Trihexyphenidyl

Identification

Name
Trihexyphenidyl
Accession Number
DB00376
Description

One of the centrally acting muscarinic antagonists used for treatment of parkinsonian disorders and drug-induced extrapyramidal movement disorders and as an antispasmodic.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 301.4662
Monoisotopic: 301.240564619
Chemical Formula
C20H31NO
Synonyms
  • Trihexifenidilo
  • Trihexyphenidyl
  • Trihexyphénidyle
  • Trihexyphenidylum
External IDs
  • Win 511

Pharmacology

Indication

Indicated for the treatment of parkinson's disease and extrapyramidal reactions caused by drugs.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Trihexyphenidyl is an anticholinergic used in the symptomatic treatment of all etiologic groups of parkinsonism and drug induced extrapyramidal reactions (except tardive dyskinesia). Trihexyphenidyl possesses both anticholinergic and antihistaminic effects, although only the former has been established as therapeutically significant in the management of parkinsonism.

Mechanism of action

Trihexyphenidyl is a selective M1 muscarinic acetylcholine receptor antagonist. It is able to discriminate between the M1 (cortical or neuronal) and the peripheral muscarinic subtypes (cardiac and glandular). Trihexyphenidyl partially blocks cholinergic activity in the CNS, which is responsible for the symptoms of Parkinson's disease. It is also thought to increase the availability of dopamine, a brain chemical that is critical in the initiation and smooth control of voluntary muscle movement.

TargetActionsOrganism
AMuscarinic acetylcholine receptor M1
antagonist
Humans
UMuscarinic acetylcholine receptor M2
antagonist
Humans
UMuscarinic acetylcholine receptor M3
antagonist
Humans
UMuscarinic acetylcholine receptor M4
antagonist
Humans
UMuscarinic acetylcholine receptor M5
antagonist
Humans
Absorption

Trihexyphenidyl is rapidly absorbed from the gastrointestinal tract.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half-life

3.3-4.1 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity

Symptoms of overdose include mydriasis, dryness of mucous membranes, red face, atonic states of bowels and bladder, and hyperthermia in high doses. Trihexyphenidyl causes agitation, confusion, and hallucinations due to its effects on the central nervous system. Untreated overdose may result in death, especially in children. Respiratory depression and cardiac arrest may be seen as premortal signs.

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.
DrugInteraction
AcetazolamideAcetazolamide may increase the central nervous system depressant (CNS depressant) activities of Trihexyphenidyl.
AcetophenazineAcetophenazine may increase the central nervous system depressant (CNS depressant) activities of Trihexyphenidyl.
AclidiniumThe risk or severity of adverse effects can be increased when Trihexyphenidyl is combined with Aclidinium.
AdenosineThe risk or severity of Tachycardia can be increased when Trihexyphenidyl is combined with Adenosine.
AgomelatineAgomelatine may increase the central nervous system depressant (CNS depressant) activities of Trihexyphenidyl.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Trihexyphenidyl.
AlimemazineAlimemazine may increase the central nervous system depressant (CNS depressant) activities of Trihexyphenidyl.
AlloinThe therapeutic efficacy of Alloin can be decreased when used in combination with Trihexyphenidyl.
AlmotriptanAlmotriptan may increase the central nervous system depressant (CNS depressant) activities of Trihexyphenidyl.
AlosetronAlosetron may increase the central nervous system depressant (CNS depressant) activities of Trihexyphenidyl.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. Taking with food may minimize stomach upset. May take before meals to mitigate dry mouth or may take after meals to reduce excess salivation.

Products

Product Ingredients
IngredientUNIICASInChI Key
Trihexyphenidyl hydrochlorideAO61G8257752-49-3QDWJJTJNXAKQKD-UHFFFAOYSA-N
Product Images
International/Other Brands
ACA (Atlantic) / Acamed (Medifive) / Altant (Panbiotic) / Apo-trihex / Artane (Sanofi Aventis) / Artine (The Central) / Atan (Newai Chem) / Benzhexol (Johnson) / Benzox (Li Ta) / Bexol (Intas) / Broflex (Alliance) / Cyclodol (Grindeks) / Dyskinil (Crescent) / Ea Ten (Heng Hsin) / Hexymer (Mersifarma) / Hipokinon (Psicofarma) / Lahexy (La Pharmaceuticals) / Pacitane (Wyeth) / Pakisonal (Takata Seiyaku) / Parales (Psyco Remedies) / Parcisol (Milve) / Pargitan (Nevada Pharma) / Parkin (Micro Synapse) / Parkinane (Eisai) / Parkines (Towa Yakuhin) / Parkinidyl (CCPC) / Parkisan (Balkanpharma) / Parkitane (Sun) / Parkizol (Hikma) / Tonaril (Chile)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Aparkane Tab 2mgTabletOralIcn Pharmaceuticals1973-12-312005-04-26Canada flag
Aparkane Tab 5mgTabletOralIcn Pharmaceuticals1973-12-312005-04-26Canada flag
Artane Elx 2mg/5mlElixirOralLederle Cyanamid Canada Inc.1967-12-311999-08-12Canada flag
Artane Tab 2mgTabletOralLederle Cyanamid Canada Inc.1951-12-311999-04-12Canada flag
Artane Tab 5mgTabletOralLederle Cyanamid Canada Inc.1951-12-311997-01-14Canada flag
Trihexyphen 5 Tab 5mgTabletOralPro Doc Limitee1982-12-312010-07-13Canada flag
Trihexyphen Tab 2mgTabletOralPro Doc Limitee1982-12-312010-07-13Canada flag
TrihexyphenidylTabletOralAa Pharma Inc1982-12-31Not applicableCanada flag
TrihexyphenidylTabletOralAa Pharma Inc1982-12-31Not applicableCanada flag
Trihexyphenidyl HydrochlorideTablet5 mg/1OralVintage Pharmaceuticals, LLC2006-10-202006-10-20US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Novo-hexidyl 2mgTabletOralNovopharm Limited1968-12-312005-08-10Canada flag
Novo-hexidyl 5mgTabletOralNovopharm Limited1967-12-312005-08-10Canada flag
Nu-trihexyphenidylTabletOralNu Pharm IncNot applicableNot applicableCanada flag
Nu-trihexyphenidylTabletOralNu Pharm IncNot applicableNot applicableCanada flag
PMS TrihexyphenidylTabletOralPharmascience Inc1987-12-31Not applicableCanada flag
PMS-trihexyphenidylTabletOralPharmascience Inc1987-12-31Not applicableCanada flag
PMS-trihexyphenidyl Elx 0.4mg/mlElixirOralPharmascience Inc1996-10-16Not applicableCanada flag
Trihexyphenidyl HydrochlorideTablet2 mg/1OralREMEDYREPACK INC.2019-11-08Not applicableUS flag
Trihexyphenidyl HydrochlorideTablet5 mg/1OralState of Florida DOH Central Pharmacy2013-01-01Not applicableUS flag
Trihexyphenidyl HydrochlorideTablet2 mg/1OralRichmond Pharmaceuticals1998-12-24Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
N04AA01 — Trihexyphenidyl
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
Piperidines / 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 / Organic oxygen compound
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
amine (CHEBI:9720)

Chemical Identifiers

UNII
6RC5V8B7PO
CAS number
144-11-6
InChI Key
HWHLPVGTWGOCJO-UHFFFAOYSA-N
InChI
InChI=1S/C20H31NO/c22-20(18-10-4-1-5-11-18,19-12-6-2-7-13-19)14-17-21-15-8-3-9-16-21/h1,4-5,10-11,19,22H,2-3,6-9,12-17H2
IUPAC Name
1-cyclohexyl-1-phenyl-3-(piperidin-1-yl)propan-1-ol
SMILES
OC(CCN1CCCCC1)(C1CCCCC1)C1=CC=CC=C1

References

General References
Not Available
Human Metabolome Database
HMDB0014520
KEGG Drug
D08638
KEGG Compound
C07171
PubChem Compound
5572
PubChem Substance
46507717
ChemSpider
5371
BindingDB
81462
RxNav
10811
ChEBI
9720
ChEMBL
CHEMBL1490
Therapeutic Targets Database
DAP001532
PharmGKB
PA164747026
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Trihexyphenidyl
AHFS Codes
  • 28:36.08 — Anticholinergic Agents
FDA label
Download (197 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentDystonias1
0RecruitingTreatmentExtrapyramidal disorder1
Not AvailableCompletedNot AvailableDYT 1 Dystonia / Primary Cervical Dystonia1

Pharmacoeconomics

Manufacturers
  • Lederle laboratories div american cyanamid co
  • Mikart inc
  • Pharmaceutical assoc inc div beach products
  • Pharmaceutical ventures ltd
  • Schering corp sub schering plough corp
  • Nylos trading co inc
  • Vangard laboratories inc div midway medical co
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • West ward pharmaceutical corp
Packagers
  • Advanced Pharmaceutical Services Inc.
  • Amerisource Health Services Corp.
  • Comprehensive Consultant Services Inc.
  • Direct Dispensing Inc.
  • Heartland Repack Services LLC
  • Kaiser Foundation Hospital
  • Mckesson Corp.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Octofoil Group Inc.
  • Pharmaceutical Association
  • Pharmaceutical Utilization Management Program VA Inc.
  • Pharmacy Service Center
  • Physicians Total Care Inc.
  • Prepak Systems Inc.
  • Qualitest
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Richmond Pharmacy
  • Vangard Labs Inc.
  • Versapharm Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
Dosage Forms
FormRouteStrength
Capsule, extended release5 MG
TabletOral2 MG
Tablet2 MG
Tablet5 MG
ElixirOral
TabletOral
SolutionOral2 mg/5mL
SyrupOral2 mg/5mL
TabletOral2 mg/1
TabletOral5 mg/1
Prices
Unit descriptionCostUnit
Trihexyphenidyl HCl 5 mg tablet0.37USD tablet
Trihexyphenidyl 5 mg tablet0.36USD tablet
Trihexyphenidyl HCl 2 mg tablet0.26USD tablet
Trihexyphenidyl 2 mg tablet0.18USD tablet
Apo-Trihex 5 mg Tablet0.07USD tablet
Apo-Trihex 2 mg Tablet0.04USD 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)258.5 °CNot Available
logP4.49SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.00314 mg/mLALOGPS
logP4.93ALOGPS
logP4.23ChemAxon
logS-5ALOGPS
pKa (Strongest Acidic)13.84ChemAxon
pKa (Strongest Basic)9.32ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area23.47 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity93.21 m3·mol-1ChemAxon
Polarizability36.73 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9156
Blood Brain Barrier+0.9523
Caco-2 permeable+0.6707
P-glycoprotein substrateSubstrate0.6943
P-glycoprotein inhibitor IInhibitor0.5993
P-glycoprotein inhibitor IINon-inhibitor0.7561
Renal organic cation transporterInhibitor0.7563
CYP450 2C9 substrateNon-substrate0.8256
CYP450 2D6 substrateNon-substrate0.7655
CYP450 3A4 substrateNon-substrate0.5746
CYP450 1A2 substrateNon-inhibitor0.9187
CYP450 2C9 inhibitorNon-inhibitor0.9126
CYP450 2D6 inhibitorInhibitor0.8966
CYP450 2C19 inhibitorNon-inhibitor0.9248
CYP450 3A4 inhibitorNon-inhibitor0.8506
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9543
Ames testNon AMES toxic0.8434
CarcinogenicityNon-carcinogens0.9238
BiodegradationNot ready biodegradable0.9253
Rat acute toxicity2.6751 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.6676
hERG inhibition (predictor II)Inhibitor0.5713
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-0002-9200000000-2092a098302f5e63b76c
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-4119000000-9ed82688d3c1b39f26eb

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
  1. 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]
  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. [PubMed:17016423]
  3. Prus AJ, Pehrson AL, Philibin SD, Wood JT, Vunck SA, Porter JH: The role of M1 muscarinic cholinergic receptors in the discriminative stimulus properties of N-desmethylclozapine and the atypical antipsychotic drug clozapine in rats. Psychopharmacology (Berl). 2009 Apr;203(2):295-301. doi: 10.1007/s00213-008-1262-0. Epub 2008 Aug 7. [PubMed:18685832]
  4. Giachetti A, Giraldo E, Ladinsky H, Montagna E: Binding and functional profiles of the selective M1 muscarinic receptor antagonists trihexyphenidyl and dicyclomine. Br J Pharmacol. 1986 Sep;89(1):83-90. [PubMed:2432979]
  5. Tanda G, Katz JL: Muscarinic preferential M(1) receptor antagonists enhance the discriminative-stimulus effects of cocaine in rats. Pharmacol Biochem Behav. 2007 Oct;87(4):400-4. Epub 2007 Jun 2. [PubMed:17631384]
  6. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002]
  7. Freedman SB, Beer MS, Harley EA: Muscarinic M1, M2 receptor binding. Relationship with functional efficacy. Eur J Pharmacol. 1988 Oct 26;156(1):133-42. [PubMed:3208836]
  8. 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
Humans
Pharmacological action
Unknown
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. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002]
  3. Freedman SB, Beer MS, Harley EA: Muscarinic M1, M2 receptor binding. Relationship with functional efficacy. Eur J Pharmacol. 1988 Oct 26;156(1):133-42. [PubMed:3208836]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002]
  3. Freedman SB, Beer MS, Harley EA: Muscarinic M1, M2 receptor binding. Relationship with functional efficacy. Eur J Pharmacol. 1988 Oct 26;156(1):133-42. [PubMed:3208836]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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. Bognar IT, Altes U, Beinhauer C, Kessler I, Fuder H: A muscarinic receptor different from the M1, M2, M3 and M4 subtypes mediates the contraction of the rabbit iris sphincter. Naunyn Schmiedebergs Arch Pharmacol. 1992 Jun;345(6):611-8. [PubMed:1635586]
  2. Dorje F, Wess J, Lambrecht G, Tacke R, Mutschler E, Brann MR: Antagonist binding profiles of five cloned human muscarinic receptor subtypes. J Pharmacol Exp Ther. 1991 Feb;256(2):727-33. [PubMed:1994002]

Drug created on June 13, 2005 07:24 / Updated on September 22, 2020 02:11

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