Identification

Name
Atropine
Accession Number
DB00572  (APRD00807, EXPT02427)
Type
Small Molecule
Groups
Approved, Vet approved
Description

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

Structure
Thumb
Synonyms
  • (±)-atropine
  • (±)-hyoscyamine
  • Atropin
  • Atropina
  • Atropine
  • Atropinum
  • dl-Hyoscyamine
  • dl-tropyltropate
  • Tropine tropate
External IDs
NSC 61810
Product Ingredients
IngredientUNIICASInChI Key
Atropine hydrochlorideEUF58V826B33952-38-4OJIPQOWZZMSBGY-RIMUKSHESA-N
Atropine sulfateKAE4PSB0Z355-48-1HOBWAPHTEJGALG-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AtroPen Auto-InjectorInjection2 mg/0.7mLIntramuscularMeridian Medical Technologies , Inc.2003-06-19Not applicableUs
AtroPen Auto-InjectorInjection0.25 mg/0.3mLIntramuscularMeridian Medical Technologies , Inc.2004-09-17Not applicableUs
AtroPen Auto-InjectorInjection1 mg/0.7mLIntramuscularMeridian Medical Technologies , Inc.2003-06-19Not applicableUs
AtroPen Auto-InjectorInjection0.5 mg/0.7mLIntramuscularMeridian Medical Technologies , Inc.2003-06-19Not applicableUs
AtropineSolution1 %OphthalmicEberth Pharmaceuticals Inc1994-12-31Not applicableCanada
AtropineSolution / drops10 mg/1mLOphthalmicAkorn2014-07-18Not applicableUs
AtropineSolution / drops10 mg/1mLOphthalmicMwi2015-03-23Not applicableUs
AtropineSolution / drops10 mg/1mLOphthalmicA-S Medication Solutions2014-07-18Not applicableUs
Atropine 1%Solution / drops1 %OphthalmicNovartis Ophthalmics Novartis Pharmaceuticals (Canada) Inc1987-12-312003-12-10Canada
Atropine Injection BPSolution0.6 mgIntramuscular; Intravenous; SubcutaneousTeligent Ou2016-01-28Not applicableCanada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
ATNAA atropine and pralidoxime chloride Auto-InjectorAtropine (2.1 mg/0.7mL) + Pralidoxime Chloride (600 mg/2mL)KitIntramuscularMeridian Medical Technologies, Inc.2002-01-17Not applicableUs
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
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
Diphenoxylate Hcl and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralStat Rx USA1979-10-29Not applicableUs
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralbryant ranch prepack2000-05-26Not applicableUs
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralMylan Pharmaceuticals Inc.1977-11-17Not applicableUs0378 041520180913 8702 kxh48l
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralAtlantic Biologicals Corps.2013-02-27Not applicableUs
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralKaiser Foundations Hospitals2010-11-30Not applicableUs
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralApotheca, Inc.1977-11-17Not applicableUs
Diphenoxylate Hydrochloride and Atropine SulfateAtropine sulfate (0.025 mg/1) + Diphenoxylate Hydrochloride (2.5 mg/1)TabletOralProficient Rx LP2017-07-07Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Atropine CareAtropine sulfate (10 mg/1mL)Solution / dropsOphthalmicAkorn, Inc1995-06-012008-06-01Us
Atropine SulfateAtropine sulfate (0.1 mg/1mL)InjectionParenteralRemedy Repack2016-06-012016-06-09Us
Atropine SulfateAtropine sulfate (0.4 mg/1mL)InjectionIntramuscular; Intravenous; SubcutaneousHF Acquisition Co LLC, DBA HealthFirst2018-10-06Not applicableUs
Atropine SulfateAtropine sulfate (0.1 mg/1mL)Injection, solutionIntravenousRemedy Repack2018-03-052018-03-05Us
Atropine SulfateAtropine sulfate (0.4 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2010-04-012017-01-18Us
Atropine SulfateAtropine sulfate (1 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousCardinal Health2011-07-07Not applicableUs
Atropine SulfateAtropine sulfate (0.1 mg/1mL)Injection, solutionIntravenousHospira, Inc.2005-08-25Not applicableUs
Atropine SulfateAtropine sulfate (1 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousAMERICAN REGENT, INC.1992-11-012011-09-29Us
Atropine SulfateAtropine sulfate (1 mg/1mL)Injection, solutionIntramuscular; Intravenous; SubcutaneousGeneral Injectables & Vaccines2013-09-19Not applicableUs
Atropine SulfateAtropine sulfate (0.1 mg/1mL)InjectionParenteralAmphastar Pharmaceuticals, Inc.1990-01-022009-12-15Us
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)
Categories
UNII
7C0697DR9I
CAS number
51-55-8
Weight
Average: 289.3694
Monoisotopic: 289.167793607
Chemical Formula
C17H23NO3
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,3R,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

Pharmacology

Indication

For the treatment of poisoning by susceptible organophosphorous nerve agents having anti-cholinesterase activity (cholinesterase inhibitors) as well as organophosphorous or carbamate insecticides.

Associated Conditions
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.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Human
AMuscarinic acetylcholine receptor M2
antagonist
Human
AMuscarinic acetylcholine receptor M3
antagonist
Human
AMuscarinic acetylcholine receptor M4
antagonist
Human
AMuscarinic acetylcholine receptor M5
antagonist
Human
UGlycine receptor subunit alpha-1
antagonist
Human
UNeuronal acetylcholine receptor subunit alpha-4Not AvailableHuman
UNeuronal acetylcholine receptor subunit beta-2Not AvailableHuman
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
1,10-PhenanthrolineThe therapeutic efficacy of Atropine can be decreased when used in combination with 1,10-Phenanthroline.
AbexinostatThe risk or severity of QTc prolongation can be increased when Atropine is combined with Abexinostat.
AcebutololThe risk or severity of QTc prolongation can be increased when Atropine is combined with Acebutolol.
AceprometazineThe risk or severity of QTc prolongation can be increased when Atropine is combined with Aceprometazine.
AcetyldigoxinThe risk or severity of QTc prolongation can be increased when Acetyldigoxin is combined with Atropine.
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.
AdenosineThe risk or severity of QTc prolongation can be increased when Atropine is combined with Adenosine.
AgmatineThe risk or severity of adverse effects can be increased when Atropine is combined with Agmatine.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Atropine.
Food Interactions
  • Avoid alcohol.
  • Take with food.

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
Not Available
External Links
Human Metabolome Database
HMDB0014712
KEGG Drug
D00113
KEGG Compound
C01479
PubChem Compound
174174
PubChem Substance
46507540
ChemSpider
10194105
BindingDB
50403547
ChEBI
78734
ChEMBL
CHEMBL517712
Therapeutic Targets Database
DAP000377
PharmGKB
PA448505
IUPHAR
320
Guide to Pharmacology
GtP Drug Page
HET
OIN
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Atropine
ATC Codes
S01FA01 — AtropineA03BA01 — AtropineA03CB03 — Atropine and psycholeptics
AHFS Codes
  • 12:08.08 — Antimuscarinics Antispasmodics
  • 52:24.00 — Mydriatics
FDA label
Download (164 KB)
MSDS
Download (73.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedBasic ScienceInsulin Resistance1
0Not Yet RecruitingPreventionIncidence of Postoperative Residual Curarization1
0RecruitingOtherBypass, Gastric / Hypoglycemia After Gastric Bypass / Post Bariatric Surgery / Sleeve Gastrectomy1
0RecruitingOtherHypoglycemia / Post Bariatricsurgery1
0RecruitingPreventionMyopia, Progressive1
1CompletedBasic SciencePre-Diabetic1
1CompletedDiagnosticDigestive Physiology / Exendin (9-39) / Gastrointestinal Hormones / Gastrointestinal Motility / Glucagon-Like Peptide 11
1CompletedDiagnosticHealthy Volunteers1
1CompletedTreatmentMyopia1
1CompletedTreatmentOrganophosphorus Poisoning1
1Not Yet RecruitingSupportive CareNear Infrared Spectroscopy / Respiratory Distress Syndrome (RDS) / Surfactant Deficiency Syndrome Neonatal1
1, 2RecruitingTreatmentMyopia1
2CompletedPreventionBradycardia1
2CompletedPreventionCoagulation Defect; Bleeding1
2CompletedPreventionVentilator-Associated Pneumonia (VAP)1
2CompletedTreatmentCardiac Arrest1
2CompletedTreatmentPhysiology, Ocular / Regional Blood Flow1
2Not Yet RecruitingTreatmentMyopia1
2RecruitingSupportive CareCancer, Breast1
2Unknown StatusTreatmentRhinitis, Seasonal, Allergic1
2, 3Active Not RecruitingTreatmentCerebral Hypoperfusion / Intubation, Endotracheal / Premedication1
2, 3Active Not RecruitingTreatmentIntubation, Endotracheal / Premedication1
2, 3CompletedPreventionHypospadias1
3CompletedDiagnosticMalignant Lymphomas1
3CompletedDiagnosticThoracic Pain1
3CompletedTreatmentAmblyopia5
3CompletedTreatmentAmblyopia / Anisometropia / Strabismus1
3CompletedTreatmentAnaesthesia therapy1
3CompletedTreatmentElective Caesarean Section Surgeries1
3CompletedTreatmentOrganophosphate Poisoning1
3CompletedTreatmentPain NOS1
3CompletedTreatmentAdjunct to general anesthesia therapy1
3Enrolling by InvitationOtherMyopia1
3RecruitingTreatmentMyopia2
3TerminatedTreatmentAmblyopia1
4CompletedDiagnosticIntraocular Pressure Changes During Tracheal Extubation1
4CompletedPreventionArrythmias / Respiratory Arrest1
4CompletedPreventionBradycardia1
4CompletedPreventionIntubation, Endotracheal1
4CompletedTreatmentAdverse Reaction to Belladonna or Atropine / Bradycardia / Neostigmine Adverse Reaction1
4CompletedTreatmentAmblyopia1
4CompletedTreatmentArterial Hypotension / Cesarean Section / Pregnancy / Spinal Anaesthesia1
4CompletedTreatmentCesarean Section / Post-Operative Nausea and Vomiting (PONV) / Spinal Anaesthesia1
4CompletedTreatmentComplication of Ventilation Therapy / Observation of Neuromuscular Block / Postoperative Recovery1
4CompletedTreatmentConscious Sedation Failure During Procedure1
4CompletedTreatmentGall Stone Disease1
4CompletedTreatmentInadequate or Impaired Respiratory Function / Pain NOS1
4CompletedTreatmentIntubations / Newborns / Preterms1
4CompletedTreatmentMajor Abdominal Surgery1
4CompletedTreatmentMild Cognitive Impairment (MCI)1
4CompletedTreatmentReversal of Skeletal Muscle Relaxant / Underdosing of Skeletal Muscle Relaxants for Laparotomy1
4CompletedTreatmentSedation, Conscious1
4Not Yet RecruitingTreatmentGynecology / Surgery, Laparoscopic1
4Not Yet RecruitingTreatmentNeuromuscular Block1
4RecruitingOtherAdverse Drug Events / Cataracts / Mydriasis1
4RecruitingPreventionLower Extremity Fractures1
4RecruitingPreventionMyopia1
4RecruitingTreatmentAnesthesiology Management1
4RecruitingTreatmentNeuromuscular Blockade1
4RecruitingTreatmentPost-operative Residual Curarization1
4Unknown StatusPreventionBradycardia / Hypoxemia1
4Unknown StatusPreventionMyopia1
4Unknown StatusTreatmentNeuromuscular Blockade1
4WithdrawnNot AvailableNeuromuscular Blockade1
Not AvailableActive Not RecruitingPreventionArterial Hypotension1
Not AvailableCompletedNot AvailableArrythmias / Bradycardia1
Not AvailableCompletedNot AvailableDeath, Sudden,Cardiac / Heart Arrest1
Not AvailableCompletedNot AvailableHealthy Volunteers1
Not AvailableCompletedNot AvailableIntubation; Difficult1
Not AvailableCompletedPreventionDiastolic Dysfunction1
Not AvailableCompletedPreventionSpinal Anaesthesia1
Not AvailableCompletedScreeningPost Operative Cognitive Dysfunction1
Not AvailableCompletedSupportive CareSialorrhea1
Not AvailableCompletedTreatmentAnesthesia-induced Negative Hemodynamic Effects1
Not AvailableCompletedTreatmentMyopia1
Not AvailableCompletedTreatmentMyopia Progression1
Not AvailableEnrolling by InvitationOtherCatecholaminergic Polymorphic Ventricular Tachycardia (CPVT)1
Not AvailableRecruitingDiagnosticBlood Coagulation Tests ( INR, APTT)1
Not AvailableRecruitingPreventionMyopia1
Not AvailableRecruitingPreventionSpinal Anaesthesia1
Not AvailableSuspendedTreatmentPaediatric Flexible Bronchoscopy1
Not AvailableUnknown StatusBasic ScienceThe Focus of This Study is to Evaluete the Significances of the Vagal Cholinerg Nervuos System for the Effect of GLP-1 by Using Atropin Administration1
Not AvailableUnknown StatusPreventionAnaesthesia therapy / Catheter Site Discomfort / Complications / Urinary Bladder Neoplasms1

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
KitIntramuscular
InjectionIntramuscular0.25 mg/0.3mL
InjectionIntramuscular0.5 mg/0.7mL
InjectionIntramuscular1 mg/0.7mL
InjectionIntramuscular2 mg/0.7mL
SolutionOphthalmic1 %
Solution / dropsOphthalmic1 %
SolutionIntramuscular; Intravenous; Subcutaneous0.4 mg
OintmentOphthalmic1 %
InjectionIntramuscular; Intravenous; Subcutaneous0.4 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; Subcutaneous.05 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, solutionIntravenous0.1 mg/1mL
Injection, solutionIntravenous1 mg/1mL
OintmentOphthalmic10 mg/1g
SolutionOphthalmic1 mg/1mL
SolutionOphthalmic10 mg/1mL
Solution / dropsOphthalmic10 mg/1mL
LiquidIntravenous.1 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.3 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.8 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.6 mg
SolutionIntramuscular; Intravenous; Subcutaneous1 mg
SolutionIntramuscular; Intravenous; Subcutaneous0.5 mg
SolutionIntramuscular; Intravenous; Subcutaneous3 mg
SolutionIntramuscular; Intravenous; Subcutaneous.6 mg
Solution / dropsOphthalmic10 mg
CapsuleOral
SolutionOral
LiquidOral
ElixirOral
Tablet, extended releaseOral
Tablet, film coated, extended releaseOral
Injection, solutionIntravenous
InjectionIntravenous
TabletOral
Solution / dropsOphthalmic
LiquidOphthalmic1 %
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 °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 Solubility2.52 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

Taxonomy

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
Tropane alkaloid / Beta-hydroxy acid / Monocyclic benzene moiety / Hydroxy acid / Piperidine / Benzenoid / N-alkylpyrrolidine / Pyrrolidine / Amino acid or derivatives / Carboxylic acid ester
show 18 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
racemate (CHEBI:16684) / Tropane alkaloids, Alkaloids, Tropan alkaloids (C01479)

Targets

Kind
Protein
Organism
Human
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. [PubMed:7855217]
  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:17139284]
  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:17016423]
Kind
Protein
Organism
Human
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. [PubMed:16248990]
  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:17087737]
  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:15333678]
  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:17588565]
  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:16188951]
  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:7855217]
Kind
Protein
Organism
Human
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. [PubMed:7855217]
  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:17139284]
  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:17016423]
Kind
Protein
Organism
Human
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. [PubMed:7855217]
  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:17139284]
  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:17016423]
Kind
Protein
Organism
Human
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. [PubMed:7855217]
  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:17139284]
  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:17016423]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
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. [PubMed:15081878]
Kind
Protein
Organism
Human
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. [PubMed:15733544]
Kind
Protein
Organism
Human
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. [PubMed:15733544]

Transporters

Kind
Protein
Organism
Human
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. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on November 18, 2018 13:31