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Identification
NameChlorthalidone
Accession NumberDB00310  (APRD00127)
TypeSmall Molecule
GroupsApproved
Description

A benzenesulfonamide-phthalimidine that tautomerizes to a benzophenones form. It is considered a thiazide-like diuretic. [PubChem]

Structure
Thumb
Synonyms
1-keto-3-(3'-Sulfamyl-4'-chlorophenyl)-3-hydroxyisoindoline
1-oxo-3-(3-Sulfamyl-4-chlorophenyl)-3-hydroxyisoindoline
2-chloro-5-(1-Hydroxy-3-oxo-1-isoindolinyl)benzenesulfonamide
2-chloro-5-(2,3-dihydro-1-Hydroxy-3-oxo-1H-isoindol-1-yl)benzenesulfonamide
3-(4'-chloro-3'-Sulfamoylphenyl)-3-hydroxyphthalimidine
3-Hydroxy-3-(4-chloro-3-sulfamylphenyl)phthalimidine
Chlorphthalidolone
Chlortalidone
Chlorthalidone
Phthalamodine
Phthalamudine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Chlorthalidonetablet50 mgoralAa Pharma Inc1976-12-31Not applicableCanada
Chlorthalidone 100mg Tabletstablet100 mgoralLaboratoires Confab IncNot applicableNot applicableCanada
Chlorthalidone 50mg Tabletstablet50 mgoralLaboratoires Confab IncNot applicableNot applicableCanada
Chlorthalidone Tab 100mgtablet100 mgoralDuchesnay Inc1978-12-312003-07-18Canada
Chlorthalidone Tab 100mgtablet100 mgoralPro Doc Limitee1978-12-311999-08-12Canada
Chlorthalidone Tab 50mgtablet50 mgoralDuchesnay Inc1978-12-312003-07-18Canada
Chlorthalidone Tab 50mgtablet50 mgoralPro Doc Limitee1978-12-311999-08-12Canada
Hygroton 50mgtablet50 mgoralNovartis Pharmaceuticals Canada Inc1968-12-311999-08-04Canada
Novo-thalidone Tab 100mgtablet100 mgoralNovopharm Limited1975-12-312005-08-10Canada
Novo-thalidone Tab 50mgtablet50 mgoralNovopharm Limited1975-12-312005-08-10Canada
Thalitonetablet15 mg/1oralMonarch Pharmaceuticals, Inc1988-12-20Not applicableUs
Uridon Tab 100mgtablet100 mgoralIcn Canada Ltd.1970-12-312005-04-26Canada
Uridon Tab 50mgtablet50 mgoralIcn Canada Ltd.1974-12-312005-04-26Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo Chlorthalidone Tab 100mgtablet100 mgoralApotex Inc1976-12-31Not applicableCanada
Chlorthalidonetablet25 mg/1oralPhysicians Total Care, Inc.2003-06-09Not applicableUs
Chlorthalidonetablet25 mg/1oralKAISER FOUNDATION HOSPITALS2009-06-08Not applicableUs
Chlorthalidonetablet50 mg/1oralA S Medication Solutions1981-02-26Not applicableUs
Chlorthalidonetablet25 mg/1oralMylan Institutional Inc.2013-05-03Not applicableUs
Chlorthalidonetablet25 mg/1oralA S Medication Solutions1981-02-26Not applicableUs
Chlorthalidonetablet50 mg/1oralA S Medication Solutions Llc1981-02-26Not applicableUs
Chlorthalidonetablet50 mg/1oralSun Pharmaceutical Industries, Inc.2016-02-12Not applicableUs
Chlorthalidonetablet25 mg/1oralA S Medication Solutions Llc1981-02-26Not applicableUs
Chlorthalidonetablet25 mg/1oralSun Pharmaceutical Industries, Inc.2016-02-12Not applicableUs
Chlorthalidonetablet50 mg/1oralAphena Pharma Solutions Tennessee, Llc1981-02-26Not applicableUs
Chlorthalidonetablet25 mg/1oralRebel Distributors Corp2009-11-18Not applicableUs
Chlorthalidonetablet25 mg/1oralbryant ranch prepack1981-02-26Not applicableUs
Chlorthalidonetablet25 mg/1oralMylan Pharmaceuticals Inc.1981-02-26Not applicableUs
Chlorthalidonetablet25 mg/1oralPd Rx Pharmaceuticals, Inc.2009-11-18Not applicableUs
Chlorthalidonetablet50 mg/1oralMylan Pharmaceuticals Inc.1981-02-26Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
HygrotonNovartis
SaluretinBalkanpharma
Brand mixtures
NameLabellerIngredients
Apo-atenidoneApotex Inc
Atenolol and ChlorthalidoneMylan Pharmaceuticals Inc.
ClorpresMylan Pharmaceuticals Inc.
Combipres 0.1/15 TabBoehringer Ingelheim (Canada) Ltd Ltee
EdarbyclorTakeda Pharmaceuticals America, Inc.
Ntp-atenolol/chlorthalidoneTeva Canada Limited
TenoreticAstra Zeneca Pharmaceuticals Lp
Tenoretic 100/25mg TabAstrazeneca Canada Inc
Tenoretic 50/25mg TabAstrazeneca Canada Inc
Teva-atenolol/chlorthalidoneTeva Canada Limited
SaltsNot Available
Categories
UNIIQ0MQD1073Q
CAS number77-36-1
WeightAverage: 338.766
Monoisotopic: 338.012805247
Chemical FormulaC14H11ClN2O4S
InChI KeyInChIKey=JIVPVXMEBJLZRO-UHFFFAOYSA-N
InChI
InChI=1S/C14H11ClN2O4S/c15-11-6-5-8(7-12(11)22(16,20)21)14(19)10-4-2-1-3-9(10)13(18)17-14/h1-7,19H,(H,17,18)(H2,16,20,21)
IUPAC Name
2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1H-isoindol-1-yl)benzene-1-sulfonamide
SMILES
NS(=O)(=O)C1=C(Cl)C=CC(=C1)C1(O)NC(=O)C2=CC=CC=C12
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as isoindolones. These are aromatic polycyclic compounds that an isoindole bearing a ketone.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIsoindoles and derivatives
Sub ClassIsoindolines
Direct ParentIsoindolones
Alternative Parents
Substituents
  • Isoindolone
  • Benzenesulfonamide
  • Isoindole
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Aminosulfonyl compound
  • Sulfonyl
  • Sulfonic acid derivative
  • Sulfonamide
  • Secondary carboxylic acid amide
  • Lactam
  • Carboxamide group
  • Azacycle
  • Carboxylic acid derivative
  • Alkanolamine
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor management of hypertension either as the sole therapeutic agent or to enhance the effect of other antihypertensive drugs in the more severe forms of hypertension.
PharmacodynamicsChlorthalidone, a monosulfonamyl diuretic, differs form other thiazide diuretics in that a double ring system is incorporated into its structure. Chlorthalidone is used alone or with atenolol in the management of hypertension and edema.
Mechanism of actionChlorthalidone inhibits sodium ion transport across the renal tubular epithelium in the cortical diluting segment of the ascending limb of the loop of Henle. By increasing the delivery of sodium to the distal renal tubule, Chlorthalidone indirectly increases potassium excretion via the sodium-potassium exchange mechanism.
Related Articles
AbsorptionAbsorbed relatively rapidly after oral administration.
Volume of distributionNot Available
Protein bindingHigh (75% [58% to albumin])
Metabolism

Liver

Route of eliminationThe major portion of the drug is excreted unchanged by the kidneys.
Half life40 hours
ClearanceNot Available
ToxicitySymptoms of overdose include nausea, weakness, dizziness and disturbances of electrolyte balance.
Affected organisms
  • Humans and other mammals
Pathways
PathwayCategorySMPDB ID
Chlorthalidone Action PathwayDrug actionSMP00122
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.5447
Caco-2 permeable-0.6272
P-glycoprotein substrateNon-substrate0.767
P-glycoprotein inhibitor INon-inhibitor0.9603
P-glycoprotein inhibitor IINon-inhibitor0.9573
Renal organic cation transporterNon-inhibitor0.891
CYP450 2C9 substrateNon-substrate0.6403
CYP450 2D6 substrateNon-substrate0.822
CYP450 3A4 substrateNon-substrate0.6369
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9299
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8193
Ames testNon AMES toxic0.7277
CarcinogenicityNon-carcinogens0.5752
BiodegradationNot ready biodegradable1.0
Rat acute toxicity1.8623 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9968
hERG inhibition (predictor II)Non-inhibitor0.8914
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Abbott laboratories pharmaceutical products div
  • Ascot hosp pharmaceuticals inc div travenol laboratories inc
  • Clonmel healthcare ltd
  • Ivax pharmaceuticals inc
  • Kv pharmaceutical co
  • Mutual pharmaceutical co inc
  • Mylan pharmaceuticals inc
  • Pioneer pharmaceuticals inc
  • Pliva inc
  • Purepac pharmaceutical co
  • Sandoz inc
  • Superpharm corp
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Vangard laboratories inc div midway medical co
  • Warner chilcott div warner lambert co
  • Watson laboratories inc
  • Sanofi aventis us llc
  • Monarch pharmaceuticals inc
Packagers
Dosage forms
FormRouteStrength
Tabletoral100 mg
Tabletoral25 mg/1
Tabletoral50 mg/1
Tabletoral50 mg
Tabletoral
Tabletoral15 mg/1
Prices
Unit descriptionCostUnit
Tenoretic 100 100-25 mg tablet2.91USD tablet
Tenoretic 100 tablet2.91USD tablet
Tenoretic 50 50-25 mg tablet2.18USD tablet
Tenoretic 50 tablet2.07USD tablet
Thalitone 15 mg tablet1.55USD tablet
Chlorthalidone 100 mg tablet1.07USD tablet
Chlorthalidone 50 mg tablet0.46USD tablet
Chlorthalidone 25 mg tablet0.28USD tablet
Apo-Chlorthalidone 50 mg Tablet0.13USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7157584 No2005-05-222025-05-22Us
US7572920 No2005-01-072025-01-07Us
US9066936 No2008-03-262028-03-26Us
US9169238 No2010-02-252030-02-25Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point239 °CPhysProp
water solubility120 mg/L (at 20 °C)MERCK INDEX (1996)
logP0.85BERTHOD,A ET AL. (1999)
Predicted Properties
PropertyValueSource
Water Solubility0.0528 mg/mLALOGPS
logP1.27ALOGPS
logP1.6ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)8.58ChemAxon
pKa (Strongest Basic)-2.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area109.49 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity81.3 m3·mol-1ChemAxon
Polarizability31.23 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Graf, W., Schmid, E. and Stoll, W.G.; US Patent 3,055,904; September 25,1962; assigned
to Geigy Chemical Corporation.

General ReferencesNot Available
External Links
ATC CodesC03BA04C03BB04C03EA06
AHFS Codes
  • 40:28.24
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetohexamideThe therapeutic efficacy of Acetohexamide can be decreased when used in combination with Chlorthalidone.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Acetylsalicylic acid is combined with Chlorthalidone.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Chlorthalidone.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Chlorthalidone.
AlfuzosinAlfuzosin may increase the hypotensive activities of Chlorthalidone.
AllopurinolThe risk of a hypersensitivity reaction to Allopurinol is increased when it is combined with Chlorthalidone.
AlogliptinThe therapeutic efficacy of Alogliptin can be decreased when used in combination with Chlorthalidone.
AmifostineChlorthalidone may increase the hypotensive activities of Amifostine.
BrimonidineBrimonidine may increase the antihypertensive activities of Chlorthalidone.
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Chlorthalidone.
ButabarbitalButabarbital may increase the orthostatic hypotensive activities of Chlorthalidone.
ButethalButethal may increase the orthostatic hypotensive activities of Chlorthalidone.
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Chlorthalidone.
CaffeineThe risk or severity of adverse effects can be increased when Caffeine is combined with Chlorthalidone.
CanagliflozinThe therapeutic efficacy of Canagliflozin can be decreased when used in combination with Chlorthalidone.
CarbamazepineThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Carbamazepine.
ChlorphenamineThe risk or severity of adverse effects can be increased when Chlorphenamine is combined with Chlorthalidone.
ChlorpropamideThe therapeutic efficacy of Chlorpropamide can be decreased when used in combination with Chlorthalidone.
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Chlorthalidone.
ColesevelamColesevelam can cause a decrease in the absorption of Chlorthalidone resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclophosphamideThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Cyclophosphamide.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Chlorthalidone.
DiazoxideThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Diazoxide.
DigoxinThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Digoxin.
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Chlorthalidone.
DihydrotachysterolChlorthalidone may increase the hypercalcemic activities of Dihydrotachysterol.
DofetilideChlorthalidone may increase the QTc-prolonging activities of Dofetilide.
DuloxetineChlorthalidone may increase the orthostatic hypotensive activities of Duloxetine.
EthanolEthanol may increase the orthostatic hypotensive activities of Chlorthalidone.
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Chlorthalidone.
FludrocortisoneFludrocortisone may increase the hypokalemic activities of Chlorthalidone.
FlunisolideFlunisolide may increase the hypokalemic activities of Chlorthalidone.
GliclazideThe therapeutic efficacy of Gliclazide can be decreased when used in combination with Chlorthalidone.
GlimepirideThe therapeutic efficacy of Glimepiride can be decreased when used in combination with Chlorthalidone.
GliquidoneThe therapeutic efficacy of Gliquidone can be decreased when used in combination with Chlorthalidone.
GlyburideThe therapeutic efficacy of Glyburide can be decreased when used in combination with Chlorthalidone.
HeptabarbitalHeptabarbital may increase the orthostatic hypotensive activities of Chlorthalidone.
HexobarbitalHexobarbital may increase the orthostatic hypotensive activities of Chlorthalidone.
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Chlorthalidone.
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Chlorthalidone.
InfliximabThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Infliximab.
Insulin AspartThe therapeutic efficacy of Insulin Aspart can be decreased when used in combination with Chlorthalidone.
Insulin DetemirThe therapeutic efficacy of Insulin Detemir can be decreased when used in combination with Chlorthalidone.
Insulin GlargineThe therapeutic efficacy of Insulin Glargine can be decreased when used in combination with Chlorthalidone.
Insulin GlulisineThe therapeutic efficacy of Insulin Glulisine can be decreased when used in combination with Chlorthalidone.
Insulin HumanThe therapeutic efficacy of Insulin Regular can be decreased when used in combination with Chlorthalidone.
Insulin LisproThe therapeutic efficacy of Insulin Lispro can be decreased when used in combination with Chlorthalidone.
IvabradineChlorthalidone may increase the arrhythmogenic activities of Ivabradine.
LevodopaChlorthalidone may increase the orthostatic hypotensive activities of Levodopa.
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Chlorthalidone.
LicoriceLicorice may increase the hypokalemic activities of Chlorthalidone.
LinagliptinThe therapeutic efficacy of Linagliptin can be decreased when used in combination with Chlorthalidone.
LithiumChlorthalidone may decrease the excretion rate of Lithium which could result in a lower serum level and potentially a reduction in efficacy.
MecamylamineThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Mecamylamine.
MetforminThe therapeutic efficacy of Metformin can be decreased when used in combination with Chlorthalidone.
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Chlorthalidone.
MethohexitalMethohexital may increase the orthostatic hypotensive activities of Chlorthalidone.
MethylphenidateMethylphenidate may decrease the antihypertensive activities of Chlorthalidone.
MolsidomineMolsidomine may increase the hypotensive activities of Chlorthalidone.
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Chlorthalidone.
MoxonidineMoxonidine may increase the hypotensive activities of Chlorthalidone.
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Chlorthalidone.
NicorandilNicorandil may increase the hypotensive activities of Chlorthalidone.
ObinutuzumabChlorthalidone may increase the hypotensive activities of Obinutuzumab.
OrciprenalineOrciprenaline may increase the hypokalemic activities of Chlorthalidone.
OxcarbazepineThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Oxcarbazepine.
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Chlorthalidone.
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Chlorthalidone.
ParoxetineParoxetine may increase the activities of Chlorthalidone.
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Chlorthalidone.
PentobarbitalPentobarbital may increase the orthostatic hypotensive activities of Chlorthalidone.
PentoxifyllinePentoxifylline may increase the hypotensive activities of Chlorthalidone.
PerindoprilChlorthalidone may increase the hypotensive activities of Perindopril.
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Chlorthalidone.
PhenelzinePhenelzine may increase the orthostatic hypotensive activities of Chlorthalidone.
PorfimerChlorthalidone may increase the photosensitizing activities of Porfimer.
PrimidonePrimidone may increase the orthostatic hypotensive activities of Chlorthalidone.
ProcyclidineThe serum concentration of Chlorthalidone can be increased when it is combined with Procyclidine.
QuinineQuinine may increase the hypotensive activities of Chlorthalidone.
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Chlorthalidone.
RepaglinideThe therapeutic efficacy of Repaglinide can be decreased when used in combination with Chlorthalidone.
RisperidoneChlorthalidone may increase the hypotensive activities of Risperidone.
RituximabChlorthalidone may increase the hypotensive activities of Rituximab.
SaxagliptinThe therapeutic efficacy of Saxagliptin can be decreased when used in combination with Chlorthalidone.
SecobarbitalSecobarbital may increase the orthostatic hypotensive activities of Chlorthalidone.
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Chlorthalidone.
SulpirideThe risk or severity of adverse effects can be increased when Chlorthalidone is combined with Sulpiride.
TadalafilTadalafil may increase the antihypertensive activities of Chlorthalidone.
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Chlorthalidone.
TolbutamideThe therapeutic efficacy of Tolbutamide can be decreased when used in combination with Chlorthalidone.
TopiramateChlorthalidone may increase the hypokalemic activities of Topiramate.
ToremifeneChlorthalidone may increase the hypercalcemic activities of Toremifene.
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Chlorthalidone.
TranylcypromineTranylcypromine may increase the orthostatic hypotensive activities of Chlorthalidone.
TreprostinilTreprostinil may increase the hypotensive activities of Chlorthalidone.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Chlorthalidone.
VardenafilVardenafil may increase the antihypertensive activities of Chlorthalidone.
VerteporfinChlorthalidone may increase the photosensitizing activities of Verteporfin.
VildagliptinThe therapeutic efficacy of Vildagliptin can be decreased when used in combination with Chlorthalidone.
YohimbineYohimbine may decrease the antihypertensive activities of Chlorthalidone.
Food Interactions
  • Take with food (increases availability).

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
inhibitor
General Function:
Sodium:potassium:chloride symporter activity
Specific Function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume.
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular Weight:
121449.13 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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on June 25, 2016 01:52