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1289003

USP

Gentamicin sulfate

United States Pharmacopeia (USP) Reference Standard

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Synonym(s):
Gentamicin sulfate salt, Gentamicin C complex sulfate.
CAS Number:
1405-41-0
EC Number:
215-778-9
MDL number:
MFCD00270181
UNSPSC Code:
41116107
PubChem Substance ID:
329749933
NACRES:
NA.24

grade

pharmaceutical primary standard

API family

gentamicin

manufacturer/tradename

USP

application(s)

pharmaceutical (small molecule)

format

neat

SMILES string

O=S(O)(O)=O.O[C@]1(C)[C@@H]([C@@H](O)[C@@H](O[C@@H]2[C@@H](O)[C@H](O[C@H]3O[C@@](CC[C@H]3N)([C@@H](C)NC)[H])[C@@H](N)C[C@H]2N)OC1)NC.O[C@]4(C)[C@@H]([C@@H](O)[C@@H](O[C@@H]5[C@@H](O)[C@H](O[C@H]6O[C@@](CC[C@H]6N)([C@@H](C)N)[H])[C@@H](N)C[C@H]5N)OC4)NC.O[

InChI

1S/C21H43N5O7.C20H41N5O7.C19H39N5O7.H2O4S/c1-9(25-3)13-6-5-10(22)19(31-13)32-16-11(23)7-12(24)17(14(16)27)33-20-15(28)18(26-4)21(2,29)8-30-20;1-8(21)12-5-4-9(22)18(30-12)31-15-10(23)6-11(24)16(13(15)26)32-19-14(27)17(25-3)20(2,28)7-29-19;1-19(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;1-5(2,3)4/h9-20,25-29H,5-8,22-24H2,1-4H3;8-19,25-28H,4-7,21-24H2,1-3H3;8-18,24-27H,3-7,20-23H2,1-2H3;(H2,1,2,3,4)/t9-,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+;8-,9-,10+,11-,12+,13+,14-,15-,16+,17-,18-,19-,20+;8-,9+,10-,11+,12-,13+,14+,15-,16+,17+,18+,19-;/m110./s1

InChI key

RDEIXVOBVLKYNT-HDZPSJEVSA-N

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General description

Gentamicin Sulfate, consisting of sulfate salts, is a medication derived from antibiotic substances produced during the growth of Micromonospora purpurea bacterium.

Application

Gentamicin sulfate USP reference standard, intended for use in specified quality tests and assays as specified in the USP compendia.
Also, for use with USP monographs such as:
  • Gentamicin Sulfate Cream
  • Gentamicin Sulfate Ointment
  • Gentamicin Sulfate Ophthalmic Ointment
  • Gentamicin Sulfate Ophthalmic Solution
  • Gentamicin Sulfate and Betamethasone Valerate Topical Solution
  • Gentamicin Sulfate and Betamethasone Acetate Ophthalmic Solution
  • Gentamicin Sulfate and Betamethasone Valerate Otic Solution
  • Gentamicin and Prednisolone Acetate Ophthalmic Ointment

Biochem/physiol Actions

Mode of action: Gentamicin causes codon misreading by binding to the 30S ribosomal subunit, blocking the translocation of peptidyl-tRNA from the acceptor site to the donor site. The bactericidal effect of gentamicin on Pseudomonas aeruginosa is exerted by the binding of gentamicin to the outer membrane, where it displaces natural cations, destabilizes the membrane, and forms holes in the cell surface.

Antimicrobial spectrum: Includes Gram-negative and Gram-positive bacteria, including strains resistant to tetracycline, chloramphenicol, kanamycin and colistin, particularly strains of Pseudomonas, Proteus, Staphylococcus and Streptococcus.

Caution

Sterile solutions should be stored at 2-8°C. Solutions have also been shown to be stable at room temperature and in boiling aqueous buffers of pH 2-142.

Analysis Note

These products are for test and assay use only. They are not meant for administration to humans or animals and cannot be used to diagnose, treat, or cure diseases of any kind.  ​

Other Notes

This product is part of the USP Biologics program.

Legal Information

This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the issuing Pharmacopoeia.For further information and support please go to the website of the issuing Pharmacopoeia.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H317

Hazard Classifications

Skin Sens. 1

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

监管及禁止进口产品

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Gentamicin Sulfate and Betamethasone Valerate Ointment
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 2103-2103 (2013)
Gentamicin Sulfate
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 43(3), 2100-2100 (2020)
Gentamicin Injection
United States Pharmacopeia and National Formulary
United States Pharmacopeia, 2099-2099 (2018)

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