Identification

Summary

Atropine is a muscarinic antagonist used to treat poisoning by muscarinic agents, including organophosphates and other drugs.

Brand Names
Atnaa, Atropen, Busulfex, Donnatal, Duodote, Enlon-plus, Isopto Atropine, Lomotil, Minims Atropine Sulphate, Motofen, Phenohytro
Generic Name
Atropine
DrugBank Accession Number
DB00572
Background

Atropine is an alkaloid originally synthesized from Atropa belladonna. It is a racemic mixture of d-and l-hyoscyamine, of which only l-hyoscyamine is pharmacologically active.3,8 Atropine is generally available as a sulfate salt and can be administered by intravenous, subcutaneous, intramuscular, intraosseous, endotracheal and ophthalmic methods. Oral atropine is only available in combination products.1,9 Atropine is a competitive, reversible antagonist of muscarinic receptors that blocks the effects of acetylcholine and other choline esters.1,5,6,8 It has a variety of therapeutic applications, including pupil dilation and the treatment of anticholinergic poisoning and symptomatic bradycardia in the absence of reversible causes.1 Atropine is a relatively inexpensive drug and is included in the World Health Organization List of Essential Medicines.4

Type
Small Molecule
Groups
Approved, Vet approved
Structure
Weight
Average: 289.3694
Monoisotopic: 289.167793607
Chemical Formula
C17H23NO3
Synonyms
  • (±)-atropine
  • (±)-hyoscyamine
  • Atropin
  • Atropina
  • Atropine
  • Atropinum
  • dl-Hyoscyamine
  • dl-tropyltropate
  • Tropine tropate
External IDs
  • NSC 61810

Pharmacology

Indication

The intravenous, intramuscular, subcutaneous, intraosseous and endotracheal use of atropine is indicated for the temporary blockade of severe or life-threatening muscarinic effects.5,8 The intramuscular use of atropine in the form of a pen injector is indicated for the treatment of poisoning by susceptible organophosphorus nerve agents having cholinesterase activity as well as organophosphorus or carbamate insecticides in adult and pediatric patients.6 The ophthalmic use of atropine is indicated for mydriasis, cycloplegia, and penalization of the healthy eye in the treatment of amblyopia.7

In combination with difenoxin or diphenoxylate (tablets for oral use), atropine is indicated as adjunctive therapy in the management of acute nonspecific diarrhea.9,11

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Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Atropine is an antimuscarinic agent that antagonizes the effects of acetylcholine.5,6,8 In small doses, atropine slows heart rate, and tachycardia develops due to paralysis of vagal control. Compared to scopolamine, atropine has a more potent and prolonged effect on the heart, intestine and bronchial muscle, but a weaker effect on the iris, ciliary body and certain secretory glands. Atropine leads to increased respiratory rate and depth of respiration, possibly due to the drug-induced bronchiolar dilatation rather than its mild effect on vagal excitation.8

At an adequate dose, atropine abolishes different types of reflex vagal cardiac slowing or asystole. Atropine can be used to prevent or abolish bradycardia or asystole induced by the injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus.8 When vagal activity is an etiologic factor, atropine may also lessen the degree of partial heart block. In clinical doses, atropine 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.8 The use of topical atropine in the eye induces mydriasis by inhibiting the contraction of the circular pupillary sphincter muscle normally stimulated by acetylcholine. This results in the contraction of the countering radial pupillary dilator muscle and pupil dilation.7

The use of atropine may precipitate acute glaucoma and convert partial organic pyloric stenosis into complete obstruction. Atropine may also lead to complete urinary retention in patients with prostatic hypertrophy and cause the thickening of bronchial secretions and formation of viscid plugs in patients with chronic lung disease.8

Mechanism of action

Atropine binds to and inhibits muscarinic acetylcholine receptors, competitively blocking the effects of acetylcholine and other choline esters.5,6,8 It acts as a reversible non-specific antagonist of muscarinic receptors, showing affinity for the M1, M2, M3, M4 and M5 receptor subtypes.2 Atropine antagonizes the effects of acetylcholine on tissues innervated by postganglionic cholinergic nerves, such as smooth muscle, cardiac tissue, exocrine glands and the central nervous system. Also, it acts in less innervated smooth muscle that responds to endogenous acetylcholine.3,5 The actions of atropine can be overcome by increasing the concentration of acetylcholine at receptor sites (for instance, the use of anticholinesterase agents that inhibit the hydrolysis of acetylcholine).8

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
AMuscarinic acetylcholine receptor M2
antagonist
Humans
AMuscarinic acetylcholine receptor M3
antagonist
Humans
AMuscarinic acetylcholine receptor M4
antagonist
Humans
AMuscarinic acetylcholine receptor M5
antagonist
Humans
UGlycine receptor subunit alpha-1
antagonist
Humans
UNeuronal acetylcholine receptor subunit alpha-4Not AvailableHumans
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHumans
Absorption

Intravenous atropine follows a non-linear pharmacokinetic model at doses between 0.5 and 4 mg.8 After intramuscular administration, atropine is rapidly absorbed. In adults given 1.67 mg of atropine intramuscularly, the Cmax was 9.6 ng/mL and the Tmax went from 3 to 60 minutes.6 In healthy subjects given 30 µL of atropine ophthalmic solution, the Cmax and Tmax were 288 pg/mL and 28 minutes, respectively.7 Atropine is well absorbed in the gastrointestinal tract and rapidly delivered to systemic circulation. When administered intramuscularly, atropine has a bioavailability of 50%.2 The AUC0-INF and Cmax of atropine are higher in females than males (15%).6

Volume of distribution

Atropine is distributed throughout the body. Following intravenous administration, the total apparent volume of distribution of atropine ranged between 1.0 and 1.7 L/kg.3

Protein binding

The protein binding of atropine ranges from 14% to 44%,3,5,6 and is saturable between 2 and 20 μg/mL.5

Metabolism

Atropine is mainly metabolized by enzymatic hydrolysis in the liver.5,6,8 The major metabolites of atropine are noratropine, atropin-n-oxide, tropine, and tropic acid. The metabolism of atropine is inhibited by organophosphate pesticides.5,8

Route of elimination

Approximately 13 to 50% of atropine is excreted unchanged in the urine.5,6,8 In healthy volunteers given intravenous atropine, 29% of tropine was excreted in urine, along with 15% of an unidentified metabolite.3

Half-life

Following intravenous and intramuscular doses of atropine, half-life values range from approximately 2 to 4 hours.3,8 In geriatric patients (65-75 years old), intravenous atropine has a longer half-life (10 hours). Also, the half-life of atropine is slightly shorter (approximately 20 minutes) in females than in males.6

In healthy volunteers given 30 µL of atropine sulfate by topical ocular administration, the half-life of atropine was approximately 2.5 hours.7

Clearance

Following intravenous administration, the total clearance of atropine ranged between 5.9 and 6.8 mL/min/kg.3 Exercise, before and after intramuscular administration, decreases the clearance of atropine.5

Adverse Effects
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Toxicity

High doses of atropine may cause palpitation, dilated pupils, difficulty swallowing, hot dry skin, thirst, dizziness, restlessness, tremor, fatigue and ataxia. Toxic doses of atropine lead to restlessness and excitement, hallucinations, delirium and coma.8 In cases of severe intoxication, atropine can cause a circulatory collapse, leading to a decline in blood pressure and respiratory failure that may ensue in death following paralysis and coma.6,8

In case of atropine overdose, supportive treatment should be administered. Provide artificial respiration with oxygen if respiration is depressed, and follow cooling methods to reduce atropine-induced fever, especially in pediatric patients. In case of urinary retention, catheterization may be required. Atropine is mainly eliminated through the kidney; therefore, urinary output must be maintained and increased if possible. In case of atropine-induced photophobia, the room should be darkened.6 A short-acting barbiturate or diazepam may be given as needed to control marked excitement and convulsions; however, large doses should be avoided since central depressant action may coincide with the depression that occurs late in atropine poisoning. Central stimulants are not recommended.8 The acute oral toxicity (LD50) of atropine in mice is 75 mg/kg.10

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-Benzodiazepine1,2-Benzodiazepine may increase the central nervous system depressant (CNS depressant) activities of Atropine.
AcebutololAtropine may increase the arrhythmogenic activities of Acebutolol.
AceclofenacThe risk or severity of hypertension can be increased when Atropine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Atropine is combined with Acemetacin.
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Atropine.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Atropine.
AcetyldigitoxinAcetyldigitoxin may increase the arrhythmogenic activities of Atropine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Atropine is combined with Acetylsalicylic acid.
AclidiniumThe risk or severity of adverse effects can be increased when Atropine is combined with Aclidinium.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Atropine.
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Food Interactions
  • Avoid alcohol.
  • Take with food. Food reduces irritation.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Atropine hydrochlorideEUF58V826B33952-38-4OJIPQOWZZMSBGY-RIMUKSHESA-N
Atropine sulfate03J5ZE7KA55908-99-6JPKKQJKQTPNWTR-CHYDPLAESA-N
Atropine sulfate anhydrousKAE4PSB0Z355-48-1HOBWAPHTEJGALG-AADVZIIPSA-N
Product Images
International/Other Brands
Anespin (Oriental Chemical Works) / Antol (Ying Yuan) / AtroPen (Meridian) / Atropt (Sigma) / Atrospan (Fischer) / Bellapan (Farmapol) / Dysurgal (MaxMedic) / Kintropine (Synpac-Kingdom) / Tromine (The Central)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Alcon AtropineSolution1 % w/vOphthalmicAlcon, Inc.1964-12-31Not applicableCanada flag
ATROPEN Auto-InjectorInjection2 mg/0.7mLIntramuscularMeridian Medical Technologies LLC2003-06-19Not applicableUS flag
ATROPEN Auto-InjectorInjection0.25 mg/0.3mLIntramuscularMeridian Medical Technologies LLC2004-09-17Not applicableUS flag
ATROPEN Auto-InjectorInjection1 mg/0.7mLIntramuscularMeridian Medical Technologies LLC2003-06-19Not applicableUS flag
ATROPEN Auto-InjectorInjection2 mg/0.7mLIntramuscularMeridian Medical Technologies LLC1973-05-15Not applicableUS flag
ATROPEN Auto-InjectorInjection0.5 mg/0.7mLIntramuscularMeridian Medical Technologies LLC2003-06-19Not applicableUS flag
AtropineSolution / drops10 mg/1mLOphthalmicAkorn2014-07-18Not applicableUS flag
AtropineSolution / drops10 mg/1mLOphthalmicA-S Medication Solutions2014-07-18Not applicableUS flag
AtropineSolution1 %OphthalmicPharma Stulln Inc.1994-12-31Not applicableCanada flag
AtropineSolution / drops10 mg/1mLOphthalmicAkorn2022-05-02Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AtropineSolution / drops10 mg/1mLOphthalmicAmneal Pharmaceuticals NY LLC2022-07-19Not applicableUS flag
AtropineSolution / drops10 mg/1mLOphthalmicAmneal Pharmaceuticals NY LLC2022-07-19Not applicableUS flag
AtropineSolution / drops10 mg/1mLOphthalmicApotex Corp.2021-11-26Not applicableUS flag
AtropineSolution / drops10 mg/1mLOphthalmicAmneal Pharmaceuticals NY LLC2022-07-19Not applicableUS flag
Atropine SulfateInjection0.1 mg/1mLIntravenousAccord Healthcare, Inc.,2021-07-30Not applicableUS flag
Atropine SulfateInjection, solution0.4 mg/1mLIntravenousAMERICAN REGENT, INC.2022-08-02Not applicableUS flag
Atropine SulfateInjection0.1 mg/1mLIntravenousHF Acquisition Co LLC, DBA HealthFirst2021-04-25Not applicableUS flag
Atropine SulfateInjection0.4 mg/1mLEndotracheal; Intramedullary; Intramuscular; Intravenous; SubcutaneousHikma Pharmaceuticals USA Inc.2021-12-01Not applicableUS flag
Atropine SulfateInjection, solution0.4 mg/1mLEndotracheal; Intramedullary; Intramuscular; Intravenous; SubcutaneousMedical Purchasing Solutions, Llc2021-03-25Not applicableUS flag
Atropine SulfateInjection0.1 mg/1mLIntravenousREMEDYREPACK INC.2021-06-14Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
ISOPTO ATROPINE STERILE OPHTHALMIC SOLUTION 1%Solution1 %OphthalmicALCON PTE LTD1990-04-17Not applicable
ยูเมด้า อะโทรปินSolution0.5 mg/1mlบริษัท ยูเมด้า จำกัด1999-09-212020-08-23Thailand flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ATNAA atropine and pralidoxime chloride Auto-InjectorAtropine (2.1 mg/0.7mL) + Pralidoxime chloride (600 mg/2mL)KitIntramuscularMeridian Medical Technologies, LLC2002-01-17Not applicableUS flag
BEAMOTIL TABLETSAtropine sulfate anhydrous (0.025 mg) + Diphenoxylate hydrochloride (2.5 mg)Tablet, film coatedOralBEACONS PHARMACEUTICALS PTE. LTD.1991-06-01Not applicable
DHAMOTIL TABLETAtropine sulfate anhydrous (0.025 mg) + Diphenoxylate hydrochloride (2.5 mg)Tablet, film coatedOralDRUG HOUSES OF AUSTRALIA PTE. LTD.1991-01-29Not applicable
Diban CapAtropine sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg) + Scopolamine (3.3 mcg)CapsuleOralWyeth Ayerst Canada Inc.1998-02-182001-01-30Canada flag
Diban CapAtropine sulfate (9.7 mcg) + Attapulgite (300 mg) + Hyoscyamine sulfate (0.0519 mg) + Opium (12 mg) + Pectin (71.4 mg) + Scopolamine (3.3 mcg)CapsuleOralAyerst Laboratories1992-12-311999-04-12Canada flag
Diphenoxylate Hcl and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate hydrochloride (2.5 mg/1)TabletOralStat Rx USA1979-10-29Not applicableUS flag
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate hydrochloride (2.5 mg/1)TabletOralMcKesson Contract Packaging1977-11-172017-09-30US flag
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate hydrochloride (2.5 mg/1)TabletOralA-S Medication Solutions2013-02-27Not applicableUS flag
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate hydrochloride (2.5 mg/1)TabletOralKAISER FOUNDATION HOSPITALS2010-11-302017-08-31US flag
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate hydrochloride (2.5 mg/1)TabletOralSpecGx LLC2020-10-30Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
ATROPIN GALEN 0,25 MG 10 AMPULAtropine sulfate anhydrous (0.25 mg)SolutionIntramuscular; Intravenous; SubcutaneousGALEN İLAÇ SAN.VE TİC.A.Ş2020-08-14Not applicableTurkey flag
ATROPIN GALEN 0,5 MG 10 AMPULAtropine sulfate anhydrous (0.5 mg)SolutionIntramuscular; Intravenous; SubcutaneousGALEN İLAÇ SAN.VE TİC.A.Ş2020-08-14Not applicableTurkey flag
ATROPIN GALEN 1 MG 10 AMPULAtropine sulfate anhydrous (1 mg)SolutionIntramuscular; Intravenous; SubcutaneousGALEN İLAÇ SAN.VE TİC.A.Ş2020-08-14Not applicableTurkey flag
Atropine CareAtropine sulfate anhydrous (10 mg/1mL)Solution / dropsOphthalmicAkorn, Inc1995-06-012008-06-01US flag
Atropine SulfateAtropine sulfate (0.4 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousMedical Purchasing Solutions, Llc1971-01-01Not applicableUS flag
Atropine SulfateAtropine sulfate (0.4 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousHF Acquisition Co LLC, DBA HealthFirst2018-10-06Not applicableUS flag
Atropine SulfateAtropine sulfate (0.4 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines, Inc2010-04-012017-01-18US flag
Atropine SulfateAtropine sulfate (1 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousMedical Purchasing Solutions, Llc1992-12-01Not applicableUS flag
Atropine SulfateAtropine sulfate (0.1 mg/1mL)Injection, solutionIntravenousA-S Medication Solutions2005-10-252019-04-30US flag
Atropine SulfateAtropine sulfate (0.4 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousHikma Pharmaceuticals USA Inc.1971-01-01Not applicableUS flag

Categories

ATC Codes
S01FA01 — AtropineA03CB03 — Atropine and psycholepticsA03BA01 — Atropine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane.
Kingdom
Organic compounds
Super Class
Alkaloids and derivatives
Class
Tropane alkaloids
Sub Class
Not Available
Direct Parent
Tropane alkaloids
Alternative Parents
Beta hydroxy acids and derivatives / Piperidines / N-alkylpyrrolidines / Benzene and substituted derivatives / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Primary alcohols
show 4 more
Substituents
Alcohol / Amine / Amino acid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Beta-hydroxy acid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
racemate (CHEBI:16684) / Tropane alkaloids, Alkaloids, Tropan alkaloids (C01479)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
7C0697DR9I
CAS number
51-55-8
InChI Key
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?
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

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 References
  1. McLendon K, Preuss CV: Atropine . [Article]
  2. Buels KS, Fryer AD: Muscarinic receptor antagonists: effects on pulmonary function. Handb Exp Pharmacol. 2012;(208):317-41. doi: 10.1007/978-3-642-23274-9_14. [Article]
  3. Kanto J, Klotz U: Pharmacokinetic implications for the clinical use of atropine, scopolamine and glycopyrrolate. Acta Anaesthesiol Scand. 1988 Feb;32(2):69-78. doi: 10.1111/j.1399-6576.1988.tb02691.x. [Article]
  4. Smulyan H: The Beat Goes On: The Story of Five Ageless Cardiac Drugs. Am J Med Sci. 2018 Nov;356(5):441-450. doi: 10.1016/j.amjms.2018.04.011. Epub 2018 Apr 25. [Article]
  5. FDA Approved Drug Products: Atropine sulfate injection for intravenous use [Link]
  6. FDA Approved Drug Products: ATROPEN (atropine) injection for intramuscular use [Link]
  7. FDA Approved Drug Products: ISOPTO ATROPINE (atropine sulfate) ophthalmic solution for topical ophthalmic use [Link]
  8. FDA Approved Drug Products: Atropine sulfate injection, for intravenous, intramuscular, subcutaneous, intraosseous or endotracheal use. [Link]
  9. FDA Approved Drug Products: MOTOFEN (difenoxin and atropine sulphate) tablets for oral use [Link]
  10. Cayman chemical: Atropine SDS [Link]
  11. FDA Approved Drug Products: LOMOTIL (diphenoxylate hydrochloride and atropine sulfate) tablets for oral use [Link]
Human Metabolome Database
HMDB0014712
KEGG Drug
D00113
KEGG Compound
C01479
PubChem Compound
174174
PubChem Substance
46507540
ChemSpider
10194105
BindingDB
50403547
RxNav
1223
ChEBI
78734
ChEMBL
CHEMBL517712
Therapeutic Targets Database
DAP000377
PharmGKB
PA448505
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
OIN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Atropine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedBasic ScienceMyopia (Disorder)1
4CompletedDiagnosticIntraocular Pressure Changes During Tracheal Extubation1
4CompletedPreventionAlzheimer's Disease (AD) / Delirium, Dementia, Amnestic, Cognitive Disorders / Mild Cognitive Impairment (MCI)1
4CompletedPreventionArrhythmia / Respiratory Arrest (Disorder)1
4CompletedPreventionBradycardia1
4CompletedPreventionBradycardia / Dexmedetomidine / Spinal Anesthesia therapy1
4CompletedPreventionIntubation, Endotracheal1
4CompletedPreventionMyopia (Disorder)1
4CompletedScreeningAnesthesia; Functional1
4CompletedSupportive CareNausea / Vomiting1

Pharmacoeconomics

Manufacturers
  • Meridian medical technologies inc
  • Solvay pharmaceuticals
  • United states army office surgeon general
  • Hospira inc
  • Mission pharmacal co
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Akorn Inc.
  • Alcon Laboratories
  • American Regent
  • Amphastar Pharmaceuticals
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Baroli
  • Bausch & Lomb Inc.
  • Baxter International Inc.
  • Bioniche Pharma
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Clipper Distributing Co. LLC
  • Contract Pharm
  • Dispensing Solutions
  • E. Fougera and Co.
  • Falcon Pharmaceuticals Ltd.
  • General Injectables and Vaccines Inc.
  • Hawthorn Pharmaceuticals
  • Hope Pharmaceuticals
  • Hospira Inc.
  • Luitpold Pharmaceuticals Inc.
  • Mallinckrodt Inc.
  • Mckesson Corp.
  • Meridian Medical Technologies Inc.
  • MWI Veterinary Supply Co.
  • Nycomed Inc.
  • Ocumed Inc.
  • OMJ Pharmaceuticals
  • PD-Rx Pharmaceuticals Inc.
  • Pharmedium
  • Physicians Total Care Inc.
  • Prometic Pharma Inc.
  • Rx Veterinary Products
  • Spectrum Pharmaceuticals
  • Teva Pharmaceutical Industries Ltd.
  • Vedco Inc.
  • Wa Butler Co.
Dosage Forms
FormRouteStrength
InjectionIntramuscular; Intravenous; Subcutaneous
KitIntramuscular
InjectionIntramuscular0.25 mg/0.3mL
Injection, solutionParenteral
SolutionIntramuscular; Intravenous; Subcutaneous
SolutionConjunctival; Ophthalmic10 mg
Injection, solutionIntravenous0.5 %
Injection, solutionIntravenous1 %
OintmentOphthalmic0.5 g/100ml
OintmentOphthalmic0.5 %
OintmentOphthalmic1 g/100ml
Solution / dropsOphthalmic10 MG/ML
Solution / dropsOphthalmic5 MG/ML
SolutionOphthalmic
Injection, solution0.1 MG/ML
Injection, solutionParenteral0.21 MG/ML
Injection, solutionParenteral1 MG/ML
SolutionIntravenous; Subcutaneous1 mg
SolutionIntravenous1 mg
SolutionIntramuscular; Intravenous; Subcutaneous1 mg
SolutionIntramuscular; Subcutaneous1 mg
Tablet
Solution / dropsOphthalmic1 %
Solution / dropsOphthalmic10 mg/1mL
SolutionIntramuscular; Intravenous; Subcutaneous0.4 mg / mL
InjectionIntramuscular; Intravenous; Subcutaneous600 mcg/ml
OintmentOphthalmic1 %
Injection
InjectionEndotracheal; Intramedullary; Intramuscular; Intravenous; Subcutaneous0.4 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous0.4 mg/1mL
InjectionIntravenous0.05 mg/1mL
InjectionIntravenous0.1 mg/1mL
InjectionIntravenous; Parenteral0.1 mg/1mL
InjectionParenteral0.1 mg/1mL
Injection, solutionEndotracheal; Intramedullary; Intramuscular; Intravenous; Subcutaneous0.4 mg/1mL
Injection, solutionEndotracheal; Intramuscular; Intravenous; Subcutaneous0.05 mg/1mL
Injection, solutionEndotracheal; Intramuscular; Intravenous; Subcutaneous0.1 mg/1mL
Injection, solutionIntramuscular0.1 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous0.1 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous0.4 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous0.4 mg/0.5mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous1 mg/1mL
Injection, solutionIntravenous0.05 mg/1mL
Injection, solutionIntravenous0.1 mg/1mL
Injection, solutionIntravenous0.4 mg/1mL
Injection, solutionIntravenous1 mg/1mL
OintmentOphthalmic10 mg/1g
SolutionOphthalmic1 mg/1mL
LiquidIntravenous.1 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous0.3 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous0.8 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous0.6 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous0.5 mg / 5 mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg / 5 mL
SolutionIntramuscular; Intravenous; Subcutaneous3 mg / 10 mL
SolutionIntramuscular; Intravenous; Subcutaneous.6 mg / mL
SolutionIntramuscular; Intravenous; Subcutaneous1 mg / 10 mL
Solution0.6 mg/1ml
InjectionIntramuscular; Intravenous; Subcutaneous0.6 mg/ml
InjectionParenteral
InjectionParenteral1 mg/ml
Injection, solution
Injection, solutionParenteral0.5 mg/ml
SolutionParenteral1 mg
Solution / dropsOphthalmic10 mg / mL
SolutionOphthalmic10.0 mg/ml
Tablet, film coatedOral0.025 mg
Solution / dropsOphthalmic
CapsuleOral
TabletOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
Injection, solutionIntravenous
InjectionIntravenous
SolutionOphthalmic10 mg/1mL
SolutionOphthalmic1 %
TabletOral2.5 mg
OintmentOphthalmic
LiquidOral
SolutionOral
TabletOral0.025 mg
Injection, solutionIntramuscular; Intravenous; Subcutaneous600 mcg/ml
SolutionOphthalmic1 % w/v
Solution / dropsOphthalmic1 % w/v
Solution / dropsOphthalmic0.025 % W/V
InjectionIntramuscular0.5 mg/0.7mL
InjectionIntramuscular1 mg/0.7mL
InjectionIntramuscular2 mg/0.7mL
Solution / dropsOphthalmic
InjectionIntramuscular; Intravenous; Subcutaneous1 mg/ml
ElixirOral
LiquidOphthalmic1 %
SyrupOral0.025 mg/5ml
Injection, solutionIntramuscular; Intravenous; Subcutaneous
Tablet
Solution0.5 mg/1ml
Solution1 mg/1ml
Tablet0.6 mg
Solution
Suspension
Prices
Unit descriptionCostUnit
Atropine Sulfate 1% Solution 15ml Bottle101.27USD bottle
Isopto Atropine 1% Solution 15ml Bottle34.65USD bottle
Atropine powder34.48USD g
Isopto Atropine 1% Solution 5ml Bottle26.59USD bottle
Atropine Sulfate 1% Solution 5ml Bottle16.82USD bottle
Atropine Sulfate 1% Ointment 3.5 gm Tube15.92USD tube
Atropine-Care 1% Solution 2ml Bottle7.99USD bottle
Isopto atropine 1% eye drops5.06USD ml
Atropine-ns 1 mg/2.5 ml syr4.8USD ml
Atropine-ns 0.8 mg/2 ml syr3.9USD ml
Atropine 1% eye drops2.88USD ml
Atropine sulfate powder2.06USD g
Atropine care 1% eye drops2.03USD ml
Atropine-ns 2 mg/5 ml syringe1.92USD ml
Atropine Sulfate 0.4 mg/ml1.6USD ml
Atropine Sulfate 0.6 mg/ml1.6USD ml
Atropine 1 mg/ml vial1.44USD ml
Atropine Sulfate 0.4 mg/ml Solution1.22USD ml
Atropine 0.4 mg/0.5 ml ampul1.2USD ampul
Atropine 1 mg/ml ampul1.2USD ml
Atropine 0.4 mg/ml vial0.96USD ml
Isopto Atropine 1 % Solution0.68USD ml
Sal-tropine 0.4 mg tablet0.36USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)118.5 °CPharmacology in Clinical Neurosciences: A Quick Guide. (2020). Germany: Springer Singapore.
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 Solubility2.52 mg/mLALOGPS
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
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9286
Blood Brain Barrier+0.9569
Caco-2 permeable+0.8866
P-glycoprotein substrateSubstrate0.5
P-glycoprotein inhibitor INon-inhibitor0.6542
P-glycoprotein inhibitor IINon-inhibitor0.8595
Renal organic cation transporterInhibitor0.7956
CYP450 2C9 substrateNon-substrate0.7041
CYP450 2D6 substrateNon-substrate0.6838
CYP450 3A4 substrateSubstrate0.5496
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9275
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9285
CYP450 3A4 inhibitorNon-inhibitor0.95
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9113
Ames testNon AMES toxic0.7742
CarcinogenicityNon-carcinogens0.9631
BiodegradationReady biodegradable0.5527
Rat acute toxicity2.7305 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8354
hERG inhibition (predictor II)Inhibitor0.5378
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (7.92 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0090000000-b8bc13dbb3c507a0f6b6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-0190000000-c8603eb138fb8f0e3404
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00dl-3940000000-da1a38da6babdc138c49
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-006x-9700000000-2f9f7ce546a61df93bfa
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9300000000-6a976c404c7b299bbdd6
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0006-9200000000-0eb0ff987d891c85a047
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0090000000-59d025c22f64675dc295
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-0090000000-661bc87f4d92ae6353d7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-1960000000-dafd68e61cc5909f5dec
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-00dl-7900000000-48d355c9eef2af0979cc
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9300000000-659231292b6eba371158
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-00di-2900000000-3d5f34ceb343969b3c91
LC-MS/MS Spectrum - LC-ESI-ITTOF , positiveLC-MS/MSsplash10-00fr-0900000000-a216bda74712aba9b341
MS/MS Spectrum - , positiveLC-MS/MSsplash10-006x-6951100000-dad9042cce0338579e31

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM1
Uniprot ID
P11229
Uniprot Name
Muscarinic acetylcholine receptor M1
Molecular Weight
51420.375 Da
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. [Article]
  2. Buels KS, Fryer AD: Muscarinic receptor antagonists: effects on pulmonary function. Handb Exp Pharmacol. 2012;(208):317-41. doi: 10.1007/978-3-642-23274-9_14. [Article]
  3. Wall SJ, Yasuda RP, Li M, Ciesla W, Wolfe BB: Differential regulation of subtypes m1-m5 of muscarinic receptors in forebrain by chronic atropine administration. J Pharmacol Exp Ther. 1992 Aug;262(2):584-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled acetylcholine receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM2
Uniprot ID
P08172
Uniprot Name
Muscarinic acetylcholine receptor M2
Molecular Weight
51714.605 Da
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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  7. Buels KS, Fryer AD: Muscarinic receptor antagonists: effects on pulmonary function. Handb Exp Pharmacol. 2012;(208):317-41. doi: 10.1007/978-3-642-23274-9_14. [Article]
  8. Wall SJ, Yasuda RP, Li M, Ciesla W, Wolfe BB: Differential regulation of subtypes m1-m5 of muscarinic receptors in forebrain by chronic atropine administration. J Pharmacol Exp Ther. 1992 Aug;262(2):584-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Receptor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM3
Uniprot ID
P20309
Uniprot Name
Muscarinic acetylcholine receptor M3
Molecular Weight
66127.445 Da
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. [Article]
  2. Buels KS, Fryer AD: Muscarinic receptor antagonists: effects on pulmonary function. Handb Exp Pharmacol. 2012;(208):317-41. doi: 10.1007/978-3-642-23274-9_14. [Article]
  3. Wall SJ, Yasuda RP, Li M, Ciesla W, Wolfe BB: Differential regulation of subtypes m1-m5 of muscarinic receptors in forebrain by chronic atropine administration. J Pharmacol Exp Ther. 1992 Aug;262(2):584-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Guanyl-nucleotide exchange factor activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM4
Uniprot ID
P08173
Uniprot Name
Muscarinic acetylcholine receptor M4
Molecular Weight
53048.65 Da
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. [Article]
  2. Buels KS, Fryer AD: Muscarinic receptor antagonists: effects on pulmonary function. Handb Exp Pharmacol. 2012;(208):317-41. doi: 10.1007/978-3-642-23274-9_14. [Article]
  3. Wall SJ, Yasuda RP, Li M, Ciesla W, Wolfe BB: Differential regulation of subtypes m1-m5 of muscarinic receptors in forebrain by chronic atropine administration. J Pharmacol Exp Ther. 1992 Aug;262(2):584-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Phosphatidylinositol phospholipase c activity
Specific Function
The muscarinic acetylcholine receptor mediates various cellular responses, including inhibition of adenylate cyclase, breakdown of phosphoinositides and modulation of potassium channels through the...
Gene Name
CHRM5
Uniprot ID
P08912
Uniprot Name
Muscarinic acetylcholine receptor M5
Molecular Weight
60073.205 Da
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. [Article]
  2. Buels KS, Fryer AD: Muscarinic receptor antagonists: effects on pulmonary function. Handb Exp Pharmacol. 2012;(208):317-41. doi: 10.1007/978-3-642-23274-9_14. [Article]
  3. Wall SJ, Yasuda RP, Li M, Ciesla W, Wolfe BB: Differential regulation of subtypes m1-m5 of muscarinic receptors in forebrain by chronic atropine administration. J Pharmacol Exp Ther. 1992 Aug;262(2):584-8. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Antagonist
Curator comments
Atropine is a weak antagonist of glycine receptor subunit alpha-1
General Function
Transmitter-gated ion channel activity
Specific Function
The glycine receptor is a neurotransmitter-gated ion channel. Binding of glycine to its receptor increases the chloride conductance and thus produces hyperpolarization (inhibition of neuronal firing).
Gene Name
GLRA1
Uniprot ID
P23415
Uniprot Name
Glycine receptor subunit alpha-1
Molecular Weight
52623.35 Da
References
  1. Jensen AA, Kristiansen U: Functional characterisation of the human alpha1 glycine receptor in a fluorescence-based membrane potential assay. Biochem Pharmacol. 2004 May 1;67(9):1789-99. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNA4
Uniprot ID
P43681
Uniprot Name
Neuronal acetylcholine receptor subunit alpha-4
Molecular Weight
69956.47 Da
References
  1. Smulders CJ, Zwart R, Bermudez I, van Kleef RG, Groot-Kormelink PJ, Vijverberg HP: Cholinergic drugs potentiate human nicotinic alpha4beta2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol. 2005 Feb 21;509(2-3):97-108. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Ligand-gated ion channel activity
Specific Function
After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
Gene Name
CHRNB2
Uniprot ID
P17787
Uniprot Name
Neuronal acetylcholine receptor subunit beta-2
Molecular Weight
57018.575 Da
References
  1. Smulders CJ, Zwart R, Bermudez I, van Kleef RG, Groot-Kormelink PJ, Vijverberg HP: Cholinergic drugs potentiate human nicotinic alpha4beta2 acetylcholine receptors by a competitive mechanism. Eur J Pharmacol. 2005 Feb 21;509(2-3):97-108. [Article]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. FDA Approved Drug Products: Atropine sulfate injection for subcutaneous, intramuscular or intravenous use [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [Article]

Drug created at June 13, 2005 13:24 / Updated at September 20, 2022 00:04