ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
化工社オープンプロジェクト：[email protected]AIアクセス：llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.7.8
戻る
化工社化工社 化学情報印刷レポート · 研究参考用
HCID 3467作成日：2026年10月27日

ゲンタミシン

ゲンタシコール · ゲンタマイシン · GM【ゲンタマイシン】 · リラマイシン · ゲンタベット · オキシトセラニム · セプチゲン · ゲンタルリン

https://huagongshe.com/ja/chemical/3467

ゲンタミシン の分子構造式

識別子と物理属性

CAS No.1403-66-3
分子式C21H43N5O7
平均分子量477.6 g/mol
SMILESCNC(C)C1CCC(N)C(OC2C(N)CC(N)C(OC3OCC(C)(O)C(NC)C3O)C2O)O1
InChIKeyCEAZRRDELHUEMR-UHFFFAOYSA-N
PubChem CID3467
ChEMBLCHEMBL329592
EC No.215-765-8
現地名ゲンタミシン

化学・物理的性質

XLogP-4.1
極性表面積200
水素結合供与体数8
水素結合受容体数12
回転可能結合数7
重原子数33
形式電荷0
複雑度636
物質分類Other Uses -> Pharmaceuticals
医薬品Pharmaceuticals
LogP（分配係数）-3.1
Color/FormWhite amorphous powder
溶解度Freely soluble in waterSoluble in pyridine, dimethylformamide, in acidic media with salt formationmoderately soluble in methanol, ethanol, acetonepractically insoluble in benzene, halogenated hydrocarbons1.26e+01 g/L
Human DrugsBreast FeedingLactationMilk, HumanAnti-Infective AgentsAntibacterial AgentsAminoglycosidesAccess group antibiotics
Animal DrugsActive Ingredients (Gentamicin) -> FDA GreenbookPharmaceuticals -> Animal Drugs -> Approved in Taiwan
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.Melts with decomposition between 220 °C and 240 °C. /Gentamycin sulfate/
融点102-108 °C105 °C (decomposition)102-108°
Optical RotationSpecific optical rotation: +146 deg at 25 °C/D
Physical DescriptionSolid
Stability/Shelf LifeStable in light, air, and heat /Gentamycin sulfate/
比旋光度D25 +146°
密度1.000 g/cm3
pKa（酸解離定数）pKa 8.2(66% DMF) (Uncertain)7.9(H2O) (Uncertain)
外観・状態powder
色Colorless to light yellow
臭いOdorless
CAS データベース1403-66-3(CAS DataBase Reference)
EPAの化学物質情報Gentamicin (1403-66-3)

化学的特性

Amorphous solid. Freely soluble in water, pyridine, acid solutions; moderately soluble in methanol, ethanol, and acetone; practically insoluble in benzene and halogenated hydrocarbons.

安全性と法規制

GHS 分類DangerH317 (47.6%): May cause an allergic skin reaction [Warning Sensitization, Skin]P203, P233, P260, P261, P264, P270, P271, P272, P273, P280, P284, P302+P352, P304+P340, P318, P319, P321, P333+P317, P342+P316, P362+P364, P391, P403, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 103 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
規制情報Gentamicin: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
その他の安全情報IMAP assessments - Gentamicin: Environment tier I assessment
有害性の概要Allergic contact dermatitis reported, but raregentamycin cross reacts with neomycin, so positive patch test may reflect neomycin as the primary sensitizer[Marks, p.194-5]
FDA 要件The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including gentamicin sulfate, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Gentamicin sulfate/The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Gentamicin sulfate is included on this list. /Gentamicin sulfate/Oral dosage form new animal drugs. Gentamicin sulfate oral solution. ... Indications for use. In weanling swine for control and treatment of colibacillosis caused by strains of Escherichia coli sensitive to gentamicin, and in swine for control and treatment of swine dysentery associated with Treponema hyodysenteriae. ... Limitations. Do not slaughter treated swine for food for at least 3 days following treatment. Federal law restricts this drug to use by or on the order of a licensed veterinarian. /Gentamicin sulfate/Oral dosage form new animal drugs. Gentamicin sulfate pig pump oral solution. ... Indications for use. In neonatal swine 1 to 3 days of age for control and treatment of colibacillosis caused by strains of Escherichia coli sensitive to gentamicin. ... Limitations. For use in neonatal swine only. Do not slaughter treated swine for food for at least 14 days following treatment. /Gentamicin sulfate/

用途

解説

ゲンタマイシンC,Micromonospora purpureaまたはM.echinosporaが産生するアミノ配糖体抗生物質で，ゲンタマイシン C1：C21H43N5O7(477.59)，C2：C20H41N5O7(463.57)，および C1a：C19H39N5O7(449.54)の混合物．白色の粉末．融点102～108 ℃．[α]25D＋146°(水)．水溶性塩基性物質．細菌のリボソームの30Sと50Sの両サブユニットに結合してタンパク質合成の開始反応を阻害し，コドンの読み間違いも起こす．グラム陽性菌および緑膿菌を含むグラム陰性菌に殺菌的に作用する．硫酸塩が注射および外用で使用される．嫌気的な環境や酸性では不活性で，嫌気性菌や膿瘍の治療には使わない．副作用は，腎毒性と耳毒性で，アミノグリコシド系抗生物質のなかでも強いほうである．硫酸塩はLD50 75 mg/kg(マウス，静注)．

説明

Gentamicin is a mixture of several antibiotic components produced by fermentation of Mi cromonospora purpurea and other related soil microorganisms (hence its name is spelled with an “i” instead of a “ y”). Gentamicins C-1, C-2, and C-1a are most prominent. Gentamicin is the most important of the aminoglycoside antibiotics still in use. Gentamicin was, for example, one of the first antibiotics to have significant activity against Pseudomonas aeruginosa infections. This water-loving, opportunistic pathogen frequently is encountered in burns, pneumonias, and urinary tract infections.

使用

antibacterial

For more FDA Requirements (Complete) data for Gentamicin (11 total), please visit the HSDB record page.
Special ReportsWHOEnvironmental Health Criteria 119: Principles and Methods for the Assessment of Nephrotoxicity Associated with Exposure to Chemicals (1991)
Hazard Classes and CategoriesSkin Sens. 1 (47.6%)
保管条件Protect from light and store away from heat. Store at controlled room temperature 15 deg - 30 °C (59 deg - 86 °F). /Gentamicin, ophthalmic preparations/Store at 20 deg to 25 °C (68 deg to 77 °F) /Gentamicin, injectable preparationsGentamicin, topical preparations/
処分方法SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.
相互作用One in vitro study indicates that cytarabine may antagonize the activity of gentamicin against Klebsiella pneumoniae.Gentamicin appears to be more readily inactivated by antipseudomonal penicillins (eg, ticarcillin) than amikacin both in vitro and in vivo in patients with renal failure.Concomitant and/or sequential use of an aminoglycoside and other systemic, oral, or topical drugs that have neurotoxic, ototoxic, or nephrotoxic effects (e.g., other aminoglycosides, acyclovir, amphotericin B, bacitracin, capreomycin, certain cephalosporins, colistin, cisplatin, methoxyflurane, polymyxin B, vancomycin) may result in additive toxicity and should be avoided, if possible. /Aminoglycosides/Because of the possibility of an increased risk of ototoxicity due to additive effects or altered serum and tissue aminoglycoside concentrations, aminoglycosides should not be given concomitantly with potent diuretics such as ethacrynic acid, furosemide, urea, or mannitol. It has been suggested that concomitant use of certain anti-emetics that suppress nausea and vomiting of vestibular origin and vertigo (e.g., dimenhydrinate, meclizine) may mask symptoms of aminoglycoside-associated vestibular ototoxicity. /Aminoglycosides/For more Interactions (Complete) data for Gentamicin (12 total), please visit the HSDB record page.
HepatotoxicityIntravenous and intramuscular therapy with gentamicin has been linked to mild and asymptomatic elevations in serum alkaline phosphatase levels, but rarely affects aminotransferase levels or bilirubin, and changes resolve rapidly once gentamicin is stopped. Only isolated case reports of acute liver injury with jaundice have been associated with aminoglycoside therapy including gentamicin, most of which are not very convincing. The hepatic injury described in these reports is typically mixed but can evolve into a cholestatic hepatitis. The latency to onset is rapid, occurring within 1 to 3 weeks and is typically associated with skin rash, fever and sometimes eosinophilia. Recovery typically occurs within 1 to 2 months and chronic injury has not been described. Aminoglycosides are not listed or mentioned in large case series of drug induced liver disease and acute liver failurethus, hepatic injury due to gentamicin is rare if it occurs at all.
生態毒性値LD50Species: Apis mellifera (Honey Bee) adulttopical >25.4 ug/bee
環境中動態TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that gentamicin is expected to have very high mobility in soil(SRC). The estimated pKb of gentamicin is 9.0(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of gentamicin from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.8X10-31 atm-cu m/mole(SRC), using a fragment constant estimation method(5). Gentamicin is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 1.8X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2017).AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 10(SRC), determined from a structure estimation method(2), indicates that gentamicin is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 9.8X10-31 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from an estimated log Kow of -1.88(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2017).ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), gentamicin, which has an estimated vapor pressure of 1,8X10-13 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase gentamicin may be removed from the air by wet and dry deposition(SRC). Gentamicin does not contain chromophores that absorb at wavelengths >290 nm(4) and, therefore, is not expected to be susceptible to direct photolysis by sunlight(SRC).
有害作用Skin Sensitizer - An agent that can induce an allergic reaction in the skin.Characteristically, gentamicin reaches high concentrations in the renal cortex and the inner ear. The latter may be injured, leading to auditory and, especially, vestibular dysfunction. The first manifestation of cochlear damage is often high-pitched tinnitus, which may last a few weeks after the gentamicin is interrupted. A high-frequency hearing loss may be present in almost two-thirds of patients receiving aminoglycosides, including gentamicin, but only a small number report hearing impairment. The vestibular toxicity manifests as nausea, vomiting, balance disorder, and vertigo within the first 2 weeks. A chronic phase, which may persist for about 2 months, is marked by ataxia and, not infrequently, leaves residual dysfunction. Gentamicin tends to accumulate in renal proximal tubular cells and can cause damage. Hence, mild proteinuria and a reduction in glomerular filtration rate are potential consequences of gentamicin use, with 14% of users experiencing these effects in a review. Once proximal tubular cells retain regenerative capacity, renal injury and its consequences are often reversible. Compared with the high-dose and extended-interval dosing approach, the divided-dose scheme implies a longer duration of gentamicin serum concentrations above the toxicity threshold, resulting in a higher risk of ototoxicity and nephrotoxicity.
毒性の概要IDENTIFICATION AND USE: Gentamicin sulfate is an aminoglycoside antibiotic. Gentamicin is widely used in the treatment of severe infections. It is active against many strains of Gram-negative bacteria and Streptococus aureus. It is inactive against anaerobes and poorly active against Streptococus hemolyticus and Pneumococcus. HUMAN EXPOSURE AND TOXICITY: Main risks and target organs: The main toxic effects are vestibular damage, deafness and renal dysfunction. The damage on the vestibular portion of the eighth cranial nerve appears to be greater than that on the cochlear portion. The main target organs are the eighth cranial nerves and the kidneys. Damage to eighth cranial nerve (both divisions) resulting in tinnitus, deafness, nausea, vomiting, vertigo, dizziness and nystagmus, and nephrotoxicity causing acute tubular necrosis resulting in renal failure. Loss of hearing, dizziness, vertigo, ataxia, nausea, vomiting and renal impairment developing in a patient on gentamicin therapy suggests a diagnosis of gentamicin toxicity. Other toxic features are muscular paralysis and respiratory depression. As gentamicin accumulates in the renal cortex, a critical concentration is reached when the concentrating ability of the kidney becomes impaired. Nephrotoxicity appears to be related to the duration for which the trough serum concentration exceeds 2 ug/ml. The exact mechanism of toxicity is unknown. Ototoxicity and vestibular toxicity seem most highly correlated with elevated peak concentrations (greater than 10 ug/mL) of gentamicin. Gentamicin accumulates in endolymph and perilymph and progressive destruction of ventricular and cochlear cells occurs. Repeated courses of gentamicin may produce progressive destruction of cells leading to deafness. Gentamicin appears to damage the vestibular portion more than the cochlear portion. Neuromuscular blockade with acute muscular paralysis and apnea may occur rarely. Most episodes have occurred in association with anesthesia or administration of other neuromuscular blockers but may also occur after intrapleural or intraperitoneal instillation of large doses of gentamicin or other aminoglycosides. This phenomenon may occur after intravenous or intramuscular administration. ANIMAL STUDIES: Clinical signs of intoxication in rodents included convulsions, prostration, hypoactivity, polydipsia, dyspnoea and ataxia. Dogs exhibited muscle tremors, salivation, and anorexia. Histopathological examination of kidneys from dogs that died up to 13 days after dosing revealed necrosis of the proximal convoluted tubule. Groups of 3 female Rhesus monkeys were injected i.m. with doses of 0, 6 or 30 mg/kg bw/day gentamicin in an aqueous vehicle for 3 weeks. Adverse clinical signs were limited to the 30 mg/kg bw/day group, which included pronounced facial paling and ptosis, markedly disturbed equilibrium from day 20, and depressed food intake and body- weight gain from week 2 onwards. Electron microscopy of renal tubules from the 30 mg/kg bw/day monkeys revealed myeloid bodies present in both tubular cells and lumen, increased phagosomes, disappearance of brush borders and sloughing of epithelial cells from the basement membrane. Groups of beagle dogs (4/sex/group) were administered oral doses of 0, 2, 10, or 60 mg/kg bw/day gentamicin in capsules for 14 weeks. Emesis and diarrhoea were observed occasionally in treated dogs. The only postmortem change was interstitial nephritis observed in 2 animals in the high-dose group. Gentamicin had negative effects on sperm parameters and testis apoptosis in rats. No treatment-related changes in pregnancy rate, litter size and weight, prenatal mortality or fetal abnormalities were reported in 2 generation study in rats. Gentamicin was tested in vitro for its ability to induce forward gene mutation in Chinese hamster ovary cells at concentrations of 128-5000 ug/mL and chromosomal aberrations in these cells at concentrations of 800-5000 ug/mL, both with and without metabolic activation. It was also tested in vivo for its ability to induce nuclear anomalies in mouse bone-marrow cells at intravenous doses of 20-80 mg/kg bw, the highest dose being the maximum tolerated dose. There was no indication of mutagenic activity.The main toxicity that occurs from gentamicin systemic use is nephrotoxicity. Although a rare event, hypersensitivity reactions secondary to gentamicin administration can be severe, to the extent that cases requiring intensive care unit admissions exist in the literature. There is no antidote for gentamicin toxicity, and the approach for gentamicin-induced hypersensitivity reaction is drug suspension combined with supportive treatment. The possible hypersensitivity manifestations are urticaria, eosinophilia, delayed-type hypersensitivity reaction (Stevens-Johnson syndrome and toxic epidermal necrolysis), angioedema, and anaphylactic shock. The clinical manifestations should guide the treatment strategy. In case of hypotension or even anaphylactic shock, intravenous fluids and vasoactive agents are the primary therapeutic options. Oxygen supplementation or mechanical ventilation may be necessary if respiratory distress occurs. When Stevens-Johnson syndrome or toxic epidermal necrolysis develops, the mainstay of treatment includes wound care, pain control, fluid and electrolyte management, and monitoring of superinfections. Nephrotoxicity, one of the most common adverse effects of gentamicin use, is associated with the therapy duration and not with serum concentrations. Generally, the glomerular filtration rate decrement is small and transient, and rarely progresses to oliguric-anuric renal failure. Likewise, ototoxicity is more common in long-term gentamicin therapy. Furthermore, cochlear and vestibular damage sometimes is irreversible and can be accumulated after repetitive gentamicin exposureaspirin use may attenuate this ototoxicity risk.
Soil Adsorption/MobilityUsing a structure estimation method based on molecular connectivity indices(1), the Koc of gentamicin can be estimated to be 10(SRC). According to a classification scheme(2), this estimated Koc value suggests that gentamicin is expected to have very high mobility in soil. The estimated pKb of gentamicin is 9.0(3), indicating that this compound will exist partially in the cation form in the environment and cations generally adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Aromatic amines are expected to bind strongly to humus or organic matter in soils due to the high reactivity of the aromatic amino group(5,6), suggesting that mobility may be much lower in some soils(SRC).
Natural Pollution SourcesGentamicin is a fermentation product of Micromonospora purpurea or M. echinospora and other variants(1).
Human Toxicity Excerpts/SIGNS AND SYMPTOMS/ Serious adverse effects on both vestibular and auditory branches of the eighth nerve have been reported, primarily in patients with renal impairment (especially if dialysis is required), and in patients on high doses and/or prolonged therapy. Symptoms include dizziness, vertigo, tinnitus, roaring in the ears and hearing loss, which, as with other aminoglycosides, may be irreversible. Hearing loss is usually manifested initially by diminution of high-tone acuity. Other factors which may increase the risk of toxicity include excessive dosage, dehydration and previous exposure to other ototoxic drugs. Peripheral neuropathy or encephalopathy, including numbness, skin tingling, muscle twitching, convulsions and a myasthenia gravis-like syndrome, have been reported./SIGNS AND SYMPTOMS/ Serious sensitivity reactions, such as anaphylaxis and dermatologic reactions including exfoliative dermatitis, toxic epidermal necrolysis, erythema multiforme, angioedema, and Stevens-Johnson syndrome, have been reported rarely in patients receiving aminoglycosidesfatalities have occurred rarely. Cross-sensitivity occurs among the aminoglycosides. /Aminoglycosides//CASE REPORTS/ A 65-year-old man with end-stage renal disease on continuous ambulatory peritoneal dialysis accidentally received an acute massive overdose of gentamicin as a treatment of peritonitis. The patient developed acute vestibular dysfunction and hearing loss following the overdose. His serum gentamicin had reached the extremely toxic level of 220 ug/mL. To remove the gentamicin, the patient received hemodialysis and hemoperfusion immediately. This was followed by two more courses of hemodialysis during the following 2 days. The gentamicin level was brought down to 10 ug/mL after the third hemodialysis. Moderate and persistent high-frequency hearing loss was documented with serial audiograms. The patient made a gradual but incomplete recovery from the vestibular dysfunction. ..../CASE REPORTS/ A healthy 14-month-old girl received gentamicin 500 mg (56 mg/kg) intravenously as empiric therapy given fever. The overdosage was quickly recognized and the child transferred to a pediatric referral center. Two hours after administration, serum creatinine was 0.3 mg/dL, though serum gentamicin level was 89 mg/L. Hemodialysis was initiated approximately 4 hr after gentamicin was given and stopped 4 hr later, with a serum gentamicin level of 3.4 mg/L. Gentamicin level 4 hr after completion of hemodialysis was 2.3 mg/L. Three months later, the child's serum creatinine was 0.3 mg/dL, urinalysis showed no blood or protein, and audiometry showed normal hearing bilaterally at all frequencies. This child demonstrated the highest gentamicin level recorded in a patient with normal renal function. Her case demonstrates that prompt hemodialysis in this circumstance rapidly clears gentamicin without rebound. If left untreated, long-term adverse sequellae for hearing or renal function were possiblehemodialysis may have altered these outcomes.For more Human Toxicity Excerpts (Complete) data for Gentamicin (17 total), please visit the HSDB record page.
Fish/Seafood ConcentrationsGentamicin was tested for but not detected in Australian farmed yellowtail kingfish (Seriola lalandi) and mulloway (Argyrosomus hololepidotus), farmed in Arno Bay and Whyalla, Spencer Gulf, South Australiadetection limit = 0.1 mg/kg(1).
Artificial Pollution SourcesGentamicin's production and administration as a a veterinary and human medication(1) may result in its release to the environment through various waste streams(SRC).
Drug Induced Liver InjuryDrug-Induced Liver Injury Severity and Toxicity (DILIst)GentamicinDILI NegativeIntramuscularIntravenousDOI:10.1016/j.drudis.2019.09.022
有害物質データ1403-66-3(Hazardous Substances Data)