Amikacin

Names

[ Name ]:
Amikacin

[Synonym ]:
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

Biological Activity

[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 >> Infection

Signaling 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

MSDS

Click to get detail MSDS

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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