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Identification
NameKetamine
Accession NumberDB01221  (APRD00493)
TypeSmall Molecule
GroupsApproved
Description

A cyclohexanone derivative used for induction of anesthesia. Its mechanism of action is not well understood, but ketamine can block NMDA receptors (receptors, N-methyl-D-aspartate) and may interact with sigma receptors. [PubChem]

Structure
Thumb
Synonyms
SynonymLanguageCode
(+-)-KetamineNot AvailableNot Available
(±)-ketamineNot AvailableNot Available
2-(2-Chloro-phenyl)-2-methylamino-cyclohexanoneNot AvailableNot Available
2-(methylamino)-2-(2-chlorophenyl)cyclohexanoneNot AvailableNot Available
2-(o-chlorophenyl)-2-(methylamino)-cyclohexanoneNot AvailableNot Available
DL-ketamineNot AvailableNot Available
KetaminaNot AvailableNot Available
KETAMINENot AvailableNot Available
KetaminumNot AvailableNot Available
NMDANot AvailableNot Available
Special kNot AvailableNot Available
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ketalarinjection10 mg/mLintramuscular; intravenousJHP Pharmaceuticals LLC2007-10-01Not AvailableUs
Ketalarinjection50 mg/mLintramuscular; intravenousJHP Pharmaceuticals LLC2007-10-01Not AvailableUs
Ketalarinjection100 mg/mLintramuscular; intravenousJHP Pharmaceuticals LLC2007-10-01Not AvailableUs
Ketamine Hydrochlorideinjection10 mg/mLintramuscular; intravenousJHP Pharmaceuticals, LLC2012-06-01Not AvailableUs
Ketamine Hydrochlorideinjection50 mg/mLintramuscular; intravenousJHP Pharmaceuticals, LLC2012-06-01Not AvailableUs
Ketamine Hydrochlorideinjection100 mg/mLintramuscular; intravenousJHP Pharmaceuticals, LLC2012-06-01Not AvailableUs
Ketalarinjection10 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2012-10-17Not AvailableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ketamine Hydrochlorideinjection, solution, concentrate100 mg/mLintramuscular; intravenousHospira, Inc.1996-06-27Not AvailableUs
Ketamine Hydrochlorideinjection, solution, concentrate50 mg/mLintramuscular; intravenousHospira, Inc.1996-06-27Not AvailableUs
Ketamine Hydrochlorideinjection, solution, concentrate50 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2012-10-11Not AvailableUs
Ketamine Hydrochlorideinjection, solution, concentrate100 mg/mLintramuscular; intravenousGeneral Injectables & Vaccines, Inc2012-10-16Not AvailableUs
Ketamine Hydrochlorideinjection, solution, concentrate50 mg/mLintramuscular; intravenousPhysicians Total Care, Inc.2002-03-12Not AvailableUs
Ketamine Hydrochlorideinjection, solution50 mg/mLintramuscular; intravenousMylan Institutional LLC2013-06-04Not AvailableUs
Ketamine Hydrochlorideinjection, solution100 mg/mLintramuscular; intravenousMylan Institutional LLC2013-06-04Not AvailableUs
Ketamine Hydrochlorideinjection, solution10 mg/mLintramuscular; intravenousMylan Institutional LLC2013-06-04Not AvailableUs
Over the Counter ProductsNot Available
International Brands
NameCompany
KetajectBristol-Myers Squibb
KetanestParke Davis
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ketamine hydrochloride
1867-66-9
Thumb
  • InChI Key: VCMGMSHEPQENPE-UHFFFAOYNA-N
  • Monoisotopic Mass: 273.068719585
  • Average Mass: 274.186
DBSALT000396
Categories
CAS number6740-88-1
WeightAverage: 237.725
Monoisotopic: 237.092041846
Chemical FormulaC13H16ClNO
InChI KeyYQEZLKZALYSWHR-UHFFFAOYSA-N
InChI
InChI=1S/C13H16ClNO/c1-15-13(9-5-4-8-12(13)16)10-6-2-3-7-11(10)14/h2-3,6-7,15H,4-5,8-9H2,1H3
IUPAC Name
2-(2-chlorophenyl)-2-(methylamino)cyclohexan-1-one
SMILES
CNC1(CCCCC1=O)C1=CC=CC=C1Cl
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassHalobenzenes
Direct ParentChlorobenzenes
Alternative Parents
Substituents
  • Aralkylamine
  • Cyclohexylamine
  • Cyclohexanone
  • Chlorobenzene
  • Aryl halide
  • Aryl chloride
  • Cyclic ketone
  • Ketone
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor use as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation.
PharmacodynamicsKetamine is a rapid-acting general anesthetic producing an anesthetic state characterized by profound analgesia, normal pharyngeal-laryngeal reflexes, normal or slightly enhanced skeletal muscle tone, cardiovascular and respiratory stimulation, and occasionally a transient and minimal respiratory depression. Ketamine is indicated as the sole anesthetic agent for diagnostic and surgical procedures that do not require skeletal muscle relaxation. The anesthetic state produced by Ketamine has been termed “dissociative anesthesia” in that it appears to selectively interrupt association pathways of the brain before producing somesthetic sensory blockade. It may selectively depress the thalamoneocortical system before significantly obtunding the more ancient cerebral centers and pathways (reticularactivating and limbic systems).
Mechanism of actionKetamine has several clinically useful properties, including analgesia and less cardiorespiratory depressant effects than other anaesthetic agents, it also causes some stimulation of the cardiocascular system. Ketamine has been reported to produce general as well as local anaesthesia. It interacts with N-methyl-D-aspartate (NMDA) receptors, opioid receptors, monoaminergic receptors, muscarinic receptors and voltage sensitive Ca ion channels. Unlike other general anaesthetic agents, ketamine does not interact with GABA receptors.
AbsorptionRapidly absorbed following parenteral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

SubstrateEnzymesProduct
Ketamine
NorketamineDetails
Ketamine
Not Available
6-HydroxyketamineDetails
Ketamine
Not Available
5-HydroxyketamineDetails
Ketamine
Not Available
4-HydroxyketamineDetails
Norketamine
Not Available
4-HydroxynorketamineDetails
Norketamine
Not Available
5-HydroxynorketamineDetails
Norketamine
Not Available
6-HydroxynorketamineDetails
6-Hydroxyketamine
Not Available
6-HydroxynorketamineDetails
5-Hydroxyketamine
Not Available
5-HydroxynorketamineDetails
4-Hydroxyketamine
Not Available
4-HydroxynorketamineDetails
Route of eliminationNot Available
Half life2.5-3 hours.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9826
Caco-2 permeable+0.6326
P-glycoprotein substrateSubstrate0.5753
P-glycoprotein inhibitor INon-inhibitor0.5948
P-glycoprotein inhibitor IINon-inhibitor0.8383
Renal organic cation transporterNon-inhibitor0.6737
CYP450 2C9 substrateNon-substrate0.6363
CYP450 2D6 substrateSubstrate0.8918
CYP450 3A4 substrateSubstrate0.7407
CYP450 1A2 substrateNon-inhibitor0.7323
CYP450 2C9 substrateNon-inhibitor0.7985
CYP450 2D6 substrateNon-inhibitor0.6912
CYP450 2C19 substrateNon-inhibitor0.5347
CYP450 3A4 substrateNon-inhibitor0.8253
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5426
Ames testNon AMES toxic0.7223
CarcinogenicityNon-carcinogens0.8878
BiodegradationNot ready biodegradable0.9937
Rat acute toxicity2.3939 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8859
hERG inhibition (predictor II)Inhibitor0.6047
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injectionintramuscular; intravenous10 mg/mL
Injectionintramuscular; intravenous100 mg/mL
Injectionintramuscular; intravenous50 mg/mL
Injection, solutionintramuscular; intravenous10 mg/mL
Injection, solutionintramuscular; intravenous100 mg/mL
Injection, solutionintramuscular; intravenous50 mg/mL
Injection, solution, concentrateintramuscular; intravenous100 mg/mL
Injection, solution, concentrateintramuscular; intravenous50 mg/mL
Prices
Unit descriptionCostUnit
Ketamine hcl powder7.22USD g
Ketamine hcl-ns 50 mg/5 ml syr2.82USD ml
Ketamine 100 mg/ml vial2.36USD ml
Ketalar 100 mg/ml vial1.95USD ml
Ketamine hcl-ns 100 mg/10 ml1.95USD ml
Ketamine HCl 50 mg/ml Solution1.77USD ml
Ketalar 10 mg/ml vial0.99USD ml
Ketamine 10 mg/ml vial0.99USD ml
Ketalar 50 mg/ml vial0.75USD ml
Ketamine 50 mg/ml vial0.61USD ml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point92-93U.S. Patent 3,254,124.
logP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0464 mg/mLALOGPS
logP2.69ALOGPS
logP3.35ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.78ChemAxon
pKa (Strongest Basic)7.45ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area29.1 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity65.55 m3·mol-1ChemAxon
Polarizability24.97 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

John A. Flores, Kenton L. Crowley, “Process for the preparation of ketamine ointment.” U.S. Patent US5817699, issued June, 1995.

US5817699
General Reference
  1. Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. Pubmed
  2. Bergman SA: Ketamine: review of its pharmacology and its use in pediatric anesthesia. Anesth Prog. 1999 Winter;46(1):10-20. Pubmed
  3. Bonanno FG: Ketamine in war/tropical surgery (a final tribute to the racemic mixture). Injury. 2002 May;33(4):323-7. Pubmed
  4. Lankenau SE, Sanders B, Bloom JJ, Hathazi D, Alarcon E, Tortu S, Clatts MC: First injection of ketamine among young injection drug users (IDUs) in three U.S. cities. Drug Alcohol Depend. 2007 Mar 16;87(2-3):183-93. Epub 2006 Sep 18. Pubmed
  5. Reboso Morales JA, Gonzalez Miranda F: [Ketamine] Rev Esp Anestesiol Reanim. 1999 Mar;46(3):111-22. Pubmed
External Links
ATC CodesN01AX03
AHFS Codes
  • 28:04.00
  • 28:04.92
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (67.5 KB)
Interactions
Drug Interactions
Drug
MemantineIncreased risk of CNS adverse effects with this association
TelithromycinTelithromycin may reduce clearance of Ketamine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Ketamine if Telithromycin is initiated, discontinued or dose changed.
ThiotepaThiotepa, a strong CYP2B6 inhibitor, may decrease the metabolism and clearance of Ketamine, a CYP2B6 substrate. Consider alternate therapy or monitor for changes in the therapeutic and adverse effects of Ketamine if Thiotepa is initiated, discontinued or dose changed.
TolbutamideTolbutamide, a strong CYP2C9 inhibitor, may decrease the metabolism and clearance of Ketamine. Consider alternate therapy or monitor for changes in Ketamine therapeutic and adverse effects if Tolbutamide is initiated, discontinued or dose changed.
VoriconazoleVoriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of ketamine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of ketamine if voriconazole is initiated, discontinued or dose changed.
Food InteractionsNot Available

Targets

1. Glutamate receptor ionotropic, NMDA 3A

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Glutamate receptor ionotropic, NMDA 3A Q8TCU5 Details

References:

  1. Smothers CT, Woodward JJ: Pharmacological characterization of glycine-activated currents in HEK 293 cells expressing N-methyl-D-aspartate NR1 and NR3 subunits. J Pharmacol Exp Ther. 2007 Aug;322(2):739-48. Epub 2007 May 14. Pubmed
  2. Harrison NL, Simmonds MA: Quantitative studies on some antagonists of N-methyl D-aspartate in slices of rat cerebral cortex. Br J Pharmacol. 1985 Feb;84(2):381-91. Pubmed
  3. Sinner B, Graf BM: Ketamine. Handb Exp Pharmacol. 2008;(182):313-33. Pubmed
  4. Radovanovic D, Pjevic M: [Ketamine: the past 30 years and its future] Med Pregl. 2003 Sep-Oct;56(9-10):439-45. Pubmed

2. Substance-P receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Substance-P receptor P25103 Details

References:

  1. Okamoto T, Minami K, Uezono Y, Ogata J, Shiraishi M, Shigematsu A, Ueta Y: The inhibitory effects of ketamine and pentobarbital on substance p receptors expressed in Xenopus oocytes. Anesth Analg. 2003 Jul;97(1):104-10, table of contents. Pubmed

3. D(2) dopamine receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist partial agonist

Components

Name UniProt ID Details
D(2) dopamine receptor P14416 Details

References:

  1. Seeman P, Guan HC, Hirbec H: Dopamine D2High receptors stimulated by phencyclidines, lysergic acid diethylamide, salvinorin A, and modafinil. Synapse. 2009 Aug;63(8):698-704. Pubmed

4. Delta-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Delta-type opioid receptor P41143 Details

References:

  1. Smith DJ, Pekoe GM, Martin LL, Coalgate B: The interaction of ketamine with the opiate receptor. Life Sci. 1980 Mar 10;26(10):789-95. Pubmed
  2. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. Pubmed

5. Sodium-dependent noradrenaline transporter

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sodium-dependent noradrenaline transporter P23975 Details

References:

  1. Salt PJ, Barnes PK, Beswick FJ: Inhibition of neuronal and extraneuronal uptake of noradrenaline by ketamine in the isolated perfused rat heart. Br J Anaesth. 1979 Sep;51(9):835-8. Pubmed

6. Kappa-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Kappa-type opioid receptor P41145 Details

References:

  1. Smith DJ, Pekoe GM, Martin LL, Coalgate B: The interaction of ketamine with the opiate receptor. Life Sci. 1980 Mar 10;26(10):789-95. Pubmed
  2. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. Pubmed

7. Mu-type opioid receptor

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Mu-type opioid receptor P35372 Details

References:

  1. Smith DJ, Pekoe GM, Martin LL, Coalgate B: The interaction of ketamine with the opiate receptor. Life Sci. 1980 Mar 10;26(10):789-95. Pubmed
  2. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. Pubmed

8. Muscarinic acetylcholine receptor

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: binder

Components

Name UniProt ID Details
Muscarinic acetylcholine receptor M1 P11229 Details
Muscarinic acetylcholine receptor M2 P08172 Details
Muscarinic acetylcholine receptor M3 P20309 Details
Muscarinic acetylcholine receptor M4 P08173 Details
Muscarinic acetylcholine receptor M5 P08912 Details

References:

  1. Hustveit O, Maurset A, Oye I: Interaction of the chiral forms of ketamine with opioid, phencyclidine, sigma and muscarinic receptors. Pharmacol Toxicol. 1995 Dec;77(6):355-9. Pubmed

9. 5-hydroxytryptamine receptor 2

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 2A P28223 Details
5-hydroxytryptamine receptor 2B P41595 Details
5-hydroxytryptamine receptor 2C P28335 Details

References:

  1. Martin LL, Bouchal RL, Smith DJ: Ketamine inhibits serotonin uptake in vivo. Neuropharmacology. 1982 Feb;21(2):113-8. Pubmed

10. 5-hydroxytryptamine receptor 1

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
5-hydroxytryptamine receptor 1A P08908 Details
5-hydroxytryptamine receptor 1B P28222 Details
5-hydroxytryptamine receptor 1D P28221 Details
5-hydroxytryptamine receptor 1E P28566 Details
5-hydroxytryptamine receptor 1F P30939 Details

References:

  1. Martin LL, Bouchal RL, Smith DJ: Ketamine inhibits serotonin uptake in vivo. Neuropharmacology. 1982 Feb;21(2):113-8. Pubmed

Enzymes

1. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. 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. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. 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

3. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed
  2. 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

4. Prostaglandin G/H synthase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Prostaglandin G/H synthase 1 P23219 Details

References:

  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. Pubmed

5. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 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

Transporters

1. Multidrug resistance protein 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

References:

  1. Mahar Doan KM, Humphreys JE, Webster LO, Wring SA, Shampine LJ, Serabjit-Singh CJ, Adkison KK, Polli JW: Passive permeability and P-glycoprotein-mediated efflux differentiate central nervous system (CNS) and non-CNS marketed drugs. J Pharmacol Exp Ther. 2002 Dec;303(3):1029-37. Pubmed

Comments
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Drug created on June 13, 2005 07:24 / Updated on March 03, 2014 21:13