OIN

(1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCT-3-YL (2R)-3-HYDROXY-2-PHENYLPROPANOATE

Created:2004-06-01
Last modified:  2021-03-01

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Chemical Details

Formal Charge0
Atom Count44
Chiral Atom Count3
Bond Count46
Aromatic Bond Count6
2D diagram of OIN
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Chemical Component Summary

Name(1R,5S)-8-METHYL-8-AZABICYCLO[3.2.1]OCT-3-YL (2R)-3-HYDROXY-2-PHENYLPROPANOATE
SynonymsATROPINE
Systematic Name (OpenEye OEToolkits)[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenyl-propanoate
FormulaC17 H23 N O3
Molecular Weight289.369
TypeNON-POLYMER

Chemical Descriptors

TypeProgramVersionDescriptor
SMILESACDLabs10.04O=C(OC2CC1N(C)C(CC1)C2)C(c3ccccc3)CO
SMILESCACTVS3.341CN1[CH]2CC[CH]1CC(C2)OC(=O)[CH](CO)c3ccccc3
SMILESOpenEye OEToolkits1.5.0CN1C2CCC1CC(C2)OC(=O)C(CO)c3ccccc3
Canonical SMILESCACTVS3.341 CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)[C@H](CO)c3ccccc3
Canonical SMILESOpenEye OEToolkits1.5.0 CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)[C@H](CO)c3ccccc3
InChIInChI1.03 InChI=1S/C17H23NO3/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12/h2-6,13-16,19H,7-11H2,1H3/t13-,14+,15-,16-/m1/s1
InChIKeyInChI1.03 RKUNBYITZUJHSG-QKPAOTATSA-N

Drug Info: DrugBank

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
DrugBank IDDB00572 
NameAtropine
Groups
  • approved
  • vet_approved
DescriptionAtropine is an alkaloid originally synthesized from Atropa belladonna. It is a racemic mixture of d-and l-hyoscyamine, of which only l-hyoscyamine is pharmacologically active.[A251670,L42835] Atropine is generally available as a sulfate salt and can be administered by intravenous, subcutaneous, intramuscular, intraosseous, endotracheal and ophthalmic methods. Oral atropine is only available in combination products.[A251660,L42840] Atropine is a competitive, reversible antagonist of muscarinic receptors that blocks the effects of acetylcholine and other choline esters.[A251660,L42815,L42825,L42835] It has a variety of therapeutic applications, including pupil dilation and the treatment of anticholinergic poisoning and symptomatic bradycardia in the absence of reversible causes.[A251660] Atropine is a relatively inexpensive drug and is included in the World Health Organization List of Essential Medicines.[A251675]
Synonyms
  • dl-tropyltropate
  • dl-Hyoscyamine
  • (±)-atropine
  • Atropina
  • Atropine sulfate
Brand Names
  • Donnatal Tab
  • Atropine Injection Bp 0.4mg/ml
  • Se-donna Pb Hyos
  • Atropine Sulfate Injection
  • Phenobarbital, Hyoscyamine Sulfate, Atropine Sulfate, Scopolamine Hydrobromide
IndicationThe intravenous, intramuscular, subcutaneous, intraosseous and endotracheal use of atropine is indicated for the temporary blockade of severe or life-threatening muscarinic effects.[L42815,L42835] The intramuscular use of atropine in the form of a pen injector is indicated for the treatment of poisoning by susceptible organophosphorus nerve agents having cholinesterase activity as well as organophosphorus or carbamate insecticides in adult and pediatric patients.[L42825] The ophthalmic use of atropine is indicated for mydriasis, cycloplegia, and penalization of the healthy eye in the treatment of amblyopia.[L42830] In combination with difenoxin or diphenoxylate (tablets for oral use), atropine is indicated as adjunctive therapy in the management of acute nonspecific diarrhea.[L42840,L42865]
Categories
  • Adjuvants, Anesthesia
  • Agents producing tachycardia
  • Agents that produce hypertension
  • Alimentary Tract and Metabolism
  • Alkaloids
ATC-Code
  • S01FA01
  • A03CB03
  • V03AB54
  • A03BA01
CAS number51-55-8

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License
NameTarget SequencePharmacological ActionActions
Muscarinic acetylcholine receptor M1MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...unknownantagonist
Muscarinic acetylcholine receptor M2MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...unknownantagonist
Muscarinic acetylcholine receptor M3MTLHNNSTTSPLFPNISSSWIHSPSDAGLPPGTVTHFGSYNVSRAAGNFS...unknownantagonist
Muscarinic acetylcholine receptor M4MANFTPVNGSSGNQSVRLVTSSSHNRYETVEMVFIATVTGSLSLVTVVGN...unknownantagonist
Muscarinic acetylcholine receptor M5MEGDSYHNATTVNGTPVNHQPLERHRLWEVITIAAVTAVVSLITIVGNVL...unknownantagonist
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
CCDC/CSD BIHWEX, WALPIJ