L-フェニレフリン
L-フェニレフリン · m-シンパトール · m-シネフリン · 1-(m-ヒドロキシフェニル)-2-(メチルアミノ)エタノール · 1-(3-ヒドロキシフェニル)-2-(メチルアミノ)エタノール · 1-(m-ヒドロキシフェニル)-2-メチルアミノエタノール · m-[2-(メチルアミノ)-1-ヒドロキシエチル]フェノール · α-[(メチルアミノ)メチル]-3-ヒドロキシベンゼンメタノール

識別子と物理属性
| CAS No. | 59-42-7 |
|---|---|
| 分子式 | C9H13NO2 |
| 平均分子量 | 167.2 g/mol |
| 単同位体質量 | 167.09462866 g/mol |
| SMILES | CNC[C@H](O)c1cccc(O)c1 |
| InChIKey | SONNWYBIRXJNDC-VIFPVBQESA-N |
| PubChem CID | 6041 |
| ChEMBL | CHEMBL1215 |
| ChEBI | CHEBI:8093 |
| EC No. | 200-424-8 |
| DTXSID | DTXSID9023465 |
| 現地名 | L-フェニレフリン |
化学・物理的性質
| XLogP | -0.3 |
|---|---|
| 極性表面積 | 52.5 |
| 水素結合供与体数 | 3 |
| 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 | 130 |
| 医薬品 | Pharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Listed in ZINC15 |
| LogP(分配係数) | -0.31 |
| 溶解度 | Freely soluble in waterFREELY SOL IN GLYCERIN /PHENYLEPHRINE HYDROCHLORIDE/水に溶けにくく、メタノールに溶けにくく、エタノールに溶けにくい (96%)。希鉱酸および希アルカリ金属水酸化物溶液に可溶です。 |
| Human Drugs | Breast FeedingLactationMilk, HumanAdrenergic AgentsAdrenergic Alpha-AgonistsAntiglaucoma AgentsSympathomimeticsVasoconstrictor AgentsNasal Decongestants |
| 融点 | 140-145 °C169-172 °C171°C |
| Physical Description | Solid |
| Stability/Shelf Life | Solutions of phenylephrine hydrochloride that have been diluted in 5% dextrose injection are stable for at least 48 hours at pH 3.5-7.5. /Phenylephrine hydrochloride/Prolonged exposure to air or strong light may cause oxidation and discoloration. |
| Dissociation Constants | 8.97pKa = 8.97 |
| Collision Cross Section | 138.7 Ų [M-H]- [CCS Type: DTBuffer gas: N2Ionization: ESI-Dataset: TOXCASTSource Identifier: DTXSID3021142] |
| Other Experimental Properties | CRYSTALSBITTERMP: 140-145 °CFREELY SOL IN WATER OR ALCOHOLSPECIFIC OPTICAL ROTATION: -46.2 TO -47.2 DEG @ 25 °C/DAQ SOLN IS NEUTRAL TO LITMUS PAPER /PHENYLEPHRINE HYDROCHLORIDE/WHITE TO OFF-WHITE, CRYSTALLINE POWDERPKA: 7.6 /PHENYLEPHRINE HYDROCHLORIDE/ODORLESS, /PHENYLEPHRINE HYDROCHLORIDE/ |
| 沸点 | 295.79°C (rough estimate) |
| 密度 | 1.1222 (rough estimate) |
| 屈折率 | -55.5 ° (C=5, 1mol/L HCl) |
| 貯蔵条件 | -20°C Freezer, Under inert atmosphere |
| 外観・状態 | Solid |
| pKa(酸解離定数) | pKa 8.9 (Uncertain) |
| 色 | ホワイトからオフホワイト |
| 主な用途 | 医薬品(低分子化合物) |
| InChI | InChI=1/C9H13NO2/c1-10-6-9(12)7-3-2-4-8(11)5-7/h2-5,9-12H,6H2,1H3/t9-/s3 |
| InChIKey | SONNWYBIRXJNDC-DJEYLCQNNA-N |
| SMILES | [C@H](C1C=CC=C(O)C=1)(O)CNC |&1:0,r| |
| CAS データベース | 59-42-7(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzenemethanol, 3-hydroxy-«alpha»-[(methylamino)methyl]-, (r)-(59-42-7) |
化学的特性
White or almost white, crystalline powder.
安全性と法規制
| GHS 分類 | WarningH302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 109 reports by companies from 4 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | REACH registered substance: Phenylephrine (EC: 200-424-8) |
| その他の安全情報 | IMAP assessments - Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (R)-: Environment tier I assessment |
| FDA 要件 | The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl phenylephrine hydrochloride, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act. /Phenylephrine Hydrochloride/Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: phenylephrine hydrochloride (less than 0.08 percent) is included in ophthalmic vasoconstrictor drug products. /Phenylephrine hydrochloride/Nasal decongestant active active ingredients. The active ingredient of the product consists of any of the following when used in the dosage limits and in the dosage forms established for each ingredient. Oral nasal decongestants: phenylephrine hydrochloride, phenylephrine bitartrate in an effervescent dosage form. Topical nasal decongestants: Phenylephrine hydrochloride. /Phenylephrine hydrochloridePhenylephrine bitartrate/Vasoconstrictor active ingredients. The active ingredient of the product consists of any of the following when used in the concentration or within the concentration range established for each ingredient. Phenylephrine hydrochloride 0.25 percent.Ophthalmic vasoconstrictors. The active ingredient of the product consists of one of the following, within the established concentration for each ingredient. Phenylephrine hydrochloride, 0.08 to 0.2 percent. |
| Special Reports | DHHS/NTPToxicology & Carcinogenesis Studies of Phenylephrine Hydrochloride in F344/N Rats and B6C3F1 Mice (Feed Studies) Technical Report Series No. 322 (1987) NIH Publication No. 87-2578 |
用途
解説
フェニレフリンは,交感神経興奮薬の一つ。ネオシネフリンともいう。メタヒドロキシ-ω-クロロアセトフェノンとメチルアミンとを希釈アルコール中で反応させて合成する。交感神経興奮作用をもつので,部分的血管収縮,瞳孔散大,鼻孔充血除去などに用いられる。アドレナリンとよく似た化学構造をもち,とくにα‐アドレナリン作動性受容体に対する選択性が高い薬物として知られる。末梢血管の収縮による血圧上昇作用が強く,持続的である。フェニレフリンの塩酸塩とその溶液は,日本薬局方,アメリカ薬局方などに収載されており,急性低血圧の昇圧薬,鼻づまりの点鼻液,瞳孔散大のための点眼薬などとして使われる。【粕谷 豊】株式会社平凡社 世界大百科事典 第2版について 情報
説明
This synthetic drug has both chemical and pharmacological similarities to norepinephrine. A characteristic quality of phenylephrine is the distinctly expressed selectivity to α- adrenoreceptors, especially α1-adrenoreceptors. Although phenylephrine increases the contractibility of blood vessels, in practical terms it is not considered a cardiostimulant.
来歴
Phenylephrine was first patented in 1927 and was first introduced for medical use in 1938. It is available as a generic medication. Unlike pseudoephedrine, abuse of phenylephrine is very uncommon. Its effectiveness as an oral nasal decongestant has been questioned. In 2023, a U.S. Food and Drug Administration (FDA) panel concluded that the drug was ineffective as a nasal decongestant when taken orally, performing no better than placebo. In November 2024, FDA announced it is proposing to remove oral phenylephrine as an active ingredient that can be used in over-the-counter (OTC) monograph drug products for the temporary relief of nasal congestion after an agency review of the available data determined that oral phenylephrine is not effective for this use.
使用
L-Phenylephrine is an adrenergic α1A receptor agonist (Ki = 1.4 μM) that demonstrates selectivity against the α1B and α1C receptor subtypes (Kis = 23.9 and 47.8 μM, respectively). By stimulating adrenergic α1 receptors, L-phenylephrine can induce aortic smooth muscle contractions, although reported relative affinity and potency values in rabbit are 5-fold weaker compared to that of L-norepinephrine. This compound is frequently used to precontract smooth muscle in preparations designed to study the properties of various vasodilator agents. Because L-phenylephrine acts on adrenergic α1 receptors in the arterioles of the nasal mucosa to produce constriction, it has been examined clinically as an oral decongestant.
一般的な説明
(Neo-Synephrine, a prototypical selectivedirect-acting 1-agonist) differs from E only inlacking a p-OH group. It is orally active, and its DOA isabout twice that of E because it lacks the catechol moietyand thus is not metabolized by COMT. However, its oralbioavailability is less than 10% because of its hydrophilicproperties (log P=0.3), intestinal 3 -O-glucuronidation/sulfation and metabolism by MAO. Lacking the p-OHgroup, it is less potent than E and NE but it is a selectiveα1-agonist and thus a potent vasoconstrictor. It is usedsimilarly to metaraminol and methoxamine for hypotension.Another use is in the treatment of severe hypotensionresulting from either shock or drug administration. It alsohas widespread use as a nonprescription nasal decongestantin both oral and topical preparations. When applied tomucous membranes, it reduces congestion and swelling byconstricting the blood vessels of the membranes. In theeye, it is used to dilate the pupil and to treat open-angleglaucoma. In addition, it is used in spinal anesthesia toprolong the anesthesia and to prevent a drop in blood pressureduring the procedure. It is relatively nontoxic and produceslittle CNS stimulation. Metaraminol is just anotherexample.