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Identification
NameAtropine
Accession NumberDB00572  (APRD00807, EXPT02427)
TypeSmall Molecule
GroupsApproved
Description

An alkaloid, originally from Atropa belladonna, but found in other plants, mainly solanaceae. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+-)-AtropineNot AvailableNot Available
(+-)-HyoscyamineNot AvailableNot Available
(+,-)-Tropyl tropateNot AvailableNot Available
(±)-atropineNot AvailableNot Available
(±)-hyoscyamineNot AvailableNot Available
(3-Endo)-8-methyl-8-azabicyclo[3.2.1]oct-3-yl tropateNot AvailableNot Available
[(1S,5R)-8-Methyl-8-azabicyclo[3.2.1]oct-3-yl] 3-hydroxy-2-phenyl-propanoateNot AvailableNot Available
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl 3-hydroxy-2-phenylpropanoateNot AvailableNot Available
8-Methyl-8-azabicyclo[3.2.1]oct-3-yl tropateNot AvailableNot Available
AtropinGermanNot Available
AtropinaItalian/SpanishINN
AtropineFrenchINN
AtropinumLatinINN
dl-HyoscyamineNot AvailableNot Available
dl-tropyltropateNot AvailableNot Available
MydriasineNot AvailableIS
Tropine tropateNot AvailableNot Available
Salts
Name/CAS Structure Properties
Atropine Sulfate
55-48-1
Thumb
  • InChI Key: HOBWAPHTEJGALG-UHFFFAOYNA-N
  • Monoisotopic Mass: 676.302966456
  • Average Mass: 676.817
DBSALT000281
Brand names
NameCompany
AnespinOriental Chemical Works
AntolYing Yuan
AtroPenMeridian
AtroptSigma
AtrospanFischer
BellapanFarmapol
DysurgalMaxMedic
KintropineSynpac-Kingdom
TromineThe Central
Brand mixtures
Brand NameIngredients
ATNAAAtropine + Pralidoxime chloride
AtridolAtropine and Diphenoxylate
DibanAtropine Sulfate + Attapulgite (Activated) + Hyoscyamine Sulfate + Opium + Pectin + Scopolamine Hydrobromide
DonnagelAtropine Sulfate + Hyoscyamine Sulfate + Kaolin + Pectin + Scopolamine Hydrobromide
DonnatalAtropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
Donnatal ElixirAtropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
Donnatal ExtentabsAtropine Sulfate + Hyoscyamine Sulfate + Phenobarbital + Scopolamine Hydrobromide
DuoDote Atropine and Pralidoxime
Enlon-PlusAtropine and Edrophonium Chloride
LomotilAtropine and Diphenoxylate
LonoxAtropine and Diphenoxylate
MotofenAtropine and Difenoxin
ReasecAtropine and Diphenoxylate
SpascupreelAconite + Atropine Sulfate + Chamomile + Citrullus Colocynthis + Copper Sulfate + Gelsemium Sempervirens + Magnesium Phosphate Dibasic + Mushroom + Passion Flower
Stmerin DAtropine and Isoprenaline
Categories
CAS number51-55-8
WeightAverage: 289.3694
Monoisotopic: 289.167793607
Chemical FormulaC17H23NO3
InChI KeyRKUNBYITZUJHSG-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?
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
Mass Specshow(7.92 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylacetic Acid Derivatives
Direct parentPhenylacetic Acid Derivatives
Alternative parentsTropanes; Beta Hydroxy Acids and Derivatives; Piperidines; Pyrrolidines; Tertiary Amines; Carboxylic Acid Esters; Ethers; Enolates; Primary Alcohols; Polyamines
Substituentsbeta-hydroxy acid; hydroxy acid; piperidine; pyrrolidine; tertiary amine; carboxylic acid ester; primary alcohol; ether; polyamine; carboxylic acid derivative; enolate; organonitrogen compound; amine; alcohol
Classification descriptionThis compound belongs to the phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
Pharmacology
IndicationFor the treatment of poisoning by susceptible organophosphorous nerve agents having cholinesterase activity as well as organophosphorous or carbamate insecticides.
PharmacodynamicsAtropine, 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 actionAtropine binds to and inhibit muscarinic acetylcholine receptors, producing a wide range of anticholinergic effects.
AbsorptionAtropine 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 distributionNot Available
Protein bindingThe 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 eliminationMuch of the drug is destroyed by enzymatic hydrolysis, particularly in the liver; from 13 to 50% is excreted unchanged in the urine.
Half life3.0 ± 0.9 hours in adults. The half-life of atropine is slightly shorter (approximately 20 minutes) in females than males.
ClearanceNot Available
ToxicityOral, 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
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9286
Blood Brain Barrier + 0.9569
Caco-2 permeable + 0.8866
P-glycoprotein substrate Substrate 0.5
P-glycoprotein inhibitor I Non-inhibitor 0.6542
P-glycoprotein inhibitor II Non-inhibitor 0.8595
Renal organic cation transporter Inhibitor 0.7956
CYP450 2C9 substrate Non-substrate 0.7041
CYP450 2D6 substrate Non-substrate 0.6838
CYP450 3A4 substrate Substrate 0.5496
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9275
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9285
CYP450 3A4 substrate Non-inhibitor 0.95
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9113
Ames test Non AMES toxic 0.7742
Carcinogenicity Non-carcinogens 0.9631
Biodegradation Ready biodegradable 0.5527
Rat acute toxicity 2.7305 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8354
hERG inhibition (predictor II) Inhibitor 0.5378
Pharmacoeconomics
Manufacturers
  • Meridian medical technologies inc
  • Solvay pharmaceuticals
  • United states army office surgeon general
  • Hospira inc
  • Mission pharmacal co
Packagers
Dosage forms
FormRouteStrength
LiquidOphthalmic
LiquidOral
OintmentOphthalmic
SolutionIntramuscular
SolutionIntravenous
SolutionOphthalmic
Solution / dropsOral
TabletOral
Prices
Unit descriptionCostUnit
Atropine Sulfate 1% Solution 15ml Bottle101.27USDbottle
Isopto Atropine 1% Solution 15ml Bottle34.65USDbottle
Atropine powder34.48USDg
Isopto Atropine 1% Solution 5ml Bottle26.59USDbottle
Atropine Sulfate 1% Solution 5ml Bottle16.82USDbottle
Atropine Sulfate 1% Ointment 3.5 gm Tube15.92USDtube
Atropine-Care 1% Solution 2ml Bottle7.99USDbottle
Isopto atropine 1% eye drops5.06USDml
Atropine-ns 1 mg/2.5 ml syr4.8USDml
Atropine-ns 0.8 mg/2 ml syr3.9USDml
Atropine 1% eye drops2.88USDml
Atropine sulfate powder2.06USDg
Atropine care 1% eye drops2.03USDml
Atropine-ns 2 mg/5 ml syringe1.92USDml
Atropine Sulfate 0.4 mg/ml1.6USDml
Atropine Sulfate 0.6 mg/ml1.6USDml
Atropine 1 mg/ml vial1.44USDml
Atropine Sulfate 0.4 mg/ml Solution1.22USDml
Atropine 0.4 mg/0.5 ml ampul1.2USDampul
Atropine 1 mg/ml ampul1.2USDml
Atropine 0.4 mg/ml vial0.96USDml
Isopto Atropine 1 % Solution0.68USDml
Sal-tropine 0.4 mg tablet0.36USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point118.5 °CPhysProp
water solubility2200 mg/L (at 25 °C)DEHN,WM (1917)
logP1.83HANSCH,C ET AL. (1995)
logS-2.12ADME Research, USCD
pKa9.43SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility2.52ALOGPS
logP2.19ALOGPS
logP1.57ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)15.15ChemAxon
pKa (Strongest Basic)9.39ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area49.77 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.82 m3·mol-1ChemAxon
Polarizability31.28 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Pei-Chang Wu, Hsi-Kung Kuo, Po-Chiung Fang, Jong-Jer Lee, Chih-Hsin Chen, “Low-concentration atropine solution for preventing myopia progression and preparing method thereof.” U.S. Patent US20070254914, issued November 01, 2007.

US20070254914
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00113
KEGG CompoundC01479
BindingDB50241332
ChEBI16684
ChEMBLCHEMBL517712
Therapeutic Targets DatabaseDAP000377
PharmGKBPA448505
IUPHAR320
Guide to Pharmacology320
HETOIN
Drug Product Database715492
RxListhttp://www.rxlist.com/cgi/generic3/atropen.htm
Drugs.comhttp://www.drugs.com/cdi/atropine-drops.html
WikipediaAtropine
ATC CodesA03BA01A03BB02N04AC30S01FA01S01FA05
AHFS Codes
  • 52:24.00
  • 12:08.08
  • 92:02.00*
PDB Entries
FDA labelshow(164 KB)
MSDSshow(73.5 KB)
Interactions
Drug Interactions
Drug
CinitaprideAnticholinergic agents like atropine may reduce the action of cinitapride.
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
HaloperidolThe anticholinergic increases the risk of psychosis and tardive dyskinesia
TacrineThe 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.
TrimethobenzamideTrimethobenzamide and Atropine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Atropine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TrospiumTrospium 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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M2 P08172 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M3 P20309 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M4 P08173 Details

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

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M5 P08912 Details

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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 1A2 P05177 Details

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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11