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Identification
NameMethylphenidate
Accession NumberDB00422  (APRD00657)
TypeSmall Molecule
GroupsApproved, Investigational
Description

A central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy. Its mechanisms appear to be similar to those of dextroamphetamine. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
alpha-Phenyl-2-piperidineacetic acid methyl esterNot AvailableNot Available
DaytranaNot AvailableNot Available
Methyl alpha-phenyl-alpha-(2-piperidyl)acetateNot AvailableNot Available
Methyl alpha-phenyl-alpha-2-piperidinylacetateNot AvailableNot Available
Methyl phenidylacetateNot AvailableNot Available
MethylphenidanNot AvailableNot Available
MethylphenidateNot AvailableNot Available
MethylphenidatumLatinINN
MetilfenidatoItalianINN
MPHNot AvailableNot Available
Salts
Name/CAS Structure Properties
Methylphenidate Hydrochloride
Thumb
  • InChI Key: JUMYIBMBTDDLNG-UHFFFAOYNA-N
  • Monoisotopic Mass: 269.118256596
  • Average Mass: 269.767
DBSALT000117
Brand names
NameCompany
ConcertaNot Available
DaytranaNoven Therapeutics, LLC
Equasym XLNot Available
Medikinet XLNot Available
MetadateNot Available
MethylinNot Available
QuillivantNot Available
Quillivant XRNextWave Pharmaceuticals
RiphenidateNot Available
RitalinNovartis
Rubifen SRNot Available
Brand mixturesNot Available
Categories
CAS number113-45-1
WeightAverage: 233.3062
Monoisotopic: 233.141578857
Chemical FormulaC14H19NO2
InChI KeyDUGOZIWVEXMGBE-UHFFFAOYSA-N
InChI
InChI=1S/C14H19NO2/c1-17-14(16)13(11-7-3-2-4-8-11)12-9-5-6-10-15-12/h2-4,7-8,12-13,15H,5-6,9-10H2,1H3
IUPAC Name
methyl 2-phenyl-2-(piperidin-2-yl)acetate
SMILES
COC(=O)C(C1CCCCN1)C1=CC=CC=C1
Mass Specshow(7.79 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenylacetic Acid Derivatives
Direct parentPhenylacetic Acid Derivatives
Alternative parentsPiperidines; Carboxylic Acid Esters; Ethers; Enolates; Dialkylamines; Polyamines
Substituentspiperidine; carboxylic acid ester; secondary amine; secondary aliphatic amine; enolate; polyamine; carboxylic acid derivative; ether; amine; organonitrogen compound
Classification descriptionThis compound belongs to the phenylacetic acid derivatives. These are compounds containing a phenylacetic acid moiety, which consists of a phenyl group substituted at the second position by an acetic acid.
Pharmacology
IndicationFor use as an integral part of a total treatment program which typically includes other remedial measures (psychological, educational, social) for a stabilizing effect in children with a behavioral syndrome characterized by the following group of developmentally inappropriate symptoms: moderate-to-severe distractibility, short attention span, hyperactivity, emotional lability, and impulsivity.
PharmacodynamicsMethylphenidate is a central nervous system stimulant used most commonly in the treatment of attention-deficit disorders in children and for narcolepsy. Methylphenidate also blocks the reuptake of norepinephrine and dopamine. Its mechanisms appear to be similar to those of dextroamphetamine. Furthermore, it is a racemic mixture comprised of the d- and l-threo enantiomers. The d-threo enantiomer is more pharmacologically active than the l-threo enantiomer.
Mechanism of actionMethylphenidate blocks dopamine uptake in central adrenergic neurons by blocking dopamine transport or carrier proteins. Methylphenidate acts at the brain stem arousal system and the cerebral cortex and causes increased sympathomimetic activity in the central nervous system. Alteration of serotonergic pathways via changes in dopamine transport may result.
AbsorptionReadily absorbed in a biphasic manner when orally administered (tablets) to children diagnosed with ADHD and to healthy adults. In children and adults males, after administration of a single oral dose of Ritalin LA and Ritalin given in two doses 4 hours apart, peak plasma concentration is reached approximately 2 hours for the first phase and 5-6 hours for the second phase. The absolute oral bioavailability of methylphenidate in children was 22±8% for d-methylphenidate and 5±3% for l-methylphenidate. These low values suggest that methylphenidate is highly metabolized presystemically.
Volume of distribution

d-methylphenidate = 2.65 L/kg;
l-methylphenidate = 1.80 L/kg;

Protein bindingBinding to plasma proteins is low (10%-33%).
Metabolism

Methylphenidate is hepatically metabolized. More specifically, it is rapidly and extensively metabolized by carboxylesterase CES1A1. Via this enzyme, methylphenidate undergoes de-esterification to ritalinic acid (a-phenyl-2-piperidine acetic acid, PPAA), which has little to no pharmacologic activity.

Route of eliminationAfter oral administration of an immediate release formulation of methylphenidate, 78%-97% of the dose is excreted in the urine and 1%-3% in the feces in the form of metabolites within 48-96 hours. Only small quantities (<1%) of unchanged methylphenidate appear in the urine. Most of the dose is excreted in the urine as ritalinic acid (60%-86%), the remainder being accounted for by minor metabolites.
Half lifed-methylphenidate = 3-4 hours; l-methylphenidate = 1-3 hours; Ritalinic acid = 3-4 hours;
Clearance

Systemic clearance for Ritalin LA and Ritalin tablets is as follows:
d-methylphenidate= 0.40±0.12 L/h/kg;
l-methylphenidate = 0.73±0.28 L/h/kg;

ToxicitySymptoms of overdose include vomiting, agitation, tremors, hyperreflexia, muscle twitching, convulsions (may be followed by coma), euphoria, confusion, hallucinations, delirium, sweating, flushing, headache, hyperpyrexia, tachycardia, palpitations, cardiac arrhythmias, hypertension, mydriasis, and dryness of mucous membranes. LD50=190mg/kg (orally in mice)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9941
Blood Brain Barrier + 0.9663
Caco-2 permeable + 0.6564
P-glycoprotein substrate Substrate 0.5466
P-glycoprotein inhibitor I Non-inhibitor 0.7964
P-glycoprotein inhibitor II Non-inhibitor 0.9601
Renal organic cation transporter Inhibitor 0.532
CYP450 2C9 substrate Non-substrate 0.7897
CYP450 2D6 substrate Non-substrate 0.9116
CYP450 3A4 substrate Non-substrate 0.5985
CYP450 1A2 substrate Non-inhibitor 0.592
CYP450 2C9 substrate Non-inhibitor 0.897
CYP450 2D6 substrate Non-inhibitor 0.5245
CYP450 2C19 substrate Non-inhibitor 0.9265
CYP450 3A4 substrate Non-inhibitor 0.8539
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9328
Ames test Non AMES toxic 0.9133
Carcinogenicity Non-carcinogens 0.9648
Biodegradation Not ready biodegradable 0.5759
Rat acute toxicity 2.7718 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.8466
hERG inhibition (predictor II) Non-inhibitor 0.7491
Pharmacoeconomics
Manufacturers
  • Shire development inc
  • Ucb inc
  • Novartis pharmaceuticals corp
  • Mallinckrodt inc
  • Tris pharma inc
  • Ortho mcneil janssen pharmaceutical inc
  • Able laboratories inc
  • Actavis elizabeth llc
  • Watson laboratories inc
  • Ortho-McNeil-Janssen Pharmaceuticals, Inc.
Packagers
Dosage forms
FormRouteStrength
Capsule, extended releaseOral
PatchTransdermal10 mg/9 hr; 15 mg/9 hr; 20 mg/9 hr; 30 mg/9 hr
SolutionOral5 mg/mL; 10mg/5mL
Suspension, extended releaseOral25 mg/5 mL
TabletOral5 mg, 10 mg, 20 mg
Tablet, chewableOral2.5 mg, 5 mg, 10 mg
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Daytrana 30 15 mg/9hr Patches Box175.64USDbox
Daytrana 30 30 mg/9hr Patches Box174.73USDbox
Daytrana 30 10 mg/9hr Patches Box172.78USDbox
Daytrana 30 20 mg/9hr Patches Box168.72USDbox
Methylphenidate hcl powder44.62USDg
Concerta er 54 mg tablet25.45USDtablet
Concerta er 36 mg tablet23.38USDtablet
Concerta er 27 mg tablet22.65USDtablet
Concerta er 18 mg tablet22.11USDtablet
Metadate cd 50 mg capsule7.08USDcapsule
Metadate cd 60 mg capsule7.02USDcapsule
Concerta 54 mg Controlled Release Tabs6.18USDtab
Metadate cd 40 mg capsule5.77USDcapsule
Concerta 36 mg Controlled Release Tabs5.72USDtab
Focalin xr 30 mg capsule5.42USDcapsule
Focalin XR 20 mg 24 Hour Capsule5.31USDcapsule
Daytrana 10 mg/9 hr patch5.16USDpatch
Daytrana 15 mg/9 hr patch5.16USDpatch
Daytrana 20 mg/9 hour patch5.16USDpatch
Daytrana 30 mg/9 hour patch5.16USDpatch
Focalin xr 15 mg capsule5.16USDcapsule
Focalin xr 20 mg capsule5.16USDcapsule
Focalin XR 30 mg 24 Hour Capsule5.15USDcapsule
Focalin xr 10 mg capsule5.02USDcapsule
Concerta 18 mg Controlled Release Tabs5.0USDtab
Concerta 27 mg Controlled Release Tabs5.0USDtab
Focalin XR 10 mg 24 Hour Capsule4.96USDcapsule
Focalin xr 5 mg capsule4.95USDcapsule
Concerta 54 mg tablet sa4.91USDtablet
Focalin XR 15 mg 24 Hour Capsule4.89USDcapsule
Focalin XR 5 mg 24 Hour Capsule4.83USDcapsule
Ritalin la 40 mg capsule4.55USDcapsule
Concerta 36 mg tablet sa4.51USDtablet
Ritalin la 30 mg capsule4.43USDcapsule
Ritalin LA 10 mg 24 Hour Capsule4.42USDcapsule
Ritalin LA 20 mg 24 Hour Capsule4.42USDcapsule
Ritalin LA 30 mg 24 Hour Capsule4.42USDcapsule
Ritalin LA 40 mg 24 Hour Capsule4.42USDcapsule
Concerta 27 mg tablet sa4.37USDtablet
Ritalin la 10 mg capsule4.33USDcapsule
Ritalin la 20 mg capsule4.33USDcapsule
Concerta 18 mg tablet sa4.27USDtablet
Metadate cd 20 mg capsule4.24USDcapsule
Metadate cd 30 mg capsule4.24USDcapsule
Metadate cd 10 mg capsule4.2USDcapsule
Methylphenidate er 10 mg tablet3.24USDtablet
Ritalin SR 20 mg Controlled Release Tabs3.0USDtab
Ritalin sr 20 mg tablet2.67USDtablet
Ritalin 20 mg tablet1.87USDtablet
Focalin 10 mg tablet1.7USDtablet
Ritalin 5 mg tablet1.42USDtablet
Metadate er 20 mg tablet1.32USDtablet
Methylin ER 20 mg Controlled Release Tabs1.3USDtab
Ritalin 10 mg tablet1.29USDtablet
Metadate er 10 mg tablet sa1.28USDtablet
Focalin 5 mg tablet1.26USDtablet
Methylphenidate HCl CR 20 mg Controlled Release Tabs1.2USDtab
Methylin er 20 mg tablet1.12USDtablet
Methylphenidate HCl 20 mg tablet1.05USDtablet
Methylin ER 10 mg1.0USDtab
Methylphenidate HCl 10 mg tablet0.95USDtablet
Methylphenidate HCl 5 mg tablet0.94USDtablet
Methylin er 10 mg tablet0.84USDtablet
Focalin 2.5 mg tablet0.76USDtablet
Methylin 20 mg tablet0.69USDtablet
Methylphenidate 20 mg tablet0.69USDtablet
Ritalin 20 mg Tablet0.67USDtablet
Ritalin Sr 20 mg Extended-Release Tablet0.67USDtablet
Methylin 10 mg tablet0.48USDtablet
Methylphenidate 10 mg tablet0.48USDtablet
Ritalin 10 mg Tablet0.38USDtablet
Apo-Methylphenidate 20 mg Tablet0.37USDtablet
Apo-Methylphenidate Sr 20 mg Extended-Release Tablet0.37USDtablet
Pms-Methylphenidate 20 mg Tablet0.37USDtablet
Sandoz Methylphenidate 20 mg Extended-Release Tablet0.37USDtablet
Methylin 5 mg tablet0.33USDtablet
Methylphenidate 5 mg tablet0.33USDtablet
Apo-Methylphenidate 10 mg Tablet0.17USDtablet
Pms-Methylphenidate 10 mg Tablet0.17USDtablet
Pms-Methylphenidate 5 mg Tablet0.1USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
CountryPatent NumberApprovedExpires (estimated)
United States76918802004-10-072024-10-07
United States59584461992-12-122012-12-12
Canada23556442009-01-202019-12-17
Canada22648522005-11-012017-09-16
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point224-226 °CNot Available
water solubility1255mg/LNot Available
logP0.20HANSCH,C ET AL. (1995), pH 7.2
pKa8.77SANGSTER,J (1994)
Predicted Properties
PropertyValueSource
Water Solubility0.182ALOGPS
logP1.47ALOGPS
logP2.25ChemAxon
logS-3.1ALOGPS
pKa (Strongest Basic)9.09ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity66.73 m3·mol-1ChemAxon
Polarizability26.21 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
References
Synthesis Reference

DrugSyn.org

US2512572
General Reference
  1. Keating GM, McClellan K, Jarvis B: Methylphenidate (OROS formulation). CNS Drugs. 2001;15(6):495-500; discussion 501-3. Pubmed
  2. Markowitz JS, DeVane CL, Pestreich LK, Patrick KS, Muniz R: A comprehensive in vitro screening of d-, l-, and dl-threo-methylphenidate: an exploratory study. J Child Adolesc Psychopharmacol. 2006 Dec;16(6):687-98. Pubmed
  3. Fone KC, Nutt DJ: Stimulants: use and abuse in the treatment of attention deficit hyperactivity disorder. Curr Opin Pharmacol. 2005 Feb;5(1):87-93. Pubmed
  4. Sharma RP, Javaid JI, Pandey GN, Easton M, Davis JM: Pharmacological effects of methylphenidate on plasma homovanillic acid and growth hormone. Psychiatry Res. 1990 Apr;32(1):9-17. Pubmed
  5. Shults T, Kownacki AA, Woods WE, Valentine R, Dougherty J, Tobin T: Pharmacokinetics and behavioral effects of methylphenidate in Thoroughbred horses. Am J Vet Res. 1981 May;42(5):722-6. Pubmed
    #FDA label
External Links
ResourceLink
KEGG DrugD04999
KEGG CompoundC07196
PubChem Compound4158
PubChem Substance46505929
ChemSpider4015
ChEBI6887
ChEMBLCHEMBL796
Therapeutic Targets DatabaseDAP000024
PharmGKBPA450464
Drug Product Database2249332
RxListhttp://www.rxlist.com/cgi/generic/methphen.htm
Drugs.comhttp://www.drugs.com/methylphenidate.html
PDRhealthhttp://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/rit1383.shtml
WikipediaMethylphenidate
ATC CodesN06BA04
AHFS Codes
  • 28:20.92
PDB EntriesNot Available
FDA labelshow(178 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AliskirenMonitor therapy due to reduced antihypertensive effect of aliskiren.
CarbamazepineCarbamazepine may decrease the effect of methylphendiate.
CyclosporineMethylphenidate increases the effect and toxicity of cyclosporine
GuanethidineMethylphenidate may decrease the effect of guanethidine.
IsocarboxazidPossible hypertensive crisis with this combination
PhenelzinePossible hypertensive crisis with this combination
RasagilinePossible hypertensive crisis with this combination.
TrandolaprilMethylphenidate may antagonize the antihypertensive effect of Trandolapril. Monitor for changes in blood pressure if Methylphenidate is initiated, discontinued or dose changed.
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of Methylphenidate. Concomitant therapy is contraindicated.
Food Interactions
  • Avoid alcohol.
  • Avoid excessive quantities of coffee or tea (Caffeine).
  • Take on empty stomach: 1 hour before or 2 hours after meals.

Targets

1. Sodium-dependent dopamine transporter

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent dopamine transporter Q01959 Details

References:

  1. Volkow ND, Fowler JS, Gatley SJ, Dewey SL, Wang GJ, Logan J, Ding YS, Franceschi D, Gifford A, Morgan A, Pappas N, King P: Comparable changes in synaptic dopamine induced by methylphenidate and by cocaine in the baboon brain. Synapse. 1999 Jan;31(1):59-66. Pubmed
  2. Wayment HK, Deutsch H, Schweri MM, Schenk JO: Effects of methylphenidate analogues on phenethylamine substrates for the striatal dopamine transporter: potential as amphetamine antagonists? J Neurochem. 1999 Mar;72(3):1266-74. Pubmed
  3. Dresel SH, Kung MP, Huang X, Plossl K, Hou C, Shiue CY, Karp J, Kung HF: In vivo imaging of serotonin transporters with [99mTc]TRODAT-1 in nonhuman primates. Eur J Nucl Med. 1999 Apr;26(4):342-7. Pubmed
  4. Volkow ND, Wang GJ, Fowler JS, Fischman M, Foltin R, Abumrad NN, Gatley SJ, Logan J, Wong C, Gifford A, Ding YS, Hitzemann R, Pappas N: Methylphenidate and cocaine have a similar in vivo potency to block dopamine transporters in the human brain. Life Sci. 1999;65(1):PL7-12. Pubmed
  5. Izenwasser S, Coy AE, Ladenheim B, Loeloff RJ, Cadet JL, French D: Chronic methylphenidate alters locomotor activity and dopamine transporters differently from cocaine. Eur J Pharmacol. 1999 Jun 4;373(2-3):187-93. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed
  7. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  8. Viggiano D, Vallone D, Sadile A: Dysfunctions in dopamine systems and ADHD: evidence from animals and modeling. Neural Plast. 2004;11(1-2):97-114. Pubmed
  9. Tilley MR, Gu HH: The effects of methylphenidate on knockin mice with a methylphenidate-resistant dopamine transporter. J Pharmacol Exp Ther. 2008 Nov;327(2):554-60. Epub 2008 Aug 12. Pubmed

2. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Yang L, Wang YF, Li J, Faraone SV: Association of norepinephrine transporter gene with methylphenidate response. J Am Acad Child Adolesc Psychiatry. 2004 Sep;43(9):1154-8. Pubmed
  2. Williard RL, Middaugh LD, Zhu HJ, Patrick KS: Methylphenidate and its ethanol transesterification metabolite ethylphenidate: brain disposition, monoamine transporters and motor activity. Behav Pharmacol. 2007 Feb;18(1):39-51. Pubmed
  3. Chuhan YS, Taukulis HK: Impairment of single-trial memory formation by oral methylphenidate in the rat. Neurobiol Learn Mem. 2006 Mar;85(2):125-31. Epub 2005 Oct 24. Pubmed
  4. Gray JD, Punsoni M, Tabori NE, Melton JT, Fanslow V, Ward MJ, Zupan B, Menzer D, Rice J, Drake CT, Romeo RD, Brake WG, Torres-Reveron A, Milner TA: Methylphenidate administration to juvenile rats alters brain areas involved in cognition, motivated behaviors, appetite, and stress. J Neurosci. 2007 Jul 4;27(27):7196-207. Pubmed
  5. Sandoval V, Riddle EL, Ugarte YV, Hanson GR, Fleckenstein AE: Methamphetamine-induced rapid and reversible changes in dopamine transporter function: an in vitro model. J Neurosci. 2001 Feb 15;21(4):1413-9. Pubmed
  6. Tatsumi M, Groshan K, Blakely RD, Richelson E: Pharmacological profile of antidepressants and related compounds at human monoamine transporters. Eur J Pharmacol. 1997 Dec 11;340(2-3):249-58. Pubmed
  7. Tilley MR, Gu HH: The effects of methylphenidate on knockin mice with a methylphenidate-resistant dopamine transporter. J Pharmacol Exp Ther. 2008 Nov;327(2):554-60. Epub 2008 Aug 12. Pubmed

3. Sodium-dependent serotonin transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Sodium-dependent serotonin transporter P31645 Details

References:

  1. Dresel SH, Kung MP, Huang X, Plossl K, Hou C, Shiue CY, Karp J, Kung HF: In vivo imaging of serotonin transporters with [99mTc]TRODAT-1 in nonhuman primates. Eur J Nucl Med. 1999 Apr;26(4):342-7. Pubmed
  2. Izenwasser S, Coy AE, Ladenheim B, Loeloff RJ, Cadet JL, French D: Chronic methylphenidate alters locomotor activity and dopamine transporters differently from cocaine. Eur J Pharmacol. 1999 Jun 4;373(2-3):187-93. Pubmed
  3. Stehouwer JS, Jarkas N, Zeng F, Voll RJ, Williams L, Owens MJ, Votaw JR, Goodman MM: Synthesis, radiosynthesis, and biological evaluation of carbon-11 labeled 2beta-carbomethoxy-3beta-(3’-((Z)-2-haloethenyl)phenyl)nortropanes: candidate radioligands for in vivo imaging of the serotonin transporter with positron emission tomography. J Med Chem. 2006 Nov 16;49(23):6760-7. Pubmed

Enzymes

1. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Carboxylesterase

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Carboxylesterase Q6LAP9 Details

References:

  1. FDA label

Comments
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Drug created on June 13, 2005 07:24 / Updated on October 08, 2013 14:24