페닐에프린

페닐레프린 · 페닐에프린 · PHENYLEPHRINE BASE · Phenylephrin · L-PHENYLEPHRINE · (R)-3-(1-Hydroxy-2-(methylamino)ethyl)phenol · PHENYLPHRINE · (r)-phenylephrine

https://huagongshe.com/ko/chemical/6041

식별자 및 물리적 특성

CAS No.	59-42-7
분자식	C9H13NO2
평균 분자량	167.2 g/mol
단동위원소 질량	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
현지명	페닐에프린

화학 및 물리적 성질

XLogP	-0.3
극성 표면적	52.5
수소 결합 공여자 수	3
수소 결합 수용자 수	3
회전 가능 결합 수	3
무거운 원자 수	12
형식 전하	0
복잡도	130
의약품	Pharmaceuticals -> Used in SwitzerlandPharmaceuticals -> Listed in ZINC15
LogP(분배 계수)	-0.31
용해도	Freely soluble in waterFREELY SOL IN GLYCERIN /PHENYLEPHRINE HYDROCHLORIDE/물에 약간 용해되고, 메탄올에 조금 용해되며, 에탄올에 약간 용해됩니다(96%). 묽은 무기산과 묽은 알칼리 수산화물 용액에 용해됩니다.
Human Drugs	Breast FeedingLactationMilk, HumanAdrenergic AgentsAdrenergic Alpha-AgonistsAntiglaucoma AgentsSympathomimeticsVasoconstrictor AgentsNasal Decongestants
녹는점	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 Å² [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/
끓는 점	295.79°C (rough estimate)
밀도	1.1222 (rough estimate)
굴절률	-55.5 ° (C=5, 1mol/L HCl)
저장 조건	-20°C Freezer, Under inert atmosphere
물리적 상태	Solid
pKa(산도 계수)	pKa 8.9 (Uncertain)
색상	흰색에서 황백색까지
주요 응용	의약품(소분자)
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\|
NIST	Benzenemethanol, 3-hydroxy-«alpha»-[(methylamino)methyl]-, (r)-(59-42-7)

화학적 성질

White or almost white, crystalline powder.

안전 및 규제

GHS 분류	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.
규제 정보	REACH registered substance: Phenylephrine (EC: 200-424-8)
기타 안전 정보	IMAP assessments - Benzenemethanol, 3-hydroxy-.alpha.-[(methylamino)methyl]-, (R)-: Environment tier I assessment
FDA 요건	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

용도

개요

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.

역사

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.

용도

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.

일반 설명

(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.