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

Stem definitionDrug idCAS RN
sympathomimetic, phenethyl derivatives 1960 51-41-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • norepinephrine
  • (R)-Norepinephrine
  • arterenol
  • levarterenol
  • noradrenaline
  • norepinephrine bitartrate
  • (-)-noradrenaline
Precursor of epinephrine that is secreted by the ADRENAL MEDULLA and is a widespread central and autonomic neurotransmitter. Norepinephrine is the principal transmitter of most postganglionic sympathetic fibers, and of the diffuse projection system in the brain that arises from the LOCUS CERULEUS. It is also found in plants and is used pharmacologically as a sympathomimetic.
  • Molecular weight: 169.18
  • Formula: C8H11NO3
  • CLOGP: -0.99
  • LIPINSKI: 0
  • HAC: 4
  • HDO: 4
  • TPSA: 86.71
  • ALOGS: -1.13
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
6 mg P

ADMET properties:

PropertyValueReference
BA (Bioavailability) 3 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
July 13, 1950 FDA HOSPIRA

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 ineffective 346.06 113.04 116 313 101508 2256148
Stress cardiomyopathy 185.97 113.04 32 397 1429 2356227
Hypotension 155.44 113.04 49 380 32387 2325269
Shock 136.40 113.04 29 400 3975 2353681
Cardiac arrest 125.62 113.04 35 394 14895 2342761
Multiple organ dysfunction syndrome 122.85 113.04 30 399 7611 2350045

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 ineffective 201.93 74.16 77 304 63724 1682676
Hypotension 92.58 74.16 36 345 29618 1716782
Cardiac arrest 77.91 74.16 27 354 15903 1730497
Metabolic acidosis 77.62 74.16 21 360 5381 1741019
Stress cardiomyopathy 76.74 74.16 13 368 348 1746052
Multiple organ dysfunction syndrome 74.93 74.16 23 358 9219 1737181

Pharmacologic Action:

SourceCodeDescription
ATC C01CA03 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES
Adrenergic and dopaminergic agents
MeSH PA D018663 Adrenergic Agents
MeSH PA D000322 Adrenergic Agonists
MeSH PA D000316 Adrenergic alpha-Agonists
FDA EPC N0000175570 Catecholamine
FDA CS M0003647 Catecholamines
MeSH PA D002317 Cardiovascular Agents
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D014662 Vasoconstrictor Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchiectasis indication 12295008 DOID:9563
Bronchitis indication 32398004 DOID:6132
Low blood pressure indication 45007003
Pulmonary emphysema indication 87433001
Asthma indication 195967001 DOID:2841
Asthma management indication 406162001
Acute exacerbation of asthma indication 708038006
Hypovolemia contraindication 28560003
Hypercapnia contraindication 29596007
Hypertensive disorder contraindication 38341003 DOID:10763
Hypoxia contraindication 389086002
Thrombosis contraindication 439127006
Occlusive Vascular Disease contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.41 acidic
pKa2 12.03 acidic
pKa3 12.63 acidic
pKa4 8.83 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
Alpha-1A adrenergic receptor GPCR AGONIST Ki 5.82 CHEMBL CHEMBL
Alpha-2C adrenergic receptor GPCR AGONIST Ki 7.20 CHEMBL CHEMBL
Beta-2 adrenergic receptor GPCR AGONIST Kd 5.40 CHEMBL CHEMBL
Alpha-1D adrenergic receptor GPCR AGONIST Ki 7.40 IUPHAR CHEMBL
Beta-1 adrenergic receptor GPCR AGONIST Ki 6 IUPHAR CHEMBL
Alpha-2A adrenergic receptor GPCR AGONIST Ki 7.18 CHEMBL CHEMBL
Alpha-1B adrenergic receptor GPCR AGONIST Ki 4.69 CHEMBL CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 6.48 PDSP
Beta-3 adrenergic receptor GPCR Ki 5.37 PDSP
Sodium-dependent dopamine transporter Transporter Ki 5.07 PDSP
Beta-1 adrenergic receptor GPCR Ki 6.90 CHEMBL
Alpha-2B adrenergic receptor GPCR Ki 7.11 CHEMBL
Adrenergic receptor alpha-1 GPCR Ki 6.41 CHEMBL
Beta-2 adrenergic receptor GPCR Ki 5.38 CHEMBL
Beta-1 adrenergic receptor GPCR Ki 6.40 CHEMBL
Alpha-1A adrenergic receptor GPCR Ki 6.35 CHEMBL
Alpha-1B adrenergic receptor GPCR Ki 6.58 CHEMBL
Adrenergic receptor alpha-2 GPCR Ki 8.32 CHEMBL
Beta-2 adrenergic receptor GPCR Ki 5.22 CHEMBL
Adrenergic receptor alpha GPCR IC50 7.80 CHEMBL
Beta-2 adrenergic receptor GPCR Ki 5.30 CHEMBL
Adrenergic receptor beta GPCR IC50 6 CHEMBL
Mu-type opioid receptor GPCR Ki 4.85 CHEMBL

External reference:

IDSource
4019859 VUID
N0000147945 NUI
C0028351 UMLSCUI
D00076 KEGG_DRUG
111130009 SNOMEDCT_US
4019859 VANDF
7512 RXNORM
45555007 SNOMEDCT_US
d00323 MMSL
2706 MMSL
004718 NDDF
439260 PUBCHEM_CID
CHEBI:33569 CHEBI
CHEMBL1437 ChEMBL_ID
DB00368 DRUGBANK_ID
IFY5PE3ZRW UNII
108341-18-0 SECONDARY_CAS_RN
E5E PDB_CHEM_ID
LNR PDB_CHEM_ID
33 INN_ID
505 IUPHAR_LIGAND_ID
CHEMBL1356607 ChEMBL_ID
CHEMBL1434513 ChEMBL_ID
D009638 MESH_DESCRIPTOR_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Norepinephrine Bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 0143-9318 INJECTION 1 mg INTRAVENOUS ANDA 12 sections
Levophed HUMAN PRESCRIPTION DRUG LABEL 1 0409-1443 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS NDA 12 sections
LEVOPHED HUMAN PRESCRIPTION DRUG LABEL 1 0409-3375 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS NDA 12 sections
Norepinephrine Bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 0703-1153 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS ANDA 12 sections
NOREPINEPHRINE BITARTRATE HUMAN PRESCRIPTION DRUG LABEL 1 0781-3755 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS ANDA 12 sections
Norepinephrine bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 36000-162 INJECTION 1 mg INTRAVENOUS ANDA 12 sections
LEVOPHED(R) NOREPINEPHRINE BITARTRATE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1315 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS NDA 12 sections
Norepinephrine Bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 52533-164 INJECTION, SOLUTION 64 ug INTRAVENOUS unapproved drug other 7 sections
Norepinephrine Bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 52533-165 INJECTION, SOLUTION 16 ug INTRAVENOUS unapproved drug other 7 sections
Norepinephrine Bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 52533-166 INJECTION, SOLUTION 32 ug INTRAVENOUS unapproved drug other 7 sections
Norepinephrine bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 67457-852 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS ANDA 11 sections
Norepinephrine Bitartrate HUMAN PRESCRIPTION DRUG LABEL 1 70121-1576 INJECTION, SOLUTION, CONCENTRATE 1 mg INTRAVENOUS ANDA 11 sections
Viatrexx-Neuro 3 HUMAN PRESCRIPTION DRUG LABEL 15 73069-373 INJECTION 201 [kp_C] INTRAVENOUS unapproved drug other 11 sections