Identification

Name
Meperidine
Accession Number
DB00454  (APRD00074)
Type
Small Molecule
Groups
Approved
Description

A narcotic analgesic that can be used for the relief of most types of moderate to severe pain, including postoperative pain and the pain of labor. Prolonged use may lead to dependence of the morphine type; withdrawal symptoms appear more rapidly than with morphine and are of shorter duration.

Structure
Thumb
Synonyms
  • Isonipecaïne
  • Meperidina
  • Pethidin
  • Pethidine
  • Péthidine
  • Pethidinum
  • Petidina
  • Petydyna
External IDs
IDS-NP-001
Product Ingredients
IngredientUNIICASInChI Key
Meperidine hydrochlorideN8E7F7Q17050-13-5WCNLCIJMFAJCPX-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
DemerolTablet50 mg/1OralPhysicians Total Care, Inc.2007-10-242012-06-30Us
DemerolInjection, solution50 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2006-02-24Not applicableUs
DemerolInjection, solution75 mg/1.5mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2006-03-22Not applicableUs
DemerolTablet100 mg/1OralValidus Pharmaceuticals LLC1942-11-10Not applicableUs
DemerolTablet50 mgOralSanofi Aventis1944-12-31Not applicableCanada
DemerolInjection, solution100 mg/1mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.2003-03-11Not applicableUs
DemerolInjection, solution50 mg/1mLIntramuscular; Intravenous; SubcutaneousPhysicians Total Care, Inc.2007-08-21Not applicableUs
DemerolInjection, solution25 mg/0.5mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-12-29Not applicableUs
DemerolInjection, solution50 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2007-02-062007-02-06Us
DemerolInjection, solution50 mg/1mLIntramuscular; Intravenous; SubcutaneousHospira, Inc.2005-09-13Not applicableUs
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Meperidine HydrochlorideTablet75 mg/1OralMikart, Inc.2009-06-24Not applicableUs
Meperidine HydrochlorideInjection25 mg/1mLIntramuscular; Intravenous; SubcutaneousWest Ward Pharmaceutical1975-01-22Not applicableUs
Meperidine HydrochlorideTablet100 mg/1OralEpic Pharma, LLC2011-05-05Not applicableUs
Meperidine HydrochlorideTablet50 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2007-01-04Not applicableUs
Meperidine HydrochlorideSolution50 mg/5mLOralWest-Ward Pharmaceuticals Corp.1985-01-30Not applicableUs
Meperidine HydrochlorideInjection75 mg/1mLIntramuscular; Intravenous; SubcutaneousBaxter Laboratories1990-09-302013-04-30Us
Meperidine HydrochlorideTablet50 mg/1OralWest-Ward Pharmaceuticals Corp.1997-03-12Not applicableUs
Meperidine HydrochlorideInjection25 mg/1mLIntramuscular; Intravenous; SubcutaneousBaxter Laboratories1990-09-302013-04-30Us
Meperidine HydrochlorideTablet100 mg/1OralBarr Laboratories1996-10-112016-07-31Us00555 0382 02 nlmimage10 22421140
Meperidine HydrochlorideTablet50 mg/1Oralbryant ranch prepack1998-12-17Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Meperidine HClMeperidine hydrochloride (10 mg/1mL)Injection, solutionIntravenousCantrell Drug Company2014-08-13Not applicableUs
Meperidine Hcl and Promethazine HclMeperidine hydrochloride (50 mg/1) + Promethazine hydrochloride (25 mg/1)CapsuleOralPhysicians Total Care, Inc.2004-09-032013-01-15Us
Meperidine Hydrochloride and Promethazine HydrochlorideMeperidine hydrochloride (50 mg/1) + Promethazine hydrochloride (25 mg/1)CapsuleOralEci Pharmaceuticals Llc2013-02-192018-07-24Us
International/Other Brands
Dolantin (sanofi-aventis) / Dolcontral (mibe) / Dolosal (Cristália) / Dolsin (Biotika) / Lydol (Sopharma) / Mialgin (Zentiva) / Petidin (Nycomed)
Categories
UNII
9E338QE28F
CAS number
57-42-1
Weight
Average: 247.3327
Monoisotopic: 247.157228921
Chemical Formula
C15H21NO2
InChI Key
XADCESSVHJOZHK-UHFFFAOYSA-N
InChI
InChI=1S/C15H21NO2/c1-3-18-14(17)15(9-11-16(2)12-10-15)13-7-5-4-6-8-13/h4-8H,3,9-12H2,1-2H3
IUPAC Name
ethyl 1-methyl-4-phenylpiperidine-4-carboxylate
SMILES
CCOC(=O)C1(CCN(C)CC1)C1=CC=CC=C1

Pharmacology

Indication

Used to control moderate to severe pain.

Associated Conditions
Pharmacodynamics

Meperidine is a synthetic opiate agonist belonging to the phenylpiperidine class. Meperidine may produce less smooth muscle spasm, constipation, and depression of the cough reflex than equivalent doses of morphine. The onset of action is lightly more rapid than with morphine, and the duration of action is slightly shorter. The chemical structure of meperidine is similar to local anesthetics. Meperidine is recommended for relief of moderate to severe acute pain and has the unique ability to interrupt postoperative shivering and shaking chills induced by amphotericin B. Meperidine has also been used for intravenous regional anesthesia, peripheral nerve blocks and intraarticular, epidural and spinal analgesia. Meperidine is considered a second-line agent for the treatment of acute pain.

Mechanism of action

Meperidine is primarily a kappa-opiate receptor agonist and also has local anesthetic effects. Meperidine has more affinity for the kappa-receptor than morphine. Opiate receptors are coupled with G-protein receptors and function as both positive and negative regulators of synaptic transmission via G-proteins that activate effector proteins. Binding of the opiate stimulates the exchange of GTP for GDP on the G-protein complex. As the effector system is adenylate cyclase and cAMP located at the inner surface of the plasma membrane, opioids decrease intracellular cAMP by inhibiting adenylate cyclase. Subsequently, the release of nociceptive neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline is inhibited. Opioids also inhibit the release of vasopressin, somatostatin, insulin and glucagon. Opioids close N-type voltage-operated calcium channels (OP2-receptor agonist) and open calcium-dependent inwardly rectifying potassium channels (OP3 and OP1 receptor agonist). This results in hyperpolarization and reduced neuronal excitability.

TargetActionsOrganism
AKappa-type opioid receptorNot AvailableHuman
UGlutamate receptor ionotropic, NMDA 1
antagonist
Human
UGlutamate receptor ionotropic, NMDA 2B
antagonist
Human
UGlutamate receptor ionotropic, NMDA 2A
antagonist
Human
UGlutamate receptor ionotropic, NMDA 2C
antagonist
Human
UGlutamate receptor ionotropic, NMDA 2D
antagonist
Human
UMuscarinic acetylcholine receptor
binder
Human
UMu-type opioid receptor
agonist
Human
USodium-dependent dopamine transporter
inhibitor
Human
USodium-dependent noradrenaline transporter
inhibitor
Human
USodium-dependent serotonin transporter
binding
Human
ULiver carboxylesterase 1Not AvailableHuman
Absorption

The oral bioavailability of meperidine in patients with normal hepatic function is 50-60% due to extensive first-pass metabolism. Bioavailability increases to 80-90% in patients with hepatic impairment (e.g. liver cirrhosis). Meperidine is less than half as effective when administered orally compared to parenteral administration. One study reported that 80-85% of the drug administered intramuscularly was absorbed within 6 hours of intragluteal injection in health adults; however, inter-individual variation and patient-specific variable appear to cause considerable variations in absorption upon IM injection.

Volume of distribution

Meperidine crosses the placenta and is distributed into breast milk.

Protein binding

60-80% bound to plasma proteins, primarily albumin and α1-acid glycoprotein. The presence of cirrhosis or active viral hepatitis does not appear to affect the extent of protein binding.

Metabolism

Meperidine is metabolized in the liver by hydrolysis to meperidinic acid followed by partial conjugation with glucuronic acid. Meperidine also undergoes N-demethylation to normeperidine, which then undergoes hydrolysis and partial conjugation. Normeperidine is about half as potent as meperidine, but it has twice the CNS stimulation effects.

Route of elimination

Excreted in the urine. The proportion of drug that is excreted unchanged or as metabolites is dependent on pH. When urine pH is uncontrolled, 5-30% of the meperidine dose is excreted as normeperidine and approximately 5% is excreted unchanged. Meperidine and normeperidine are found in acidic urine, while the free and conjugated forms of meperidinic and normperidinic acids are found in alkaline urine.

Half life

Initial distribution phase (t1/2 α) = 2-11 minutes; terminal elimination phase (t1/2 β) = 3-5 hours. In patients with hepatic dysfunction (e.g. liver cirrhosis or active viral hepatitis) the t1/2 β is prolonged to 7-11 hours.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of Meperidine can be decreased when combined with (R)-warfarin.
(S)-WarfarinThe metabolism of Meperidine can be decreased when combined with (S)-Warfarin.
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Meperidine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Meperidine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Meperidine is combined with 3,4-Methylenedioxyamphetamine.
3,5-diiodothyropropionic acidThe metabolism of Meperidine can be decreased when combined with 3,5-diiodothyropropionic acid.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Meperidine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be increased when combined with Meperidine.
4-MethoxyamphetamineThe metabolism of Meperidine can be decreased when combined with 4-Methoxyamphetamine.
5-androstenedioneThe metabolism of Meperidine can be decreased when combined with 5-androstenedione.
Food Interactions
  • Take without regard to meals. Avoid alcohol.

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0014597
KEGG Drug
D08343
KEGG Compound
C07128
PubChem Compound
4058
PubChem Substance
46506899
ChemSpider
3918
BindingDB
50026752
ChEBI
6754
ChEMBL
CHEMBL607
Therapeutic Targets Database
DAP000230
PharmGKB
PA450369
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Meperidine
ATC Codes
N02AB72 — Pethidine, combinations with psycholepticsN02AB52 — Pethidine, combinations excl. psycholepticsN02AG03 — Pethidine and antispasmodicsN02AB02 — Pethidine
AHFS Codes
  • 28:08.08 — Opiate Agonists
FDA label
Download (173 KB)
MSDS
Download (6.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1RecruitingTreatmentGraft Versus Host Disease (GVHD) / Sickle Cell Disorders1
2CompletedPreventionPostspinal Shivering1
2CompletedTreatmentShivering Caused by Spinal Anesthesia1
2Not Yet RecruitingPreventionPost Anaesthetic Shivering1
2Not Yet RecruitingTreatmentAnalgesia / Obstetrical1
2Not Yet RecruitingTreatmentObstetrical analgesia therapy2
2Unknown StatusDiagnosticEffect of Meperidine or Drotaverine on Effacement and Dilatation of the Cervix During Labor in Full Term Primigravidae1
2, 3RecruitingOtherLow Dose of Pethidine for Subarachnoid Anesthesia1
2, 3RecruitingTreatmentObstetrical analgesia therapy / Obstetrical Anesthesia / Postpartum Depression1
2, 3RecruitingTreatmentPain NOS1
3CompletedTreatmentElective Caesarean Section Surgeries1
3RecruitingTreatmentAcute Ischemic Stroke (AIS)1
3RecruitingTreatmentCesarean Section Complications1
3Unknown StatusTreatmentSciatica1
4CompletedNot AvailableDisorders of Gallbladder, Biliary Tract and Pancrease1
4CompletedDiagnosticAlteration of Cognitive Function / Gastrointestinal Dysfunction1
4CompletedSupportive CareColonoscopy1
4CompletedSupportive CareInfertilities1
4CompletedTreatmentArrested Active Phase of Labor as Antepartum Condition1
4CompletedTreatmentCholangiocarcinomas / Choledocholithiasis / Malignant Neoplasm of Pancreas / Pancreatitis1
4CompletedTreatmentComplications1
4CompletedTreatmentDiagnostic Colonoscopy Screening1
4CompletedTreatmentFeeling Anxious / Hepatitis, Chronic / Liver Cirrhosis1
4CompletedTreatmentLabour Pain1
4CompletedTreatmentPain NOS / Quality of Life1
4CompletedTreatmentPain Relief in Labour1
4Not Yet RecruitingTreatmentFirst Labor Stage / Humanizing Deliver / Labor Onset / Labour Pain / Natural Childbirth / Parturition1
4RecruitingTreatmentAnalgesia / Urolithiasis1
4Unknown StatusTreatmentLaparoscopic Nissen Fundoplication1
Not AvailableCompletedNot AvailableLabour Pain1
Not AvailableCompletedNot AvailableRenal Failure1
Not AvailableCompletedDiagnosticEsophagogastroduodenoscopy1
Not AvailableCompletedDiagnosticPatients Undergoing Diagnostic EGD1
Not AvailableCompletedPreventionPost-Operative Nausea and Vomiting (PONV)1
Not AvailableCompletedSupportive CareRespiration Disorders1
Not AvailableCompletedTreatmentCesarean Section1
Not AvailableCompletedTreatmentColonoscopy1
Not AvailableRecruitingNot AvailableObstetric Labor / Pregnancy1
Not AvailableRecruitingNot AvailableRenal Failure1
Not AvailableRecruitingTreatmentLabour Pain1
Not AvailableUnknown StatusSupportive CarePacemaker Implantation / Pain NOS1

Pharmacoeconomics

Manufacturers
  • Hospira inc
  • Sanofi aventis us llc
  • Abbott laboratories pharmaceutical products div
  • Astrazeneca lp
  • Baxter healthcare corp anesthesia and critical care
  • Baxter healthcare corp anesthesia critical care
  • Elkins sinn div ah robins co inc
  • International medication systems ltd
  • Parke davis div warner lambert co
  • Watson laboratories inc
  • International medication system
  • Mallinckrodt chemical inc
  • Roxane laboratories inc
  • Barr laboratories inc
  • Caraco pharmaceutical laboratories ltd
  • Duramed pharmaceuticals inc sub barr laboratories inc
  • Mallinckrodt inc
  • Mikah pharma llc
  • Mikart inc
  • Mutual pharmaceutical co inc
  • Vintage pharmaceuticals inc
  • Wyeth ayerst laboratories
Packagers
  • AstraZeneca Inc.
  • Barr Pharmaceuticals
  • Baxter International Inc.
  • Bayer Healthcare
  • Caraco Pharmaceutical Labs
  • D.M. Graham Laboratories Inc.
  • Diversified Healthcare Services Inc.
  • Hawkins Inc.
  • Hospira Inc.
  • Lake Erie Medical and Surgical Supply
  • Mallinckrodt Inc.
  • Nucare Pharmaceuticals Inc.
  • Pharmedium
  • Physicians Total Care Inc.
  • Qualitest
  • Roxane Labs
  • Sanofi-Aventis Inc.
  • Vintage Pharmaceuticals Inc.
Dosage forms
FormRouteStrength
Injection, solutionIntramuscular; Intravenous; Subcutaneous100 mg/2mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous100 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous25 mg/0.5mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous25 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous50 mg/1mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous75 mg/1.5mL
Injection, solutionIntramuscular; Intravenous; Subcutaneous75 mg/1mL
SyrupOral50 mg/5mL
TabletOral50 mg
LiquidIntramuscular; Intravenous; Subcutaneous50 mg
LiquidIntramuscular; Subcutaneous50 mg
LiquidIntramuscular; Intravenous; Subcutaneous100 mg
LiquidIntramuscular; Subcutaneous100 mg
SolutionIntramuscular; Subcutaneous100 mg
SolutionIntramuscular; Subcutaneous50 mg
LiquidIntramuscular; Intravenous; Subcutaneous75 mg
TabletOral50 mg/1
CapsuleOral
SolutionIntramuscular; Intravenous; Subcutaneous100 mg
SolutionIntramuscular; Intravenous; Subcutaneous10 mg
SolutionIntramuscular; Intravenous; Subcutaneous25 mg
SolutionIntramuscular; Intravenous; Subcutaneous50 mg
SolutionIntramuscular; Intravenous; Subcutaneous75 mg
InjectionIntramuscular50 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous100 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous25 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous50 mg/1mL
InjectionIntramuscular; Intravenous; Subcutaneous75 mg/1mL
Injection, solutionIntravenous10 mg/1mL
SolutionOral50 mg/5mL
TabletOral100 mg/1
TabletOral150 mg/1
TabletOral75 mg/1
SolutionIntravenous10 mg
Prices
Unit descriptionCostUnit
Meperidine HCl 100 mg/ml vial33.99USD vial
Meperidine hcl powder10.51USD g
Demerol 100 mg tablet3.33USD tablet
Demerol 100 mg/ml vial1.79USD ml
Demerol 50 mg tablet1.71USD tablet
Meperidine HCl 100 mg tablet1.33USD tablet
Meperidine 100 mg tablet1.31USD tablet
Demerol 100 mg/ml ampul1.1USD ml
Meperidine Hydrochloride 100 mg/ml1.1USD ml
Meperidine Hydrochloride 75 mg/ml1.04USD ml
Meperidine Hydrochloride 50 mg/ml0.98USD ml
Meperidine HCl 50 mg tablet0.93USD tablet
Demerol 50 mg/ml vial0.85USD ml
Meperidine 10 mg/ml syringe0.85USD ml
Meperidine 50 mg tablet0.69USD tablet
Demerol 50 mg/ml ampul0.58USD ml
Meperidine 10 mg/ml cartrdge0.3USD ml
Demerol 50 mg Tablet0.16USD tablet
Meperidine HCl 50 mg/5ml Solution0.14USD ml
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)270 °CPhysProp
water solubility3220 mg/L (at 30 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP2.72SANGSTER (1994)
logS-1.89ADME Research, USCD
pKa8.59SANGSTER (1994)
Predicted Properties
PropertyValueSource
Water Solubility1.11 mg/mLALOGPS
logP2.9ALOGPS
logP2.46ChemAxon
logS-2.4ALOGPS
pKa (Strongest Basic)8.16ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity72.48 m3·mol-1ChemAxon
Polarizability28.09 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9947
Blood Brain Barrier+0.9876
Caco-2 permeable+0.6683
P-glycoprotein substrateSubstrate0.7821
P-glycoprotein inhibitor IInhibitor0.5174
P-glycoprotein inhibitor IIInhibitor0.5401
Renal organic cation transporterInhibitor0.6375
CYP450 2C9 substrateNon-substrate0.8593
CYP450 2D6 substrateSubstrate0.8826
CYP450 3A4 substrateSubstrate0.5073
CYP450 1A2 substrateNon-inhibitor0.6897
CYP450 2C9 inhibitorNon-inhibitor0.6691
CYP450 2D6 inhibitorInhibitor0.7415
CYP450 2C19 inhibitorNon-inhibitor0.7635
CYP450 3A4 inhibitorNon-inhibitor0.6876
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5547
Ames testNon AMES toxic0.8694
CarcinogenicityNon-carcinogens0.8355
BiodegradationNot ready biodegradable0.9145
Rat acute toxicity3.1526 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8593
hERG inhibition (predictor II)Inhibitor0.5813
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
GC-MS Spectrum - EI-BGC-MSsplash10-00dl-9310000000-9f5598127b487d9339dc
GC-MS Spectrum - CI-BGC-MSsplash10-0002-0090000000-bcf24d9e6302b6454d0e
Mass Spectrum (Electron Ionization)MSsplash10-00di-9620000000-7309f4ee3918ea05f00d
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
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0090000000-2d9035995cbed82a8382
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0190000000-96507adebcd15f1cb917
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-1490000000-d1e318ddf3f73eb8db30
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-7970000000-d3f460862fa9a6d8be1f
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00di-8910000000-b45b7154182933942536
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00dl-9800000000-e79c047f6c6a8c9c0033

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylpiperidines. These are compounds containing a phenylpiperidine skeleton, which consists of a piperidine bound to a phenyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Piperidines
Sub Class
Phenylpiperidines
Direct Parent
Phenylpiperidines
Alternative Parents
Piperidinecarboxylic acids / Aralkylamines / Benzene and substituted derivatives / Trialkylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Azacyclic compounds / Organopnictogen compounds / Organic oxides
show 2 more
Substituents
Phenylpiperidine / Piperidinecarboxylic acid / Aralkylamine / Monocyclic benzene moiety / Benzenoid / Amino acid or derivatives / Carboxylic acid ester / Tertiary amine / Tertiary aliphatic amine / Carboxylic acid derivative
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines (CHEBI:6754)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
General Function
Opioid receptor activity
Specific Function
G-protein coupled opioid receptor that functions as receptor for endogenous alpha-neoendorphins and dynorphins, but has low affinity for beta-endorphins. Also functions as receptor for various synt...
Gene Name
OPRK1
Uniprot ID
P41145
Uniprot Name
Kappa-type opioid receptor
Molecular Weight
42644.665 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]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Voltage-gated cation channel activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. This protein plays a key role in synaptic p...
Gene Name
GRIN1
Uniprot ID
Q05586
Uniprot Name
Glutamate receptor ionotropic, NMDA 1
Molecular Weight
105371.945 Da
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine. In concert with DAPK1 at extrasynaptic site...
Gene Name
GRIN2B
Uniprot ID
Q13224
Uniprot Name
Glutamate receptor ionotropic, NMDA 2B
Molecular Weight
166365.885 Da
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Zinc ion binding
Specific Function
NMDA receptor subtype of glutamate-gated ion channels possesses high calcium permeability and voltage-dependent sensitivity to magnesium. Activation requires binding of agonist to both types of sub...
Gene Name
GRIN2A
Uniprot ID
Q12879
Uniprot Name
Glutamate receptor ionotropic, NMDA 2A
Molecular Weight
165281.215 Da
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Nmda glutamate receptor activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine.
Gene Name
GRIN2C
Uniprot ID
Q14957
Uniprot Name
Glutamate receptor ionotropic, NMDA 2C
Molecular Weight
134207.77 Da
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Antagonist
General Function
Nmda glutamate receptor activity
Specific Function
NMDA receptor subtype of glutamate-gated ion channels with high calcium permeability and voltage-dependent sensitivity to magnesium. Mediated by glycine.
Gene Name
GRIN2D
Uniprot ID
O15399
Uniprot Name
Glutamate receptor ionotropic, NMDA 2D
Molecular Weight
143750.685 Da
References
  1. Yamakura T, Sakimura K, Shimoji K: N-methyl-D-aspartate receptor channel block by meperidine is dependent on extracellular pH. Anesth Analg. 2000 Apr;90(4):928-32. [PubMed:10735801]
Kind
Protein group
Organism
Human
Pharmacological action
Unknown
Actions
Binder
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...

Components:
References
  1. Hustveit O: Binding of fentanyl and pethidine to muscarinic receptors in rat brain. Jpn J Pharmacol. 1994 Jan;64(1):57-9. [PubMed:8164394]
Details
8. Mu-type opioid receptor
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Voltage-gated calcium channel activity
Specific Function
Receptor for endogenous opioids such as beta-endorphin and endomorphin. Receptor for natural and synthetic opioids including morphine, heroin, DAMGO, fentanyl, etorphine, buprenorphin and methadone...
Gene Name
OPRM1
Uniprot ID
P35372
Uniprot Name
Mu-type opioid receptor
Molecular Weight
44778.855 Da
References
  1. Poulain R, Horvath D, Bonnet B, Eckhoff C, Chapelain B, Bodinier MC, Deprez B: From hit to lead. Combining two complementary methods for focused library design. Application to mu opiate ligands. J Med Chem. 2001 Oct 11;44(21):3378-90. [PubMed:11585443]
  2. Bryant, Bronwen (2010). Pharmacology for Health Professionals (Paperback) (3rd ed.). Chatswood: Mosby Australia. [ISBN:978-0-7295-3929-6]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Lomenzo SA, Izenwasser S, Gerdes RM, Katz JL, Kopajtic T, Trudell ML: Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine. Bioorg Med Chem Lett. 1999 Dec 6;9(23):3273-6. [PubMed:10612583]
  2. Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML: Synthesis and biological evaluation of meperidine analogues at monoamine transporters. J Med Chem. 2005 Mar 10;48(5):1336-43. [PubMed:15743177]
  3. Gu X, Izenwasser S, Wade D, Housman A, Gulasey G, Rhoden JB, Savoie CD, Mobley DL, Lomenzo SA, Trudell ML: Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. Bioorg Med Chem. 2010 Dec 1;18(23):8356-64. doi: 10.1016/j.bmc.2010.09.060. Epub 2010 Sep 29. [PubMed:20980153]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML: Synthesis and biological evaluation of meperidine analogues at monoamine transporters. J Med Chem. 2005 Mar 10;48(5):1336-43. [PubMed:15743177]
  2. Gu X, Izenwasser S, Wade D, Housman A, Gulasey G, Rhoden JB, Savoie CD, Mobley DL, Lomenzo SA, Trudell ML: Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. Bioorg Med Chem. 2010 Dec 1;18(23):8356-64. doi: 10.1016/j.bmc.2010.09.060. Epub 2010 Sep 29. [PubMed:20980153]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Binding
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. Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML: Synthesis and biological evaluation of meperidine analogues at monoamine transporters. J Med Chem. 2005 Mar 10;48(5):1336-43. [PubMed:15743177]
  2. Gu X, Izenwasser S, Wade D, Housman A, Gulasey G, Rhoden JB, Savoie CD, Mobley DL, Lomenzo SA, Trudell ML: Synthesis and structure-activity studies of benzyl ester meperidine and normeperidine derivatives as selective serotonin transporter ligands. Bioorg Med Chem. 2010 Dec 1;18(23):8356-64. doi: 10.1016/j.bmc.2010.09.060. Epub 2010 Sep 29. [PubMed:20980153]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Triglyceride lipase activity
Specific Function
Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acy...
Gene Name
CES1
Uniprot ID
P23141
Uniprot Name
Liver carboxylesterase 1
Molecular Weight
62520.62 Da
References
  1. Zhang J, Burnell JC, Dumaual N, Bosron WF: Binding and hydrolysis of meperidine by human liver carboxylesterase hCE-1. J Pharmacol Exp Ther. 1999 Jul;290(1):314-8. [PubMed:10381793]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
Inducer
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. Rane A, Liu Z, Henderson CJ, Wolf CR: Divergent regulation of cytochrome P450 enzymes by morphine and pethidine: a neuroendocrine mechanism? Mol Pharmacol. 1995 Jan;47(1):57-64. [PubMed:7838134]
  2. Buck ML: Is Meperidine the Drug That Just Won't Die? J Pediatr Pharmacol Ther. 2011 Jul;16(3):167-9. doi: 10.5863/1551-6776-16.3.167. [PubMed:22479158]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Ramirez J, Innocenti F, Schuetz EG, Flockhart DA, Relling MV, Santucci R, Ratain MJ: CYP2B6, CYP3A4, and CYP2C19 are responsible for the in vitro N-demethylation of meperidine in human liver microsomes. Drug Metab Dispos. 2004 Sep;32(9):930-6. [PubMed:15319333]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
Curator comments
In vitro data support this enzyme action.
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
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 oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Rane A, Liu Z, Henderson CJ, Wolf CR: Divergent regulation of cytochrome P450 enzymes by morphine and pethidine: a neuroendocrine mechanism? Mol Pharmacol. 1995 Jan;47(1):57-64. [PubMed:7838134]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Edwards DJ, Svensson CK, Visco JP, Lalka D: Clinical pharmacokinetics of pethidine: 1982. Clin Pharmacokinet. 1982 Sep-Oct;7(5):421-33. [PubMed:6754208]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Edwards DJ, Svensson CK, Visco JP, Lalka D: Clinical pharmacokinetics of pethidine: 1982. Clin Pharmacokinet. 1982 Sep-Oct;7(5):421-33. [PubMed:6754208]

Drug created on June 13, 2005 07:24 / Updated on November 17, 2018 07:09