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Procyclidine
Identification
- Name
- Procyclidine
- Accession Number
- DB00387
- Description
A muscarinic antagonist that crosses the blood-brain barrier and is used in the treatment of drug-induced extrapyramidal disorders and in parkinsonism.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Procyclidine (DB00387)
- Weight
- Average: 287.4397
Monoisotopic: 287.224914555 - Chemical Formula
- C19H29NO
- Synonyms
- 1-cyclohexyl-1-phenyl-3-pyrrolidin-1-yl-propan-1-ol hydrochloride
- 1-Cyclohexyl-1-phenyl-3-pyrrolidino-1-propanol
- Prociclidina
- Procyclidin
- Procyclidine
- Procyclidinum
- Tricyclamol
Pharmacology
- Indication
For the treatment of all forms of Parkinson's Disease, as well as control of extrapyramidal reactions induced by antipsychotic agents.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
Procyclidine has an atropine-like action on parasympathetic-innervated peripheral structures including smooth muscle. It's antispasmodic effects are thought to be related to the blockage of central cholinergic receptors M1, M2 and M4. It is used to treat symptomatic Parkinsonism and extrapyramidal dysfunction caused by antipsychotic agents.
- Mechanism of action
The mechanism of action is unknown. It is thought that Procyclidine acts by blocking central cholinergic receptors, and thus balancing cholinergic and dopaminergic activity in the basal ganglia. Many of its effects are due to its pharmacologic similarities with atropine. Procyclidine exerts an antispasmodic effect on smooth muscle, and may produce mydriasis and reduction in salivation.
Target Actions Organism AMuscarinic acetylcholine receptor M1 antagonistHumans AMuscarinic acetylcholine receptor M2 antagonistHumans AMuscarinic acetylcholine receptor M4 antagonistHumans AMuscarinic acetylcholine receptor M3 antagonistHumans - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
Approximately 100% bound to albumin.
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
LD50=60 mg/kg (IV in mice)
- Affected organisms
- Humans and other mammals
- 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.
Drug Interaction Unlock Additional DataAcetazolamide Acetazolamide may increase the central nervous system depressant (CNS depressant) activities of Procyclidine. Acetophenazine Acetophenazine may increase the central nervous system depressant (CNS depressant) activities of Procyclidine. Aclidinium The risk or severity of adverse effects can be increased when Procyclidine is combined with Aclidinium. Adenosine The risk or severity of Tachycardia can be increased when Procyclidine is combined with Adenosine. Agomelatine Agomelatine may increase the central nervous system depressant (CNS depressant) activities of Procyclidine. Alfentanil The risk or severity of adverse effects can be increased when Alfentanil is combined with Procyclidine. Alimemazine Alimemazine may increase the central nervous system depressant (CNS depressant) activities of Procyclidine. Alloin The therapeutic efficacy of Alloin can be decreased when used in combination with Procyclidine. Almotriptan Almotriptan may increase the central nervous system depressant (CNS depressant) activities of Procyclidine. Alosetron Alosetron may increase the central nervous system depressant (CNS depressant) activities of Procyclidine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Take with or without food. Taking with food may reduce the adverse effects of procyclidine.
Products
- Product Ingredients
Ingredient UNII CAS InChI Key Procyclidine hydrochloride CQC932Z7YW 1508-76-5 ZFSPFXJSEHCTTR-UHFFFAOYSA-N - International/Other Brands
- Arpicolin (Rosemont) / Extranil (General Pharma) / Kdrine (Opsonin) / Kemadren (GlaxoSmithKline) / Osnervan (Aspen) / Prodine (Psyco Remedies) / Proimer (Cho Dang)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataKemadrin Tablet 5 mg/1 Oral Monarch Pharmaceuticals, Inc. 1955-05-26 2008-10-22 US 
Kemadrin Elx Elixir Oral Glaxosmithkline Inc 1968-12-31 2004-08-05 Canada 
Kemadrin Tab 5mg Tablet Oral Glaxosmithkline Inc 1956-12-31 2004-12-02 Canada Procyclid Elx Elixir Oral Icn Pharmaceuticals 1980-12-31 2005-04-26 Canada Procyclid Tab 5mg Tablet Oral Icn Pharmaceuticals 1974-12-31 2005-04-26 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataPdp-procyclidine Tablet Oral Pendopharm Division Of Pharmascience Inc 1985-12-31 Not applicable Canada Pdp-procyclidine Elixir Oral Pendopharm Division Of Pharmascience Inc 1984-12-31 Not applicable Canada Pdp-procyclidine Tablet Oral Pendopharm Division Of Pharmascience Inc 1985-12-31 Not applicable Canada Pendo-procyclidine Tablet Oral Pendopharm Division Of Pharmascience Inc Not applicable Not applicable Canada PHL-procyclidine Tablets Tablet Oral Pharmel Inc 1998-02-17 2010-11-03 Canada PHL-procyclidine Tablets Tablet Oral Pharmel Inc 1998-02-17 2010-11-03 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- ATC Codes
- N04AA04 — Procyclidine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
- Kingdom
- Organic compounds
- Super Class
- Organic nitrogen compounds
- Class
- Organonitrogen compounds
- Sub Class
- Amines
- Direct Parent
- Aralkylamines
- Alternative Parents
- N-alkylpyrrolidines / Benzene and substituted derivatives / Tertiary alcohols / 1,3-aminoalcohols / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,3-aminoalcohol / Alcohol / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Benzenoid / Hydrocarbon derivative / Monocyclic benzene moiety / N-alkylpyrrolidine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- tertiary alcohol, pyrrolidines (CHEBI:8448)
Chemical Identifiers
- UNII
- C6QE1Q1TKR
- CAS number
- 77-37-2
- InChI Key
- WYDUSKDSKCASEF-UHFFFAOYSA-N
- InChI
- InChI=1S/C19H29NO/c21-19(17-9-3-1-4-10-17,18-11-5-2-6-12-18)13-16-20-14-7-8-15-20/h1,3-4,9-10,18,21H,2,5-8,11-16H2
- IUPAC Name
- 1-cyclohexyl-1-phenyl-3-(pyrrolidin-1-yl)propan-1-ol
- SMILES
- OC(CCN1CCCC1)(C1CCCCC1)C1=CC=CC=C1
References
- General References
- Theodoridis GC, Stark L: Central role of solar information flow in pregenetic evolution. J Theor Biol. 1971 Jun;31(3):377-88. [PubMed:5556140]
- External Links
- Human Metabolome Database
- HMDB0014531
- KEGG Drug
- D08425
- KEGG Compound
- C07378
- PubChem Compound
- 4919
- PubChem Substance
- 46505553
- ChemSpider
- 4750
- BindingDB
- 50062598
- 8718
- ChEBI
- 8448
- ChEMBL
- CHEMBL86715
- Therapeutic Targets Database
- DAP001110
- PharmGKB
- PA164784001
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Procyclidine
- AHFS Codes
- 28:36.08 — Anticholinergic Agents
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Monarch pharmaceuticals inc
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 5 mg/1 Tablet 5 mg Elixir Oral Tablet Oral - Prices
Unit description Cost Unit Pms-Procyclidine 2.5 mg Tablet 0.06USD tablet Pms-Procyclidine 0.5 mg/ml Elixir 0.03USD ml Pms-Procyclidine 5 mg Tablet 0.03USD tablet DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 86 °C PhysProp water solubility Moderately soluble in water, ~ 30 mg/ml Not Available logP 4.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.00984 mg/mL ALOGPS logP 4.13 ALOGPS logP 3.79 ChemAxon logS -4.5 ALOGPS pKa (Strongest Acidic) 13.84 ChemAxon pKa (Strongest Basic) 9.45 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 23.47 Å2 ChemAxon Rotatable Bond Count 5 ChemAxon Refractivity 88.6 m3·mol-1 ChemAxon Polarizability 34.43 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9822 Blood Brain Barrier + 0.9734 Caco-2 permeable + 0.6388 P-glycoprotein substrate Substrate 0.6324 P-glycoprotein inhibitor I Non-inhibitor 0.51 P-glycoprotein inhibitor II Non-inhibitor 0.5877 Renal organic cation transporter Inhibitor 0.7954 CYP450 2C9 substrate Non-substrate 0.7956 CYP450 2D6 substrate Non-substrate 0.7907 CYP450 3A4 substrate Non-substrate 0.5427 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.915 CYP450 2D6 inhibitor Inhibitor 0.8931 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.8308 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682 Ames test Non AMES toxic 0.841 Carcinogenicity Non-carcinogens 0.9142 Biodegradation Not ready biodegradable 0.9178 Rat acute toxicity 2.7861 LD50, mol/kg Not applicable hERG inhibition (predictor I) Strong inhibitor 0.6498 hERG inhibition (predictor II) Inhibitor 0.5597
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Mass Spectrum (Electron Ionization) MS splash10-001i-9010000000-7d7f1b16f54aaca37f10 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 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
- 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
- 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]
- 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]
- Larson EW, Pfenning MA, Richelson E: Selectivity of antimuscarinic compounds for muscarinic receptors of human brain and heart. Psychopharmacology (Berl). 1991;103(2):162-5. [PubMed:2027917]
- Waelbroeck M, Camus J, Tastenoy M, Lambrecht G, Mutschler E, Tacke R, Christophe J: Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. Eur J Pharmacol. 1990 Sep 18;189(2-3):135-42. [PubMed:2253700]
- Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420]
- Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023]
- 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
- 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]
- 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]
- Larson EW, Pfenning MA, Richelson E: Selectivity of antimuscarinic compounds for muscarinic receptors of human brain and heart. Psychopharmacology (Berl). 1991;103(2):162-5. [PubMed:2027917]
- Waelbroeck M, Camus J, Tastenoy M, Lambrecht G, Mutschler E, Tacke R, Christophe J: Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. Eur J Pharmacol. 1990 Sep 18;189(2-3):135-42. [PubMed:2253700]
- Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420]
- Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023]
- 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
- 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]
- 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]
- Waelbroeck M, Camus J, Tastenoy M, Lambrecht G, Mutschler E, Tacke R, Christophe J: Stereoselectivity of procyclidine binding to muscarinic receptor subtypes M1, M2 and M4. Eur J Pharmacol. 1990 Sep 18;189(2-3):135-42. [PubMed:2253700]
- Alberts P: Classification of the presynaptic muscarinic receptor subtype that regulates 3H-acetylcholine secretion in the guinea pig urinary bladder in vitro. J Pharmacol Exp Ther. 1995 Jul;274(1):458-68. [PubMed:7616431]
- Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420]
- Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023]
- 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
- Myhrer T: Identification of neuronal target areas for nerve agents and specification of receptors for pharmacological treatment. Neurotoxicology. 2010 Dec;31(6):629-38. doi: 10.1016/j.neuro.2010.07.002. Epub 2010 Jul 17. [PubMed:20624420]
- Waelbroeck M, Camus J, Tastenoy M, Mutschler E, Strohmann C, Tacke R, Schjelderup L, Aasen A, Lambrecht G, Christophe J: Stereoselective interaction of procyclidine, hexahydro-difenidol, hexbutinol and oxyphencyclimine, and of related antagonists, with four muscarinic receptors. Eur J Pharmacol. 1992 Sep 1;227(1):33-42. [PubMed:1426023]
Drug created on June 13, 2005 07:24 / Updated on September 25, 2020 15:13
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