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

Stem definitionDrug idCAS RN
835 113775-47-6

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • dexmedetomidine
  • (S)-Medetomidine
  • dexmedetomidine hydrochloride
  • dexdor
  • dexmedetomidine HCl
  • MPV1440
A imidazole derivative that is an agonist of ADRENERGIC ALPHA-2 RECEPTORS. It is closely-related to MEDETOMIDINE, which is the racemic form of this compound.
  • Molecular weight: 200.29
  • Formula: C13H16N2
  • CLOGP: 3.11
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 1
  • TPSA: 28.68
  • ALOGS: -3.06
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1 mg P

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.09 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
Vd (Volume of distribution) 1.60 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 11 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.06 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 2.20 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Dec. 17, 1999 FDA HOSPIRA
Jan. 29, 2001 PMDA Abbott Japan, Maruishi Pharmaceutical

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
Bradycardia 167.78 32.72 83 3153 70973 53274857
Product administered to patient of inappropriate age 99.74 32.72 25 3211 2811 53343019
Agitation 94.12 32.72 53 3183 58573 53287257
Delirium 81.88 32.72 43 3193 41386 53304444
Floppy iris syndrome 75.96 32.72 12 3224 118 53345712
Upper airway obstruction 73.54 32.72 15 3221 664 53345166
Glossoptosis 67.95 32.72 10 3226 58 53345772
Respiratory acidosis 67.32 32.72 22 3214 6366 53339464
Sinus arrest 63.56 32.72 16 3220 1828 53344002
Hypotension 62.87 32.72 77 3159 253999 53091831
Respiratory depression 62.66 32.72 25 3211 12781 53333049
Laryngeal stenosis 59.66 32.72 13 3223 793 53345037
Cardiac arrest 56.14 32.72 46 3190 93621 53252209
Generalised tonic-clonic seizure 54.38 32.72 29 3207 28729 53317101
Hepatic function abnormal 50.22 32.72 30 3206 36869 53308961
Withdrawal syndrome 49.74 32.72 24 3212 19277 53326553
Tachyphylaxis 47.71 32.72 9 3227 264 53345566
Drug interaction 45.55 32.72 61 3175 219268 53126562
Product closure removal difficult 44.75 32.72 6 3230 15 53345815
Ventricular dysfunction 42.86 32.72 13 3223 2950 53342880
Respiratory failure 41.52 32.72 40 3196 100472 53245358
Local anaesthetic systemic toxicity 40.70 32.72 9 3227 587 53345243
Abdominal compartment syndrome 40.08 32.72 9 3227 630 53345200
Acute respiratory distress syndrome 39.84 32.72 22 3214 23310 53322520
Hyperthermia 39.39 32.72 16 3220 8553 53337277
Laryngospasm 38.67 32.72 12 3224 2938 53342892
Device pacing issue 36.58 32.72 6 3230 76 53345754
Hypernatraemia 35.40 32.72 14 3222 6983 53338847

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
Bradycardia 219.78 23.79 134 4620 71428 32437344
Cardiac arrest 149.72 23.79 119 4635 96657 32412115
Hyperthermia 138.95 23.79 54 4700 10674 32498098
Diabetes insipidus 132.46 23.79 37 4717 2595 32506177
Delirium 92.07 23.79 65 4689 43981 32464791
Arteriospasm coronary 86.02 23.79 27 4727 2833 32505939
Product administered to patient of inappropriate age 82.35 23.79 26 4728 2780 32505992
Seizure like phenomena 77.08 23.79 18 4736 612 32508160
Postoperative ileus 75.24 23.79 18 4736 680 32508092
Hyperthermia malignant 73.84 23.79 22 4732 1937 32506835
Drug withdrawal syndrome 67.28 23.79 40 4714 20191 32488581
Intestinal pseudo-obstruction 63.32 23.79 18 4736 1343 32507429
Hypotension 60.73 23.79 111 4643 215999 32292773
Acute motor axonal neuropathy 60.24 23.79 10 4744 51 32508721
Myoclonus 51.45 23.79 30 4724 14599 32494173
Agitation 49.73 23.79 51 4703 57185 32451587
Electrocardiogram QT prolonged 49.12 23.79 43 4711 39598 32469174
Off label use 47.73 23.79 124 4630 306196 32202576
Epidermolysis bullosa 47.11 23.79 9 4745 112 32508660
Respiratory failure 43.39 23.79 65 4689 107117 32401655
Polyuria 40.89 23.79 21 4733 7964 32500808
Upper airway obstruction 37.12 23.79 10 4744 611 32508161
Malignant catatonia 35.95 23.79 8 4746 218 32508554
Fatigue 34.87 23.79 5 4749 350696 32158076
Serotonin syndrome 34.84 23.79 26 4728 19091 32489681
Floppy iris syndrome 32.92 23.79 8 4746 323 32508449
Laryngomalacia 32.75 23.79 8 4746 330 32508442
Neuroleptic malignant syndrome 32.34 23.79 24 4730 17471 32491301
Macule 31.88 23.79 10 4744 1045 32507727
Sedation complication 30.76 23.79 10 4744 1172 32507600
Urinary bladder rupture 30.69 23.79 6 4748 85 32508687
Product use issue 30.39 23.79 38 4716 52739 32456033
Burkholderia test positive 30.32 23.79 8 4746 451 32508321
Cardiac arrest neonatal 29.88 23.79 5 4749 27 32508745
Hypernatraemia 29.24 23.79 17 4737 8216 32500556
Torsade de pointes 28.18 23.79 16 4738 7399 32501373
Ventricular fibrillation 28.14 23.79 22 4732 17288 32491484
Glossoptosis 27.86 23.79 6 4748 140 32508632
Sinus arrest 27.53 23.79 10 4744 1634 32507138
Tachypnoea 26.57 23.79 21 4733 16762 32492010
Drug withdrawal syndrome neonatal 26.18 23.79 12 4742 3552 32505220
Transcranial electrical motor evoked potential monitoring abnormal 25.78 23.79 4 4750 12 32508760
Methaemoglobinaemia 25.34 23.79 11 4743 2865 32505907
Tachycardia 25.14 23.79 43 4711 79045 32429727
Postresuscitation encephalopathy 25.09 23.79 4 4750 15 32508757
Multiple organ dysfunction syndrome 24.91 23.79 40 4714 69814 32438958
Product use in unapproved indication 24.61 23.79 45 4709 87159 32421613
Atonic urinary bladder 24.51 23.79 4 4750 18 32508754
Asthenia 24.28 23.79 3 4751 235941 32272831
Abdominal compartment syndrome 24.19 23.79 8 4746 989 32507783

Pharmacologic Action:

SourceCodeDescription
ATC N05CM18 NERVOUS SYSTEM
PSYCHOLEPTICS
HYPNOTICS AND SEDATIVES
Other hypnotics and sedatives
FDA MoA N0000009918 Adrenergic alpha2-Agonists
FDA EPC N0000175554 Central alpha-2 Adrenergic Agonist
CHEBI has role CHEBI:35569 alpha-adrenergic receptor agonist
CHEBI has role CHEBI:35717 sedatives
FDA PE N0000175975 General Anesthesia
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D058647 Adrenergic alpha-2 Receptor Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D002491 Central Nervous System Agents
MeSH PA D002492 Central Nervous System Depressants
MeSH PA D006993 Hypnotics and Sedatives
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Conscious sedation indication 314271007
Complete atrioventricular block contraindication 27885002
Hypovolemia contraindication 28560003
Hypertensive disorder contraindication 38341003 DOID:10763
Low blood pressure contraindication 45007003
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Diabetes mellitus contraindication 73211009 DOID:9351
Kidney disease contraindication 90708001 DOID:557
Disease of liver contraindication 235856003 DOID:409
Cardiac Decompensation contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 13.36 acidic
pKa2 6.76 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
EQ 200MCG BASE/50ML (EQ 4MCG BASE/ML) PRECEDEX HOSPIRA N021038 March 13, 2013 RX INJECTABLE INJECTION 8455527 Jan. 4, 2032 USE FOR SEDATION
EQ 400MCG BASE/100ML (EQ 4MCG BASE/ML) PRECEDEX HOSPIRA N021038 March 13, 2013 RX INJECTABLE INJECTION 8455527 Jan. 4, 2032 USE FOR SEDATION
EQ 80MCG BASE/20ML (EQ 4MCG BASE/ML) PRECEDEX HOSPIRA N021038 Nov. 14, 2014 RX INJECTABLE INJECTION 8455527 Jan. 4, 2032 USE FOR SEDATION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alpha-2B adrenergic receptor GPCR AGONIST Ki 9.70 IUPHAR CHEMBL
Alpha-2C adrenergic receptor GPCR AGONIST Ki 9.30 IUPHAR CHEMBL
Alpha-2A adrenergic receptor GPCR AGONIST EC50 8.82 CHEMBL CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.50 PDSP
Alpha-1A adrenergic receptor GPCR Ki 6.70 PDSP
Alpha-1D adrenergic receptor GPCR Ki 10.82 CHEMBL
Alpha-2A adrenergic receptor GPCR Ki 10.82 CHEMBL
Alpha-1A adrenergic receptor GPCR EC50 6.42 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 10.82 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 8.30 CHEMBL
Alpha-1B adrenergic receptor GPCR EC50 6.44 CHEMBL

External reference:

IDSource
4021214 VUID
N0000148660 NUI
D00514 KEGG_DRUG
145108-58-3 SECONDARY_CAS_RN
4021214 VANDF
4021215 VANDF
C0113293 UMLSCUI
CHEBI:4466 CHEBI
CZX PDB_CHEM_ID
CHEMBL778 ChEMBL_ID
DB00633 DRUGBANK_ID
CHEMBL2106195 ChEMBL_ID
D020927 MESH_DESCRIPTOR_UI
5311068 PUBCHEM_CID
6277 INN_ID
521 IUPHAR_LIGAND_ID
67VB76HONO UNII
228054 RXNORM
227894 MMSL
29394 MMSL
8598 MMSL
d04505 MMSL
008084 NDDF
008085 NDDF
116348007 SNOMEDCT_US
437750002 SNOMEDCT_US
438079000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9525 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 30 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 0143-9526 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 30 sections
Dexmedetomidine HCl HUMAN PRESCRIPTION DRUG LABEL 1 0143-9532 INJECTION 100 ug INTRAVENOUS ANDA 29 sections
DEXMEDETOMIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0338-9555 INJECTION 200 ug INTRAVENOUS ANDA 30 sections
DEXMEDETOMIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0338-9557 INJECTION 400 ug INTRAVENOUS ANDA 30 sections
PRECEDEX HUMAN PRESCRIPTION DRUG LABEL 1 0404-9938 INJECTION, SOLUTION, CONCENTRATE 100 ug INTRAVENOUS NDA 17 sections
Precedex HUMAN PRESCRIPTION DRUG LABEL 1 0409-1434 INJECTION, SOLUTION 4 ug INTRAVENOUS NDA 34 sections
Precedex HUMAN PRESCRIPTION DRUG LABEL 1 0409-1638 INJECTION, SOLUTION, CONCENTRATE 100 ug INTRAVENOUS NDA 34 sections
Precedex HUMAN PRESCRIPTION DRUG LABEL 1 0409-1660 INJECTION, SOLUTION 4 ug INTRAVENOUS NDA 34 sections
DEXMEDETOMIDINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0781-3493 INJECTION 4 ug INTRAVENOUS ANDA 29 sections
DEXMEDETOMIDINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0781-3494 INJECTION 4 ug INTRAVENOUS ANDA 29 sections
DEXMEDETOMIDINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 0781-3495 INJECTION 4 ug INTRAVENOUS ANDA 29 sections
Dexmedetomidine HUMAN PRESCRIPTION DRUG LABEL 1 16729-239 INJECTION, SOLUTION 100 ug INTRAVENOUS ANDA 28 sections
DEXMEDETOMIDINE HUMAN PRESCRIPTION DRUG LABEL 1 16729-432 INJECTION, SOLUTION 100 ug INTRAVENOUS ANDA 28 sections
Dexmedetomidine HUMAN PRESCRIPTION DRUG LABEL 1 17478-055 INJECTION, SOLUTION, CONCENTRATE 100 ug INTRAVENOUS ANDA 32 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42023-146 INJECTION, SOLUTION, CONCENTRATE 100 ug INTRAVENOUS ANDA 32 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42023-186 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 32 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 42023-187 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 32 sections
DEXMEDETOMIDINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 43066-555 INJECTION 200 ug INTRAVENOUS ANDA 30 sections
DEXMEDETOMIDINE HYDROCHLORIDE IN 0.9% SODIUM CHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 43066-557 INJECTION 400 ug INTRAVENOUS ANDA 30 sections
DEXMEDETOMIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 43066-561 INJECTION 200 ug INTRAVENOUS ANDA 30 sections
DEXMEDETOMIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 43066-565 INJECTION 400 ug INTRAVENOUS ANDA 30 sections
DEXMEDETOMIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 43598-975 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 29 sections
DEXMEDETOMIDINE HYDROCHLORIDE HUMAN PRESCRIPTION DRUG LABEL 1 43598-976 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 29 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 44567-600 INJECTION, SOLUTION, CONCENTRATE 100 ug INTRAVENOUS NDA 27 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 44567-601 INJECTION, SOLUTION, CONCENTRATE 100 ug INTRAVENOUS NDA 27 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 44567-602 INJECTION 4 ug INTRAVENOUS NDA 27 sections
Dexmedetomidine Hydrochloride HUMAN PRESCRIPTION DRUG LABEL 1 44567-603 INJECTION 4 ug INTRAVENOUS NDA 27 sections
Dexmedetomidine Hydrochloride in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 51224-015 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 33 sections
Dexmedetomidine Hydrochloride in Sodium Chloride HUMAN PRESCRIPTION DRUG LABEL 1 51224-115 INJECTION, SOLUTION 4 ug INTRAVENOUS ANDA 33 sections