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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6 entries where OIN is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	44
Chiral Atom Count	3
Bond Count	46
Aromatic Bond Count	6

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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
Synonyms	ATROPINE
Systematic Name (OpenEye OEToolkits)	[(1S,5R)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl] (2S)-3-hydroxy-2-phenyl-propanoate
Formula	C₁₇ H₂₃ N O₃
Molecular Weight	289.369
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(OC2CC1N(C)C(CC1)C2)C(c3ccccc3)CO
SMILES	CACTVS	3.341	CN1[CH]2CC[CH]1CC(C2)OC(=O)[CH](CO)c3ccccc3
SMILES	OpenEye OEToolkits	1.5.0	CN1C2CCC1CC(C2)OC(=O)C(CO)c3ccccc3
Canonical SMILES	CACTVS	3.341	CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)[C@H](CO)c3ccccc3
Canonical SMILES	OpenEye OEToolkits	1.5.0	CN1[C@H]2CC[C@@H]1CC(C2)OC(=O)[C@H](CO)c3ccccc3
InChI	InChI	1.03	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
InChIKey	InChI	1.03	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 ID	DB00572 ?
Name	Atropine
Groups	approved vet_approved
Description	Atropine 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 Atropina Atropine hydrochloride dl-Hyoscyamine (±)-atropine Atropine sulfate anhydrous Atropin Atropine Tropine tropate Atropinum (±)-hyoscyamine Atropine sulfate
Brand Names	DuoDote Atropine Ont 1% Enlon-Plus Belladonna Alkaloids with Phenobartbital Re-PB Hyos Atropine Sulfate Inj 0.3mg/ml Atropine Injection Bp 0.4mg/ml Atropine Care Atropine Sulfate Injection USP Atropisol Atropine Injection Bp 0.6mg/ml Diban Cap Phenobarbital with Belladonna Alkaloids - Mint Phenohytro Se-donna Pb Hyos Phenobarbital with Belladonna Alkaloids - Grape Motofen Phenobarbital with Belladonna Alkaloids Donnatal Tab Me-PB-Hyos Atropine Sulfate Inj 0.4mg/ml Phenobarbital, Hyoscyamine Sulfate, Atropine Sulfate and Scopolamine Hydrobromide Diphenoxylate Hcl and Atropine Sulfate Phenobarbital, Hyoscyamine Sulfate, Atropine Sulfate, Scopolamine Hydrobromide R.O.-atropine Alcon Atropine Diphenoxylate hydrochloride and atropine sulfate ATROPEN Auto-Injector Atropine Injection BP Odan-atropine Minims Atropine Sulphate Phenobarbital With Belladonna Alkaloids Re-PB Hyos Elixir Atropine Sulfate Atropine Sulphate 1% - Liq Oph Atropine 1% PB Hyos Donnatal Extentabs Srt B-Donna Vitetal Atropine Sulfate Inj 0.6mg/ml Donnatal Atropine Sulfate Inj 1mg/ml Diphenoxylate Hydrochloride and Atropine Sulfate Donnatal Elixir Atropine Sulfate Inj 0.1mg/ml Atropine sulfate Lomotil N/a Servira ATNAA atropine and pralidoxime chloride Auto-Injector Atropisol Oph Soln 1% Quadrapax Donnagel Liq Atropine Sulfate Inj 0.4mg/0.5ml Donnatal Extentabs Belladonna Alkaloids with Phenobarbital Isopto Atropine Enlon Plus Atropine Urised Atropine Sulfate Injection
Indication	The 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 Anti-Asthmatic Agents Antiarrhythmic agents Anticholinergic Agents Antidotes Antimuscarinics Antispasmodics Autonomic Agents Aza Compounds Azabicyclo Compounds Belladonna Alkaloids Belladonna Alkaloids, Tertiary Amines Belladonna and Derivatives, Plain Bronchodilator Agents BSEP/ABCB11 Substrates Cardiovascular Agents Central Nervous System Agents Cholinergic Agents Drugs for Functional Gastrointestinal Disorders Moderate Risk QTc-Prolonging Agents Muscarinic Antagonists Mydriatics Mydriatics and Cycloplegics Neurotransmitter Agents Ophthalmologicals Parasympatholytics Peripheral Nervous System Agents QTc Prolonging Agents Respiratory System Agents Sensory Organs Solanaceous Alkaloids Tropanes
ATC-Code	S01FA01 A03CB03 V03AB54 A03BA01
CAS number	51-55-8

Drug Targets

DrugBank data are sourced from datasets licensed under a Creative Common's Attribution-NonCommercial 4.0 International License

Name	Target Sequence	Pharmacological Action	Actions
Muscarinic acetylcholine receptor M1	MNTSAPPAVSPNITVLAPGKGPWQVAFIGITTGLLSLATVTGNLLVLISF...	unknown	antagonist
Muscarinic acetylcholine receptor M2	MNNSTNSSNNSLALTSPYKTFEVVFIVLVAGSLSLVTIIGNILVMVSIKV...	unknown	antagonist
Muscarinic acetylcholine receptor M3	MTLHNNSTTSPLFPNISSSWIHSPSDAGLPPGTVTHFGSYNVSRAAGNFS...	unknown	antagonist
Muscarinic acetylcholine receptor M4	MANFTPVNGSSGNQSVRLVTSSSHNRYETVEMVFIATVTGSLSLVTVVGN...	unknown	antagonist
Muscarinic acetylcholine receptor M5	MEGDSYHNATTVNGTPVNHQPLERHRLWEVITIAAVTAVVSLITIVGNVL...	unknown	antagonist
Glycine receptor subunit alpha-1	MYSFNTLRLYLWETIVFFSLAASKEAEAARSAPKPMSPSDFLDKLMGRTS...	unknown	antagonist
Neuronal acetylcholine receptor subunit alpha-4	MELGGPGAPRLLPPLLLLLGTGLLRASSHVETRAHAEERLLKKLFSGYNK...	unknown
Neuronal acetylcholine receptor subunit beta-2	MARRCGPVALLLGFGLLRLCSGVWGTDTEERLVEHLLDPSRYNKLIRPAT...	unknown
Alpha-1-acid glycoprotein 1	MALSWVLTVLSLLPLLEAQIPLCANLVPVPITNATLDRITGKWFYIASAF...	unknown	binder
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate
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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