atropine

[From New Latin Atropa, genus name of belladonna, from Greek Atropos, Atropos. See Atropos.]

For more information on atropine, visit Britannica.com.

An alkaloid, C₁₇H₂₃NO₃, with the chemical structure below. The systematic chemical name is endo-(±)-α-(hydroxymethyl)phenylacetic acid 8-methyl-8-azabicyclo[3.2.1] oct-3-yl ester, and in phamacy it is sometimes known as dl-hyoscyamine. It occurs in minute amounts

Atropine is used clinically as a mydriatic (pupil dilator). Dilation is produced by paralyzing the iris and ciliary muscles. Atropine is also administered in small doses before general anesthesia to lessen oral and air-passage secretions. Its ability to reduce these secretions is also utilized in several preparations commonly used for symptomatic relief of colds. See also Alkaloid.

Atropine is an alkaloid derived from the solanaceous plants Atropa belladonna (deadly nightshade), Hyoscyamus niger (black henbane), and Datura stramonium (thornapple). These plants contain a mixture of two closely related alkaloids, hyoscyamine and hyoscine; atropine is a mixture of two isomers of hyoscyamine. In 1867, von Bezold found that atropine blocked the slowing of the heart caused by vagal stimulation. We now know that atropine blocks the action of the neurotransmitter acetylcholine at all the nerve endings where the membrane receptors are of the so-called muscarinic type. This includes those of the parasympathetic nervous system in the heart, glandular tissue, and smooth muscle. Thus atropine causes a rise in heart rate and inhibits secretions (for example of saliva, causing a dry mouth, and of the digestive enzymes). It also relaxes smooth muscle in the gastrointestinal tract, the urinary bladder, and the bronchial trees, by preventing the effects of the normal background discharge of parasympathetic neurons to these organs.

The central nervous system also contains muscarinic receptors. Blockade of these by atropine leads to restlessness and mental excitement, and can improve the rigidity and tremor characteristic of Parkinson's disease. Large doses of atropine can cause hallucination.

Long-lasting pupillary dilation results if atropine drops are placed in the eye. The iris has both circular and radial muscles, and the balance between the tonic activities of these two muscle groups controls the pupil diameter. The circular muscle is under parasympathetic control, so when the transmitter, acetylcholine, is blocked with atropine, the pupil will dilate. It is told that Spanish ladies put atropine drops in their eyes for the allure given by large, black pupils: hence the name belladonna — ‘fine lady’.

— Alan W. Cuthbert

See also autonomic nervous system; neurotransmitter; membrane receptors.

An alkaloid that annuls parasympathetic effects and antagonizes the effects of pilocarpine. It acts directly on the effector cells, preventing the action but not the liberation of acetylcholine. It suppresses sweat and other glandular sections.

Brand names: Atreza™, AtroPen®, Atropine Care®, Atropisol®, Atrosulf 1™, Isopto® Atropine, Ocu-Tropine®, Sal-Tropine®

Chemical formula:

Drug Forms:
• Atropine Sulfate Ophthalmic drops, solution (below)
• Atropine Sulfate Solution for injection
• Atropine tablets or soluble tablets
• Atropine auto-injection
• Atropine Sulfate Ophthalmic ointment
• Atropine Sulfate Oral tablet

Español:
• Atropina Sulfato, Solución para gotas oftálmicas
• Sulfato de atropina, Solución para inyección
• Tabletas o tabletas solubles de atropina
• Auto inyección de atropina
• Sulfato de atropina, Pomada oftálmica
• Sulfato de atropina, Tableta oral

Atropine Sulfate Ophthalmic drops, solution

What is this medicine?

ATROPINE can dilate your pupils before examinations and can treat different eye problems.

This medicine may be used for other purposes; ask your health care provider or pharmacist if you have questions.

What should I tell my health care provider before I take this medicine?

They need to know if you have any of these conditions:
• glaucoma
• an unusual or allergic reaction to atropine, other medicines, foods, dyes, or preservatives
• pregnant or trying to get pregnant
• breast-feeding

How should I use this medicine?

This medicine is only for use in the eye. Do not take by mouth. Follow the directions on the prescription label. Wash hands before and after use. Tilt your head back and pull your lower eyelid down with your index finger to form a pouch. Squeeze the required number of drops into the pouch. Do not blink for 30 seconds. Close your eye gently to spread the drops. Do not touch your eye or surrounding tissue with the eye dropper. Do not use your medicine more often than directed.

Talk to your pediatrician regarding the use of this medicine in children. Special care may be needed.

Overdosage: If you think you have taken too much of this medicine contact a poison control center or emergency room at once.
NOTE: This medicine is only for you. Do not share this medicine with others.

What may interact with this medicine?

Interactions are not expected. Do not use any other eye products without asking your doctor or health care professional.

This list may not describe all possible interactions. Give your health care provider a list of all the medicines, herbs, non-prescription drugs, or dietary supplements you use. Also tell them if you smoke, drink alcohol, or use illegal drugs. Some items may interact with your medicine.

What should I watch for while using this medicine?

Side effects may occur even though you are no longer using this medicine. Contact your doctor or health care professional if you are still getting side effects after several days.

You may get blurred vision. Do not drive, use machinery, or do anything that requires mental alertness until you know how this medicine affects you.

Stay out of bright light and wear sunglasses if this medicine makes your eyes more sensitive to light.

What side effects may I notice from receiving this medicine?

Side effects that you should report to your doctor or health care professional as soon as possible:
• allergic reactions like skin rash, itching or hives, swelling of the face, lips, or tongue
• breathing problems
• decrease in blood pressure
• feeling faint or lightheaded, falls

Side effects that usually do not require medical attention (report to your doctor or health care professional if they continue or are bothersome):
• eye irritation, swelling of the eyelids
• increased sensitivity of the eyes to sun or ultraviolet light

This list may not describe all possible side effects. Call your doctor for medical advice about side effects. You may report side effects to FDA at 1-800-FDA-1088.

Where should I keep my medicine?

Keep out of the reach of children.

Store between 8 and 27 degrees C (46 and 80 degrees F). Do not freeze. Throw away any unused medicine after the expiration date.

Last updated: 11/3/2003 10:44:00 AM

Important Disclaimer: The drug information provided here is for educational purposes only. It is intended to supplement, not substitute for, the diagnosis, treatment and advice of a medical professional. This drug information does not cover all possible uses, precautions, side effects and interactions. It should not be construed to indicate that this or any drug is safe for you. Consult your medical professional for guidance before using any prescription or over the counter drugs.

A drug extracted from belladonna (the juice of the deadly nightshade, Atropa belladonna), which blocks the action of acetylcholine (ACh). Since ACh is the main neurotransmitter of the parasympathetic nervous system, atropine puts this system out of action leaving the sympathetic nervous system to function unopposed. Thus, atropine mimics some actions of the sympathetic nervous system and adrenaline. Small doses of atropine cause a marked increase in heart rate. Belladonna is used in some cold-remedies for bronchitis and whooping cough.

An anticholinergic alkaloid occurring in belladonna, hyoscyamus and stramonium. It acts as a competitive antagonist of acetylcholine at muscarinic receptors, blocking stimulation of muscles and glands by parasympathetic and cholinergic sympathetic nerves; used as a smooth muscle relaxant, as a preanesthetic to reduce secretions, and as an antidote to organophosphate poisoning. Has been used as a spasmolytic in many cases of gut hypermotility, e.g. equine spasmodic colic. Has the disadvantage of causing prolonged pupillary dilatation.

• a. challenge test — used in the diagnosis of narcolepsy in dogs; pretreatment with atropine reduces the number of cataleptic attacks with exposure to food.
• a. methobromide — a synthetic muscarinic blocking agent used as a smooth muscle relaxant but less effective against poisoning with organophosphorus insecticides than atropine. Called also methylatropine.
• a. poisoning — severe toxic reaction due to overdosage of atropine. Signs include dilated pupils, absent pupillary light reflex, dry mouth, high heart rate, excitement, muscle tremor. In animals usually results from atropine overdose.
• a. sulfate — the pharmaceutical preparation in common use.

Atropine
Systematic (IUPAC) name
(8-methyl-8-azabicyclo[3.2.1]oct-3-yl) 3-hydroxy-2-phenylpropanoate
Identifiers
CAS number	51-55-8
ATC code	A03BA01 S01FA01
PubChem	174174
DrugBank	APRD00807
ChemSpider	10194105
Chemical data
Formula	C17H23NO3
Mol. mass	289.369
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	25%
Metabolism	50% hydrolysed to tropine and tropic acid
Half life	2 hours
Excretion	50% excreted unchanged in urine
Therapeutic considerations
Pregnancy cat.	C(US)
Legal status	Rx only
Routes	Oral, IV, rectal
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Atropine is a tropane alkaloid extracted from deadly nightshade (Atropa belladonna), jimsonweed (Datura stramonium), mandrake (Mandragora officinarum) and other plants of the family Solanaceae. It is a secondary metabolite of these plants and serves as a drug with a wide variety of effects. It is a competitive antagonist for the muscarinic acetylcholine receptor. It is classified as an anticholinergic drug. Being potentially deadly, it derives its name from Atropos, one of the three Fates who, according to Greek mythology, chose how a person was to die. Atropine is a core medicine in the World Health Organization's "Essential Drugs List", which is a list of minimum medical needs for a basic health care system.^[1]

Contents 1 Physiological effects and uses 1.1 Ophthalmic use 1.2 Resuscitation 1.3 Secretions and bronchoconstriction 1.4 Treatment for organophosphate poisoning 1.5 Optical penalisation 1.6 Side-effects and overdose 2 Chemistry and pharmacology 3 History 4 Natural sources 5 See also 6 References

Physiological effects and uses

Atropine increases firing of the sinoatrial node (SA) and conduction through the atrioventricular node (AV) of the heart, opposes the actions of the vagus nerve, blocks acetylcholine receptor sites, and decreases bronchial secretions.

In general, atropine lowers the parasympathetic activity of all muscles and glands regulated by the parasympathetic nervous system. This occurs because atropine is a competitive antagonist of the muscarinic acetylcholine receptors (Acetylcholine is the main neurotransmitter used by the parasympathetic nervous system). Therefore, it may cause swallowing difficulties and reduced secretions.

Ophthalmic use

Topical atropine is used as a cycloplegic, to temporarily paralyze the accommodation reflex, and as a mydriatic, to dilate the pupils. Atropine degrades slowly, typically wearing off in 7 to 14 days, so it is generally used as a therapeutic mydriatic, whereas tropicamide (a shorter-acting cholinergic antagonist) or phenylephrine (an α-adrenergic agonist) is preferred as an aid to ophthalmic examination. Atropine induces mydriasis by blocking contraction of the circular pupillary sphincter muscle, which is normally stimulated by acetylcholine release, thereby allowing the radial pupillary dilator muscle to contract and dilate the pupil. Atropine induces cycloplegia by paralyzing the ciliary muscles, whose action inhibits accommodation to allow accurate refraction in children, helps to relieve pain associated with iridocyclitis, and treats ciliary block (malignant) glaucoma. Atropine is contraindicated in patients pre-disposed to narrow angle glaucoma.

Atropine can be given to patients who have direct globe trauma.

Resuscitation

Injections of atropine are used in the treatment of bradycardia (an extremely low heart rate), asystole and pulseless electrical activity (PEA) in cardiac arrest. This works because the main action of the vagus nerve of the parasympathetic system on the heart is to decrease heart rate. Atropine blocks this action and, therefore, may speed up the heart rate. The usual dosage of atropine in bradyasystolic arrest is 0.5 to 1 mg IV push every three to five minutes, up to a maximum dose of 0.04 mg/kg. For symptomatic bradycardia, the usual dosage is 0.5 to 1.0 mg IV push, may repeat every 3 to 5 minutes up to a maximum dose of 3.0 mg^[2].

Atropine is also useful in treating second-degree heart block Mobitz Type 1 (Wenckebach block), and also third-degree heart block with a high Purkinje or AV-nodal escape rhythm. It is usually not effective in second-degree heart block Mobitz type 2, and in third-degree heart block with a low Purkinje or ventricular escape rhythm. Atropine is contraindicated in ischemia-induced conduction block, because the drug increases oxygen demand of the AV nodal tissue, thereby aggravating ischemia and the resulting heart block.

One of the main actions of the parasympathetic nervous system is to stimulate the M₂ muscarinic receptor in the heart, but atropine inhibits this action.

Secretions and bronchoconstriction

Atropine's actions on the parasympathetic nervous system inhibits salivary, sweat, and mucus glands. This can be useful in treating hyperhidrosis, and can prevent the death rattle of dying patients. Even though atropine has not been officially indicated for either of these purposes by the FDA, it has been used by physicians for these purposes.^[3]

Treatment for organophosphate poisoning

Atropine is not an actual antidote for organophosphate poisoning. However, by blocking the action of acetylcholine at muscarinic receptors, atropine also serves as a treatment for poisoning by organophosphate insecticides and nerve gases, such as Tabun (GA), Sarin (GB), Soman (GD) and VX. Troops that are likely to be attacked with chemical weapons often carry autoinjectors with atropine and obidoxime, which can be quickly injected into the thigh. Atropine is often used in conjunction with Pralidoxime chloride.

Atropine is given as a treatment for SLUDGE (Salivation, Lacrimation, Urination, Diaphoresis, Gastrointestinal motility, Emesis) symptoms caused by organophosphate poisoning.

Some of the nerve agents attack and destroy acetylcholinesterase, so the action of acetylcholine becomes prolonged. Therefore, atropine can be used to reduce the effect of acetylcholine.

Optical penalisation

In refractive and accommodative amblyopia, when occlusion is not appropriate sometimes atropine is given to induce blur in the good eye.^[4]

Side-effects and overdose

Adverse reactions to atropine include ventricular fibrillation, supraventricular or ventricular tachycardia, dizziness, nausea, blurred vision, loss of balance, dilated pupils, photophobia, and, possibly, notably in the elderly, extreme confusion, extreme dissociative hallucinations, and excitation. These latter effects are because atropine is able to cross the blood-brain barrier. Because of the hallucinogenic properties, some have used the drug recreationally, though this is potentially dangerous and often unpleasant.

In overdoses, atropine is poisonous. Atropine is sometimes added to other potentially addictive drugs, particularly anti-diarrhea opioid drugs such as diphenoxylate or difenoxin, wherein the secretion-reducing effects of the atropine can also aid the anti-diarrhea effects.

Although atropine treats bradycardia (slow heart rate) in emergency settings, it can cause paradoxical heart rate slowing when given at very low doses, presumably as a result of central action in the CNS.^[5]

The antidote to atropine is physostigmine or pilocarpine.

A common mnemonic used to describe the physiologic manifestations of atropine overdose is: "hot as a hare, blind as a bat, dry as a bone, red as a beet, and mad as a hatter".^[6] These associations reflect the specific changes of warm, dry skin from decreased sweating, blurry vision, decreased sweating/lacrimation, vasodilation, and central nervous system effects on muscarinic receptors, type 4 and 5. This set of symptoms is known as anticholinergic toxidrome, and may also be caused by other drugs with anticholinergic effects, such as diphenhydramine, phenothiazine antipsychotics and benztropine.^[7]

Chemistry and pharmacology

Atropine is a racemic mixture of D-hyoscyamine and L-hyoscyamine, with most of its physiological effects due to L-hyoscyamine. Its pharmacological effects are due to binding to muscarinic acetylcholine receptors. It is an antimuscarinic agent.

The most common atropine compound used in medicine is atropine sulfate (C₁₇H₂₃NO₃)₂·H₂SO₄·H₂O, the full chemical name is 1α H, 5α H-Tropan-3-α ol (±)-tropate(ester), sulfate monohydrate.

History

Mandragora (mandrake) was described by Theophrastus in the fourth century B.C. for treatment of wounds, gout, and sleeplessness, and as a love potion. By the first century A.D. Dioscorides recognized wine of mandrake as an anaesthetic for treatment of pain or sleeplessness, to be given prior to surgery or cautery.^[6] The use of Solanaceae containing tropane alkaloids for anesthesia, often in combination with opium, persisted throughout the Roman and Islamic Empires and continued in Europe until superseded by the use of ether, chloroform, and other modern anesthetics.

Atropine extracts from the Egyptian henbane were used by Cleopatra in the last century B.C. to dilate her pupils, in the hope that she would appear more alluring. In the Renaissance, women used the juice of the berries of Atropa belladonna to enlarge the pupils of their eyes, for cosmetic reasons; "bella donna" is Italian for "beautiful lady".^[8] This practice resumed briefly in the late nineteenth- and early twentieth-century in Paris.

The mydriatic effects of atropine were studied among others by the German chemist Friedrich Ferdinand Runge (1795–1867). In 1831, the pharmacist Mein succeeded the pure crystalline isolation of atropine. The substance was first synthesized by German chemist Richard Willstätter in 1901.

Atropinic shock therapy, also known as atropinic coma therapy, is an old and rarely-used method. It consists of induction of atropinic coma by rapid intravenous infusion of atropine. Atropinic shock treatment is considered safe with careful monitoring and preparation, but it entails prolonged coma (between four and five hours), and it has many unpleasant side-effects, such as blurred vision.^{[citation needed]}

Natural sources

Atropine is found in many members of the Solanaceae family. The most commonly-found sources are Atropa belladonna, Datura inoxia, D. metel, and D. stramonium. Other sources include members of the Brugmansia and Hyoscyamus genera. The Nicotiana genus (including the tobacco plant, N. tabacum) is also found in the Solanaceae family, but these plants do not contain atropine or other tropane alkaloids.

See also

• Mark I NAAK
• Atropine coma therapy

References

1. ^ "WHO Model List of Essential Medicines" (PDF). World Health Organization. March 2005. http://whqlibdoc.who.int/hq/2005/a87017_eng.pdf. Retrieved 2006-03-12. 
2. ^ * Bryan E, Bledsoe; Robert S. Porter, Richard A. Cherry (2004). "Ch. 3". Intermediate Emergency Care. Upper Saddle River, NJ: Pearson Prentice Hill. pp. 260. ISBN 0-13-113607-0. 
3. ^ Untitled Document
4. ^ Georgievski Z, Koklanis K, Leone J. Fixation behaviour in the treatment of amblyopia using atropine. Clinical and Experimental Ophthalmology 2008; 36 (Suppl 2): A764–A765. [Link]
5. ^ * Rang HP, Dale MM, Ritter JM, Flower RJ (2007). "Ch. 10". Rang and Dale's Pharmacology. Elsevier Churchill Livingstone. pp. 153. ISBN 0-443-06911-5. 
6. ^ ^{a b} Robert S. Holzman, MD (1998-07). "The Legacy of Atropos". Anesthesiology 89 (1): 241-249. http://www.anesthesiology.org/pt/re/anes/fulltext.00000542-199807000-00030.htm;jsessionid=GSJKLv9vLCdQSmpp6vH3xdhnzWN1hy3s7JqMNFpWkHhLbKJT5vLM!741375937!-949856145!8091!-1#P89. Retrieved 2007-05-21.  citing J. Arena, Poisoning: Toxicology-Symptoms-Treatments, 3rd edition. Springfield, Charles C. Thomas, 1974, p 345
7. ^ Szajewski J (1995). "Acute anticholinergic syndrome". IPCS Intox Databank. http://www.intox.org/databank/documents/treat/treate/trt05_e.htm. Retrieved 2007-05-22. 
8. ^ Scrub Notes: A Medical Student Blog: Why Monica Bellucci Might Take Atropine

v • d • e Anticholinergics Nicotinic antagonists Ganglionic nondepolarizing: Hexamethonium, Mecamylamine, Pentolinium, Trimetaphan depolarizing: Nicotine (high doses) note: in PNS, ganglionic blocker can have direct antinicotinic action at preganglionic terminal, but simulate indirect antimuscarinic activities at postganglionic terminal Neuromuscular Non-depolarising Curare alkaloids Alcuronium · Dimethyltubocurarine · Tubocurarine 4° ammonium short duration: Mivacurium intermediate: Atracurium/Cisatracurium · Fazadinium · Rocuronium (short onset) · Vecuronium long: Doxacurium · Metocurine · Pancuronium · Pipecuronium unsorted: Gallamine · Hexafluronium Depolarising choline derivatives (Suxamethonium, Succinylcholine) · Decamethonium Muscarinic antagonists nonpolar/tertiary/CNS: Atropine · Scopolamine · Hyoscyamine · antiparkinson drugs (Benzatropine, Trihexyphenidyl, Biperiden) polar/quarternary/non-CNS: Glycopyrrolate · Ipratropium · M1 (Pirenzepine, Telenzepine) · M3 (Tiotropium, Darifenacin, Vedaclidine) unsorted: Tropicamide · Cyclopentolate · Dicycloverine · Tolterodine · Oxybutynin · Homatropine  · Orphenadrine · Diphenhydramine · Other ethanolamine class first-generation antihistamines Indirect acetylcholine synthesis inhibitor (Hemicholinium-3) · vesicle storage inhibitor (Vesamicol) · acetylcholine release inhibitor (Botulinum toxin) · acetylcholine release stimulator (Alpha-latrotoxin) · acetylcholinesterase reactivators (Pralidoxime, Obidoxime)

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v • d • e Ophthalmologicals: mydriatics and cycloplegics (S01F) Anticholinergics/antimuscarinics Atropine - Scopolamine - Methylscopolamine - Cyclopentolate - Homatropine - Tropicamide Sympathomimetics Phenylephrine - Ephedrine - Ibopamine

v • d • e Ancient anaesthesia Plants/animals Aconite • Argyreia speciosa • Castoreum • Cannabis • Coca • Deadly nightshade • Henbane • Lactucarium • Mandrake • Metel nut • Opium • Poison hemlock • Saussurea • Toloatzin • Willow People Abulcasis • Avenzoar • Avicenna • Celsus • Dioscorides • Galen • Hippocrates • Rhazes • Sabuncuoğlu • Sushrutha • Theophrastus • Zhang Compounds Aconitine • Δ9-THC • Atropine • Cocaine • Coniine • Hyoscyamine • Morphine • Salicylate • Scopolamine

v • d • e Deliriants (anticholinergic hallucinogens) Tropanes Atropine • CAR-226,086 • Hyoscyamine • Scopolamine Benzilates Benactyzine • CAR-301,060 • CAR-302,196 • CAR-302,282 • CAR-302,368 • CAR-302,537 • CAR-302,668 • CS-27349 • Ditran • EA-3167 • EA-3443 • EA-3580 • EA-3834 • N-Ethyl-3-piperidyl benzilate • N-Methyl-3-piperidyl benzilate • 3-Quinuclidinyl benzilate • WIN-2299 Antihistamines Benzhydryl compounds (Cyclizine • Dimenhydrinate • Diphenhydramine), Doxylamine • Promethazine Others Benzydamine • Dicyclomine • Biperiden • Trihexyphenidyl

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