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1403-66-3

Basic Information
CAS No.: 1403-66-3
Name: Gentamicin
Molecular Structure:
Molecular Structure of 1403-66-3 (Gentamicin)
Formula: C21H43N5O7
Molecular Weight: 477.60
Synonyms: Centicin;Gentacycol;Gentamycin;Gentavet;Lyramycin;Oksitselanim;Septigen;
EINECS: 215-765-8
Density: 1.3 g/cm3
Melting Point: 102-108°
Boiling Point: 669.4 °C at 760 mmHg
Flash Point: 358.6 °C
Appearance: clear amber liquid.
PSA: 627.17000
LogP: -1.62550
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    Gentamycin

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    Gentamycin

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Consensus Reports

GENTAMYCIN(1403-66-3) is reported in EPA Genetic Toxicology Program.

Specification

The Gentamycin is an organic compound with the formula C21H43N5O7. The IUPAC name of this chemical is 2-[4,6-diamino-3-[3-amino-6-[1-(methylamino)ethyl]oxan-2-yl]oxy-2-hydroxycyclohexyl]oxy-5-methyl-4-(methylamino)oxane-3,5-diol. With the CAS registry number 1403-66-3, it is also named as (1R,2S,3S,4R,6S)-4,6-diamino-3-{[3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl]oxy}-2-hydroxycyclohexyl 2-amino-2,3,4,6,7-pentadeoxy-6-(methylamino)-β-L-lyxo-heptopyranoside. The product's classification codes are Drug / Therapeutic Agent; Human Data; Mutation data; Natural Product; Reproductive Effect.The Gentamycin is a complex of three different closely related aminoglycoside sulfates, Gentamicins C1, C2, and C1(subA), obtained from Micromonospora purpurea and related species. They are broad-spectrum antibiotics, but may cause ear and kidney damage. They act to inhibit protein synthesis .

Physical properties about Gentamycin are:
 (1)ACD/LogP: -1.89; (2)# of Rule of 5 Violations: 2; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 12; (8)#H bond donors: 11; (9)#Freely Rotating Bonds: 13; (10)Polar Surface Area: 80.81 Å2; (11)Index of Refraction: 1.583; (12)Molar Refractivity: 122.64 cm3; (13)Molar Volume: 366.8 cm3; (14)Polarizability: 48.61×10-24cm3; (15)Surface Tension: 62.7 dyne/cm; (16)Density: 1.3 g/cm3; (17)Flash Point: 358.6 °C; (18)Enthalpy of Vaporization: 112.58 kJ/mol; (19)Boiling Point: 669.4 °C at 760 mmHg; (20)Vapour Pressure: 8.85E-21 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O[C@]3(C)[C@H](NC)[C@@H](O)[C@@H](O[C@H]2[C@H](N)C[C@H](N)[C@@H](O[C@H]1O[C@H](C(NC)C)CC[C@H]1N)[C@@H]2O)OC3
(2)InChI: InChI=1/C21H43N5O7/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/h9-20,25-29H,5-8,22-24H2,1-4H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
(3)InChIKey: CEAZRRDELHUEMR-URQXQFDEBJ
(4)Std. InChI: InChI=1S/C21H43N5O7/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/h9-20,25-29H,5-8,22-24H2,1-4H3/t9?,10-,11+,12-,13+,14+,15-,16-,17+,18-,19-,20-,21+/m1/s1
(5)Std. InChIKey: CEAZRRDELHUEMR-URQXQFDESA-N

The toxicity data is of Gentamicin as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 intramuscular 430mg/kg (430mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
cat LD50 intraperitoneal 304mg/kg (304mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
cat LD50 intravenous 88mg/kg (88mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
dog LD50 intramuscular 750mg/kg (750mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
dog LD50 intraperitoneal 710mg/kg (710mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
dog LD50 intravenous 184mg/kg (184mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
guinea pig LD50 intraperitoneal 530mg/kg (530mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
guinea pig LD50 subcutaneous 740mg/kg (740mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
human TDLo intravenous 2mg/kg (2mg/kg) KIDNEY, URETER, AND BLADDER: OTHER CHANGES New England Journal of Medicine. Vol. 303, Pg. 1002, 1980.
human TDLo intravenous 23mg/kg/1Y-I (23mg/kg) PERIPHERAL NERVE AND SENSATION: SENSORY CHANGE INVOLVING TRIGEMINAL NERVE Archives of Internal Medicine. Vol. 138, Pg. 1621, 1978.
infant TDLo intramuscular 20mg/kg (20mg/kg) KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)" Pediatrics. Vol. 77, Pg. 848, 1986.
man TDLo intramuscular 8mg/kg/2W-I (8mg/kg) SENSE ORGANS AND SPECIAL SENSES: VISUAL FIELD CHANGES: EYE

SENSE ORGANS AND SPECIAL SENSES: HEMORRHAGE: EYE

SKIN AND APPENDAGES (SKIN): HAIR: OTHER
JAMA, Journal of the American Medical Association. Vol. 211, Pg. 123, 1970.
mouse LD50 intramuscular 167mg/kg (167mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: ATAXIA
Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
mouse LD50 intraperitoneal 235mg/kg (235mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
mouse LD50 intravenous 43500ug/kg (43.5mg/kg)   Antibiotiki. Vol. 21, Pg. 532, 1976.
mouse LD50 oral 10gm/kg (10000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Japanese Journal of Antibiotics. Vol. 30, Pg. 386, 1977.
mouse LD50 subcutaneous 274mg/kg (274mg/kg)   Toxicology and Applied Pharmacology. Vol. 25, Pg. 398, 1973.
rabbit LD50 intramuscular 780mg/kg (780mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rabbit LD50 intraperitoneal 1350mg/kg (1350mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rabbit LD50 intravenous 81mg/kg (81mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rabbit LD50 subcutaneous 1230mg/kg (1230mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 11, 1966.
rat LD50 intramuscular 463mg/kg (463mg/kg)   Japanese Journal of Antibiotics. Vol. 35, Pg. 461, 1982.
rat LD50 intraperitoneal 735mg/kg (735mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 intravenous 70mg/kg (70mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
rat LD50 oral 6600mg/kg (6600mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: OTHER CHANGES
Archives des Maladies Professionnelles de Medecine du Travail et de Securite Sociale. Vol. 39, Pg. 259, 1978.
rat LD50 subcutaneous 710mg/kg (710mg/kg)   Journal of International Medical Research. Vol. 2, Pg. 100, 1974.
women TDLo intravenous 8200ug/kg/12D (8.2mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHANGES IN VESTIBULAR FUNCTIONS: EAR

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)
Acta Pathologica et Microbiologica Scandinavica, Section B: Microbiology and Immunology. Vol. 81(Suppl,