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Details

Stereochemistry RACEMIC
Molecular Formula C17H23NO3.C6H8O7
Molecular Weight 481.4929
Optical Activity ( + / - )
Defined Stereocenters 3 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATROPINE CITRATE

SMILES

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

InChI

InChIKey=PVFKXEKWGWYDSO-RIMUKSHESA-N
InChI=1S/C17H23NO3.C6H8O7/c1-18-13-7-8-14(18)10-15(9-13)21-17(20)16(11-19)12-5-3-2-4-6-12;7-3(8)1-6(13,5(11)12)2-4(9)10/h2-6,13-16,19H,7-11H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)/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

Molecular Formula C6H8O7
Molecular Weight 192.1235
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
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.

Originator

Curator's Comment: Atropine was first obtained from the deadly nightshade (Atropa belladonna) by M. Brandes in 1819.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
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
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
9.6 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
43245 pg × min/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.1 h
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
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
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

Doses

DosePopulationAdverse events​
0.1 mg/kg single, intravenous
Dose: 0.1 mg/kg
Route: intravenous
Route: single
Dose: 0.1 mg/kg
Sources:
unhealthy, 10 years
Health Status: unhealthy
Age Group: 10 years
Sex: M
Sources:
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:
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:
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:
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:
1 mg single, sublingual
Overdose
Dose: 1 mg
Route: sublingual
Route: single
Dose: 1 mg
Sources:
unhealthy
Health Status: unhealthy
Sources:
Other AEs: Adverse event...
Other AEs:
Adverse event (severe)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 10 years
Health Status: unhealthy
Age Group: 10 years
Sex: M
Sources:
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:
unhealthy, 10 years
Health Status: unhealthy
Age Group: 10 years
Sex: M
Sources:
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:
unhealthy, 10 years
Health Status: unhealthy
Age Group: 10 years
Sex: M
Sources:
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:
unhealthy, 10 years
Health Status: unhealthy
Age Group: 10 years
Sex: M
Sources:
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:
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:
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:
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:
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:
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:
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:
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:
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:
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:
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:
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:
Adverse event severe
1 mg single, sublingual
Overdose
Dose: 1 mg
Route: sublingual
Route: single
Dose: 1 mg
Sources:
unhealthy
Health Status: unhealthy
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1.2 uM]
yes [IC50 39 uM]
yes [IC50 466 uM]
PubMed

PubMed

TitleDatePubMed
Endothelin receptors in human and guinea-pig gallbladder muscle.
2001-04-20
Localisation and neural control of the release of calcitonin gene-related peptide (CGRP) from the isolated perfused porcine ileum.
2001-04-20
Orally administered atropine enhances motor cortex excitability: a transcranial magnetic stimulation study in human subjects.
2001-03-16
Neural-epithelial cell interplay: in vitro evidence that vagal mediators increase PGE2 production by human nasal epithelial cells.
2001-03-03
5-Hydroxytryptamine and atropine inhibit nicotinic receptors in submucosal neurons.
2001-03-02
Activation of the parasympathetic nervous system is necessary for normal meal-induced insulin secretion in rhesus macaques.
2001-03
From 'captive' agonism to insurmountable antagonism: demonstrating the power of analytical pharmacology.
2001-03
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration.
2001-03
Low-affinity M(2) receptor binding state mediates mouse atrial bradycardia: comparative effects of carbamylcholine and the M(1) receptor agonists sabcomeline and xanomeline.
2001-03
Respective roles of carbamylcholine and cyclic adenosine monophosphate in their synergistic regulation of cell cycle in thyroid primary cultures.
2001-03
Role of a central muscarinic cholinergic pathway for relaxation of the proximal urethra during the voiding phase in rats.
2001-03
Initiation of distension-induced descending peristaltic reflex in opossum esophagus: role of muscle contractility.
2001-03
Muscarinic stimulation increases basal Ca(2+) and inhibits spontaneous Ca(2+) transients in murine colonic myocytes.
2001-03
Photochemical N-demethylation of alkaloids.
2001-02-26
Facilitation of transmitter release in the urinary bladders of neonatal and adult rats via alpha1-adrenoceptors.
2001-02-23
Binding of nicotinic ligands to and nicotine-induced calcium signaling in Trypanosoma cruzi.
2001-02-23
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.
2001-02-16
Characterisation of the prejunctional inhibitory muscarinic receptor on cholinergic nerves in the rat urinary bladder.
2001-02-16
[Availability of antidotes in French emergency medical aid units].
2001-02-03
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001-02-02
Muscarinic receptor subtypes and calcium signaling in Fischer rat thyroid cells.
2001-02-01
Acetylcholine-evoked calcium increases in Deiters' cells of the guinea pig cochlea suggest alpha9-like receptors.
2001-02-01
Differences in electromechanical coupling between bradykinin and the nonpeptide kinin B2 receptor agonist, FR 190997, in the circular muscle of guinea-pig colon.
2001-02
Accelerated dobutamine stress testing: safety and feasibility in patients with known or suspected coronary artery disease.
2001-02
On the mechanisms of cholinergic control of the sinoatrial node discharge.
2001-02
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.
2001-02
Antispasmodic activity of the fruits of Helicteres isora Linn.
2001-02
Sublingual hyoscyamine sulfate in combination with ketorolac tromethamine for ureteral colic: a randomized, double-blind, controlled trial.
2001-02
Reversal of rocuronium with edrophonium during propofol versus sevoflurane anesthesia.
2001-02
Role of preoptic and anterior hypothalamic cholinergic input on water intake and body temperature.
2001-01-19
[Atropine. Principles and rules of utilization].
2001-01-15
Determination of scopolamine in human serum and microdialysis samples by liquid chromatography-tandem mass spectrometry.
2001-01-05
Role of PAG in the antinociception evoked from the medial or central amygdala in rats.
2001-01-01
[Experiences with cycloplegic drops in German-speaking centers of pediatric ophthalmology and stabology--results of a 1999 survey].
2001-01
Preanaesthetic use of atropine in small animals.
2001-01
On the interactions between antimuscarinic atropine and NMDA receptor antagonists in anticholinesterase-treated mice.
2001-01
Mechanisms of acetylcholine-induced vasorelaxation in high K+-stimulated rabbit renal arteries.
2001-01
Increase of peak expiratory flow by atropine is dependent on circadian rhythm.
2001-01
High concentration sevoflurane induction of anesthesia accelerates onset of vecuronium neuromuscular blockade.
2001-01
[Marked bradycardia during anesthetic induction treated with temporary cardiac pacing in a patient with latent sick sinus syndrome].
2001-01
Tachykinins contribute to nerve-mediated contractions in the human esophagus.
2001-01
Influence of patient posture on oxygen saturation during fibre-optic bronchoscopy.
2001-01
A clinico-epidemiological study of organophosphorus poisoning at a rural-based teaching hospital in eastern Nepal.
2001-01
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation.
2001-01
Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells.
2001-01
Hypotensive infarction of the spinal cord in a rhesus macaque (Macaca mulatta).
2001-01
Spectral analysis of circadian rhythms in heart rate variability of dogs.
2001-01
Effects of VIP and NO on the motor activity of vascularly perfused rat proximal colon.
2001-01
Unplanned administration of atropine, succinylcholine and lidocaine.
2001-01
Neuropharmacological actions of some binuclear lanthanide(III) complexes.
2001-01
Patents

Sample Use Guides

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 Mon Mar 31 18:08:37 GMT 2025
Edited
by admin
on Mon Mar 31 18:08:37 GMT 2025
Record UNII
058DSI3OLC
Record Status Validated (UNII)
Record Version
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Name Type Language
ATROPINE CITRATE
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER ENDO-, 2-HYDROXY-1,2,3-PROPANETRICARBOXYLATE (SALT)
Preferred Name English
Code System Code Type Description
PUBCHEM
71587492
Created by admin on Mon Mar 31 18:08:37 GMT 2025 , Edited by admin on Mon Mar 31 18:08:37 GMT 2025
PRIMARY
CAS
137414-35-8
Created by admin on Mon Mar 31 18:08:37 GMT 2025 , Edited by admin on Mon Mar 31 18:08:37 GMT 2025
PRIMARY
FDA UNII
058DSI3OLC
Created by admin on Mon Mar 31 18:08:37 GMT 2025 , Edited by admin on Mon Mar 31 18:08:37 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY