Atropine sulfate

First marketed in 1921

Details

Stereochemistry	RACEMIC
Molecular Formula	2C17H23NO3.H2O.H2O4S
Molecular Weight	694.833
Optical Activity	( + / - )
Defined Stereocenters	6 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.OS(O)(=O)=O.CN1[C@H]2CC[C@@H]1C[C@@H](C2)OC(=O)C(CO)C3=CC=CC=C3.CN4[C@H]5CC[C@@H]4C[C@@H](C5)OC(=O)C(CO)C6=CC=CC=C6

InChI

InChIKey=JPKKQJKQTPNWTR-CHYDPLAESA-N

InChI=1S/2C17H23NO3.H2O4S.H2O/c2*1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;1-5(2,3)4;/h2*2-6,13-16,19H,7-11H2,1H3;(H2,1,2,3,4);1H2/t2*13-,14+,15+,16?;;

HIDE SMILES / InChI

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 2849	9.34 null [pKi]
Muscarinic acetylcholine receptor M2 121 Target ID: CHEMBL211 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2849	8.95 null [pKi]
Muscarinic acetylcholine receptor M3 160 Target ID: CHEMBL245 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2014/206289s000lbl.pdf	Antagonist 2849	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 8583	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 2001
Organophosphorus poisoning 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8583	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 2001
Increased salivary flow 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8583	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 2001
Vagus nerve activation 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8583	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 2001
Muscarinic mushroom poisoning 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/021146s015lbl.pdf	Primary	Approved 8583	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 2001

C_max

Value	Dose	Analyte	Population
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
860 pg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3046815	0.4 mg single, ocular dose: 0.4 mg 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

AUC

Value	Dose	Co-administered	Analyte	Population
43245 pg × min/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3046815	0.4 mg single, ocular dose: 0.4 mg 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
OCT1 620 OCT2 779 OCT3 159

Drug as perpetrator

Target	Modality	Activity
OCT1 656	inhibitor 4027 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 1.2 uM]
OCT2 782	inhibitor 4027 Sources: http://www.ncbi.nlm.nih.gov/pubmed/16263091	yes [IC50 39 uM]
OCT3 161	inhibitor 4027 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
eMolecules	478873	https://www.emolecules.com/cgi-bin/more?vid=478873
MolPort	MolPort-001-742-593	https://www.molport.com/shop/molecule-link/MolPort-001-742-593

PubMed

Title	Date	PubMed
Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways.	2000 Dec	11112886
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
Cardiovascular studies on different classes of soft drugs.	2000 Mar	10756546
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.	2001	11114406
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.	2001 Feb	11181424
Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial.	2001 Feb	11174230
Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats.	2001 Feb	11158985
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells.	2001 Feb 1	11172738
Mechanisms of acetylcholine-induced vasorelaxation in high K+-stimulated rabbit renal arteries.	2001 Jan	11217061
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
Spectral analysis of circadian rhythms in heart rate variability of dogs.	2001 Jan	11197557
Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat.	2001 Jan 1	11149716
Effects of preemptive atropine administration on incidence of medetomidine-induced bradycardia in dogs.	2001 Jan 1	11149715
Role of preoptic and anterior hypothalamic cholinergic input on water intake and body temperature.	2001 Jan 19	11166703
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry.	2001 Jan 5	11204211
Low-affinity M(2) receptor binding state mediates mouse atrial bradycardia: comparative effects of carbamylcholine and the M(1) receptor agonists sabcomeline and xanomeline.	2001 Mar	11181912
Respective roles of carbamylcholine and cyclic adenosine monophosphate in their synergistic regulation of cell cycle in thyroid primary cultures.	2001 Mar	11181542
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.

Name

Type

Language

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-(±)-, SULPHATE (2:1) (SALT), MONOHYDRATE

Preferred Name

English

Atropine sulfate

Common Name

English

ATROPINI SULFAS [WHO-IP LATIN]

Common Name

English

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-, 8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, ENDO-(±)-, SULFATE (2:1) (SALT), MONOHYDRATE

Systematic Name

English

ATROPINUM SULPHURICUM

Common Name

English

ATROPINE SULFATE [WHO-IP]

Common Name

English

Atropine sulfate hydrate [JAN]

Common Name

English

ATROPINE SULFATE [ORANGE BOOK]

Common Name

English

ATROPINE SULPHATE

Common Name

English

LONOX COMPONENT ATROPINE SULFATE

Common Name

English

Atropine sulfate monohydrate

Common Name

English

1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (±)-TROPATE (ESTER), SULPHATE (2:1) (SALT) MONOHYDRATE

Systematic Name

English

ISOPTO ATROPINE

Brand Name

English

ATROPINE SULFATE [USP MONOGRAPH]

Common Name

English

DI-ATRO COMPONENT ATROPINE SULFATE

Common Name

English

LO-TROL COMPONENT ATROPINE SULFATE

Common Name

English

NSC-755889

Code

English

Atropine sulfate hydrate

Common Name

English

MOTOFEN COMPONENT ATROPINE SULFATE

Common Name

English

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)- (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, SULFATE (2:1) (SALT), MONOHYDRATE

Systematic Name

English

SYD-101

Code

English

COLONAID COMPONENT ATROPINE SULFATE

Common Name

English

ENLON-PLUS COMPONENT ATROPINE SULFATE

Common Name

English

ATROPINE SULFATE [USP-RS]

Common Name

English

ATROPINE SULFATE [VANDF]

Common Name

English

ATROPT

Brand Name

English

BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)- (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, SULPHATE (2:1) (SALT), MONOHYDRATE

Systematic Name

English

(±)-ENDO-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL .ALPHA.-(HYDROXYMETHYL)BENZENEACETATE SULFATE (2:1) (SALT) MONOHYDRATE

Systematic Name

English

ATROPISOL

Brand Name

English

Atropine sulfate [MART.]

Common Name

English

LOMOTIL COMPONENT ATROPINE SULFATE

Common Name

English

LOGEN COMPONENT ATROPINE SULFATE

Common Name

English

Atropine sulfate monohydrate [WHO-DD]

Common Name

English

Atropine sulfate monohydrate [MI]

Common Name

English

Atropine sulfate [EP MONOGRAPH]

Common Name

English

ATROPINUM SULPHURICUM [HPUS]

Common Name

English

LOW-QUEL COMPONENT ATROPINE SULFATE

Common Name

English

1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (±)-TROPATE (ESTER), SULFATE (2:1) (SALT) MONOHYDRATE

Systematic Name

English

LOMANATE COMPONENT ATROPINE SULFATE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29704