Kanamycin A Sulfate

HCID 441374CAS 25389-94-0
Substructure searchFind similar structures

Basic information

Standard SMILES
NC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H](N)C[C@@H]2N)[C@H](O)[C@@H](O)[C@@H]1O.O=S(=O)(O)O
InChIKey
OOYGSFOGFJDDHP-KMCOLRRFSA-N
Molecular formula
C18H38N4O15S
Average molar mass
582.6 g/mol
Monoisotopic mass
582.20543769

Names & identifiers

Preferred name
Kanamycin A Sulfate
IUPAC
(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol;sulfuric acid
English name
Kanamycin sulfate
Molecular formula
C18H38N4O15S
Molecular weight
582.58

Names & synonyms

Kanamycin A sulfateKanamycin A sulphateDTXSID1047524J80EX28SMQEINECS 223-347-1(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-3-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-2-hydroxycyclohexyl]oxyoxane-3,4,5-triol;sulfuric acidCHEBI:6109DTXCID9027524KANAMYCIN A SULFATE [MI]KANAMYCIN SULFATE [USP-RS]KANAMYCIN SULFATE [USP MONOGRAPH]KANAMYCIN MONOSULFATE [EP MONOGRAPH]
Show more names
KANAMYCIN MONOSULFATEKANAMYCIN ACID SULFATEKANAMYCIN SULPHATEKantrexklebcilKanamycin AcidKanamycin monosulfate CRSkanoKAMYCINKantrim
KANAMYCIN SULFATE (USP-RS)KANAMYCIN SULFATE (USP MONOGRAPH)D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL(1->4))-2-DEOXY-, SULFATE (1:1) (SALT)D-STREPTAMINE, O-3-AMINO-3-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL(1->6)-O-(6-AMINO-6-DEOXY-.ALPHA.-D-GLUCOPYRANOSYL(1->4))-2-DEOXY-, SULPHATE (1:1) (SALT)D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl(1->6)-O-(6-amino-6-deoxy-alpha-D-glucopyranosyl(1->4))-2-deoxy-, sulfate (1:1) (salt)KANAMYCIN MONOSULFATE (EP MONOGRAPH)Kanaplex(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-((1R,2R,3S,4R,6S)-4,6-diamino-3-((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)oxy-2-hydroxycyclohexyl)oxyoxane-3,4,5-triol;sulfuric acid

Database identifiers

CAS
25389-94-0、3847-27-6、64013-70-3
PubChem CID
441374
DTXSID
DTXSID1047524
ChEMBL
CHEMBL1446
ChEBI
CHEBI:6109
UNII
J80EX28SMQ
EC Number
223-347-1、613-414-7

Properties

Computed structural properties

Topological polar surface area
366 Ų
Hydrogen bond donors
13
Hydrogen bond acceptors
19
Rotatable bonds
6
Heavy atoms
38

Experimental & physicochemical properties

Collision Cross Section221.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
250 °C · 250°C
alpha
112 · +112~+123°(D/20℃)(c=1,H2O)(calculated on the dried basis)
Density
1.3619 · 1.3619 (rough estimate)
refractive index
117.5 ° · 117.5 ° (C=1, H2O)
storage temp.
2 · 2-8°C
solubility
2 O: · H2O: 10-50 mg/mL As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 5 days.

Safety & regulation

GHS classification

GHS Classification · 6 items

This chemical does not meet GHS hazard criteria for 1% (1 of 96) of reports.

Danger

H360 (69.8%): May damage fertility or the unborn child [Danger Reproductive toxicity]；H372 (29.2%): Causes damage to organs through prolonged or repeated exposure [Danger Specific target organ toxicity, repeated exposure]；H400 (29.2%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]；H410 (29.2%): Very toxic to aquatic life with long lasting effects [Warning Hazardous to the aquatic environment, long-term hazard]

P203, P260, P264, P270, P273, P280, P318, P319, P391, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 96 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.；Reported as not meeting GHS hazard criteria per 1 of 96 reports by companies.；There are 9 notifications provided by 95 of 96 reports by companies with hazard statement code(s).；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and Categories · 2 items

Repr. 1B (69.8%)；STOT RE 1 (29.2%)；Aquatic Acute 1 (29.2%)；Aquatic Chronic 1 (29.2%)

Repr. 1B (100%)

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
rtecs
NZ3225030
hs_code
29419020
Toxicity
LD50 in mice: 20.7 g/kg orally; 1450 mg/kg i.p. (Zel'tser)
risk_code
61

Chemistry & industry

Uses & manufacturing

Use ClassificationAnimal Drugs -> FDA Approved Animal Drug Products (Green Book) -> Active Ingredients
Applications · 6 items

DescriptionKanamycin sulfate has been well known as desirable antibiotics, which shows an obvious curative effect on serious infections caused by gram-negative bacteria such as Escherichia coil, Klebsiella, Proteus, Pneumonia, Enterobacter aerogenes and Shigella. Clinically, this substance is mainly used for infections caused by sensitive bacteria including pulmonary infection, urinary tract infection, biliary tract infection, sepsis, and abdominal cavity infection. For example, the effective antibacterial activity of kanamycin sulfate has been demonstrated by the treatment of acute gonorrheal urethritis in men, showing that a single parenterally administered dose of 2 mg of kanamycin sulfate cured 144 (93%) of 155 men with acute gonorrheal urethritis.1 Moreover, kanamycin sulfate was found to be a valuable drug in the treatment of serious infections in infants and children through an analysis of 140 cases treated during a two-year period.2

DescriptionKanamycin was found by Umezawa et al. in the culture broth of Streptomyces kanamyceticus in 1957. It is produced with other components, kanamycins B (bekanamycin) and C, which are also separated during the purification. The compound shows much lower toxicity than the earlier aminoglycosides, streptomycin and neomycin, and strong activity against a wide range of gram-positive and gram-negative bacteria, including Mycobacterium. Kanamycin has been used clinically for treatment of such serious infections as dysentery, salmonellosis, and tuberculosis.

UsesKanamycin monosulfate, is used as an aminoglycoside antibiotic. Kanamycin can be used as a selection agent in several types of isolation media.Kanamycin sulfate from Streptomyces kanamyceticus has been used in tissue culture media. Kanamycin sulfate can also be used as a selection agent for cells transformed with kanamycin B resistance gene. It is recommended for use in cell culture applications at 100mg/mL.

UsesAntibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. Comprised of three components, kanamycin A, the major component, and kanamycins B and C, two minor congeners. Antibacterial.

UsesKanamycin sulfate is an antibacterial agent similar to neomycin.

General DescriptionKanamycin sulfate is a broad spectrum aminoglycoside-antibiotic derived from Streptomyces kanamyceticus. It is used as an additive in culture media for the isolation of group D streptococci on Kanamycin Esculin Azide Agar and for selection of transformed plant cells containing the neomycin phosphotransferase on a kanamycin-medium. Kanamycin sulfate can also be used as a selection agent for cells transformed with kanamycin B resistance gene. It is recommended for use in cell culture applications at 2 mL/L.

Upstream & downstream products

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

Additional notes

DefinitionA broadspectrum antibiotic.

Related reactions

11 records
New reaction record

Linked notes

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