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Atropine information


Atropine
Clinical data
Trade namesAtropen, others
Other namesDaturin[1]
AHFS/Drugs.comMonograph
MedlinePlusa682487
License data
  • US DailyMed: Atropine
Pregnancy
category
  • AU: A
Routes of
administration
By mouth, intravenous, intramuscular, rectal, ophthalmic
Drug classantimuscarinic (anticholinergic)
ATC code
  • A03BA01 (WHO) S01FA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • US: ℞-only[3][4]
Pharmacokinetic data
Bioavailability25%
Metabolism≥50% hydrolysed to tropine and tropic acid
Onset of actionc. 1 minute[5]
Elimination half-life2 hours
Duration of action30 to 60 min[5]
Excretion15–50% excreted unchanged in urine
Identifiers
IUPAC name
  • (RS)-(8-Methyl-8-azabicyclo[3.2.1]oct-3-yl) 3-hydroxy-2-phenylpropanoate
CAS Number
  • 51-55-8 checkY
PubChem CID
  • 174174
IUPHAR/BPS
  • 320
DrugBank
  • DB00572 checkY
ChemSpider
  • 10194105 checkY
UNII
  • 7C0697DR9I
KEGG
  • D00113 checkY
ChEBI
  • CHEBI:16684 checkY
ChEMBL
  • ChEMBL517712
ECHA InfoCard100.000.096 Edit this at Wikidata
Chemical and physical data
FormulaC17H23NO3
Molar mass289.375 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN3[C@H]1CC[C@@H]3C[C@@H](C1)OC(=O)C(CO)c2ccccc2
InChI
  • InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15+,16? checkY
  • Key:RKUNBYITZUJHSG-SPUOUPEWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Atropine is a tropane alkaloid and anticholinergic medication used to treat certain types of nerve agent and pesticide poisonings as well as some types of slow heart rate, and to decrease saliva production during surgery.[6] It is typically given intravenously or by injection into a muscle.[6] Eye drops are also available which are used to treat uveitis and early amblyopia.[7][8] The intravenous solution usually begins working within a minute and lasts half an hour to an hour.[5] Large doses may be required to treat some poisonings.[6]

Common side effects include dry mouth, abnormally large pupils, urinary retention, constipation, and a fast heart rate.[6] It should generally not be used in people with closed-angle glaucoma.[6] While there is no evidence that its use during pregnancy causes birth defects, this has not been well studied so sound clinical judgment should be used.[9] It is likely safe during breastfeeding.[9] It is an antimuscarinic (a type of anticholinergic) that works by inhibiting the parasympathetic nervous system.[6]

Atropine occurs naturally in a number of plants of the nightshade family, including deadly nightshade (belladonna), Jimson weed, and mandrake.[10] It was first isolated in 1833,[11] It is on the World Health Organization's List of Essential Medicines.[12] It is available as a generic medication.[6][13][14]

  1. ^ Rafinesque CS (1828). Medical Flora; Or, Manual of the Medical Botany of the United States of ... - Constantine Samuel Rafinesque - Internet Archive. Atkinson & Alexander. p. 148. Retrieved 2012-11-07.
  2. ^ "AusPAR: Atropine sulfate monohydrate". Therapeutic Goods Administration (TGA). 31 May 2022. Archived from the original on 31 May 2022. Retrieved 12 June 2022.
  3. ^ Cite error: The named reference Atropine sulfate FDA label was invoked but never defined (see the help page).
  4. ^ "Atropine- atropine sulfate solution/ drops". DailyMed. 22 February 2022. Archived from the original on 16 March 2022. Retrieved 16 March 2022.
  5. ^ a b c Barash PG (2009). Clinical anesthesia (6th ed.). Philadelphia: Wolters Kluwer/Lippincott Williams & Wilkins. p. 525. ISBN 9780781787635. Archived from the original on 2015-11-24.
  6. ^ a b c d e f g "Atropine". The American Society of Health-System Pharmacists. Archived from the original on 2015-07-12. Retrieved Aug 13, 2015.
  7. ^ Hamilton RJ, Duffy AN, Stone D, Spencer A (2014). Tarascon pharmacopoeia (15 ed.). Jones & Bartlett Publishers. p. 386. ISBN 9781284056716. Archived from the original on 2015-10-02.
  8. ^ "Amblyopia (Lazy Eye)". National Eye Institute. 2019-07-02. Archived from the original on 2020-01-31. Retrieved 2020-01-31. Putting special eye drops in the stronger eye. A once-a-day drop of the drug atropine can temporarily blur near vision, which forces the brain to use the other eye. For some children, this treatment works as well as an eye patch, and some parents find it easier to use (for example, because young children may try to pull off eye patches).
  9. ^ a b "Atropine Pregnancy and Breastfeeding Warnings". Archived from the original on 6 September 2015. Retrieved 14 August 2015.
  10. ^ Brust JC (2004). Neurological aspects of substance abuse (2 ed.). Philadelphia: Elsevier. p. 310. ISBN 9780750673136. Archived from the original on 2015-10-02.
  11. ^ Ainsworth S (2014). Neonatal Formulary: Drug Use in Pregnancy and the First Year of Life. John Wiley & Sons. p. 94. ISBN 9781118819593. Archived from the original on 2015-10-02.
  12. ^ World Health Organization (2021). World Health Organization model list of essential medicines: 22nd list (2021). Geneva: World Health Organization. hdl:10665/345533. WHO/MHP/HPS/EML/2021.02.
  13. ^ Hamilton RJ (2014). Tarascon pharmacopoeia (15 ed.). Jones & Bartlett Publishers. p. 386. ISBN 9781284056716. Archived from the original on 2015-10-02.
  14. ^ "Competitive Generic Therapy Approvals". U.S. Food and Drug Administration (FDA). 29 June 2023. Archived from the original on 29 June 2023. Retrieved 29 June 2023.

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Atropine

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combination drug with atropine for the treatment of diarrhea. Diphenoxylate is an opioid and acts by slowing intestinal contractions; the atropine is present to...

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Hyoscyamine

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the levorotary isomer of atropine (third of the three major nightshade alkaloids) and thus sometimes known as levo-atropine. In 2021, it was the 272nd...

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Atropa belladonna

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toxic when ingested, containing tropane alkaloids. These toxins include atropine, scopolamine, and hyoscyamine, which cause delirium and hallucinations...

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ATNAA

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delivery vehicle to be used in lieu of the Mark I NAAK. The ATNAA provides atropine and pralidoxime chloride in a single delivery system, although the two...

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Anticholinergic

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Organophosphate based nerve agent poisoning, such as VX, sarin, tabun, and soman (atropine is favoured in conjunction with an oxime, usually pralidoxime) Anticholinergics...

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Pralidoxime

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acetylcholinesterase. It is used to treat organophosphate poisoning in conjunction with atropine and either diazepam or midazolam. It is a white solid. Pralidoxime, 2-pyridinaldoxime...

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Cholinergic blocking drug

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Antimuscarinic agents (also known as muscarinic antagonists), including atropine and hyoscine, block acetylcholine at the muscarinic acetylcholine receptors...

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Ipratropium bromide

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the BAN and the USAN) obtained by treating atropine with isopropyl bromide, thus the name: isopropyl + atropine.[citation needed] It is chemically related...

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Muscarinic antagonist

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nervous system (CNS) than atropine due to its ability to cross the blood–brain barrier. At higher-than-therapeutic doses, atropine and scopolamine cause CNS...

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Tropinesterase

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The enzyme tropinesterase (EC 3.1.1.10) catalyzes the reaction atropine + H2O ⇌ {\displaystyle \rightleftharpoons } tropine + tropate This enzyme belongs...

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Floater

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to either conservative management or vitrectomy. Dropping low doses of atropine onto the eye dilates the pupil, thus reducing shadow formation on the retina...

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Datura stramonium

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individual seed contains about 0.1 mg of atropine, and the approximate fatal dose for adult humans is >10 mg atropine or >2–4 mg scopolamine. Datura intoxication...

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Cholinergic crisis

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(constricted pupils). This crisis may be masked by the concomitant use of atropine along with cholinesterase inhibitor medication in order to prevent side...

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Plant secondary metabolism

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organic compound containing nitrogen and it is from tropane that atropine is derived. Atropine is synthesized by a reaction between tropine and tropate, catalyzed...

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Cycloplegia

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is usually due to topical application of muscarinic antagonists such as atropine and cyclopentolate. Belladonna alkaloids are used for testing the error...

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Tropine

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stramonium). It can be prepared by hydrolysis of atropine or other solanaceous alkaloids. Pseudotropine Atropine Tropinone Tropane alkaloid "8-Methyl-8-azabicyclo[3...

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Difenoxin

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Difenoxin (Motofen, R-15403) is an opioid drug used, often in combination with atropine, to treat diarrhea. It is the principal metabolite of diphenoxylate.: 558 ...

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Tensilon test

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2018. A 10 mg edrophonium chloride syringe and a 2 mg atropine syringe are prepared. Atropine is prepared for immediate use in case cholinergic crisis...

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Autonomic drug

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cramps in the intestines. Patients with bradycardia are treated with atropine. Atropine is a muscarinic antagonist, which can obstruct the muscarinic receptor...

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Datura

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New and Old Worlds due to the presence of the alkaloids scopolamine and atropine, which are also produced by plants associated with Old World medicine such...

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Mark I NAAK

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Antidote Kit") is a dual-chamber autoinjector: Two anti-nerve agent drugs—atropine sulfate and pralidoxime chloride—each in injectable form, constitute the...

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Muscarinic acetylcholine receptor

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over sympathetic activity. Hence, inhibition of M2 receptors (e.g. by atropine) will cause a raise in heart rate. They also moderately reduce contractile...

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WHO Model List of Essential Medicines

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Lidocaine/epinephrine (lidocaine + epinephrine) Complementary: Ephedrineα Atropine Midazolam Morphine Oxygen Acetylsalicylic acid (aspirin) Ibuprofen Paracetamol...

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Tropane

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is mainly known for the other alkaloids derived from it, which include atropine and cocaine, among others. Tropane alkaloids occur in plants of the families...

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Dimenhydrinate

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users report a side-effect profile consistent with tropane alkaloid (e.g. atropine) poisoning as both show antagonism of muscarinic acetylcholine receptors...

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Apoatropine

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include atropine, hyoscyamine, and hyoscine. Though apoatropine is found in various plants, it can also be prepared by the dehydration of atropine using...

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