Home > Compound List > Compound details
80012-43-7 molecular structure
click picture or here to close

2,4-diazatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),3,7(12),8,10,15,17-heptaen-3-amine

ChemBase ID: 631
Molecular Formular: C16H15N3
Molecular Mass: 249.3104
Monoisotopic Mass: 249.1265975
SMILES and InChIs

SMILES:
N12C(c3c(Cc4c1cccc4)cccc3)CN=C2N
Canonical SMILES:
NC1=NCC2N1c1ccccc1Cc1c2cccc1
InChI:
InChI=1S/C16H15N3/c17-16-18-10-15-13-7-3-1-5-11(13)9-12-6-2-4-8-14(12)19(15)16/h1-8,15H,9-10H2,(H2,17,18)
InChIKey:
WHWZLSFABNNENI-UHFFFAOYSA-N

Cite this record

CBID:631 http://www.chembase.cn/molecule-631.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2,4-diazatetracyclo[12.4.0.0^{2,6}.0^{7,12}]octadeca-1(14),3,7(12),8,10,15,17-heptaen-3-amine
IUPAC Traditional name
epinastine
Brand Name
Elestat
Synonyms
Epinastina [Spanish]
Epinastinum [Latin]
epinastine
Epinastine
CAS Number
80012-43-7
PubChem SID
46509056
160964094
PubChem CID
3241

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00751 external link
PubChem 3241 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
H Acceptors H Donor
LogD (pH = 5.5) 0.7146667  LogD (pH = 7.4) 1.72546 
Log P 3.073111  Molar Refractivity 76.9014 cm3
Polarizability 28.761738 Å3 Polar Surface Area 41.62 Å2
Rotatable Bonds Lipinski's Rule of Five true 
Log P 2.53  LOG S -3.18 
Solubility (Water) 1.63e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Hydrophobicity(logP)
3.1 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00751 external link
Item Information
Drug Groups approved; investigational
Description Epinastine is used for the prevention of itching associated with allergic conjunctivitis. It has a multi-action effect that inhibits the allergic response in 3 ways: 1. stabilizes mast cells by preventing mast cell degranulation to control the allergic response, 2. prevents histamine binding to both the H1- and H2-receptors to stop itching and provide lasting protection, and 3. prevents the release of proinflammatory chemical mediators from the blood vessel to halt progression of the allergic response.
Indication For the prevention of itching associated with allergic conjunctivitis.
Pharmacology Epinastine is an antihistamine and an inhibitor of histamine release from the mast cell for topical administration to the eyes. Epinastine is indicated for the prevention of itching associated with allergic conjunctivitis. Epinastine is a topically active, direct H1-receptor antagonist and an inhibitor of the release of histamine from the mast cell. Epinastine is selective for the histamine H1-receptor and has affinity for the histamine H2 receptor. Epinastine also possesses affinity for the a1-, a2-, and 5-HT2 -receptors. Epinastine does not penetrate the blood/brain barrier and, therefore, is not expected to induce side effects of the central nervous system.
Affected Organisms
Humans and other mammals
Biotransformation Mainly excreted unchanged, less than 10% metabolized.
Absorption The absolute bioavailability of epinastine is about 40%.
Half Life 12 hours
Protein Binding 64%
Elimination Epinastine is mainly excreted unchanged. The renal elimination is mainly via active tubular secretion.
Clearance * 56 L/hr [patients with allergic conjunctivitis receiving one drop of ELESTAT? ophthalmic solution in each eye twice daily for seven days]
References
Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. [Pubmed]
Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Walther G, Daniel H, Bechtel WD, Brandt K: New tetracyclic guanidine derivatives with H1-antihistaminic properties. Chemistry of epinastine. Arzneimittelforschung. 1990 Apr;40(4):440-6. Pubmed
  • • Schilling JC, Adamus WS, Kuthan H: Antihistaminic activity and side effect profile of epinastine and terfenadine in healthy volunteers. Int J Clin Pharmacol Ther Toxicol. 1990 Dec;28(12):493-7. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle