pethidine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
analgesics, pethidine derivatives 1690 57-42-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • meperidine
  • pethidine
  • isonipecaine
  • meperidol
  • pethanol
  • pethidin
  • meperidine hydrochloride
  • pethidine hydrochloride
  • meperidine HCl
  • pethidine HCl
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.
  • Molecular weight: 247.34
  • Formula: C15H21NO2
  • CLOGP: 2.23
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 0
  • TPSA: 29.54
  • ALOGS: -2.35
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P
0.40 g R

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 3.22 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 13 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 60.65 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 52 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 2.30 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 4.90 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.42 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 7.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 10, 1942 FDA SANOFI AVENTIS US

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 4189.25 13.74 1875 13768 241950 46428469
Contrast media allergy 341.44 13.74 86 15557 1713 46668706
Drug intolerance 198.46 13.74 245 15398 146804 46523615
International normalised ratio fluctuation 191.86 13.74 57 15586 2136 46668283
Obliterative bronchiolitis 141.73 13.74 43 15600 1732 46668687
Upper respiratory tract infection 98.83 13.74 114 15529 63442 46606977
Bloody discharge 96.53 13.74 28 15615 963 46669456
Treatment failure 81.40 13.74 126 15517 92961 46577458
Psoriasis 72.38 13.74 109 15534 78495 46591924
Serotonin syndrome 72.28 13.74 62 15581 24158 46646261
Lyme disease 69.11 13.74 27 15616 2336 46668083
Vomiting 66.97 13.74 314 15329 452480 46217939
Herpes zoster 60.88 13.74 93 15550 67779 46602640
Respiratory arrest 56.50 13.74 63 15580 33753 46636666
Urticaria 49.74 13.74 117 15526 117775 46552644
Infusion related reaction 47.75 13.74 105 15538 101103 46569316
Nausea 44.94 13.74 387 15256 687067 45983352
Bronchitis chronic 42.85 13.74 23 15620 4144 46666275
Rash 34.75 13.74 221 15422 356291 46314128
Anaphylactic reaction 32.00 13.74 61 15582 53051 46617368
Hallucination 29.64 13.74 57 15586 49894 46620525
Arteriospasm coronary 29.10 13.74 17 15626 3604 46666815
Neonatal seizure 26.73 13.74 8 15635 307 46670112
Neonatal respiratory depression 25.79 13.74 6 15637 84 46670335
Hypertension 25.15 13.74 131 15512 196225 46474194
Therapeutic product effect incomplete 25.08 13.74 70 15573 78083 46592336
Product dose omission issue 24.43 13.74 13 15630 168507 46501912
Pulse absent 24.21 13.74 17 15626 4939 46665480
Unresponsive to stimuli 23.25 13.74 40 15603 32134 46638285
Diarrhoea 23.03 13.74 103 15540 559499 46110920
Dactylitis 22.60 13.74 10 15633 1183 46669236
Alopecia 21.47 13.74 14 15629 162400 46508019
Death 21.24 13.74 51 15592 335497 46334922
Injection site pain 21.08 13.74 5 15638 107147 46563272
Tarsal tunnel syndrome 20.99 13.74 8 15635 647 46669772
Pancreatic carcinoma recurrent 20.48 13.74 5 15638 87 46670332
Drug abuser 20.39 13.74 13 15630 3220 46667199
Thrombocytopenia 20.20 13.74 90 15553 126491 46543928
Moaning 19.98 13.74 8 15635 738 46669681
Pain 19.73 13.74 245 15398 476703 46193716
Methaemoglobinaemia 19.65 13.74 11 15632 2151 46668268
Extremity contracture 19.46 13.74 9 15634 1180 46669239
Cardiac aneurysm 19.29 13.74 8 15635 808 46669611
Condition aggravated 19.11 13.74 33 15610 245019 46425400
Acute kidney injury 19.09 13.74 31 15612 235824 46434595
Joint swelling 18.69 13.74 107 15536 165966 46504453
Fatigue 18.46 13.74 124 15519 608573 46061846
Lip dry 18.39 13.74 12 15631 3092 46667327
Limb mass 18.19 13.74 11 15632 2483 46667936
Respiratory alkalosis 17.80 13.74 11 15632 2580 46667839
Purpura senile 17.67 13.74 7 15636 628 46669791
Asthenia 16.87 13.74 51 15592 311024 46359395
Breath sounds absent 16.25 13.74 5 15638 211 46670208
Emotional distress 15.77 13.74 33 15610 30674 46639745
Procedural complication 15.48 13.74 13 15630 4917 46665502
Vestibular disorder 15.35 13.74 8 15635 1358 46669061
Encephalopathy neonatal 15.03 13.74 3 15640 19 46670400
Iodine allergy 15.02 13.74 6 15637 550 46669869
Gastrointestinal inflammation 14.88 13.74 12 15631 4289 46666130
Pickwickian syndrome 14.35 13.74 5 15638 313 46670106
Nervous system disorder 14.30 13.74 22 15621 16107 46654312
Maternal drugs affecting foetus 14.21 13.74 13 15630 5505 46664914
Resorption bone increased 13.82 13.74 7 15636 1120 46669299

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 494.54 14.98 261 6554 68258 29877405
Chills 64.85 14.98 81 6734 72257 29873406
Serotonin syndrome 57.87 14.98 41 6774 17850 29927813
Drug dependence 35.22 14.98 33 6782 21262 29924401
Respiratory depression 29.64 14.98 23 6792 11480 29934183
Drug abuser 26.62 14.98 15 6800 4386 29941277
Sedation 24.47 14.98 24 6791 16349 29929314
Drug withdrawal syndrome 24.11 14.98 26 6789 19783 29925880
Administration related reaction 22.09 14.98 5 6810 93 29945570
Intra-abdominal haemorrhage 20.89 14.98 10 6805 2092 29943571
Oesophageal mucosa erythema 20.77 14.98 4 6811 32 29945631
Procedural complication 18.58 14.98 12 6803 4485 29941178
Mucosal atrophy 17.90 14.98 4 6811 70 29945593
Carditis 17.59 14.98 4 6811 76 29945587
Gastrointestinal scarring 16.43 14.98 4 6811 103 29945560
Respiratory arrest 16.11 14.98 26 6789 29232 29916431
Anal stenosis 15.75 14.98 4 6811 123 29945540
Cytokine release syndrome 15.66 14.98 15 6800 9918 29935745

Pharmacologic Action:

SourceCodeDescription
ATC N02AB02 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Phenylpiperidine derivatives
ATC N02AB52 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Phenylpiperidine derivatives
ATC N02AB72 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Phenylpiperidine derivatives
ATC N02AG03 NERVOUS SYSTEM
ANALGESICS
OPIOIDS
Opioids in combination with antispasmodics
MeSH PA D000759 Adjuvants, Anesthesia
MeSH PA D000700 Analgesics
MeSH PA D000701 Analgesics, Opioid
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D009294 Narcotics
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
FDA MoA N0000175684 Full Opioid Agonists
FDA EPC N0000175690 Opioid Agonist
CHEBI has role CHEBI:35482 narcotic analgesics
CHEBI has role CHEBI:53784 antispasmodics
CHEBI has role CHEBI:55322 mu opioid agonist
CHEBI has role CHEBI:59282 kappa-opioid receptor agonists

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
General anesthesia indication 50697003
Severe pain indication 76948002
Labor pain indication 247412007
Local anesthesia indication 386761002
Sedation as Adjunct to Anesthesia indication
Dependent drug abuse contraindication 6525002
Necrosis contraindication 6574001
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Hyperbilirubinemia contraindication 14783006 DOID:2741
Neuroleptic malignant syndrome contraindication 15244003 DOID:14464
Agranulocytosis contraindication 17182001 DOID:12987
Jaundice contraindication 18165001
Lowered convulsive threshold contraindication 19260006
Disorder of the central nervous system contraindication 23853001 DOID:331
Alcohol intoxication contraindication 25702006
Gangrene contraindication 36024000
Hypothyroidism contraindication 40930008 DOID:1459
Myxedema contraindication 43153006 DOID:11634
Low blood pressure contraindication 45007003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Thrombophlebitis contraindication 64156001 DOID:3875
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Poisoning by acetaminophen contraindication 70273001
Sleep apnea contraindication 73430006 DOID:0050847
Extrapyramidal disease contraindication 76349003
Urethral stricture contraindication 76618002
Decreased respiratory function contraindication 80954004
Disorder of brain contraindication 81308009 DOID:936
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Cor pulmonale contraindication 83291003 DOID:8515
Epilepsy contraindication 84757009 DOID:1826
Leukopenia contraindication 84828003 DOID:615
Gastrointestinal obstruction contraindication 126765001
Hb SS disease contraindication 127040003 DOID:10923
Seizure disorder contraindication 128613002
Drug-induced psychosis contraindication 191483003 DOID:1742
Disease of liver contraindication 235856003 DOID:409
Bladder outflow obstruction contraindication 236645006
Pyloric obstruction contraindication 244815007
Benign prostatic hyperplasia contraindication 266569009
Pheochromocytoma contraindication 302835009
Bone marrow depression contraindication 307762000
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Angle-closure glaucoma contraindication 392291006 DOID:13550
Breastfeeding (mother) contraindication 413712001
Central nervous system depression contraindication 418072004
Acute exacerbation of asthma contraindication 708038006
Injection Site Sequelae contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.56 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Mu-type opioid receptor GPCR AGONIST Ki 6.04 CHEMBL CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 6.49 CHEMBL
Glutamate receptor ionotropic, NMDA 3A Ion channel WOMBAT-PK
Kappa-type opioid receptor GPCR Ki 5.63 WOMBAT-PK
Sodium-dependent dopamine transporter Transporter WOMBAT-PK
Sodium-dependent dopamine transporter Transporter Ki 4.75 CHEMBL
Mu-type opioid receptor GPCR Ki 6.35 CHEMBL
Opioid receptor GPCR IC50 6.30 CHEMBL
Opioid receptor GPCR EC50 6.15 CHEMBL
Sodium-dependent serotonin transporter Transporter Ki 6.39 CHEMBL

External reference:

IDSource
4019813 VUID
N0000147902 NUI
D01383 KEGG_DRUG
50-13-5 SECONDARY_CAS_RN
4018030 VANDF
4019813 VANDF
C0025376 UMLSCUI
CHEBI:6754 CHEBI
CHEMBL607 ChEMBL_ID
CHEMBL1701 ChEMBL_ID
D008614 MESH_DESCRIPTOR_UI
DB00454 DRUGBANK_ID
7221 IUPHAR_LIGAND_ID
411 INN_ID
9E338QE28F UNII
4058 PUBCHEM_CID
103755 RXNORM
1858 MMSL
5046 MMSL
d00017 MMSL
001542 NDDF
004620 NDDF
2878005 SNOMEDCT_US
387298007 SNOMEDCT_US
54544005 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Meperidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-3545 SOLUTION 50 mg ORAL ANDA 32 sections
Meperidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-4595 TABLET 50 mg ORAL ANDA 32 sections
Meperidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-4596 TABLET 100 mg ORAL ANDA 32 sections
Meperidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0054-8595 TABLET 50 mg ORAL ANDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1176 INJECTION, SOLUTION 25 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1178 INJECTION, SOLUTION 50 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1179 INJECTION, SOLUTION 75 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1180 INJECTION, SOLUTION 100 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1181 INJECTION, SOLUTION 50 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1201 INJECTION, SOLUTION 100 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1203 INJECTION, SOLUTION 25 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1253 INJECTION, SOLUTION 50 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1254 INJECTION, SOLUTION 75 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1255 INJECTION, SOLUTION 100 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1256 INJECTION, SOLUTION 100 mg INTRAMUSCULAR NDA 32 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1362 INJECTION, SOLUTION 25 mg INTRAMUSCULAR NDA 35 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1377 INJECTION, SOLUTION 100 mg INTRAMUSCULAR NDA 35 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-1418 INJECTION, SOLUTION 50 mg INTRAMUSCULAR NDA 35 sections
DEMEROL HUMAN PRESCRIPTION DRUG LABEL 1 0409-2033 INJECTION, SOLUTION 75 mg INTRAMUSCULAR NDA 35 sections
MEPERIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0641-6052 INJECTION 25 mg INTRAMUSCULAR ANDA 30 sections
MEPERIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0641-6053 INJECTION 50 mg INTRAMUSCULAR ANDA 30 sections
MEPERIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0641-6054 INJECTION 100 mg INTRAMUSCULAR ANDA 30 sections
Demerol HUMAN PRESCRIPTION DRUG LABEL 1 30698-335 TABLET 50 mg ORAL NDA 32 sections
Demerol HUMAN PRESCRIPTION DRUG LABEL 1 30698-337 TABLET 100 mg ORAL NDA 32 sections
Meperidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-050 TABLET 50 mg ORAL ANDA 30 sections
Meperidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42806-051 TABLET 100 mg ORAL ANDA 30 sections
meperidine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 46672-829 TABLET 50 mg ORAL ANDA 30 sections
meperidine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 46672-830 TABLET 75 mg ORAL ANDA 30 sections
meperidine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 46672-831 TABLET 100 mg ORAL ANDA 30 sections
meperidine hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 46672-832 TABLET 150 mg ORAL ANDA 30 sections