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

Stem definitionDrug idCAS RN
sympathomimetics 1024 299-42-3

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • ephedrine sulphate
  • ephedrine
  • ephedrin
  • ephedrine sulfate
  • ephedrine hydrochloride
  • ephedrine HCl
A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.
  • Molecular weight: 165.24
  • Formula: C10H15NO
  • CLOGP: 0.89
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 2
  • TPSA: 32.26
  • ALOGS: -1.30
  • ROTB: 3

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
50 mg P
8 mg N
50 mg O

ADMET properties:

None

Approvals:

DateAgencyCompanyOrphan
None FDA

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
Hypotension 94.08 26.47 84 2382 253992 53092608
Exposure during pregnancy 94.03 26.47 63 2403 124797 53221803
Bradycardia 84.43 26.47 48 2418 71008 53275592
Anaphylactic shock 69.48 26.47 29 2437 21864 53324736
Cardiac arrest 58.05 26.47 42 2424 93625 53252975
Mental status changes postoperative 52.30 26.47 9 2457 206 53346394
Live birth 51.32 26.47 21 2445 15038 53331562
Confusion postoperative 50.88 26.47 9 2457 243 53346357
Tachycardia 48.41 26.47 40 2426 108172 53238428
Procedural hypotension 46.62 26.47 11 2455 1262 53345338
Oliguria 46.11 26.47 17 2449 9221 53337379
Procedural hypertension 43.67 26.47 8 2458 264 53346336
Maternal exposure during delivery 43.21 26.47 10 2456 1055 53345545
Cardio-respiratory arrest 40.17 26.47 28 2438 58730 53287870
Anterior spinal artery syndrome 37.79 26.47 6 2460 82 53346518
Blood pressure decreased 34.36 26.47 26 2440 61843 53284757
Ventricular tachycardia 32.38 26.47 16 2450 17746 53328854
Serotonin syndrome 31.72 26.47 18 2448 26388 53320212
Maternal exposure during pregnancy 30.97 26.47 37 2429 155602 53190998
Spinal cord injury 30.67 26.47 7 2459 694 53345906
Antidepressant drug level above therapeutic 28.83 26.47 6 2460 387 53346213
Metabolic alkalosis 28.66 26.47 9 2457 3010 53343590
Postmortem blood drug level increased 26.69 26.47 6 2460 556 53346044
Arteriospasm coronary 26.67 26.47 9 2457 3768 53342832
Angle closure glaucoma 26.55 26.47 8 2458 2332 53344268

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
Anaphylactic shock 69.13 30.18 26 1474 15008 32497018
Toxicity to various agents 56.62 30.18 54 1446 177987 32334039
Hypertonia neonatal 46.87 30.18 9 1491 386 32511640
Locked-in syndrome 43.64 30.18 8 1492 266 32511760
Agitation neonatal 37.66 30.18 9 1491 1093 32510933
Delayed recovery from anaesthesia 35.04 30.18 8 1492 797 32511229
Hypotension 31.68 30.18 44 1456 216066 32295960

Pharmacologic Action:

SourceCodeDescription
ATC C01CA26 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
CARDIAC STIMULANTS EXCL. CARDIAC GLYCOSIDES
Adrenergic and dopaminergic agents
ATC R01AA03 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Sympathomimetics, plain
ATC R01AB05 RESPIRATORY SYSTEM
NASAL PREPARATIONS
DECONGESTANTS AND OTHER NASAL PREPARATIONS FOR TOPICAL USE
Sympathomimetics, combinations excl. corticosteroids
ATC R03CA02 RESPIRATORY SYSTEM
DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
ADRENERGICS FOR SYSTEMIC USE
Alpha- and beta-adrenoreceptor agonists
ATC S01FB02 SENSORY ORGANS
OPHTHALMOLOGICALS
MYDRIATICS AND CYCLOPLEGICS
Sympathomimetics excl. antiglaucoma preparations
ATC A08AA56 ALIMENTARY TRACT AND METABOLISM
ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
ANTIOBESITY PREPARATIONS, EXCL. DIET PRODUCTS
Centrally acting antiobesity products
FDA MoA N0000000209 Adrenergic alpha-Agonists
FDA MoA N0000000245 Adrenergic beta-Agonists
FDA PE N0000009456 Increased Norepinephrine Activity
FDA EPC N0000175552 alpha-Adrenergic Agonist
FDA EPC N0000175555 beta-Adrenergic Agonist
MeSH PA D018663 Adrenergic Agents
MeSH PA D002317 Cardiovascular Agents
MeSH PA D002491 Central Nervous System Agents
MeSH PA D000697 Central Nervous System Stimulants
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D013566 Sympathomimetics
MeSH PA D014662 Vasoconstrictor Agents
CHEBI has role CHEBI:35524 sympathomimetic
CHEBI has role CHEBI:35703 Xenobiotic
CHEBI has role CHEBI:76924 plant metabolites
CHEBI has role CHEBI:77715 decongestants
CHEBI has role CHEBI:78298 environmental contaminants
FDA EPC N0000192563 Norepinephrine Releasing Agent

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Bronchospasm indication 4386001
Sinus headache indication 4969004
Vasomotor rhinitis indication 8229003 DOID:4730
Bronchitis indication 32398004 DOID:6132
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Rhinitis indication 70076002 DOID:4483
Sneezing indication 76067001
Common cold indication 82272006 DOID:10459
Headache disorder indication 230461009
Influenza-like symptoms indication 315642008
Seasonal allergic rhinitis indication 367498001
Allergic conjunctivitis indication 473460002 DOID:11204
Intracranial hemorrhage contraindication 1386000
Brain damage contraindication 2470005
Goiter contraindication 3716002 DOID:12176
Ocular hypertension contraindication 4210003 DOID:9282
Gastritis contraindication 4556007 DOID:4029
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Hyperammonemia contraindication 9360008
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Asthenia contraindication 13791008
Hepatic encephalopathy contraindication 13920009 DOID:13413
Hyperkalemia contraindication 14140009
Severe chronic ulcerative colitis contraindication 14311001
Constipation contraindication 14760008 DOID:2089
Disorder of autonomic nervous system contraindication 15241006
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Pulmonary edema contraindication 19242006 DOID:11396
Hashimoto thyroiditis contraindication 21983002
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Ventricular tachycardia contraindication 25569003
Acute tuberculosis contraindication 25629007
Alcohol intoxication contraindication 25702006
Shock contraindication 27942005
Toxic megacolon contraindication 28536002 DOID:1770
Atony of colon contraindication 29479008
Hypercapnia contraindication 29596007
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Hypovolemic shock contraindication 39419009
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Third trimester pregnancy contraindication 41587001
Body fluid retention contraindication 43498006
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Pregnancy-induced hypertension contraindication 48194001
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Acidosis contraindication 51387008
Gastrointestinal perforation contraindication 51875005
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Paralytic ileus contraindication 55525008 DOID:8442
Heart disease contraindication 56265001 DOID:114
Peptic reflux disease contraindication 57643001
Multiple organ failure contraindication 57653000
Acute nephropathy contraindication 58574008
Metabolic acidosis contraindication 59455009
Hepatic failure contraindication 59927004
Ulcerative colitis contraindication 64766004 DOID:8577
Blood coagulation disorder contraindication 64779008 DOID:1247
Poisoning by phenobarbital contraindication 64921004
Arterial thrombosis contraindication 65198009
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Benign intracranial hypertension contraindication 68267002 DOID:11459
Psychotic disorder contraindication 69322001
Poisoning by acetaminophen contraindication 70273001
Abnormal vasomotor function contraindication 70670009
Arteriosclerotic vascular disease contraindication 72092001
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050847
Gastrointestinal hemorrhage contraindication 74474003
Urethral stricture contraindication 76618002
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Oliguria contraindication 83128009
Cor pulmonale contraindication 83291003 DOID:8515
Hiatal hernia contraindication 84089009 DOID:12642
Open-angle glaucoma contraindication 84494001 DOID:1067
Epilepsy contraindication 84757009 DOID:1826
Pulmonary emphysema contraindication 87433001
Kidney disease contraindication 90708001 DOID:557
Thyrotoxicosis contraindication 90739004 DOID:7997
Myasthenia gravis contraindication 91637004 DOID:437
Dermatitis herpetiformis contraindication 111196000 DOID:8505
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
Gastrointestinal obstruction contraindication 126765001
Neoplasm of brain contraindication 126952004 DOID:1319
Seizure disorder contraindication 128613002
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Liver function tests abnormal contraindication 166603001
Cystic fibrosis contraindication 190905008 DOID:1485
Drug-induced psychosis contraindication 191483003 DOID:1742
Angina pectoris contraindication 194828000
Partial atrioventricular block contraindication 195039008
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Cerebrovascular accident contraindication 230690007
Coronary artery bypass graft contraindication 232717009
Myocardial dysfunction contraindication 233928007
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Disease of liver contraindication 235856003 DOID:409
Hyporeninemic hypoaldosteronism contraindication 236464008
Bladder outflow obstruction contraindication 236645006
Morbid obesity contraindication 238136002 DOID:11981
Sepsis syndrome contraindication 238150007
Hypocomplementemic urticarial vasculitis contraindication 239945009
Rhabdomyolysis contraindication 240131006
Pyloric obstruction contraindication 244815007
Esophageal dysmotility contraindication 266434009 DOID:9192
Benign prostatic hyperplasia contraindication 266569009
Dyspnea contraindication 267036007
Edema contraindication 267038008
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Continuous fever contraindication 271751000
Drowsy contraindication 271782001
Exacerbation of asthma contraindication 281239006
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Thromboembolic disorder contraindication 371039008
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000
Smoking cessation assistance contraindication 384742004
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Cardiovascular event risk contraindication 395112001
Pseudomembranous enterocolitis contraindication 397683000
Gastric ulcer contraindication 397825006 DOID:10808
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Traumatic injury contraindication 417746004
Central nervous system depression contraindication 418072004
Porphyria contraindication 418470004
Ultrarapid metabolizer due to cytochrome p450 CYP2D6 variant contraindication 422681000
Fever greater than 100.4 Fahrenheit contraindication 426000000
Dysfunction of sphincter of Oddi contraindication 430887001
Hypertensive urgency contraindication 443482000
Smokes tobacco daily contraindication 449868002
Acute exacerbation of asthma contraindication 708038006
Acute Thromboembolic Stroke contraindication
Severe Hypoxemia contraindication
Theophylline Toxicity contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 9.22 Basic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
50MG/10ML (5MG/ML) EMERPHED NEXUS PHARMS N213407 April 17, 2020 RX SOLUTION INTRAVENOUS 11090278 May 16, 2040 USE OF EPHEDRINE SULFATE FOR TREATING HYPOTENSION
50MG/10ML (5MG/ML) EMERPHED NEXUS PHARMS N213407 April 17, 2020 RX SOLUTION INTRAVENOUS 11241400 May 16, 2040 USE OF EPHEDRINE SULFATE FOR TREATING HYPOTENSION

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Beta-2 adrenergic receptor GPCR AGONIST Ki 5.60 IUPHAR IUPHAR

External reference:

IDSource
4017462 VUID
N0000179480 NUI
D00124 KEGG_DRUG
134-72-5 SECONDARY_CAS_RN
4017462 VANDF
4018445 VANDF
4019279 VANDF
C0014479 UMLSCUI
CHEBI:15407 CHEBI
CHEMBL211456 ChEMBL_ID
DB01364 DRUGBANK_ID
CHEMBL1523964 ChEMBL_ID
CHEMBL526872 ChEMBL_ID
CHEMBL2146102 ChEMBL_ID
D004809 MESH_DESCRIPTOR_UI
9294 PUBCHEM_CID
556 IUPHAR_LIGAND_ID
GN83C131XS UNII
3966 RXNORM
3438 MMSL
4660 MMSL
4661 MMSL
6510 MMSL
71901 MMSL
d00700 MMSL
001820 NDDF
001821 NDDF
001822 NDDF
387327006 SNOMEDCT_US
387358007 SNOMEDCT_US
65026000 SNOMEDCT_US
76525000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Bronchial Asthma Relief HUMAN OTC DRUG LABEL 2 0363-2529 TABLET 12.50 mg ORAL OTC monograph final 15 sections
PRIMATENE HUMAN OTC DRUG LABEL 2 0573-2952 TABLET 12.50 mg ORAL OTC monograph final 17 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0641-6238 INJECTION 50 mg INTRAVENOUS ANDA 25 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 0781-3269 INJECTION 50 mg INTRAVENOUS ANDA 24 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 14789-014 INJECTION, SOLUTION 50 mg INTRAVENOUS unapproved drug other 17 sections
Emerphed HUMAN PRESCRIPTION DRUG LABEL 1 14789-250 INJECTION 5 mg INTRAVENOUS NDA 25 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 16714-037 INJECTION 50 mg INTRAVENOUS ANDA 24 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 17478-415 INJECTION 50 mg INTRAVENOUS NDA 25 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 17478-515 INJECTION 50 mg INTRAMUSCULAR unapproved drug other 17 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 17478-517 INJECTION 50 mg INTRAVENOUS NDA 25 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 17478-955 INJECTION 50 mg INTRAVENOUS NDA 24 sections
REZIPRES HUMAN PRESCRIPTION DRUG LABEL 1 39822-1410 INJECTION, SOLUTION 4.70 mg INTRAVENOUS NDA 25 sections
Corphedra HUMAN PRESCRIPTION DRUG LABEL 1 42023-196 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 24 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 42023-216 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 24 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 42023-216 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 24 sections
EPHEDRINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 42023-243 INJECTION 5 mg INTRAVENOUS NDA 24 sections
Ephedrine sulfate HUMAN PRESCRIPTION DRUG LABEL 1 43598-725 INJECTION 50 mg INTRAVENOUS ANDA 24 sections
EPHEDRINE SULFATE HUMAN PRESCRIPTION DRUG LABEL 1 51662-1325 INJECTION, SOLUTION 50 mg INTRAVENOUS NDA 17 sections
Akovaz HUMAN PRESCRIPTION DRUG LABEL 1 51754-4200 INJECTION 50 mg INTRAVENOUS NDA 24 sections
Akovaz HUMAN PRESCRIPTION DRUG LABEL 1 51754-4250 INJECTION 5 mg INTRAVENOUS NDA 24 sections
Ephedrine Sulfate Human Prescription Drug Label 1 55150-373 INJECTION 50 mg INTRAVENOUS ANDA 24 sections
Red Label Ephedrine Plus HUMAN OTC DRUG LABEL 2 65193-125 TABLET 12.50 mg ORAL OTC monograph final 9 sections
Ephed Plus Liquid HUMAN OTC DRUG LABEL 2 65193-180 LIQUID 25 mg ORAL OTC monograph final 8 sections
Ephed Plus HUMAN OTC DRUG LABEL 2 65193-225 TABLET 25 mg ORAL OTC monograph final 9 sections
Ephed Asthma HUMAN OTC DRUG LABEL 2 65193-320 TABLET 25 mg ORAL OTC monograph final 9 sections
Red Label Ephed Plus HUMAN OTC DRUG LABEL 2 65193-340 TABLET 12.50 mg ORAL OTC monograph final 9 sections
Ephedrine Sulfate HUMAN PRESCRIPTION DRUG LABEL 1 65219-257 INJECTION 50 mg INTRAVENOUS ANDA 24 sections
Akovaz HUMAN PRESCRIPTION DRUG LABEL 1 68001-330 INJECTION 50 mg INTRAVENOUS NDA 24 sections
Bronkaid Max HUMAN OTC DRUG LABEL 1 69536-250 TABLET, COATED 25 mg ORAL OTC MONOGRAPH FINAL 17 sections
Bronkaid Dual Action Formula HUMAN OTC DRUG LABEL 2 69536-425 TABLET, COATED 25 mg ORAL OTC MONOGRAPH FINAL 17 sections