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| CAS No.: | 1403-66-3 |
|---|---|
| Name: | Gentamicin |
| Molecular Structure: | |
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| 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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Consensus Reports
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, |