ATROPINE

First marketed in 1921

Details

Stereochemistry	RACEMIC
Molecular Formula	C17H23NO3
Molecular Weight	289.3694
Optical Activity	( + / - )
Defined Stereocenters	3 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3

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	289.3694
Charge	0
Count

Stereochemistry	EPIMERIC
Additional Stereochemistry	No
Defined Stereocenters	3 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/mesh/68001285 | 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	Potency
Muscarinic acetylcholine receptor M1 168 Target ID: CHEMBL216 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2760	9.34 null [pKi]
Muscarinic acetylcholine receptor M2 120 Target ID: CHEMBL211 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2760	8.95 null [pKi]
Muscarinic acetylcholine receptor M3 158 Target ID: CHEMBL245 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2760	9.15 null [pKi]

Conditions

Condition	Modality	Highest Phase	Product
Bradyasystolic cardiac arrest 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8360	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 9.9455042E11
Organophosphorus poisoning 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8360	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 9.9455042E11
Increased salivary flow 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8360	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 9.9455042E11
Vagus nerve activation 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8360	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 9.9455042E11
Muscarinic mushroom poisoning 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8360	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 9.9455042E11

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 n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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 n = 1 Health Status: unhealthy Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 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 n = 1 Health Status: unhealthy Age Group: 10 years Sex: M Population Size: 1 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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) n = 77 Health Status: unhealthy Condition: progressive myopia Age Group: 10.3 years (range: 2.7–16.8 years) Sex: M+F Population Size: 77 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 n = 1 Health Status: unhealthy Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/33521988

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OCT1 506 OCT2 638 OCT3 149

Drug as perpetrator

Target	Modality	Activity
OCT1 523	inhibitor 3240 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 1.2 uM]
OCT2 639	inhibitor 3240 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 39 uM]
OCT3 149	inhibitor 3240 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
ChemicalBook	CB2163178	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB2163178
MolPort	MolPort-001-742-593	https://www.molport.com/shop/molecule-link/MolPort-001-742-593
eMolecules	478873	https://www.emolecules.com/cgi-bin/more?vid=478873

PubMed

Title	Date	PubMed
Catalepsy induced by morphine or haloperidol: effects of apomorphine and anticholinergic drugs.	1976 Aug	10058
Nicotine potentiates sulpiride-induced catalepsy in mice.	1998	10958255
Progressive treatment of erectile dysfunction with intracorporeal injections of different combinations of vasoactive agents.	1999 Feb	10098948
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
Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate.	1999 Nov	10537051
Focal microinjection of carbachol into the periaqueductal gray induces seizures in the forebrain of the rat.	2000 Dec	11074189
Acute cardiac rupture during dobutamine-atropine echocardiography stress test.	2000 Feb	10668020
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
SCH 23390 affords protection against soman-evoked seizures in the freely moving guinea-pig: a concomitant neurochemical, electrophysiological and behavioural study.	2001	11114407
Differences in electromechanical coupling between bradykinin and the nonpeptide kinin B2 receptor agonist, FR 190997, in the circular muscle of guinea-pig colon.	2001 Feb	11218070
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.	2001 Feb 16	11226391
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
Effects of VIP and NO on the motor activity of vascularly perfused rat proximal colon.	2001 Jan	11179602
Unplanned administration of atropine, succinylcholine and lidocaine.	2001 Jan	11167461
Administration of atropine in the setting of acute myocardial infarction: potentiation of the ischemic process?	2001 Jan	11146027
Assessment of autonomic cardiovascular indices in non-stationary data in rats.	2001 Jan	11137443
Electrical activation of endothelium evokes vasodilation and hyperpolarization along hamster feed arteries.	2001 Jan	11123230
Role of PAG in the antinociception evoked from the medial or central amygdala in rats.	2001 Jan 1	11226714
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs.	2001 Jan 1	11149715
[Atropine. Principles and rules of utilization].	2001 Jan 15	11234098
Neural-epithelial cell interplay: in vitro evidence that vagal mediators increase PGE2 production by human nasal epithelial cells.	2001 Jan-Feb	11227912
Initiation of distension-induced descending peristaltic reflex in opossum esophagus: role of muscle contractility.	2001 Mar	11171625
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 poisoning: initial single dose of 2 mg to 3 mg, repeated every 20-30 minutes; for bradyasystolic cardiac arrest: 1 mg dose, repeated every 3-5 minutes if asystole persists; in patients with coronary artery disease: total dose should not exceed 0.03 mg/kg to 0.04 mg/kg.

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 `Wed Jul 05 23:54:02 UTC 2023` Edited by `admin` on `Wed Jul 05 23:54:02 UTC 2023`
Record UNII	7C0697DR9I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ATROPINE

Common Name

English

ATROPINE [VANDF]

Common Name

English

ATROPINE [USP MONOGRAPH]

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

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 [EP IMPURITY]

Common Name

English

Atropine [WHO-DD]

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

HOMATROPINE HYDROBROMIDE IMPURITY D [EP IMPURITY]

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