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20-September-2008 09:29:03 - Atropine Atropine Systematic IUPAC name 8-methyl-8-azabicyclo3.2.1oct-3-yl 3-hydroxy-2-phenylpropanoate Identifiers CAS number 51-55-8 ATC code A03BA01 S01FA01 PubChem 174174 DrugBank APRD00807 Chemical data Formula C17H23NO3 Mol. mass 289.369 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. CUS Legal status Rx only Routes Oral, IV, rectal Atropine is a tropane alkaloid extracted from deadly nightshade Atropa belladonna, jimsonweed Datura stramonium 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 Antidote for organophosphate poisoning 1.5 Side effects and overdose 2 Chemistry and pharmacology 3 History 4 Natural sources 5 See also 6 References Physiological effects and uses Increases firing of SA node, conduction through AV node, opposes vagus nerve, blocks acetylcholine receptor sites, decreases bronchiole secretions. Generally, atropine lowers the rest and digest 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 2 to 3 days, so is generally used as a therapeutic mydriatic, whereas tropicamide a shorter-acting cholinergic antagonist or phenylephrine an α-adrenergic agonist are preferred as an aid to ophthalmic examination. The effects of atropine can last up to two weeks. 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 is contraindicated in patients predisposed 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 slow it down. Atropine blocks that action and therefore may speed up the heart rate. The usual dose of atropine is 0.5 to 1 mg IV push every three to five minutes, up to a maximum dose of 0.04mg/kg. 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 it has not been officially indicated for either of these purposes by the FDA, it has been used by physicians for these purposes. 2 Antidote for organophosphate poisoning By blocking the action of acetylcholine at muscarinic receptors, atropine also serves as an antidote for poisoning by organophosphate insecticides and nerve gases, such as Tabun GA, Sarin GB, Soman GD and VX. Troops who 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 an antidote to SLUDGE Salivation, Lacrimation, Urination, Diaphoresis, Gastrointestinal motility, Emesis symptoms caused by organophosphate poisoning. Some of the nerve gases attack and destroy acetylcholinesterase, so the action of acetylcholine becomes prolonged. Therefore, atropine can be used to reduce the effect of acetylcholine. 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 very dangerous and often unpleasant. In overdoses, atropine is poisonous. Atropine is sometimes added to other potentially addictive drugs, particularly anti-diahorrea opioid drugs such as diphenoxylate or difenoxin where the secretion-reducing effects of the atropine can also aid the anti-diahorrea effects. This is supposed to prevent abuse of these drugs, however while the unpleasant side effects produced by the atropine may discourage abuse they certainly do not prevent it entirely,3 and these combination products can be significantly more dangerous than if the opioid was administered by itself.4 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 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 C17H23NO32·H2SO4·H2O, the full chemical name is 1α H, 5α H-Tropan-3-α ol ±-tropateester, 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. 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, but it entails prolonged coma between four and five hours, with careful monitoring and preparation, 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 References ^ WHO Model List of Essential Medicines PDF. World Health Organization March 2005. Retrieved on 2006-03-12. ^ Untitled Document ^ Rao R, Agrawal A, Pal HR, Mohan I 2005. Lomotil dependence: a note of caution. Natl Med J India 18 6: 330-1. PMID 16483040. ^ Thomas TJ, Pauze D, Love JN January 2008. Are one or two dangerous? Diphenoxylate-atropine exposure in toddlers. J Emerg Med 34 1: 71-5. doi:10.1016/j.jemermed.2007.03.051. PMID 17976801. ^ Rang HP, Dale MM, Ritter JM, Flower RJ 2007. Ch. 10, Rang and Dale's Pharmacology. Elsevier Churchill Livingstone, 153. ISBN 0-443-06911-5. ^ a b Robert S. Holzman, MD 1998-07. The Legacy of Atropos 241-249. Retrieved on 2007-05-21. citing J. Arena, Poisoning: Toxicology-Symptoms-Treatments, 3rd ion. Springfield, Charles C. Thomas, 1974, p 345 ^ Szajewski J 1995. Acute anticholinergic syndrome. IPCS Intox Databank. Retrieved on 2007-05-22. v d e Anticholinergics Nicotinic antagonists Ganglionic Mecamylamine - Trimethaphan - Hexamethonium Neuromuscular Non-depolarising Curare Alkaloids: Alcuronium - Dimethyltubocurarine - Tubocurarine Quaternary ammonium compounds: Atracurium - Cisatracurium - Doxacurium chloride - Fazadinium bromide - Gallamine - Hexafluronium - Metocurine - Mivacurium chloride - Pancuronium - Pipecuronium bromide - Rocuronium bromide,Vecuronium Depolarising Choline Derivatives: Suxamethonium - Succinylcholine Muscarinic antagonists Atropine - Scopolamine - Ipratropium - Tropicamide - Cyclopentolate - Benztropine - Dicycloverine - Tolterodine - Oxybutynin - Pirenzepine - M1 Pirenzepine - M3 Tiotropium, Darifenacin Presynaptic acetylcholine synthesis Hemicholinium-3 - acetylcholine release Botulinum toxin Other acetylcholinesterase reactivators Pralidoxime, Obidoxime note: in PNS, ganglionic blocker can have direct antinicotinic action at preganglionic terminal, but simulate indirect antimuscarinic activities at postganglionic terminal v d e Drugs for functional gastrointestinal disorders A03 Drugs for functional bowel disorders Antimuscarinics Mebeverine - Dicycloverine - Propantheline Phosphodiesterase inhibitors Papaverine - Drotaverine - Moxaverine Acting on serotonin receptors 5-HT3 antagonists Alosetron, Cilansetron - 5-HT4 agonists Mosapride, Tegaserod Other Diisopromine - Isometheptene - Phloroglucinol - Proglumide - Tridihexethyl Belladonna and derivatives antimuscarinics Atropine - Hyoscyamine - Butylscopolamine - Methylscopolamine - Scopolamine - Tincture of Belladonna - Fenoverine Propulsives primarily dopamine antagonists Metoclopramide/Bromopride, Domperidone, Alizapride - 5-HT4 agonists Cisapride - Clebopride v d e Ophthalmologicals: mydriatics and cycloplegics S01F Anticholinergics/antimuscarinics Atropine - Scopolamine - Methylscopolamine - Cyclopentolate - Homatropine - Tropicamide Sympathomimetics Phenylephrine - Ephedrine - Ibopamine v d e Anesthetic: 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 Avicenna Celsus Dioscorides Galen Hippocrates Rhazes SabuncuoÄŸlu Susrutha Theophrastus Zhang Molecules Aconitine Δ9-THC Atropine Cocaine Coniine Hyoscyamine Morphine Salicylate Scopolamine v d e Deliriants anticholinergic hallucinogens Tropanes Atropine, Hyoscyamine, Scopolamine Benzilates Benactyzine, Ditran, EA-3167, N-Ethyl-3-piperidyl benzilate, N-Methyl-3-piperidyl benzilate, 3-Quinuclidinyl benzilate Antihistamines Benzhydryl compounds Cyclizine, Dimenhydrinate, Diphenhydramine, Doxylamine, Promethazine Others Benzydamine, Dicyclomine, Biperiden, Trihexyphenidyl v d e Health Science Medicine Emergency medicine Procedures Advanced cardiac life support ACLS · Advanced life support ALS · Advanced Trauma Life Support ATLS · Basic life support BLS · Cardiopulmonary resuscitation CPR · First aid · Pediatric Advanced Life Support PALS Equipment Ambulance · Bag valve mask BVM · Chest tube · Defibrillation AED, ICD · Electrocardiogram ECG/EKG · Intraosseous infusion IO · Intravenous therapy IV · Intubation · Nasopharyngeal airway NPA · Oropharyngeal airway OPA · Pocket mask People Certified first responder CFR · Emergency medical responder EMR · Emergency medical technician EMT · Paramedic · Emergency physician Drugs Atropine · Amiodarone · Epinephrine/Adrenaline · Magnesium · Bicarbonate Other Golden hour · Emergency department · Emergency medical services · Emergency psychiatry · Medical emergency · Trauma center · Triage Retrieved from http://en..org/wiki/Atropine Categories: Natural tropane alkaloids | Antidotes | Deliriants | Muscarinic antagonists | World Health Organization essential medicinesHidden categories: All articles with statements | Articles with statements since May 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages БългарÑ?ки ÄŒesky Dansk Deutsch Español Esperanto Français Galego í•œêµì–´ Hrvatski Italiano עברית Lietuvių Magyar Nederlands 日本語 ‪Norsk bokmÃ¥l‬ Polski Português Română РуÑ?Ñ?кий Shqip SlovenÄ?ina SlovenÅ¡Ä?ina СрпÑ?ки / Srpski Suomi Svenska Türkçe УкраїнÑ?ька ä¸æ–‡ This page was last modified on 12 August 2008, at 08:01
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