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Details

Stereochemistry EPIMERIC
Molecular Formula 2C17H23NO3.H2O4S
Molecular Weight 676.8197
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATROPINE SULFATE ANHYDROUS

SMILES

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

InChI

InChIKey=HOBWAPHTEJGALG-AADVZIIPSA-N
InChI=1S/2C17H23NO3.H2O4S/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)/t2*13-,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

Molecular Formula H2O4S
Molecular Weight 98.0796
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

9.9455042E11
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

9.9455042E11
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

9.9455042E11
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

9.9455042E11
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

9.9455042E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
860 pg/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
43245 pg × min/mL
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
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
n = 1
Health Status: unhealthy
Age Group: 10 years
Sex: M
Population Size: 1
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)
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:
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
n = 1
Health Status: unhealthy
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 10 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 10 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 10 years
Sex: M
Population Size: 1
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
n = 1
Health Status: unhealthy
Age Group: 10 years
Sex: M
Population Size: 1
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)
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:
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)
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:
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)
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:
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)
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:
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)
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:
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)
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:
Adverse event severe
1 mg single, sublingual
Overdose
Dose: 1 mg
Route: sublingual
Route: single
Dose: 1 mg
Sources:
unhealthy
n = 1
Health Status: unhealthy
Population Size: 1
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
Nicotine potentiates sulpiride-induced catalepsy in mice.
1998
Altered baroreflex control of heart rate in bradykinin B2-receptor knockout mice.
1999 Dec
TIVA with propofol and remifentanil.
1999 May
Attenuation of focal adhesion kinase signaling following depletion of agonist-sensitive pools of phosphatidylinositol 4,5-bisphosphate.
1999 Nov
Effects of topical glucocorticoids on in vitro lactoferrin glandular secretion: comparison between human upper and lower airways.
2000 Dec
Focal microinjection of carbachol into the periaqueductal gray induces seizures in the forebrain of the rat.
2000 Dec
Effect of alpha-2 adrenoceptor antagonists on colonic function in rats.
2000 Jun
Cardiovascular studies on different classes of soft drugs.
2000 Mar
SCH 23390 affords protection against soman-evoked seizures in the freely moving guinea-pig: a concomitant neurochemical, electrophysiological and behavioural study.
2001
Influence of nitric oxide donors and of the alpha(2)-agonist UK-14,304 on acetylcholine release in the pig gastric fundus.
2001
Endothelin receptors in human and guinea-pig gallbladder muscle.
2001 Apr 20
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
Pharmacological characterization of muscarinic receptors in dog isolated ciliary and urinary bladder smooth muscle.
2001 Feb
Antispasmodic activity of the fruits of Helicteres isora Linn.
2001 Feb
Reversal of rocuronium with edrophonium during propofol versus sevoflurane anesthesia.
2001 Feb
Cardiac sympathetic overactivity and decreased baroreflex sensitivity in L-NAME hypertensive rats.
2001 Feb
Sympathetic control of nasal blood flow in the rat mediated by alpha(1)-adrenoceptors.
2001 Feb 16
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery.
2001 Feb 2
Facilitation of transmitter release in the urinary bladders of neonatal and adult rats via alpha1-adrenoceptors.
2001 Feb 23
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
[Experiences with cycloplegic drops in German-speaking centers of pediatric ophthalmology and stabology--results of a 1999 survey].
2001 Jan
On the interactions between antimuscarinic atropine and NMDA receptor antagonists in anticholinesterase-treated mice.
2001 Jan
Increase of peak expiratory flow by atropine is dependent on circadian rhythm.
2001 Jan
Influence of patient posture on oxygen saturation during fibre-optic bronchoscopy.
2001 Jan
Tris(2,2'-bipyridine)ruthenium(II) electrogenerated chemiluminescence of alkaloid type drugs with solid phase extraction sample preparation.
2001 Jan
Muscarinic activation of transient inward current and contraction in canine colon circular smooth muscle cells.
2001 Jan
Hypotensive infarction of the spinal cord in a rhesus macaque (Macaca mulatta).
2001 Jan
Effects of VIP and NO on the motor activity of vascularly perfused rat proximal colon.
2001 Jan
Unplanned administration of atropine, succinylcholine and lidocaine.
2001 Jan
Evidence for cocaine and methylecgonidine stimulation of M(2) muscarinic receptors in cultured human embryonic lung cells.
2001 Jan
Characterization of a novel mechanism accounting for the adverse cholinergic effects of the anticancer drug irinotecan.
2001 Jan
Comparison of myocardial blood flow during dobutamine-atropine infusion with that after dipyridamole administration in normal men.
2001 Jan
Reversal of Haemorrhagic Shock in Rats by Tetrahydroaminoacridine.
2001 Jan
Eruptive pruritic syringomas: treatment with topical atropine.
2001 Jan
Secretion and gene expression of secretory leukocyte protease inhibitor by human airway submucosal glands.
2001 Jan
Xerostomia, xerophthalmia, and plasmacytic infiltrates of the salivary glands (Sjögren's-like syndrome) in a cat.
2001 Jan 1
Activation of sympathoadrenomedullary system increases pulmonary nitric oxide production in the rabbit.
2001 Jan 12
Post-ictal analgesia: involvement of opioid, serotoninergic and cholinergic mechanisms.
2001 Jan 12
Changes in sensitivity of cholinoceptors and adrenoceptors during transhemispheric cortical reorganisation in rat SmI.
2001 Jan 12
Upregulation of immunoreactive angiotensin II release and angiotensinogen mRNA expression by high-frequency preganglionic stimulation at the canine cardiac sympathetic ganglia.
2001 Jan 19
The effect of nitrate and ammonium concentrations on growth and alkaloid accumulation of Atropa belladonna hairy roots.
2001 Jan 23
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
Neural-epithelial cell interplay: in vitro evidence that vagal mediators increase PGE2 production by human nasal epithelial cells.
2001 Jan-Feb
Evidence of alpha-adrenoceptor-mediated chronotropic action in children.
2001 Jan-Feb
Pharmacological characterization of locomotor sensitization induced by chronic phencyclidine administration.
2001 Mar
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
Respective roles of carbamylcholine and cyclic adenosine monophosphate in their synergistic regulation of cell cycle in thyroid primary cultures.
2001 Mar
Initiation of distension-induced descending peristaltic reflex in opossum esophagus: role of muscle contractility.
2001 Mar
Orally administered atropine enhances motor cortex excitability: a transcranial magnetic stimulation study in human subjects.
2001 Mar 16
Evidence for a direct action of Tityus serrulatus scorpion venom on the cardiac muscle.
2001 May
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 Sat Jun 26 11:46:55 UTC 2021
Edited
by admin
on Sat Jun 26 11:46:55 UTC 2021
Record UNII
KAE4PSB0Z3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ATROPINE SULFATE ANHYDROUS
Common Name English
ATROPINE SULFATE [WHO-DD]
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)- (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, SULFATE (2:1) (SALT)
Common Name English
BENZENEACETIC ACID, .ALPHA.-(HYDROXYMETHYL)- (3-ENDO)-8-METHYL-8-AZABICYCLO(3.2.1)OCT-3-YL ESTER, SULFATE (2:1)
Common Name English
1.ALPHA.H,5.ALPHA.H-TROPAN-3.ALPHA.-OL (+/-)-TROPATE (ESTER), SULFATE (2:1) (SALT)
Common Name English
ATROPINE SULFATE ANHYDROUS [MI]
Common Name English
NSC-26671
Code English
Code System Code Type Description
FDA UNII
KAE4PSB0Z3
Created by admin on Sat Jun 26 11:46:55 UTC 2021 , Edited by admin on Sat Jun 26 11:46:55 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-235-0
Created by admin on Sat Jun 26 11:46:55 UTC 2021 , Edited by admin on Sat Jun 26 11:46:55 UTC 2021
PRIMARY
EPA CompTox
55-48-1
Created by admin on Sat Jun 26 11:46:55 UTC 2021 , Edited by admin on Sat Jun 26 11:46:55 UTC 2021
PRIMARY
CAS
55-48-1
Created by admin on Sat Jun 26 11:46:55 UTC 2021 , Edited by admin on Sat Jun 26 11:46:55 UTC 2021
PRIMARY
MERCK INDEX
M2136
Created by admin on Sat Jun 26 11:46:55 UTC 2021 , Edited by admin on Sat Jun 26 11:46:55 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY