UNII	A08F5XTI6G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

GENETICIN

Common Name

English

G418

Common Name

English

ANTIBIOTIC G-418

Common Name

English

D-STREPTAMINE, O-2-AMINO-2,7-DIDEOXY-D-GLYCERO-.ALPHA.-D-GLUCO-HEPTOPYRANOSYL-(1->4)-O-(3-DEOXY-4-C-METHYL-3-(METHYLAMINO)-.BETA.-L-ARABINOPYRANOSYL-(1->6))-2-DEOXY-

Common Name

English

ANTIBIOTIC G 418

Common Name

English

G-418

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

204605