Sibutramine

Identification

Summary

Sibutramine is a norepinephrine, serotonin and dopamine reuptake inhibitor indicated to assist with weight loss in obesity.

Generic Name
Sibutramine
DrugBank Accession Number
DB01105
Background

Sibutramine (trade name Meridia in the USA, Reductil in Europe and other countries), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. It is a centrally acting stimulant chemically related to amphetamines thus it is classified as a Schedule IV controlled substance in the United States. In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease.

Type
Small Molecule
Groups
Approved, Illicit, Investigational, Withdrawn
Structure
Weight
Average: 279.848
Monoisotopic: 279.175377544
Chemical Formula
C17H26ClN
Synonyms
  • Sibutramina
  • Sibutramine
  • Sibutraminum
External IDs
  • HSDB 7209

Pharmacology

Indication

For the treatment of obesity.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Used in combination to manageBmi >30 kg/m2•••••••••••••••• ••• •••••••• ••• •••••••••• ••• •••••• •••••••••••
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Pharmacodynamics

Sibutramine is an orally administered agent for the treatment of obesity. Sibutramine exerts its pharmacological actions predominantly via its secondary (M1) and primary (M2) amine metabolites. The parent compound, sibutramine, is a potent inhibitor of serotonin and norepinephrine reuptake in vivo, but not in vitro. However, metabolites M1 and M2 inhibit the reuptake of these neurotransmitters both in vitro and in vivo. In human brain tissue, M1 and M2 also inhibit dopamine reuptake in vitro, but with ~3-fold lower potency than for the reuptake inhibition of serotonin or norepinephrine. Sibutramine, M1 and M2 exhibit no evidence of anticholinergic or antihistaminergic actions. In addition, receptor binding profiles show that sibutramine, M1 and M2 have low affinity for serotonin (5-HT1, 5-HT1A, 5-HT1B, 5-HT2A, 5-HT2C), norepinephrine (b, b1, b3, a1 and a2), dopamine (D1 and D2), benzodiazepine, and glutamate (NMDA) receptors. These compounds also lack monoamine oxidase inhibitory activity in vitro and in vivo.

Mechanism of action

Sibutramine produces its therapeutic effects by inhibition of norepinephrine (NE), serotonin (5-hydroxytryptamine, 5-HT), and to a lesser extent, dopamine reuptake at the neuronal synapse. By inhibiting the reuptake of these neurotransmitters, sibutramine promotes a sense of satiety and decrease in appetite, thereby reducing food intake. Data from animal studies also suggest that sibutramine may also increase energy expenditure through thermogenic effects in both the basal and fed states, but this has not been confirmed in humans. Sibutramine and its major pharmacologically active metabolites (M1 and M2) do not act via release of monoamines.

TargetActionsOrganism
ASodium-dependent dopamine transporter
inhibitor
Humans
ASodium-dependent serotonin transporter
inhibitor
Humans
ASodium-dependent noradrenaline transporter
inhibitor
Humans
Absorption

Rapid absorption following oral administration. Absolute bioavailability is not known, but at least 77% of a single oral dose of sibutramine is absorbed.

Volume of distribution

Not Available

Protein binding

97% (to human plasma proteins)

Metabolism

Hepatic

Route of elimination

Sibutramine is metabolized in the liver principally by the cytochrome P450 (3A4) isoenzyme, to desmethyl metabolites, M1 and M2. These active metabolites are further metabolized by hydroxylation and conjugation to pharmacologically inactive metabolites, M5 and M6. Approximately 85% (range 68-95%) of a single orally administered radiolabeled dose was excreted in urine and feces over a 15-day collection period with the majority of the dose (77%) excreted in the urine. The primary route of excretion for M1 and M2 is hepatic metabolism and for M5 and M6 is renal excretion.

Half-life

1.1 hours

Clearance
  • Oral cl=1750 L/h [oral administration]
Adverse Effects
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Toxicity

Side effects include dry mouth, anorexia, insomnia, constipation and headache.

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Guanine nucleotide-binding protein G(I)/G(S)/G(T) subunit beta-3---(T;T) / (C;T)C > TEffect Directly StudiedPatients with this genotype will lose weight with sibutramine.Details

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
1,2-BenzodiazepineThe risk or severity of adverse effects can be increased when 1,2-Benzodiazepine is combined with Sibutramine.
AbacavirAbacavir may decrease the excretion rate of Sibutramine which could result in a higher serum level.
AbametapirThe serum concentration of Sibutramine can be increased when it is combined with Abametapir.
AbciximabThe risk or severity of hemorrhage can be increased when Sibutramine is combined with Abciximab.
AcebutololThe serum concentration of Acebutolol can be increased when it is combined with Sibutramine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Sibutramine hydrochlorideOGM0YHD1WF125494-59-9KFNNPQDSPLWLCX-UHFFFAOYSA-N
International/Other Brands
Butramin / Medaria / Reductil
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
MeridiaCapsule10 mgOralAbbott2001-02-282010-10-12Canada flag
MeridiaCapsule5 mg/1OralAbbVie Inc2010-08-122010-12-21US flag
MeridiaCapsule15 mg/1OralAbbVie Inc2010-08-122012-12-21US flag
MeridiaCapsule15 mgOralAbbott2001-02-282010-10-12Canada flag
MeridiaCapsule10 mg/1OralAbbVie Inc2010-08-122012-12-21US flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Apo-sibutramineCapsule10 mgOralApotex Corporation2009-11-232010-10-12Canada flag
Apo-sibutramineCapsule15 mgOralApotex Corporation2009-11-232010-10-12Canada flag

Categories

ATC Codes
A08AA10 — Sibutramine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as chlorobenzenes. These are compounds containing one or more chlorine atoms attached to a benzene moiety.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Halobenzenes
Direct Parent
Chlorobenzenes
Alternative Parents
Aralkylamines / Aryl chlorides / Trialkylamines / Organopnictogen compounds / Organochlorides / Hydrocarbon derivatives
Substituents
Amine / Aralkylamine / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Chlorobenzene / Hydrocarbon derivative / Organic nitrogen compound / Organochloride / Organohalogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amino compound, organochlorine compound (CHEBI:9137)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
WV5EC51866
CAS number
106650-56-0
InChI Key
UNAANXDKBXWMLN-UHFFFAOYSA-N
InChI
InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3
IUPAC Name
{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine
SMILES
CC(C)CC(N(C)C)C1(CCC1)C1=CC=C(Cl)C=C1

References

Synthesis Reference

Chris Senanayake, "Methods of preparing didesmethylsibutramine and other sibutramine derivatives." U.S. Patent US20020183554, issued December 05, 2002.

US20020183554
General References
  1. Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [Article]
  2. Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [Article]
  3. Heal DJ, Aspley S, Prow MR, Jackson HC, Martin KF, Cheetham SC: Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine. Int J Obes Relat Metab Disord. 1998 Aug;22 Suppl 1:S18-28; discussion S29. [Article]
  4. Stock MJ: Sibutramine: a review of the pharmacology of a novel anti-obesity agent. Int J Obes Relat Metab Disord. 1997 Mar;21 Suppl 1:S25-9. [Article]
Human Metabolome Database
HMDB0015237
KEGG Drug
D08513
KEGG Compound
C07247
PubChem Compound
5210
PubChem Substance
46507740
ChemSpider
5021
BindingDB
84742
RxNav
36514
ChEBI
9137
ChEMBL
CHEMBL1419
Therapeutic Targets Database
DCL000881
PharmGKB
PA451344
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Sibutramine
FDA label
Download (134 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4CompletedTreatmentBipolar Disorder (BD) / Psychosis / Schizophrenia1
4CompletedTreatmentEating, Binge / Obesity1
4CompletedTreatmentHypertension / Obesity / Obstructive Sleep Apnea (OSA)1
4CompletedTreatmentObesity3
4CompletedTreatmentObesity / Polycystic Ovarian Syndrome (PCOS)1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • Abbott Laboratories Ltd.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • BASF Corp.
  • Bryant Ranch Prepack
  • Dispensing Solutions
  • PD-Rx Pharmaceuticals Inc.
  • Physicians Total Care Inc.
Dosage Forms
FormRouteStrength
CapsuleOral10 mg
CapsuleOral10 mg/1
CapsuleOral15 mg/1
CapsuleOral15 mg
CapsuleOral5 mg/1
Capsule, coatedOral5 mg
CapsuleOral
Capsule, coatedOral20 mg
Capsule, coatedOral10 mg
Capsule, coatedOral15 mg
Prices
Unit descriptionCostUnit
Meridia 15 mg capsule5.11USD capsule
Meridia 10 mg capsule4.02USD capsule
Meridia 5 mg capsule4.0USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5436272No1995-07-252013-01-25US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)191-192 °CNot Available
water solubility2.9 mg/mL (in pH 5.2 water)Not Available
logP5.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00094 mg/mLALOGPS
logP5.05ALOGPS
logP5.2Chemaxon
logS-5.5ALOGPS
pKa (Strongest Basic)9.77Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count1Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area3.24 Å2Chemaxon
Rotatable Bond Count5Chemaxon
Refractivity83.92 m3·mol-1Chemaxon
Polarizability32.9 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9948
Blood Brain Barrier+0.9667
Caco-2 permeable+0.6584
P-glycoprotein substrateNon-substrate0.5148
P-glycoprotein inhibitor INon-inhibitor0.718
P-glycoprotein inhibitor IIInhibitor0.5071
Renal organic cation transporterNon-inhibitor0.5805
CYP450 2C9 substrateNon-substrate0.8056
CYP450 2D6 substrateNon-substrate0.9115
CYP450 3A4 substrateSubstrate0.6969
CYP450 1A2 substrateNon-inhibitor0.7059
CYP450 2C9 inhibitorNon-inhibitor0.9205
CYP450 2D6 inhibitorNon-inhibitor0.754
CYP450 2C19 inhibitorNon-inhibitor0.7041
CYP450 3A4 inhibitorNon-inhibitor0.969
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8292
Ames testNon AMES toxic0.837
CarcinogenicityNon-carcinogens0.5808
BiodegradationNot ready biodegradable0.9903
Rat acute toxicity2.9056 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9065
hERG inhibition (predictor II)Inhibitor0.769
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-MSsplash10-07bf-9640000000-63dab33ab67c598b8779
MS/MS Spectrum - , positiveLC-MS/MSsplash10-003r-1930000000-b90a7add9041c09efb5e
MS/MS Spectrum - , positiveLC-MS/MSsplash10-005i-1930000000-524395362f2824760185
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-1390000000-a6fe4405805f7924efcf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-0290000000-4a9f12bac317b411cf10
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0aor-9800000000-c47fb04e167857b08027
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-3290000000-f89c8c2ca9f6de8d4868
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0ar0-9730000000-179c295228019890a583
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9000000000-c2b67c583566373fd487
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-168.7428162
predicted
DarkChem Lite v0.1.0
[M-H]-176.19402
predicted
DeepCCS 1.0 (2019)
[M+H]+169.3326162
predicted
DarkChem Lite v0.1.0
[M+H]+178.55203
predicted
DeepCCS 1.0 (2019)
[M+Na]+169.0024162
predicted
DarkChem Lite v0.1.0
[M+Na]+184.64519
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [Article]
  2. Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [Article]
  3. Berke EM, Morden NE: Medical management of obesity. Am Fam Physician. 2000 Jul 15;62(2):419-26. [Article]
  4. Nakagawa T, Ukai K, Ohyama T, Gomita Y, Okamura H: Effects of sibutramine on the central dopaminergic system in rodents. Neurotox Res. 2001 Jul;3(3):235-47. [Article]
  5. Krahn LE, Moore WR, Altchuler SI: Narcolepsy and obesity: remission of severe cataplexy with sibutramine. Sleep Med. 2001 Jan;2(1):63-65. [Article]
  6. Balcioglu A, Wurtman RJ: Sibutramine, a serotonin uptake inhibitor, increases dopamine concentrations in rat striatal and hypothalamic extracellular fluid. Neuropharmacology. 2000 Sep;39(12):2352-9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Serotonin:sodium symporter activity
Specific Function
Serotonin transporter whose primary function in the central nervous system involves the regulation of serotonergic signaling via transport of serotonin molecules from the synaptic cleft back into t...
Gene Name
SLC6A4
Uniprot ID
P31645
Uniprot Name
Sodium-dependent serotonin transporter
Molecular Weight
70324.165 Da
References
  1. Vazquez Roque MI, Camilleri M, Clark MM, Tepoel DA, Jensen MD, Graszer KM, Kalsy SA, Burton DD, Baxter KL, Zinsmeister AR: Alteration of gastric functions and candidate genes associated with weight reduction in response to sibutramine. Clin Gastroenterol Hepatol. 2007 Jul;5(7):829-37. Epub 2007 Jun 4. [Article]
  2. Heusser K, Engeli S, Tank J, Diedrich A, Wiesner S, Janke J, Luft FC, Jordan J: Sympathetic vasomotor tone determines blood pressure response to long-term sibutramine treatment. J Clin Endocrinol Metab. 2007 Apr;92(4):1560-3. Epub 2007 Feb 6. [Article]
  3. Jordan J, Scholze J, Matiba B, Wirth A, Hauner H, Sharma AM: Influence of Sibutramine on blood pressure: evidence from placebo-controlled trials. Int J Obes (Lond). 2005 May;29(5):509-16. [Article]
  4. Heusser K, Tank J, Diedrich A, Engeli S, Klaua S, Kruger N, Strauss A, Stoffels G, Luft FC, Jordan J: Influence of sibutramine treatment on sympathetic vasomotor tone in obese subjects. Clin Pharmacol Ther. 2006 May;79(5):500-8. [Article]
  5. Birkenfeld AL, Schroeder C, Boschmann M, Tank J, Franke G, Luft FC, Biaggioni I, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation. Circulation. 2002 Nov 5;106(19):2459-65. [Article]
  6. Birkenfeld AL, Schroeder C, Pischon T, Tank J, Luft FC, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation in obese hypertensive patients--sibutramine and blood pressure. Clin Auton Res. 2005 Jun;15(3):200-6. [Article]
  7. Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [Article]
  8. Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [Article]
  9. Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [Article]
  10. Berke EM, Morden NE: Medical management of obesity. Am Fam Physician. 2000 Jul 15;62(2):419-26. [Article]
  11. Krahn LE, Moore WR, Altchuler SI: Narcolepsy and obesity: remission of severe cataplexy with sibutramine. Sleep Med. 2001 Jan;2(1):63-65. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Norepinephrine:sodium symporter activity
Specific Function
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A2
Uniprot ID
P23975
Uniprot Name
Sodium-dependent noradrenaline transporter
Molecular Weight
69331.42 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Heusser K, Engeli S, Tank J, Diedrich A, Wiesner S, Janke J, Luft FC, Jordan J: Sympathetic vasomotor tone determines blood pressure response to long-term sibutramine treatment. J Clin Endocrinol Metab. 2007 Apr;92(4):1560-3. Epub 2007 Feb 6. [Article]
  3. Jordan J, Scholze J, Matiba B, Wirth A, Hauner H, Sharma AM: Influence of Sibutramine on blood pressure: evidence from placebo-controlled trials. Int J Obes (Lond). 2005 May;29(5):509-16. [Article]
  4. Heusser K, Tank J, Diedrich A, Engeli S, Klaua S, Kruger N, Strauss A, Stoffels G, Luft FC, Jordan J: Influence of sibutramine treatment on sympathetic vasomotor tone in obese subjects. Clin Pharmacol Ther. 2006 May;79(5):500-8. [Article]
  5. Birkenfeld AL, Schroeder C, Boschmann M, Tank J, Franke G, Luft FC, Biaggioni I, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation. Circulation. 2002 Nov 5;106(19):2459-65. [Article]
  6. Birkenfeld AL, Schroeder C, Pischon T, Tank J, Luft FC, Sharma AM, Jordan J: Paradoxical effect of sibutramine on autonomic cardiovascular regulation in obese hypertensive patients--sibutramine and blood pressure. Clin Auton Res. 2005 Jun;15(3):200-6. [Article]
  7. Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [Article]
  8. Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [Article]
  9. Gomis Barbara R: [Pharmacological treatment of obesity]. Rev Med Univ Navarra. 2004 Apr-Jun;48(2):63-5. [Article]
  10. Berke EM, Morden NE: Medical management of obesity. Am Fam Physician. 2000 Jul 15;62(2):419-26. [Article]
  11. Krahn LE, Moore WR, Altchuler SI: Narcolepsy and obesity: remission of severe cataplexy with sibutramine. Sleep Med. 2001 Jan;2(1):63-65. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. doi: 10.1517/14656566.9.12.2161 . [Article]
  2. Luque CA, Rey JA: Sibutramine: a serotonin-norepinephrine reuptake-inhibitor for the treatment of obesity. Ann Pharmacother. 1999 Sep;33(9):968-78. doi: 10.1345/aph.18319. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 02, 2024 22:55