CAS 37517-28-5|Amikacin

Introduction：Basic information about CAS 37517-28-5|Amikacin, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Amikacin BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles90
7. Synonyms

Common Name	Amikacin
CAS Number	37517-28-5	Molecular Weight	585.602
Density	1.6±0.1 g/cm3	Boiling Point	981.8±65.0 °C at 760 mmHg
Molecular Formula	C₂₂H₄₃N₅O₁₃	Melting Point	203-204ºC (sesquihydrate)
MSDS	/	Flash Point	547.6±34.3 °C

Names

Name	amikacin
Synonym	More Synonyms

Amikacin BiologicalActivity

Description	Amikacin (BAY 41-6551), a semisynthetic analog of kanamycin, is very active against most gram-negative bacteria including gentamicin- and tobramycin-resistant strains. Amikacin (BAY 41-6551) is ototoxic and nephrotoxic[1][2].
Related Catalog	Research Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial
References	[1]. Edson, R.S. and C.L. Terrell, The aminoglycosides. Mayo Clin Proc, 1999. 74(5): p. 519-28. [2]. Ristuccia AM, et al. An overview of amikacin. Ther Drug Monit. 1985;7(1):12-25. [3]. Siân R Kitcher, et al. ORC-13661 Protects Sensory Hair Cells From Aminoglycoside and Cisplatin Ototoxicity. JCI Insight. 2019 Aug 8;4(15):e126764.

Description

Amikacin (BAY 41-6551), a semisynthetic analog of kanamycin, is very active against most gram-negative bacteria including gentamicin- and tobramycin-resistant strains. Amikacin (BAY 41-6551) is ototoxic and nephrotoxic[1][2].

Related Catalog

Research Areas >>InfectionSignaling Pathways >>Anti-infection >>Bacterial

References

[1]. Edson, R.S. and C.L. Terrell, The aminoglycosides. Mayo Clin Proc, 1999. 74(5): p. 519-28.

[2]. Ristuccia AM, et al. An overview of amikacin. Ther Drug Monit. 1985;7(1):12-25.

[3]. Siân R Kitcher, et al. ORC-13661 Protects Sensory Hair Cells From Aminoglycoside and Cisplatin Ototoxicity. JCI Insight. 2019 Aug 8;4(15):e126764.

Chemical & Physical Properties

Density	1.6±0.1 g/cm3
Boiling Point	981.8±65.0 °C at 760 mmHg
Melting Point	203-204ºC (sesquihydrate)
Molecular Formula	C₂₂H₄₃N₅O₁₃
Molecular Weight	585.602
Flash Point	547.6±34.3 °C
Exact Mass	585.285706
PSA	331.94000
LogP	-3.34
Vapour Pressure	0.0±0.6 mmHg at 25°C
Index of Refraction	1.664
InChIKey	LKCWBDHBTVXHDL-RMDFUYIESA-N
SMILES	NCCC(O)C(=O)NC1CC(N)C(OC2OC(CN)C(O)C(O)C2O)C(O)C1OC1OC(CO)C(O)C(N)C1O

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: WK1955000

CHEMICAL NAME :: D-Streptamine, O-3-amino-3-deoxy-alpha-D-glucopyranosyl-(1-6)-O-(6-a mino-6-deoxy-alpha-D- glucopyranosyl-(1,4))-N(sup 1)-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-, (S)-

CAS REGISTRY NUMBER :: 37517-28-5

LAST UPDATED :: 199612

DATA ITEMS CITED :: 12

MOLECULAR FORMULA :: C22-H43-N5-O13

MOLECULAR WEIGHT :: 585.70

WISWESSER LINE NOTATION :: T6OTJ CQ DZ EQ F1Q BO- DL6TJ AZ CQ EMVYQ2Z BO- BT6OTJ CQ DQ EQ F1Z -S

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >6 gm/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,415,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 750 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage)

REFERENCE :: AMACCQ Antimicrobial Agents and Chemotherapy. (American Soc. for Microbiology, 1913 I St., NW, Washington, DC 20006) V.1- 1972- Volume(issue)/page/year: 13,41,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,415,1975

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 280 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JANTAJ Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo, 141, Japan) V.2-5, 1948-52; V.21- 1968- Volume(issue)/page/year: 43,858,1990

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 6200 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,415,1975 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5040 mg/kg/14D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol)

REFERENCE :: JEPTDQ Journal of Environmental Pathology and Toxicology. (Park Forest South, IL) V.1-5(3), 1977-81(?). For publisher information, see JEPOEC. Volume(issue)/page/year: 4(5-6),277,1980

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 3150 mg/kg/21D-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - changes in tubules (including acute renal failure, acute tubular necrosis) Kidney, Ureter, Bladder - urine volume increased Kidney, Ureter, Bladder - changes in bladder weight

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 33(Suppl 5),47,1985

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 4500 mg/kg/20D-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Ear) - changes in cochlear structure or function

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 65,222,1982

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - guinea pig

DOSE/DURATION :: 5600 mg/kg/4W-I

TOXIC EFFECTS :: Sense Organs and Special Senses (Ear) - changes in vestibular functions Sense Organs and Special Senses (Ear) - changes in cochlear structure or function Nutritional and Gross Metabolic - weight loss or decreased weight gain

REFERENCE :: NKRZAZ Chemotherapy (Tokyo). (Nippon Kagaku Ryoho Gakkai, 2-20-8 Kamiosaki, Shinagawa-Ku, Tokyo 141, Japan) V.1- 1953- Volume(issue)/page/year: 33(Suppl 5),90,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intramuscular

DOSE :: 90 mg/kg

SEX/DURATION :: female 8-16 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - body wall

REFERENCE :: JJANAX Japanese Journal of Antibiotics. (Japan Antibiotics Research Assoc., 2-20-8 Kamiosaki, Shinagawa-ku, Tokyo 141, Japan) V.21- 1968- Volume(issue)/page/year: 28,366,1975 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - X3198 No. of Facilities: 312 (estimated) No. of Industries: 2 No. of Occupations: 7 No. of Employees: 15838 (estimated) No. of Female Employees: 12302 (estimated)

Safety Information

Hazard Codes	Xi
Risk Phrases	R36/37/38
Safety Phrases	26-36
RIDADR	NONH for all modes of transport
WGK Germany	2
RTECS	WK1955000

Articles90

Enhancement of in vitro activity of tuberculosis drugs by addition of thioridazine is not reflected by improved in vivo therapeutic efficacy.

Tuberculosis (Edinb.) 94(6) , 701-7, (2015)

Assessment of the activity of thioridazine towards Mycobacterium tuberculosis (Mtb), in vitro and in vivo as a single drug and in combination with tuberculosis (TB) drugs.The in vitro activity of thio...

Aminoglycosides suppress the protein folding activity of the molecular chaperone HSC70: implication of a structure-activity relationship.

Chemotherapy 60(1) , 37-46, (2014)

The mechanism of aminoglycoside (AG)-induced nephrotoxicity has not been fully elucidated. We previously reported that gentamicin suppresses the functions of HSC70, a heat shock cognate protein, which...

Phenotypic heterogeneity enables uropathogenic Escherichia coli to evade killing by antibiotics and serum complement.

Infect. Immun. 83(3) , 1056-67, (2015)

Uropathogenic strains of Escherichia coli (UPEC) are the major cause of bacteremic urinary tract infections. Survival in the bloodstream is associated with different mechanisms that help to resist ser...

Synonyms

Butanamide, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2S)-

Butanimidic acid, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (1E,2S)-

kaminax

(2S)-4-amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-a-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-a-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide

novamin

1-N-[L(-)-4-Amino-2-hydroxybutyryl]kanamycin A

mikavir

D-Streptamine

AMIKACIN

bb-k8

Amikin

EINECS 253-538-5

butanamide, 4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-a-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-a-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl]-2-hydroxy-, (2S)-

(1E,2S)-4-Amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanimidic acid

Amikacin Base

Fabianol

lukadin

Biklin

amiklin

(2S)-4-Amino-N-{(1R,2S,3S,4R,5S)-5-amino-2-[(3-amino-3-deoxy-α-D-glucopyranosyl)oxy]-4-[(6-amino-6-deoxy-α-D-glucopyranosyl)oxy]-3-hydroxycyclohexyl}-2-hydroxybutanamide

O-3-Amino-3-deoxy-a-D-glucopyranosyl-(1®6)-O-[6-amino-6-deoxy-a-D-glucopyranosyl-(1®4)]-N1-(4-amino-2-hydroxy-1-oxobutyl)-2-deoxy-D-streptamine

AMK

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