Bethanechol

Identification

Summary

Bethanechol is a muscarinic agonist used to treat postoperative and postpartum nonobstructive functional urinary retention and neurogenic atony of the bladder with retention.

Brand Names

Duvoid

Generic Name

Bethanechol

DrugBank Accession Number

DB01019

Background

Bethanechol is a synthetic ester that was initially synthesized in 1935.^1,4 As a cholinergic agent, bethanechol is similar in structure and pharmacological function to acetylcholine and is used in specific cases when stimulation of the parasympathetic nervous system is necessary.^1,4 For example, bethanechol is readily used to treat postoperative or postpartum urinary retention. An advantage of bethanechol is that in contrast to acetylcholine, bethanechol is not degraded by cholinesterase allowing its effects to be longer-lasting.⁴

Type

Small Molecule

Groups

Approved

Structure

3D

Download

MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Bethanechol (DB01019)

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Weight

Average: 161.2221
Monoisotopic: 161.129002798

Chemical Formula

C₇H₁₇N₂O₂

Synonyms

• (2-hydroxypropyl)trimethylammonium carbamate
• 2-(carbamoyloxy)-N,N,N-trimethylpropan-1-aminium
• 2-carbamoyloxypropyl-trimethylazanium
• Amidopropyldimethylbetaine
• Bethanechol
• Carbamoyl-beta-methylcholine
• carbamoyl-β-methylcholine
• Carbamyl-beta-methylcholine
• carbamyl-β-methylcholine

Pharmacology

Indication

Bethanechol is indicated for the treatment of acute, functional postpartum and postoperative urinary retention. It is also indicated for the treatment of neurogenic atony of the bladder with retention.^3,4

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Associated Conditions

• Acute post-operative Urinary retention
• Neurogenic atony of the urinary bladder
• Non-obstructive postpartum urinary retention

Contraindications & Blackbox Warnings

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Pharmacodynamics

Bethanechol is selective for muscarinic receptors and has little to no impact on nicotinic receptors.¹ The charged quaternary amine in the structure of bethanechol prevents it from crossing the blood-brain barrier which minimizes central nervous system related adverse effects.¹

Mechanism of action

Bethanechol is a direct muscarinic agonist and stimulates the parasympathetic nervous system by binding to postganglionic muscarinic receptors.^2,1

Though there are 5 types of muscarinic receptors (M1, M2, M3, M4, M5), binding of bethanechol to M3 is most clinically significant since M3 receptors are present in intestinal smooth muscle and the bladder.² The cholinergic effects of bethanechol lead to increased detrusor muscle tone to promote bladder emptying and increased smooth muscle tone which restores gastrointestinal peristalsis and motility.²

As a result of selectivity for muscarinic receptors, bethanechol produces minimal to no nicotinic effects.¹

Target	Actions	Organism
AMuscarinic acetylcholine receptor M3	agonist	Humans
UMuscarinic acetylcholine receptor M1	agonist	Humans
UMuscarinic acetylcholine receptor M2	agonist	Humans
UMuscarinic acetylcholine receptor M4	agonist	Humans
UMuscarinic acetylcholine receptor M5	agonist	Humans

Absorption

After oral administration of bethanechol, maximum effectiveness of the drug on the bladder and GI tract typically occur after 60-90 minutes; however, effects may present as early as 30 minutes after administration. The duration of action of a typical oral dose of bethanechol is around 1 hour while higher doses (300-400 mg) may be effective for up to 6 hours.⁴

Subcutaneously administered bethanechol produces effects more rapidly after 5-15 minutes with maximum effectiveness achieved after 15-30 minutes. The effects of subcutaneous bethanechol subside within 2 hours of administration.⁴

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects

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Toxicity

Symptoms of bethanechol overdose include nausea, vomiting, abdominal discomfort, salivation, sweating, and flushing of the skin.⁴

In case of overdose, atropine sulfate is available as an antidote and although subcutaneous administration is preferred, it may be given intravenously in emergencies. In adults, the recommended dose of atropine is 0.6 mg and may be repeated every 2 hours based on the patient’s response. In infants and children up to 12 years of age, the recommended dose of atropine is 0.01 mg/kg (maximum single dose = 0.04 mg) and may be repeated every 2 hours until the desired response is achieved or until adverse effects of atropine limit usage.⁴

In mice, the oral LD50 of bethanechol is 1510 mg/kg.⁴

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Acebutolol	The risk or severity of adverse effects can be increased when Acebutolol is combined with Bethanechol.
Ambenonium	The risk or severity of adverse effects can be increased when Ambenonium is combined with Bethanechol.
Amikacin	The therapeutic efficacy of Bethanechol can be decreased when used in combination with Amikacin.
Aprotinin	The risk or severity of adverse effects can be increased when Aprotinin is combined with Bethanechol.
Atenolol	The risk or severity of adverse effects can be increased when Atenolol is combined with Bethanechol.
Betaine	The risk or severity of adverse effects can be increased when Betaine is combined with Bethanechol.
Betaxolol	The risk or severity of adverse effects can be increased when Betaxolol is combined with Bethanechol.
Bisoprolol	The risk or severity of adverse effects can be increased when Bisoprolol is combined with Bethanechol.
Botulinum toxin type A	The risk or severity of hypotension can be increased when Botulinum toxin type A is combined with Bethanechol.
Botulinum toxin type B	The risk or severity of hypotension can be increased when Botulinum toxin type B is combined with Bethanechol.

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Food Interactions

• Take on an empty stomach. Nausea and vomiting may occur if taken after food.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Bethanechol chloride	H4QBZ2LO84	590-63-6	XXRMYXBSBOVVBH-UHFFFAOYSA-N

Product Images

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International/Other Brands

Duvoid (Roberts) / Myotonachol (Glenwood) / Myotonine / Uro-Carb (Hamilton)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Duvoid Tablets 10 mg	Tablet	10 mg	Oral	Paladin Labs Inc	1992-12-31	Not applicable
Duvoid Tablets 25 mg	Tablet	25 mg	Oral	Paladin Labs Inc	1992-12-31	Not applicable
Duvoid Tablets 50 mg	Tablet	50 mg	Oral	Paladin Labs Inc	1992-12-31	Not applicable
Myotonachol Tablets 10mg	Tablet	10 mg	Oral	Glenwood Inc.	1993-12-31	2010-07-16
Myotonachol Tablets 25mg	Tablet	25 mg	Oral	Glenwood Inc.	1993-12-31	2010-07-16
Urecholine Inj 5mg/ml	Liquid	5 mg / mL	Subcutaneous	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1976-12-31	2003-01-31
Urecholine Tab 10mg	Tablet	10 mg / tab	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1976-12-31	2001-03-21
Urecholine Tab 25mg	Tablet	25 mg / tab	Oral	Merck Frosst Canada & Cie, Merck Frosst Canada & Co.	1976-12-31	2001-01-25

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Bethanechol Chloride	Tablet	50 mg/1	Oral	Upsher-Smith Laboratories, LLC	2010-01-24	Not applicable
Bethanechol Chloride	Tablet	25 mg/1	Oral	Major Pharmaceuticals	2010-04-01	Not applicable
Bethanechol Chloride	Tablet	50 mg/1	Oral	AvKARE, Inc.	2010-04-01	2018-09-18
Bethanechol Chloride	Tablet	10 mg/1	Oral	Eci Pharmaceuticals Llc	2020-02-15	Not applicable
Bethanechol Chloride	Tablet	25 mg/1	Oral	Physicians Total Care, Inc.	1995-08-14	Not applicable
Bethanechol Chloride	Tablet	25 mg/1	Oral	Actavis Totowa LLC	2002-07-30	2010-07-30
Bethanechol Chloride	Tablet	50 mg/1	Oral	Caraco Pharmaceutical Laboratories, Ltd.	2009-04-30	2016-12-30
Bethanechol Chloride	Tablet	25 mg/1	Oral	Rising Pharmaceuticals	2010-04-06	Not applicable
Bethanechol Chloride	Tablet	5 mg/1	Oral	Golden State Medical Supply, Inc.	2012-04-02	2015-07-01
Bethanechol Chloride	Tablet	25 mg/1	Oral	Avera McKennan Hospital	2015-06-15	2017-05-24

Categories

ATC Codes

N07AB02 — Bethanechol

• N07AB — Choline esters
• N07A — PARASYMPATHOMIMETICS
• N07 — OTHER NERVOUS SYSTEM DRUGS
• N — NERVOUS SYSTEM

Drug Categories

• Acids, Acyclic
• Amines
• Ammonium Compounds
• Autonomic Agents
• Bethanechol Compounds
• Carbamates
• Choline Esters
• Cholinergic Agents
• Cholinergic Agonists
• Muscarinic Agonists
• Nervous System
• Neurotransmitter Agents
• Nitrogen Compounds
• Onium Compounds
• Parasympathomemetic (Cholinergic) Agents
• Parasympathomimetics
• Peripheral Nervous System Agents
• Quaternary Ammonium Compounds
• Trimethyl Ammonium Compounds

Chemical TaxonomyProvided by Classyfire

Description

This compound belongs to the class of organic compounds known as tetraalkylammonium salts. These are organonitrogen compounds containing a quaternary ammonium substituted with four alkyl chains.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Quaternary ammonium salts

Direct Parent

Tetraalkylammonium salts

Alternative Parents

Carboximidic acids and derivatives / Organopnictogen compounds / Organooxygen compounds / Organic salts / Imines / Hydrocarbon derivatives / Amines / Organic cations

Substituents

Aliphatic acyclic compound / Amine / Carboximidic acid derivative / Hydrocarbon derivative / Imine / Organic cation / Organic oxygen compound / Organic salt / Organooxygen compound / Organopnictogen compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

carbamate ester, quaternary ammonium ion (CHEBI:3084)

Affected organisms

• Humans and other mammals

Chemical Identifiers

UNII

004F72P8F4

CAS number

674-38-4

InChI Key

NZUPCNDJBJXXRF-UHFFFAOYSA-O

InChI

InChI=1S/C7H16N2O2/c1-6(11-7(8)10)5-9(2,3)4/h6H,5H2,1-4H3,(H-,8,10)/p+1

IUPAC Name

1-(trimethylazaniumyl)propan-2-yl carbamate

SMILES

CC(C[N+](C)(C)C)OC(N)=O

References

Synthesis Reference

Major, R.T. and Bonnett, H.T.; U.S. Patent 2,322,375: June 22,1943; assigned to Merck & Co., Inc.

General References

1. Padda IS, Derian A: Bethanechol . [Article]
2. Bui T, Duong H: Muscarinic Agonists . [Article]
3. Pakala RS, Brown KN, Preuss CV: Cholinergic Medications . [Article]
4. DailyMed Drug Label Information: Bethanechol chloride oral tablets [Link]

External Links

Human Metabolome Database

HMDB0015154

KEGG Compound

C06850

PubChem Compound

2370

PubChem Substance

46507707

ChemSpider

2280

BindingDB

39342

RxNav

19257

ChEBI

3084

ChEMBL

CHEMBL1482

Therapeutic Targets Database

DAP000263

PharmGKB

PA448613

Guide to Pharmacology

GtP Drug Page

RxList

RxList Drug Page

Drugs.com

Drugs.com Drug Page

Wikipedia

Bethanechol

MSDS

Download (74.1 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
4	Completed	Prevention	Bladder Dysfunction	1
2	Terminated	Treatment	Eosinophilic Esophagitis (EoE)	1
1	Completed	Basic Science	Type 2 Diabetes Mellitus	1
1	Completed	Treatment	Esophageal Motility Disorders	1
0	Recruiting	Other	Malignant Neoplasm of Pancreas	1

Pharmacoeconomics

Manufacturers

• Sun pharmaceutical industries inc
• Odyssey pharmaceuticals inc
• Able laboratories inc
• Actavis totowa llc
• Amneal pharmaceutical
• Ascot hosp pharmaceuticals inc div travenol laboratories inc
• Emcure pharmaceuticals usa inc
• Impax laboratories inc
• Ivax pharmaceuticals inc sub teva pharmaceuticals usa
• Lannett holdings inc
• Lannett co inc
• Pharmax group inc
• Sandoz inc
• Upsher smith laboratories inc
• Watson laboratories inc
• Wockhardt ltd
• Wellspring pharmaceutical corp
• Glenwood inc

Packagers

• Actavis Group
• Amerisource Health Services Corp.
• Amneal Pharmaceuticals
• Ascend Laboratories LLC
• Caraco Pharmaceutical Labs
• Duramed
• Global Pharmaceuticals
• Heartland Repack Services LLC
• Impax Laboratories Inc.
• Lannett Co. Inc.
• Major Pharmaceuticals
• Medisca Inc.
• Murfreesboro Pharmaceutical Nursing Supply
• PD-Rx Pharmaceuticals Inc.
• Pharmaceutical Utilization Management Program VA Inc.
• Pharmacy Service Center
• Physicians Total Care Inc.
• Pliva Inc.
• QPharm Inc.
• Ranbaxy Laboratories
• Resource Optimization and Innovation LLC
• Sandhills Packaging Inc.
• Southwood Pharmaceuticals
• Sun Pharmaceutical Industries Ltd.
• United Research Laboratories Inc.
• USL Pharma Inc.
• Vangard Labs Inc.
• Wellspring Pharmaceutical
• Wockhardt Ltd.

Dosage Forms

Form	Route	Strength
Tablet	Oral	10 mg/1
Tablet	Oral	25 mg/1
Tablet	Oral	5 mg/1
Tablet	Oral	50 mg/1
Tablet	Oral	25 mg
Tablet	Oral	50 mg
Tablet	Oral
Liquid	Subcutaneous	5 mg / mL
Tablet	Oral	10 mg / tab
Tablet	Oral	25 mg / tab
Tablet	Oral	10 mg
Tablet	Oral	5 mg

Prices

Unit description	Cost	Unit
Bethanechol chloride powder	10.1USD	g
Urecholine 50 mg tablet	3.95USD	tablet
Urecholine 25 mg tablet	3.46USD	tablet
Bethanechol Chloride 50 mg tablet	2.97USD	tablet
Bethanechol 50 mg tablet	2.85USD	tablet
Bethanechol Chloride 25 mg tablet	1.86USD	tablet
Urecholine 10 mg tablet	1.85USD	tablet
Bethanechol 25 mg tablet	1.78USD	tablet
Bethanechol Chloride 10 mg tablet	1.39USD	tablet
Bethanechol 10 mg tablet	1.34USD	tablet
Urecholine 5 mg tablet	1.14USD	tablet
Bethanechol Chloride 5 mg tablet	0.74USD	tablet
Bethanechol 5 mg tablet	0.71USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.311 mg/mL	ALOGPS
logP	-2.8	ALOGPS
logP	-4.1	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	15.34	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	52.32 Å2	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	54.44 m3·mol-1	ChemAxon
Polarizability	17.73 Å3	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	-	0.8407
Blood Brain Barrier	+	0.9789
Caco-2 permeable	+	0.5251
P-glycoprotein substrate	Non-substrate	0.7295
P-glycoprotein inhibitor I	Non-inhibitor	0.9508
P-glycoprotein inhibitor II	Non-inhibitor	0.8371
Renal organic cation transporter	Non-inhibitor	0.9209
CYP450 2C9 substrate	Non-substrate	0.8304
CYP450 2D6 substrate	Non-substrate	0.8066
CYP450 3A4 substrate	Substrate	0.5216
CYP450 1A2 substrate	Non-inhibitor	0.9045
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.9231
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.9522
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9047
Ames test	Non AMES toxic	0.6804
Carcinogenicity	Carcinogens	0.522
Biodegradation	Not ready biodegradable	0.8058
Rat acute toxicity	2.7833 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9852
hERG inhibition (predictor II)	Non-inhibitor	0.8915

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available

Targets

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Details1. Muscarinic acetylcholine receptor M3

Kind

Protein

Organism

Humans

Pharmacological action

Yes

Actions

Agonist

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. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [Article]
2. Padda IS, Derian A: Bethanechol . [Article]
3. Bui T, Duong H: Muscarinic Agonists . [Article]

Details2. Muscarinic acetylcholine receptor M1

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

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. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [Article]
2. Padda IS, Derian A: Bethanechol . [Article]

Details3. Muscarinic acetylcholine receptor M2

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

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. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
2. 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. [Article]
3. Agrawal A, Hila A, Tutuian R, Mainie I, Castell DO: Bethanechol improves smooth muscle function in patients with severe ineffective esophageal motility. J Clin Gastroenterol. 2007 Apr;41(4):366-70. [Article]
4. Buranakarl C, Kijtawornrat A, Angkanaporn K, Komolvanich S, Bovee KC: Effects of bethanechol on canine urinary bladder smooth muscle function. Res Vet Sci. 2001 Dec;71(3):175-81. [Article]
5. Cruzblanca H: An M2-like muscarinic receptor enhances a delayed rectifier K+ current in rat sympathetic neurones. Br J Pharmacol. 2006 Oct;149(4):441-9. Epub 2006 Sep 4. [Article]
6. Padda IS, Derian A: Bethanechol . [Article]

Details4. Muscarinic acetylcholine receptor M4

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

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. Jakubik J, Bacakova L, El-Fakahany EE, Tucek S: Positive cooperativity of acetylcholine and other agonists with allosteric ligands on muscarinic acetylcholine receptors. Mol Pharmacol. 1997 Jul;52(1):172-9. [Article]
2. Padda IS, Derian A: Bethanechol . [Article]

Details5. Muscarinic acetylcholine receptor M5

Kind

Protein

Organism

Humans

Pharmacological action

Unknown

Actions

Agonist

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. Padda IS, Derian A: Bethanechol . [Article]

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Drug created at June 13, 2005 13:24 / Updated at October 26, 2021 21:40