(1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate

• ChemBase ID: 454
• Molecular Formular: C17H23NO3
• Molecular Mass: 289.36942
• Monoisotopic Mass: 289.1677936
• SMILES: O(C1C[C@@H]2N([C@@H](CC2)C1)C)C(=O)C(c1ccccc1)CO
• Canonical SMILES: OCC(c1ccccc1)C(=O)OC1C[C@@H]2CC[C@H](C1)N2C
• InChI: 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?
• InChIKey: RKUNBYITZUJHSG-PJPHBNEVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,5S)-8-methyl-8-azabicyclo[3.2.1]octan-3-yl 3-hydroxy-2-phenylpropanoate
• IUPAC Traditional name: hyoscyamine
• Brand Name: Atnaa; Atropair; Atropen; Atropin; Atropin-flexiolen; Atropine Care; Atropine Sulfate Ansyr Plastic Syringe; Atropine Sulfate S.O.P.; Atropinol; Atropisol; Atrosulf; Equipin; Eyesules; Homapin-10; Homapin-5; I-Tropine; Isopto Atropine; Isopto-atropine; Minims Atropine; Ocu-Tropine; Tropine tropate; Troyl tropate
• Synonyms: Atropin [German]; Atropina [Italian]; Atropine Sulfate; DL-Hyoscyamine; DL-Tropyl tropate; Atropine

Database IDs

• CAS Number: 51-55-8
• PubChem SID: 160963917
• PubChem CID: 174174

CALCULATED PROPERTIES

JChem

• Acid pKa: 15.1457405
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.7801015
• LogD (pH = 7.4): -0.40574417
• Log P: 1.571241
• Molar Refractivity: 80.8164 cm^3
• Polarizability: 32.034832 Å^3
• Polar Surface Area: 49.77 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.19
• LOG S: -2.06
• Solubility (Water): 2.52e+00 g/l

PROPERTIES

Physical Property

• Solubility: Highly soluble (2200 mg/L)
• Hydrophobicity(logP): 1.8

DETAILS

DrugBank - DB00572

• Drug Groups: approved
• Description: An alkaloid, originally from Atropa belladonna, but found in other plants, mainly solanaceae. [PubChem]
• Indication: For the treatment of poisoning by susceptible organophosphorous nerve agents having cholinesterase activity as well as organophosphorous or carbamate insecticides.
• Pharmacology: Atropine, a naturally occurring belladonna alkaloid, is a racemic mixture of equal parts of d- and l-hyoscyamine, whose activity is due almost entirely to the levo isomer of the drug. Atropine is commonly classified as an anticholinergic or antiparasympathetic (parasympatholytic) drug. More precisely, however, it is termed an antimuscarinic agent since it antagonizes the muscarine-like actions of acetylcholine and other choline esters. Adequate doses of atropine abolish various types of reflex vagal cardiac slowing or asystole. The drug also prevents or abolishes bradycardia or asystole produced by injection of choline esters, anticholinesterase agents or other parasympathomimetic drugs, and cardiac arrest produced by stimulation of the vagus. Atropine may also lessen the degree of partial heart block when vagal activity is an etiologic factor. Atropine in clinical doses counteracts the peripheral dilatation and abrupt decrease in blood pressure produced by choline esters. However, when given by itself, atropine does not exert a striking or uniform effect on blood vessels or blood pressure.
• Toxicity: Oral, mouse: LD₅₀ = 75 mg/kg. Symptoms of overdose includes widespread paralysis of parasympathetically innervated organs. Dry mucous membranes, widely dilated and nonresponsive pupils, tachycardia, fever and cutaneous flush are especially prominent, as are mental and neurological symptoms. In instances of severe intoxication, respiratory depression, coma, circulatory collapse and death may occur.
• Affected Organisms: Humans and other mammals
• Biotransformation: Much of the drug is destroyed by enzymatic hydrolysis, particularly in the liver. From 13 to 50% is excreted unchanged in the urine.
• Absorption: Atropine is rapidly and well absorbed after intramuscular administration. Atropine disappears rapidly from the blood and is distributed throughout the various body tissues and fluids.
• Half Life: 3.0 ± 0.9 hours in adults. The half-life of atropine is slightly shorter (approximately 20 minutes) in females than males.
• Protein Binding: The protein binding of atropine is 14 to 22% in plasma.
• Elimination: Much of the drug is destroyed by enzymatic hydrolysis, particularly in the liver; from 13 to 50% is excreted unchanged in the urine.
• External Links: Wikipedia; RxList; Drugs.com