GtoPdb Ligand ID: 320

Synonyms: Atropen® | hyoscyamine
atropine is an approved drug (FDA (1973))
Comment: Atropine is a muscarinic acetylcholine receptor (mAChR) antagonist.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: atropine

2D Structure
Click here for structure editor
Physico-chemical Properties
Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 49.77
Molecular weight 289.17
XLogP 1.83
No. Lipinski's rules broken 0
Canonical SMILES OCC(c1ccccc1)C(=O)OC1CC2CCC(C1)N2C
Isomeric SMILES OCC(c1ccccc1)C(=O)O[C@@H]1C[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?
1. Buckley NJ, Bonner TI, Buckley CM, Brann MR. (1989)
Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells.
Mol. Pharmacol., 35 (4): 469-76. [PMID:2704370]
2. Carr BJ, Mihara K, Ramachandran R, Saifeddine M, Nathanson NM, Stell WK, Hollenberg MD. (2018)
Myopia-Inhibiting Concentrations of Muscarinic Receptor Antagonists Block Activation of Alpha2A-Adrenoceptors In Vitro.
Invest. Ophthalmol. Vis. Sci., 59 (7): 2778-2791. [PMID:29860464]
3. Cheng K, Khurana S, Chen Y, Kennedy RH, Zimniak P, Raufman JP. (2002)
Lithocholylcholine, a bile acid/acetylcholine hybrid, is a muscarinic receptor antagonist.
J. Pharmacol. Exp. Ther., 303 (1): 29-35. [PMID:12235229]
4. Christopoulos A, Pierce TL, Sorman JL, El-Fakahany EE. (1998)
On the unique binding and activating properties of xanomeline at the M1 muscarinic acetylcholine receptor.
Mol. Pharmacol., 53 (6): 1120-30. [PMID:9614217]
5. Dowling MR, Charlton SJ. (2006)
Quantifying the association and dissociation rates of unlabelled antagonists at the muscarinic M3 receptor.
Br. J. Pharmacol., 148 (7): 927-37. [PMID:16847442]
6. Fruchart-Gaillard C, Mourier G, Marquer C, Ménez A, Servent D. (2006)
Identification of various allosteric interaction sites on M1 muscarinic receptor using 125I-Met35-oxidized muscarinic toxin 7.
Mol. Pharmacol., 69 (5): 1641-51. [PMID:16439611]
7. Hirose H, Aoki I, Kimura T, Fujikawa T, Numazawa T, Sasaki K, Sato A, Hasegawa T, Nishikibe M, Mitsuya M et al.. (2001)
Pharmacological properties of (2R)-N-[1-(6-aminopyridin-2-ylmethyl)piperidin-4-yl]-2-[(1R)-3,3-difluorocyclopentyl]-2-hydroxy-2-phenylacetamide: a novel mucarinic antagonist with M(2)-sparing antagonistic activity.
J. Pharmacol. Exp. Ther., 297 (2): 790-7. [PMID:11303071]
8. Huang F, Buchwald P, Browne CE, Farag HH, Wu WM, Ji F, Hochhaus G, Bodor N. (2001)
Receptor binding studies of soft anticholinergic agents.
AAPS PharmSci, 3 (4): E30. [PMID:12049493]
9. Kashihara K, Varga EV, Waite SL, Roeske WR, Yamamura HI. (1992)
Cloning of the rat M3, M4 and M5 muscarinic acetylcholine receptor genes by the polymerase chain reaction (PCR) and the pharmacological characterization of the expressed genes.
Life Sci., 51 (12): 955-71. [PMID:1325587]
10. Kovacs I, Yamamura HI, Waite SL, Varga EV, Roeske WR. (1998)
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
J. Pharmacol. Exp. Ther., 284 (2): 500-7. [PMID:9454790]
11. Maksay G, Laube B, Betz H. (1999)
Selective blocking effects of tropisetron and atropine on recombinant glycine receptors.
J. Neurochem., 73 (2): 802-6. [PMID:10428078]
12. Nelson CP, Nahorski SR, Challiss RA. (2006)
Constitutive activity and inverse agonism at the M2 muscarinic acetylcholine receptor.
J. Pharmacol. Exp. Ther., 316 (1): 279-88. [PMID:16188951]
13. Peralta EG, Ashkenazi A, Winslow JW, Smith DH, Ramachandran J, Capon DJ. (1987)
Distinct primary structures, ligand-binding properties and tissue-specific expression of four human muscarinic acetylcholine receptors.
EMBO J., 6 (13): 3923-9. [PMID:3443095]
14. Smith CM, Wallis RM. (1997)
Characterisation of [3H]-darifenacin as a novel radioligand for the study of muscarinic M3 receptors.
J. Recept. Signal Transduct. Res., 17 (1-3): 177-84. [PMID:9029489]
15. Yang Z, Ney A, Cromer BA, Ng HL, Parker MW, Lynch JW. (2007)
Tropisetron modulation of the glycine receptor: femtomolar potentiation and a molecular determinant of inhibition.
J. Neurochem., 100 (3): 758-69. [PMID:17181559]