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Identification
Name Atropine
Accession Number DB00572 (APRD00807, EXPT02427)
Type small molecule
Groups approved
Description

An alkaloid, originally from Atropa belladonna, but found in other plants, mainly solanaceae. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Atropin [German]
Atropina [Italian]
Atropine Sulfate
DL-Hyoscyamine
DL-Tropyl tropate
Salts Not Available
Brand names
Name Company
Atnaa
Atropair
Atropen
Atropin
Atropin-flexiolen
Atropine Care
Atropine Sulfate Ansyr Plastic Syringe
Atropine Sulfate S.O.P.
Atropinol
Atropisol
Atrosulf
Equipin
Eyesules
Homapin-10
Homapin-5
I-Tropine
Isopto Atropine
Isopto-atropine
Minims Atropine
Ocu-Tropine
Tropine tropate
Troyl tropate
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Brand mixtures
Brand Name Ingredients
Diban Cap Atropine Sulfate + Attapulgite (Activated) + Hyoscyamine Sulfate + Opium + Pectin + Scopolamine Hydrobromide
Donnagel Liq Atropine Sulfate + Hyoscyamine Sulfate + Kaolin + Pectin + Scopolamine Hydrobromide
Donnatal Elixir Atropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
Donnatal Extentabs Atropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
Donnatal Extentabs Srt Atropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
Donnatal Tab Atropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
Spascupreel Injeel Liq Aconite + Atropine Sulfate + Chamomile + Citrullus Colocynthis + Copper Sulfate + Gelsemium Sempervirens + Magnesium Phosphate Dibasic + Mushroom + Passion Flower
Spascupreel Tablets Aconitum + Agaricus + Atropine Sulfate + Chamomile + Citrullus Colocynthis + Copper Sulfate + Gelsemium Sempervirens + Magnesium Phosphate Dibasic + Passion Flower
Categories
  • Mydriatics
  • Bronchodilator Agents
  • Adjuvants, Anesthesia
  • Muscarinic Antagonists
  • Anti-Arrhythmia Agents
  • Parasympatholytics
CAS number 51-55-8
Weight Average: 289.3694
Monoisotopic: 289.167793607
Chemical Formula C17H23NO3
InChI Key InChIKey=RKUNBYITZUJHSG-SPUOUPEWSA-N
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?
Plain Text
IUPAC Name
(1R,3S,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
SMILES
CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C1=CC=CC=C1
Plain Text
Mass Spec show (7.92 KB)
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication For the treatment of poisoning by susceptible organophosphorous nerve agents having cholinesterase activity as well as organophosphorous or carbamate insecticides.
Pharmacodynamics Atropine, a naturally occurring belladonna alkaloid, is a racemic mixture of equal parts of d- and l-hyoscyamine, whose activity is due almost entirely to the levo isomer of the drug. Atropine is commonly classified as an anticholinergic or antiparasympathetic (parasympatholytic) drug. More precisely, however, it is termed an antimuscarinic agent since it antagonizes the muscarine-like actions of acetylcholine and other choline esters. Adequate doses of atropine abolish various types of reflex vagal cardiac slowing or asystole. The drug also prevents or abolishes bradycardia or asystole produced by injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. Atropine may also lessen the degree of partial heart block when vagal activity is an etiologic factor. Atropine in clinical doses counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure.
Mechanism of action Atropine binds to and inhibit muscarinic acetylcholine receptors, producing a wide range of anticholinergic effects.
Absorption Atropine is rapidly and well absorbed after intramuscular administration. Atropine disappears rapidly from the blood and is distributed throughout the various body tissues and fluids.
Volume of distribution Not Available
Protein binding The protein binding of atropine is 14 to 22% in plasma.
Metabolism Much of the drug is destroyed by enzymatic hydrolysis, particularly in the liver. From 13 to 50% is excreted unchanged in the urine.
Route of elimination Much of the drug is destroyed by enzymatic hydrolysis, particularly in the liver; from 13 to 50% is excreted unchanged in the urine.
Half life 3.0 ± 0.9 hours in adults. The half-life of atropine is slightly shorter (approximately 20 minutes) in females than males.
Clearance Not Available
Toxicity Oral, mouse: LD50 = 75 mg/kg. Symptoms of overdose includes widespread paralysis of parasympathetically innervated organs. Dry mucous membranes, widely dilated and nonresponsive pupils, tachycardia, fever and cutaneous flush are especially prominent, as are mental and neurological symptoms. In instances of severe intoxication, respiratory depression, coma, circulatory collapse and death may occur.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Meridian medical technologies inc
  • Solvay pharmaceuticals
  • United states army office surgeon general
  • Hospira inc
  • Mission pharmacal co
Packagers
Dosage forms
Form Route Strength
Liquid Ophthalmic
Liquid Oral
Ointment Ophthalmic
Solution Intramuscular
Solution Intravenous
Solution Ophthalmic
Solution / drops Oral
Tablet Oral
Prices
Unit description Cost Unit
Atropine Sulfate 1% Solution 15ml Bottle 101.27 USD bottle
Isopto Atropine 1% Solution 15ml Bottle 34.65 USD bottle
Atropine powder 34.48 USD g
Isopto Atropine 1% Solution 5ml Bottle 26.59 USD bottle
Atropine Sulfate 1% Solution 5ml Bottle 16.82 USD bottle
Atropine Sulfate 1% Ointment 3.5 gm Tube 15.92 USD tube
Atropine-Care 1% Solution 2ml Bottle 7.99 USD bottle
Isopto atropine 1% eye drops 5.06 USD ml
Atropine-ns 1 mg/2.5 ml syr 4.8 USD ml
Atropine-ns 0.8 mg/2 ml syr 3.9 USD ml
Atropine 1% eye drops 2.88 USD ml
Atropine sulfate powder 2.06 USD g
Atropine care 1% eye drops 2.03 USD ml
Atropine-ns 2 mg/5 ml syringe 1.92 USD ml
Atropine Sulfate 0.4 mg/ml 1.6 USD ml
Atropine Sulfate 0.6 mg/ml 1.6 USD ml
Atropine 1 mg/ml vial 1.44 USD ml
Atropine Sulfate 0.4 mg/ml Solution 1.22 USD ml
Atropine 0.4 mg/0.5 ml ampul 1.2 USD ampul
Atropine 1 mg/ml ampul 1.2 USD ml
Atropine 0.4 mg/ml vial 0.96 USD ml
Isopto Atropine 1 % Solution 0.68 USD ml
Sal-tropine 0.4 mg tablet 0.36 USD tablet
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DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 118.5 °C PhysProp
water solubility 2200 mg/L (at 25 °C) DEHN,WM (1917)
logP 1.83 HANSCH,C ET AL. (1995)
logS -2.12 ADME Research, USCD
pKa 9.43 SANGSTER (1994)
Predicted Properties
Property Value Source
water solubility 2.52e+00 g/l ALOGPS
logP 2.19 ALOGPS
logP 1.57 ChemAxon
logS -2.1 ALOGPS
pKa (strongest acidic) 15.15 ChemAxon
pKa (strongest basic) 9.39 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 49.77 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 80.82 ChemAxon
polarizability 31.28 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00113 Link_out
KEGG Compound C01479 Link_out
BindingDB 50241332 Link_out
ChEBI 16684 Link_out
ChEMBL 16684 Link_out
Therapeutic Targets Database DAP000377 Link_out
PharmGKB PA448505 Link_out
IUPHAR 320 Link_out
Guide to Pharmacology 320 Link_out
HET OIN Link_out
Drug Product Database 715492 Link_out
RxList http://www.rxlist.com/cgi/generic3/atropen.htm Link_out
Drugs.com http://www.drugs.com/cdi/atropine-drops.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Atropine Link_out
ATC Codes
  • A03BA01
  • A03BB02
  • N04AC01
  • N04AC30
  • S01FA01
  • S01FA05
  • A03BA03
AHFS Codes
  • 52:24.00
  • 12:08.08
  • 92:02.00*
PDB Entries
FDA label show (164 KB)
MSDS show (73.5 KB)
Interactions
Drug Interactions
Drug Interaction
Cinitapride Anticholinergic agents like atropine may reduce the action of cinitapride.
Donepezil Possible antagonism of action
Galantamine Possible antagonism of action
Haloperidol The anticholinergic increases the risk of psychosis and tardive dyskinesia
Tacrine The therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Atropine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
Trimethobenzamide Trimethobenzamide and Atropine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Triprolidine Triprolidine and Atropine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Trospium Trospium and Atropine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food Interactions
  • Avoid alcohol.
  • Take with food.
Targets

1. Muscarinic acetylcholine receptor M1

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P11229 Link_out
Gene: CHRM1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

2. Muscarinic acetylcholine receptor M2

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is adenylate cyclase inhibition

Organism class: human
UniProt ID: P08172 Link_out
Gene: CHRM2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Roman S, Badia A, Camps P, Munoz-Torrero D, Clos MV: Nicotinic-receptor potentiator drugs, huprine X and galantamine, increase ACh release by blocking AChE activity but not acting on nicotinic receptors. Brain Res. 2005 Nov 9;1061(2):73-9. Epub 2005 Oct 24. Pubmed
  2. Minaba M, Ichiyama S, Kojima K, Ozaki M, Kato Y: Activation of nematode G protein GOA-1 by the human muscarinic acetylcholine receptor M2 subtype. Functional coupling of G-protein-coupled receptor and G protein originated from evolutionarily distant animals. FEBS J. 2006 Dec;273(24):5508-16. Epub 2006 Nov 3. Pubmed
  3. May LT, Lin Y, Sexton PM, Christopoulos A: Regulation of M2 muscarinic acetylcholine receptor expression and signaling by prolonged exposure to allosteric modulators. J Pharmacol Exp Ther. 2005 Jan;312(1):382-90. Epub 2004 Aug 27. Pubmed
  4. Cembala TM, Forde SC, Appadu BL, Lambert DG: Allosteric interaction of the neuromuscular blockers vecuronium and pancuronium with recombinant human muscarinic M2 receptors. Eur J Pharmacol. 2007 Aug 13;569(1-2):37-40. Epub 2007 May 22. Pubmed
  5. Nelson CP, Nahorski SR, Challiss RA: Constitutive activity and inverse agonism at the M2 muscarinic acetylcholine receptor. J Pharmacol Exp Ther. 2006 Jan;316(1):279-88. Epub 2005 Sep 27. Pubmed
  6. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed

3. Muscarinic acetylcholine receptor M3

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P20309 Link_out
Gene: CHRM3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

4. Muscarinic acetylcholine receptor M4

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is inhibition of adenylate cyclase

Organism class: human
UniProt ID: P08173 Link_out
Gene: CHRM4 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

5. Muscarinic acetylcholine receptor M5

Pharmacological action: yes
Actions: antagonist

The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the action of G proteins. Primary transducing effect is Pi turnover

Organism class: human
UniProt ID: P08912 Link_out
Gene: CHRM5 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Cusack B, Nelson A, Richelson E: Binding of antidepressants to human brain receptors: focus on newer generation compounds. Psychopharmacology (Berl). 1994 May;114(4):559-65. Pubmed
  2. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  3. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
Enzymes

1. Cytochrome P450 1A2

Actions: inhibitor

Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen

UniProt ID: P05177 Link_out
Gene: CYP1A2
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19