ATROPINE

First marketed in 1921

Details

Stereochemistry	EPIMERIC
Molecular Formula	C17H23NO3
Molecular Weight	289.3701
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@@]2([H])CC[C@]1([H])C[C@@]([H])(C2)OC(=O)C([H])(CO)c3ccccc3

InChI

InChIKey=RKUNBYITZUJHSG-SPUOUPEWSA-N

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?

HIDE SMILES / InChI

Molecular Formula	C17H23NO3
Molecular Weight	289.3701
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf
Curator's Comment:: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf

Atropine inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves, and on smooth muscles which respond to endogenous acetylcholine but are not so innervated. As with other antimuscarinic agents, the major action of atropine is a competitive or surmountable antagonism which can be overcome by increasing the concentration of acetylcholine at receptor sites of the effector organ (e.g., by using anticholinesterase agents which inhibit the enzymatic destruction of acetylcholine). The receptors antagonized by atropine are the peripheral structures that are stimulated or inhibited by muscarine (i.e., exocrine glands and smooth and cardiac muscle). Responses to postganglionic cholinergic nerve stimulation also may be inhibited by atropine but this occurs less readily than with responses to injected (exogenous) choline esters. Atropine is relatively selective for muscarinic receptors. Its potency at nicotinic receptors is much lower, and actions at non-muscarinic receptors are generally undetectable clinically. Atropine does not distinguish among the M1, M2, and M3 subgroups of muscarinic receptors.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Muscarinic acetylcholine receptor M1 160 Target ID: CHEMBL216 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2577	Muscarinic mushroom poisoning	9.33999999999999986 null [pKi]
Muscarinic acetylcholine receptor M2 114 Target ID: CHEMBL211 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2577	Muscarinic mushroom poisoning	8.94999999999999929 null [pKi]
Muscarinic acetylcholine receptor M3 150 Target ID: CHEMBL245 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2577	Muscarinic mushroom poisoning	9.15000000000000036 null [pKi]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bradyasystolic cardiac arrest 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary		Approved 7997	Atropine sulfate Approved Use Atropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date 994550400000
Organophosphorus poisoning 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary		Approved 7997	Atropine sulfate Approved Use Atropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date 994550400000
Increased salivary flow 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary		Approved 7997	Atropine sulfate Approved Use Atropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date 994550400000
Vagus nerve activation 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary		Approved 7997	Atropine sulfate Approved Use Atropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date 994550400000
Muscarinic mushroom poisoning 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Muscarinic acetylcholine receptor M1 Muscarinic acetylcholine receptor M2 Muscarinic acetylcholine receptor M3	Approved 7997	Atropine sulfate Approved Use Atropine sulfate is indicated for temporary blockade of severe or life threatening muscarinic effects, e.g., as an antisialagogue, an antivagal agent, an antidote for organophosphorus or muscarinic mushroom poisoning, and to treat bradyasystolic cardiac arrest. Launch Date 994550400000

C_max

Value	Dose	Analyte	Population
860 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3046815	0.4 μg single, ocular dose: 0.4 μg route of administration: Ocular experiment type: SINGLE co-administered:	ATROPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
11.7 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3740650	1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	ATROPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
9.6 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/212319s000lbl.pdf	1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered:	ATROPINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
43245 pg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3046815	0.4 μg single, ocular dose: 0.4 μg route of administration: Ocular experiment type: SINGLE co-administered:		ATROPINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
47.6 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3740650	1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		ATROPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
4.1 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3740650	1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		ATROPINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
82% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/212319s000lbl.pdf	1.67 mg single, intramuscular dose: 1.67 mg route of administration: Intramuscular experiment type: SINGLE co-administered:		ATROPINE plasma	Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29316984	unhealthy, 10 years Health Status: unhealthy Age Group: 10 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/29316984	Disc. AE: Kounis syndrome, Chest discomfort... AEs leading to discontinuation/dose reduction: Kounis syndrome (1 patient) Chest discomfort (1 patient) Nausea (1 patient) Vomiting (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/29316984
0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	Other AEs: Photophobia, Reading disorder... Other AEs: Photophobia (70%) Reading disorder (25.9%) Headache (21.7%) Hot flushes (3.3%) Conjunctivitis (1.7%) Blepharitis (1.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
1 mg single, sublingual Overdose Dose: 1 mg Route: sublingual Route: single Dose: 1 mg Sources: https://pubmed.ncbi.nlm.nih.gov/33521988	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/33521988	Other AEs: Adverse event... Other AEs: Adverse event (severe) Sources: https://pubmed.ncbi.nlm.nih.gov/33521988

AEs

AE	Significance	Dose	Population
Chest discomfort	1 patient Disc. AE	0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29316984	unhealthy, 10 years Health Status: unhealthy Age Group: 10 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/29316984
Kounis syndrome	1 patient Disc. AE	0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29316984	unhealthy, 10 years Health Status: unhealthy Age Group: 10 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/29316984
Nausea	1 patient Disc. AE	0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29316984	unhealthy, 10 years Health Status: unhealthy Age Group: 10 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/29316984
Vomiting	1 patient Disc. AE	0.1 mg/kg single, intravenous Dose: 0.1 mg/kg Route: intravenous Route: single Dose: 0.1 mg/kg Sources: https://pubmed.ncbi.nlm.nih.gov/29316984	unhealthy, 10 years Health Status: unhealthy Age Group: 10 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/29316984
Blepharitis	1.7%	0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
Conjunctivitis	1.7%	0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
Headache	21.7%	0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
Reading disorder	25.9%	0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
Hot flushes	3.3%	0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
Photophobia	70%	0.5 % 1 times / day multiple, ophthalmic Highest studied dose Dose: 0.5 %, 1 times / day Route: ophthalmic Route: multiple Dose: 0.5 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/27101751	unhealthy, 10.3 years (range: 2.7–16.8 years) Health Status: unhealthy Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/27101751
Adverse event	severe	1 mg single, sublingual Overdose Dose: 1 mg Route: sublingual Route: single Dose: 1 mg Sources: https://pubmed.ncbi.nlm.nih.gov/33521988	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/33521988

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT2 582 OCT1 473 OCT3 139

Drug as perpetrator

Target	Modality	Activity
OCT1 488	inhibitor 2614 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 1.2 uM]
OCT2 583	inhibitor 2614 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 39 uM]
OCT3 139	inhibitor 2614 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 466 uM]

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16684	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16684
MolPort	MolPort-001-742-593	https://www.molport.com/shop/molecule-link/MolPort-001-742-593

PubMed

Title	Date	PubMed
Neurotransmitter-mediated open-field behavioral action of CGRP.	1999	10075105
The incidence of systemic side-effects following subconjunctival Mydricaine no. 1 injection.	1999 Dec	10707131
Progressive treatment of erectile dysfunction with intracorporeal injections of different combinations of vasoactive agents.	1999 Feb	10098948
Relation between the extent of coronary artery disease and tachyarrhythmias during dobutamine stress echocardiography.	1999 Mar 15	10190394
TIVA with propofol and remifentanil.	1999 May	10995163
The influence of peripheral site ligands on the reaction of symmetric and chiral organophosphates with wildtype and mutant acetylcholinesterases.	1999 May 14	10421444
Profound bradycardia and hypotension following spinal anaesthesia in a patient receiving an ACE inhibitor: an important 'drug' interaction?	1999 Nov	10713875
Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways.	2000 Dec	11112886
Effect of alpha-2 adrenoceptor antagonists on colonic function in rats.	2000 Jun	10867622
Cardiovascular studies on different classes of soft drugs.	2000 Mar	10756546
Endothelin receptors in human and guinea-pig gallbladder muscle.	2001 Apr 20	11231044
Localisation and neural control of the release of calcitonin gene-related peptide (CGRP) from the isolated perfused porcine ileum.	2001 Apr 20	11231043
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.	2001 Feb	11181424
Stimulation of M3 muscarinic receptors induces phosphorylation of the Cdc42 effector activated Cdc42Hs-associated kinase-1 via a Fyn tyrosine kinase signaling pathway.	2001 Feb 23	11087735
Influence of patient posture on oxygen saturation during fibre-optic bronchoscopy.	2001 Jan	11207018
A clinico-epidemiological study of organophosphorus poisoning at a rural-based teaching hospital in eastern Nepal.	2001 Jan	11205599
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation.	2001 Jan	11205508
Hypotensive infarction of the spinal cord in a rhesus macaque (Macaca mulatta).	2001 Jan	11199156
Neural mechanisms underlying migrating motor complex formation in mouse isolated colon.	2001 Jan	11159701
Evidence for cocaine and methylecgonidine stimulation of M(2) muscarinic receptors in cultured human embryonic lung cells.	2001 Jan	11159694
Characterization of a novel mechanism accounting for the adverse cholinergic effects of the anticancer drug irinotecan.	2001 Jan	11156563
Comparison of myocardial blood flow during dobutamine-atropine infusion with that after dipyridamole administration in normal men.	2001 Jan	11153727
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine.	2001 Jan	11150921
Eruptive pruritic syringomas: treatment with topical atropine.	2001 Jan	11148500
Administration of atropine in the setting of acute myocardial infarction: potentiation of the ischemic process?	2001 Jan	11146027
Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat.	2001 Jan 1	11149716
Activation of sympathoadrenomedullary system increases pulmonary nitric oxide production in the rabbit.	2001 Jan 12	11164390
The effect of nitrate and ammonium concentrations on growth and alkaloid accumulation of Atropa belladonna hairy roots.	2001 Jan 23	11164960
Ghrelin acts in the central nervous system to stimulate gastric acid secretion.	2001 Jan 26	11162609
Angiotensinergic and noradrenergic mechanisms in the hypothalamic paraventricular nucleus participate in the drinking response induced by activation of the subfornical organ in rats.	2001 Jan 29	11164509
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry.	2001 Jan 5	11204211
Neural-epithelial cell interplay: in vitro evidence that vagal mediators increase PGE2 production by human nasal epithelial cells.	2001 Jan-Feb	11227912
Activation of the parasympathetic nervous system is necessary for normal meal-induced insulin secretion in rhesus macaques.	2001 Mar	11238517
From 'captive' agonism to insurmountable antagonism: demonstrating the power of analytical pharmacology.	2001 Mar	11236130
Respective roles of carbamylcholine and cyclic adenosine monophosphate in their synergistic regulation of cell cycle in thyroid primary cultures.	2001 Mar	11181542
5-Hydroxytryptamine and atropine inhibit nicotinic receptors in submucosal neurons.	2001 Mar 2	11239911
The role of nitric oxide on the relaxations of rabbit corpus cavernosum induced by Androctonus australis and Buthotus judaicus scorpion venoms.	2001 May	11072041

Patents

Sample Use Guides

In Vivo Use Guide

Atropine as an antisialagogue or for antivagal effects: initial single dose of 0.5 mg to 1 mg; as an antidote for organophosporous or muscarinic mushroom

Route of Administration: Other

In Vitro Use Guide

Atropine in doses -5.44 to -4.74 log mol/L totally inhibited the contraction induced by acetylcholine and carbachol in segmental pulmonary artery specimens taken from the patients undergoing thoracic surgery.

Substance Class	Chemical Created by `admin` on `Fri Jun 25 21:11:21 UTC 2021` Edited by `admin` on `Fri Jun 25 21:11:21 UTC 2021`
Record UNII	7C0697DR9I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ATROPINE

Common Name

English

ATROPINE [USP]

Common Name

English

ATROPINE [VANDF]

Common Name

English

ATROPINE COMPONENT OF ATNAA

Common Name

English

(+/-)-HYOSCYAMINE

Common Name

English

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER

Common Name

English

ATROPEN

Brand Name

English

ATROPINE [WHO-DD]

Common Name

English

HOMATROPINE HYDROBROMIDE IMPURITY D [EP]

Common Name

English

ATROPINUM [HPUS]

Common Name

English

ATROPINE COMPONENT OF DUODOTE

Common Name

English

ATROPINE [ORANGE BOOK]

Common Name

English

DUODOTE COMPONENT ATROPINE

Common Name

English

ATROPINE ((+/-))

Common Name

English

(3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL TROPATE

Common Name

English

ATROPINE [MI]

Common Name

English

ATROPINE, (+/-)-

Common Name

English

ATNAA COMPONENT ATROPINE

Common Name

English

ATROPINE [GREEN BOOK]

Common Name

English

ATROPINE [EP MONOGRAPH]

Common Name

English

ATROPINE [MART.]

Common Name

English

ATROPINUM

Common Name

English

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-(+/-)-

Common Name

English

ATROPINE [EP]

Common Name

English

1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (+/-)-TROPATE (ESTER)

Common Name

English

ATROPINE [USP-RS]

Common Name

English

DL-HYOSCYAMINE

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000175370