ガバペンチン
ガバペンチン · 1-(アミノメチル)シクロヘキサン-1-酢酸 · ノイロンチン · 1-(アミノメチル)シクロヘキサン酢酸 · 2-[1-(アミノメチル)シクロヘキシル]酢酸 · 1-アミノメチルシクロヘキサン酢酸 · (1-アミノメチルシクロヘキシル)酢酸 · ギャバペンチン
識別子と物理属性
| CAS No. | 60142-96-3 |
|---|---|
| 分子式 | C9H17NO2 |
| 平均分子量 | 171.24 g/mol |
| 単同位体質量 | 171.12592878 g/mol |
| SMILES | NCC1(CC(=O)O)CCCCC1 |
| InChIKey | UGJMXCAKCUNAIE-UHFFFAOYSA-N |
| PubChem CID | 3446 |
| ChEMBL | CHEMBL940 |
| ChEBI | CHEBI:42797 |
| EC No. | 262-076-3 |
| DTXSID | DTXSID0020074 |
| 現地名 | ガバペンチン |
化学・物理的性質
| XLogP | -1.1 |
|---|---|
| 極性表面積 | 63.3 |
| 水素結合供与体数 | 2 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 3 |
| 重原子数 | 12 |
| 形式電荷 | 0 |
| 複雑度 | 162 |
| 物質分類 | Pharmaceutical |
| 医薬品 | Pharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Listed in ZINC15Pharmaceuticals -> Antiepileptic |
| LogP（分配係数） | log Kow = -1.10 |
| 味 | Bitter |
| Color/Form | White to off-white crystalline solidcrystals from ethanol/ether |
| 溶解度 | >100mg/mLIn water, 4.49X10+3 mg/L at 25 °CFreely soluble in waterFreely soluble in alkaline and acidic solutions>25.7 [ug/mL] (The mean of the results at pH 7.4)H2O: 10 mg/mLwater: 100mM |
| Human Drugs | Breast FeedingLactationMilk, HumanAnticonvulsantsAntimanic AgentsGABA AgentsFDA approved drugs -> Active ingredientPharmaceuticals |
| Decomposition | Hazardous decomposition products formed under fire conditions - Carbon oxides, nitrogen oxides (NOx). |
| 融点 | 162-166 °Calso reported as 165-167 °C165 - 167 °C162°C |
| Physical Description | Solid |
| Stability/Shelf Life | Stable under recommended storage conditions. |
| Dissociation Constants | 3.7pKa1 = 3.68 at 25 °C (carboxylic acid)pKa2 = 10.70 (primary amine) |
| 沸点 | 314.4±15.0 °C(Predicted) |
| 密度 | 1.058±0.06 g/cm3(Predicted) |
| 引火点 | 9℃ |
| 貯蔵条件 | 2-8°C |
| 外観・状態 | 個体 |
| pKa（酸解離定数） | pKa1 (25°) 3.68pKa2 10.70 |
| 色 | オフホワイト |
| Merck | 14,4319 |
| BRN | 2359739 |
| BCS Class | 3 |
| 安定性 | -20°C の蒸留水で最長 3 か月間保存できます。 |
| 主な用途 | 医薬品（低分子化合物） |
| InChI | 1S/C9H17NO2/c10-7-9(6-8(11)12)4-2-1-3-5-9/h1-7,10H2,(H,11,12) |
| InChIKey | UGJMXCAKCUNAIE-UHFFFAOYSA-N |
| SMILES | NCC1(CCCCC1)CC(O)=O |
| CAS データベース | 60142-96-3(CAS DataBase Reference) |
| EPAの化学物質情報 | Cyclohexaneacetic acid, 1-(aminomethyl)- (60142-96-3) |
化学的特性
White Crystalline Solid
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 30.8% (32 of 104) of reports.DangerH315 (57.7%): Causes skin irritation [Warning Skin corrosion/irritation]P203, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 104 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Gabapentin: Does not have an individual approval but may be used under an appropriate group standard |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including gabapentin, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including gabapentin enacarbil, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Gabapentin enacarbil/ |
| Hazard Classes and Categories | Skin Irrit. 2 (57.7%) |
| Hazardous Reactivities and Incompatibilities | Incompatible materials: Strong oxidizing agents. |
| 消火手順 | Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary. |
| 保管条件 | Keep container tightly closed in a dry and well-ventilated place.Store Neurontin Tablets and Capsules at 25 °C (77 °F)excursions permitted between 15 °C to 30 °C (59 °F to 86 °F) [see USP Controlled Room Temperature]. Store Neurontin Oral Solution refrigerated, 2 °C to 8 °C (36 °F to 46 °F). |
| 清掃方法 | ACCIDENTAL RELEASE MEASURES: Personal precautions, protective equipment and emergency procedures: Use personal protective equipment. Avoid dust formation. Avoid breathing vapors, mist or gas. Ensure adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust. Environmental precautions: Prevent further leakage or spillage if safe to do so. Do not let product enter drains. Methods and materials for containment and cleaning up: Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed containers for disposal. |
用途
用途
脳中の GABA を上昇させます。 抗けいれん作用を示します。
用途
GABA 脳中の GABA を上昇させます。 抗けいれん作用を示します。
説明
Gabapentin was introduced in 1993 in the UK and early 1994 in the USA as an adjunctive therapy in the treatment of refractory partial seizures and secondarily generalized tonic-clonic seizures. Although being a lipophilic analog of the neurotransmitter GABA, gabapentin appears to exert its anticonvulsive function by a GABA receptor independent mechanism, possibly involving the L-system amino acid transporter protein. Gabapentin easily crosses the blood brain barrier and exhibits a favorable pharmacokinetic profile with high tolerability. It does not interfere with the metabolism of other concomitant administered antiepileptic drugs, thus having a low potential for drug interactions. Studies are currently underway for the use of gabapentin as mono-therapy for the treatment of various seizures.
来歴
Gabapentin is a pharmacologically active amino acid, discovered by the pharmaceutical company Parke-Davis, now owned by Warner-Lambert, a division of Pfizer in 1974. Although it was first approved as a treatment for partial seizures in 1993, Pfizer pleaded guilty to illegally marketing gabapentin for unapproved uses in 2004 and was heavily fined by the US Department of Justice for defrauding public health care programs. When this adjunctive use was approved by the US Food and Drug Administration (FDA) in late 1993, Warner-Lambert released gabapentin under the brand name Neurontin, expecting it to make no more than $500,000. But the 2001 sales of Neurontin raked in $1.2 billion.
使用
Gabapentin is an Amino acid structurally related to γ-Aminobutyric Acid (GABA), designed to cross the blood brain barrier. Used as an anticonvulsant.
一般的な説明
Gabapentin and its closely related analog pregabalin,(S)-3-isobutyl-GABA, are broad-spectrum anticonvulsantswith multiple mechanisms of action.24,51 Inaddition to modulating calcium influx and stimulateGABA biosynthesis as discussed earlier, they also competefor the biosynthesis of L-glutamic acid because oftheir structural similarity to L-leucine.51 Gabapentin andpregabalin have very little liability for causing metabolicbaseddrug–drug interactions, particularly when used incombination with other AEDs because they are not metabolizedin humans. More than 95% of the drug is excretedunchanged through the kidneys. However, there are somedifferences in their bioavailability. Unlike gabapentin,which exhibits 60% bioavailability when given in lowdoses because of intestinal uptake by a saturable smallneutral L-amino acid transporter, the absorption of pregabalinis almost complete (98%) and exhibits an ideal linear pharmacokinetic profile.24 This high bioavailability of pregabalincan be attributed to its closer structure similarity tothe essential amino acid, L-leucine.