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Trade names | AKPro, D Epifrin, Diopine, Glaucothil, Pro-Epinephrine, Propine, Pivalephrine, Thilodrin, Vistapine, others |
Other names | Dipivefrin; Dipivephrine; Dipivephrin; Dipivalyl epinephrine; Dipivalylepinephrine; DPE; Epinephrine dipivalate; Epinephrine dipivalate ester; Adrenaline dipivalate; K-30081; 3,4-Dipivalyloxy-β-hydroxy-N-methylphenethylamine; 3,4-Dipivalyloxy-β-hydroxy-N-methyl-β-phenylethylamine |
AHFS/Drugs.com | International Drug Names |
MedlinePlus | a686005 |
Routes of administration | Eye drops [1] |
Drug class | Adrenergic receptor agonist; Sympathomimetic |
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Chemical and physical data | |
Formula | C19H29NO5 |
Molar mass | 351.443 g·mol−1 |
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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. [2] [3] It is available as a 0.1% ophthalmic solution (eye drop). [1] [4]
Side effects of dipivefrine include local eye reactions among others. Dipivefrine is a prodrug of epinephrine (adrenaline) and hence acts as a non-selective adrenergic receptor agonist. [5] It is a substituted phenethylamine and catecholamine and is an ester of epinephrine with much greater fat solubility. [6] [7] [8]
Dipivefrine was first described by 1975. [9] It is widely marketed throughout the world. [10] However, it is no longer available in the United States. [11]
Dipivefrine is used in the treatment of open-angle glaucoma. [2]
Use in narrow-angle glaucoma may be dangerous because it could make the eye susceptible to an attack of angle closure, [3] causing an increase in pressure and pain and possibly loss of vision.
The most common side effects of dipivefrine are burning, stinging, and other irritations of the eye. Possible but uncommon side effects are the same as those of epinephrine and include tachycardia (fast heartbeat), hypertension (high blood pressure) and arrhythmias (irregular heartbeat). [3]
Dipivefrine penetrates the cornea and is then hydrolysed to epinephrine by esterase enzymes. [8] It increases outflow of the aqueous humour and also reduces its formation (mediated by its action on α1- and α2-adrenergic receptors), thus reducing pressure inside the eye. It also increases the conductivity of trabecular filtering cells (a β2-adrenergic-receptor-mediated action). It is preferred to epinephrine because it is longer-acting, more consistent in its action, and better-tolerated. [2]
Dipivefrine, also known as epinephrine dipivalate or as 3,4-dipivalyloxy-β-hydroxy-N-methylphenethylamine, is a substituted phenethylamine and catecholamine. [6] It is the 3,4-dipivalate ester of epinephrine (adrenaline). [6]
The experimental log P of dipivefrine is 1.7 and its predicted log P ranges from 1.49 to 3.71. [6] [1] [12] It is dramatically more lipophilic (600-fold) than epinephrine, [7] [8] [4] which is highly hydrophilic and has a log P of -1.37. [13] The lipophilicity of dipivefrine allows it to penetrate the cornea much more readily (17-fold) than epinephrine. [7] [8] [4] Eye drops containing 0.1% dipivefrine have similar effectiveness to conventional eye drops containing 2% epinephrine in lowering intraocular pressure. [4]
Dipivefrine is used pharmaceutically mainly as the hydrochloride salt. [14] [10]
A similar compound that was never marketed is pivenfrine, which is the 3-pivalate ester of phenylephrine. [14]
Dipivefrine was first described in the scientific literature by 1975. [9]
Dipivefrine is the generic name of the drug and its INN , BAN , and DCF , while dipivefrin is its USAN and dipivefrina is its DCIT . [14] [10] [15] In the case of the hydrochloride salt, dipivefrine hydrochloride is its BANM while dipivefrin hydrochloride is its USAN and JAN . [14] [10] [15]
Synonyms of dipivefrine include epinephrine pivalate, adrenaline pivalate, and dipivalyl epinephrine, among others. [14] [10]
Dipivefrine has been sold under brand names including Diopine, Glaucothil, Pro-Epinephrine, Propine, Thilodrin, and Vistapine, among many others. [14] [10]
Beta blockers, also spelled β-blockers, are a class of medications that are predominantly used to manage abnormal heart rhythms (arrhythmia), and to protect the heart from a second heart attack after a first heart attack. They are also widely used to treat high blood pressure, although they are no longer the first choice for initial treatment of most patients.
Ephedrine is a central nervous system (CNS) stimulant and sympathomimetic agent that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection, it lasts about an hour, and when taken by mouth, it can last up to four hours.
Esmolol, sold under the brand name Brevibloc, is a cardio selective beta1 receptor blocker with rapid onset, a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilising activity at therapeutic dosages.
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.
An adrenergic agonist is a drug that stimulates a response from the adrenergic receptors. The five main categories of adrenergic receptors are: α1, α2, β1, β2, and β3, although there are more subtypes, and agonists vary in specificity between these receptors, and may be classified respectively. However, there are also other mechanisms of adrenergic agonism. Epinephrine and norepinephrine are endogenous and broad-spectrum. More selective agonists are more useful in pharmacology.
Betaxolol is a selective beta1 receptor blocker used in the treatment of hypertension and angina. It is also a adrenergic blocker with no partial agonist action and minimal membrane stabilizing activity. Being selective for beta1 receptors, it typically has fewer systemic side effects than non-selective beta-blockers, for example, not causing bronchospasm as timolol may. Betaxolol also shows greater affinity for beta1 receptors than metoprolol. In addition to its effect on the heart, betaxolol reduces the pressure within the eye. This effect is thought to be caused by reducing the production of the liquid within the eye. The precise mechanism of this effect is not known. The reduction in intraocular pressure reduces the risk of damage to the optic nerve and loss of vision in patients with elevated intraocular pressure due to glaucoma.
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.
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.
Carteolol is a non-selective beta blocker used to treat glaucoma. It is administered in the form of eye drops.
Levobetaxolol is a drug used to lower the pressure in the eye in treating conditions such as glaucoma. It is marketed as a 0.25 or 0.5% ophthalmic solution of levobetaxolol hydrochloride under the trade name Betaxon. Levobetaxolol is a beta-adrenergic receptor inhibitor.
Corbadrine, sold under the brand name Neo-Cobefrine and also known as levonordefrin and α-methylnorepinephrine, is a catecholamine sympathomimetic used as a topical nasal decongestant and vasoconstrictor in dentistry in the United States. It is usually used in a pre-mixed solution with local anesthetics, such as mepivacaine.
Ibopamine is a sympathomimetic drug, designed as a prodrug of epinine, used in ophthalmology. It induces mydriasis. It also has been investigated for use in the treatment of congestive heart failure.
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.
Adrenaline, also known as epinephrine, is a hormone and medication which is involved in regulating visceral functions. It appears as a white microcrystalline granule. Adrenaline is normally produced by the adrenal glands and by a small number of neurons in the medulla oblongata. It plays an essential role in the fight-or-flight response by increasing blood flow to muscles, heart output by acting on the SA node, pupil dilation response, and blood sugar level. It does this by binding to alpha and beta receptors. It is found in many animals, including humans, and some single-celled organisms. It has also been isolated from the plant Scoparia dulcis found in Northern Vietnam.
Deoxyepinephrine, also known by the common names N-methyldopamine and epinine, is an organic compound and natural product that is structurally related to the important neurotransmitters dopamine and epinephrine. All three of these compounds also belong to the catecholamine family. The pharmacology of epinine largely resembles that of its "parent", dopamine. Epinine has been found in plants, insects and animals. It is also of significance as the active metabolic breakdown product of the prodrug ibopamine, which has been used to treat congestive heart failure.
Tafluprost is a prostaglandin analogue. It is used topically to control the progression of open-angle glaucoma and in the management of ocular hypertension, alone or in combination with other medication. It reduces intraocular pressure by increasing the outflow of aqueous fluid from the eyes.
Phenylethanolamine, or β-hydroxyphenethylamine, is a trace amine with a structure similar to those of other trace phenethylamines as well as the catecholamine neurotransmitters dopamine, norepinephrine, and epinephrine. As an organic compound, phenylethanolamine is a β-hydroxylated phenethylamine that is also structurally related to a number of synthetic drugs in the substituted phenethylamine class. In common with these compounds, phenylethanolamine has strong cardiovascular activity and, under the name Apophedrin, has been used as a drug to produce topical vasoconstriction.
Pivenfrine, also known as pivalylphenylephrine or phenylephrine pivalate, is a sympathomimetic and mydriatic agent which was never marketed. It is the 3-pivalyl ester of phenylephrine. Pivenfrine has much greater lipophilicity than phenylephrine. Higher lipophilicity is known to greatly improve corneal permeability, as in dipivefrine. Another related compound is etilefrine pivalate.
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.
Epinephrine, also known as adrenaline, is a medication and hormone. As a medication, it is used to treat several conditions, including anaphylaxis, cardiac arrest, asthma, and superficial bleeding. Inhaled epinephrine may be used to improve the symptoms of croup. It may also be used for asthma when other treatments are not effective. It is given intravenously, by injection into a muscle, by inhalation, or by injection just under the skin.