Clinical data | |
---|---|
Trade names | Vasoxine, Vasoxyl, Vasylox, others |
Other names | Methoxamedrine; 2,6-Dimethoxy-β-hydroxy-α-methylphenethylamine; 2,6-Dimethoxy-β-hydroxyamphetamine |
AHFS/Drugs.com | International Drug Names |
Routes of administration | Oral, injection [1] |
ATC code | |
Pharmacokinetic data | |
Elimination half-life | 3 hours |
Excretion | Urine |
Identifiers | |
| |
CAS Number | |
PubChem CID | |
IUPHAR/BPS | |
DrugBank | |
ChemSpider | |
UNII | |
KEGG | |
ChEMBL | |
CompTox Dashboard (EPA) | |
ECHA InfoCard | 100.006.244 |
Chemical and physical data | |
Formula | C11H17NO3 |
Molar mass | 211.261 g·mol−1 |
3D model (JSmol) | |
| |
| |
(verify) |
Methoxamine, sold under the brand names Vasoxine, Vasoxyl, and Vasylox among others, is a sympathomimetic medication used as an antihypotensive agent. [2] [3] [4] [5] It has mostly or entirely been discontinued. [6]
The drug is an α1-adrenergic receptor agonist. [4] [ additional citation(s) needed ]
The long duration of action of methoxamine has been said to have rendered it obsolete in modern clinical practice. [2]
Methoxamine is an α1-adrenergic receptor agonist. [2] It is described as a long-acting α1-adrenergic receptor agonist and this is contrasted with phenylephrine which is said to be short-acting. [2] Phenylephrine is 5 to 10 times more potent than methoxamine and has a 3-fold higher maximal effect. [2]
Methoxamine, also known as 2,6-dimethoxy-β-hydroxy-α-methylphenethylamine or as 2,6-dimethoxy-β-hydroxyamphetamine, is a substituted phenethylamine and amphetamine derivative. [3]
It is somewhat similar in chemical structure to those of desglymidodrine (3,6-dimethoxy-β-hydroxyphenethylamine), dimetofrine (3,5-dimethoxy-4,β-dihydroxy-N-methylphenethylamine), 2,5-dimethoxyamphetamine (2,5-DMA), and butaxamine ((1S,2S)-3,6-dimethoxy-β-hydroxy-N-tert-butylamphetamine).
Methoxamine was synthesized by 1944. [3] It was marketed in the United States by 1949. [1]
Methoxamine is the generic name of the drug and its INN and BAN , while méthoxamine is its DCF and methoxamina is its DCIT . [3] [4] [6] In the case of the hydrochloride salt, its generic name is methoxamine hydrochloride and this is its USAN , BANM , and JAN . [3] [4] [7] [6] A synonym of methoxamine is methoxamedrine. [4] The drug has been sold under brand names including Idasal, Mexan, Pressomin, Vasosterol, Vasoxine, Vasoxyl, and Vasylox. [3] [4] [6]
Methoxamine has been marketed in Canada, the Czech Republic, Ireland, Japan, Spain, the United Kingdom, and the United States and was available in these countries in 2000. [4] [6] However, it was discontinued in Canada and the United Kingdom by 2004. [7] It has also been discontinued in the United States. [1] By 2016, methoxamine appeared to remain available only in Japan. [6]
Phenylephrine, sold under the brand names Neosynephrine and Sudafed PE among numerous others, is a medication used as a decongestant for uncomplicated nasal congestion, used to dilate the pupil, used to increase blood pressure, and used to relieve hemorrhoids. It can be taken by mouth, as a nasal spray, given by injection into a vein or muscle, applied to the skin, or as a rectal suppository.
Midodrine, sold under the brand names ProAmatine and Orvaten among others, is a vasopressor or antihypotensive medication used to treat orthostatic hypotension and urinary incontinence. It is taken by mouth.
Isoprenaline, also known as isoproterenol and sold under the brand name Isuprel among others, is a sympathomimetic medication which is used in the treatment of acute bradycardia, heart block, and rarely for asthma, among other indications. It is used by injection into a vein, muscle, fat, or the heart, by inhalation, and in the past under the tongue or into the rectum.
Dipivefrine, or dipivefrin, also known as epinephrine pivalate and sold under the brand name Propine among others, is a sympathomimetic medication which is used in the treatment of open-angle glaucoma. It is available as a 0.1% ophthalmic solution.
Ritodrine, sold under the brand name Yutopar, is a tocolytic drug used to stop premature labor. This drug has been removed from the US market, according to FDA Orange Book. It was available in oral tablets or as an injection and was typically used as the hydrochloride salt.
Metaraminol, also known as metaradrine and sold under the brand names Aramine and Pressonex among others, is a sympathomimetic medication which is used in the prevention and treatment of hypotension, particularly as a complication of anesthesia. It is given by intramuscular or intravenous administration.
Xamoterol, sold under the brand names Corwin, Carwin, Corwil, and Xamtol among others, is a cardiac stimulant which is used in the treatment of heart failure. It acts as a selective partial agonist of the β1-adrenergic receptor with around 50% intrinsic sympathomimetic activity (ISA). The drug has no significant β2-adrenergic receptor agonistic activity. Xamoterol provides cardiac stimulation at rest but acts as a blocker during exercise. It is taken by mouth.
Ifenprodil, sold under the brand names Cerocral, Dilvax, and Vadilex, is a cerebral vasodilator that has been marketed in some countries, including in Japan, Hong Kong, and France. It is currently under development for treatment of a variety of additional indications.
Prenalterol, sold under the brand name Hyprenan, is a sympathomimetic agent and cardiac stimulant which acts as a β1-adrenergic receptor partial agonist and is used in the treatment of heart failure. It has selectivity for the β1-adrenergic receptor. Its partial agonist activity or intrinsic sympathomimetic activity is about 60%. It is said to have much greater impact on myocardial contractility than on heart rate. The drug has been marketed in Denmark, Norway, and Sweden.
Dimetofrine, also known as dimethophrine or dimetophrine and sold under the brand names Dovida, Pressamina, and Superten, is a medication described as a sympathomimetic, vasoconstrictor, and cardiac stimulant. It is said to be similarly or less effective than midodrine in the treatment of orthostatic hypotension and shows substantially lower potency.
Norfenefrine, also known as meta-octopamine or norphenylephrine and sold under the brand name Novadral among others, is a sympathomimetic medication which is used in the treatment of hypotension. Along with its structural isomer p-octopamine and the tyramines, norfenefrine is a naturally occurring endogenous trace amine and plays a role as a minor neurotransmitter in the brain.
Etilefrine, sold under the brand name Effortil among others, is a sympathomimetic medication used as an antihypotensive agent to treat orthostatic hypotension. It is usually used by mouth, but is also available as an injectable.
Oxyfedrine, sold under the brand names Ildamen and Myofedrin among others, is a sympathomimetic agent and coronary vasodilator which is used in the treatment of coronary heart disease, angina pectoris, and acute myocardial infarction. It is taken by mouth or intravenously.
Amidephrine, or amidefrine, sold under the brand name Fentrinol among others, is a selective α1-adrenergic receptor agonist which is described as an adrenergic or sympathomimetic, vasoconstrictor, and topical nasal decongestant used to treat allergic rhinitis. It is used as the mesylate salt, which has the generic names amidefrine mesilate and amidephrine mesylate. The drug is a substituted phenethylamine derivative and is also known as 3-methylsulfonamidyl-β-hydroxy-N-methylphenethylamine. As of 2000, it remained marketed only in Austria.
Iproheptine, sold under the brand names Metron and Susat, is a nasal decongestant which has been marketed in Japan. It is described as a vasoconstrictor and antihistamine. The drug is available over-the-counter in Japan.
Oxilofrine, sold under the brand names Carnigen and Suprifen among others, is a sympathomimetic medication which has been used as an antihypotensive agent and cough suppressant. It is taken by mouth.
Methylephedrine, sold under the brand name Metheph among others, is a sympathomimetic medication described as an antiasthmatic agent and used to treat coughing and nasal congestion. It is reported to be used in various over-the-counter cough and cold preparations throughout the world, including Japan.
Norepinephrine, also known as noradrenaline and sold under the brand name Levophed among others, is a medication used to treat people with very low blood pressure. It is the typical medication used in sepsis if low blood pressure does not improve following intravenous fluids. It is the same molecule as the hormone and neurotransmitter norepinephrine. It is given by slow injection into a vein.
Dextrofemine, sold under the brand names Marsyl and Dysmalgine, is a uterine spasmolytic and muscle relaxant of the amphetamine family. It is the dextrorotatory enantiomer of racefemine. The drug acts as a β-adrenergic receptor agonist and sympathomimetic. It was marketed in France in 1966 but appears to no longer be marketed. Other tocolytics with similar chemical structures as phenethylamines or amphetamines include bedoradrine, buphenine, fenoterol, hexoprenaline, isoxsuprine, ritodrine, and terbutaline.
Clorprenaline, also known as isoprophenamine and known as clorprenaline hydrochloride in the case of the hydrochloride salt, is a sympathomimetic and bronchodilator medication which is marketed in Japan. It acts as a β-adrenergic receptor agonist or as a β-sympathomimetic. Brand names of clorprenaline in Japan are numerous and include Asnormal, Bazarl, Bronchon, Clopinerin, Conselt, Cosmoline, Fusca, Kalutein, Pentadoll, Restanolon, and Troberin. The drug was first described in the literature by 1956.
{{cite web}}
: CS1 maint: unfit URL (link)