Epinephrine bitartrateProduct ingredient for Epinephrine

Name
Epinephrine bitartrate
Drug Entry
Epinephrine

Epinephrine, also known as adrenaline, is a hormone and neurotransmitter and produced by the adrenal glands that can also be used as a drug due to its various important functions. Though it has long been used in the treatment of hypersensitivity reactions, epinephrine in the auto-injector form (EpiPen) has been available since 1987 in the USA. Many new products/biosimilars and dosage routes have been approved under various names over the last several decades 10, 11, 12. On August 16, 2018, Teva Pharmaceuticals USA gained approval to market its generic epinephrine auto-injector in 0.3 mg and 0.15 mg strengths 8. Dosage delivery routes for epinephrine include intravenous, inhalation, nebulization, intramuscular injection, and subcutaneous injection.

In general, the most common uses of parenteral epinephrine are to relieve respiratory distress due to bronchospasm, to provide rapid relief of hypersensitivity (anaphylactic or anaphylactoid) reactions to drugs, animal serums and other allergens, and to prolong the action of infiltration anesthetics 20. In addition to the above functions, epinephrine is the primary drug administered during cardiopulmonary resuscitation (CPR) to reverse cardiac arrest 3, 4. It can be used in severe cases of croup 14.

Accession Number
DBSALT000788
Structure
Synonyms
Adrenaline Acid Tartrate / epinephrine acid tartrate
UNII
30Q7KI53AK
CAS Number
51-42-3
Weight
Average: 333.2913
Monoisotopic: 333.105981211
Chemical Formula
C13H19NO9
InChI Key
YLXIPWWIOISBDD-NDAAPVSOSA-N
InChI
InChI=1S/C9H13NO3.C4H6O6/c1-10-5-9(13)6-2-3-7(11)8(12)4-6;5-1(3(7)8)2(6)4(9)10/h2-4,9-13H,5H2,1H3;1-2,5-6H,(H,7,8)(H,9,10)/t9-;1-,2-/m01/s1
IUPAC Name
(2R,3R)-2,3-dihydroxybutanedioic acid; 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
SMILES
[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O.[H][C@](O)(CNC)C1=CC(O)=C(O)C=C1
PubChem Compound
5815
ChemSpider
5610
ChEBI
774769
ChEMBL
CHEMBL1200818
Wikipedia
Epinephrine_(medication)
Predicted Properties
PropertyValueSource
Water Solubility18.6 mg/mLALOGPS
logP-0.82ALOGPS
logP-0.43Chemaxon
logS-0.99ALOGPS
pKa (Strongest Acidic)9.69Chemaxon
pKa (Strongest Basic)8.91Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count4Chemaxon
Polar Surface Area72.72 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity49.23 m3·mol-1Chemaxon
Polarizability18.91 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon