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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 of ATROPINE

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
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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 TargetPharmacologyConditionPotency
9.34 null [pKi]
8.95 null [pKi]
9.15 null [pKi]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Atropine sulfate
Primary
Atropine sulfate
Primary
Atropine sulfate
Primary
Atropine sulfate
Primary
Atropine sulfate

Cmax

ValueDoseCo-administeredAnalytePopulation
9.6 ng/mL
1.67 mg single, intramuscular
ATROPINE plasma
Homo sapiens
860 pg/mL
0.4 mg single, ocular
ATROPINE plasma
Homo sapiens
11.7 ng/mL
1.67 mg single, intramuscular
ATROPINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
43245 pg × min/mL
0.4 mg single, ocular
ATROPINE plasma
Homo sapiens
47.6 ng × h/mL
1.67 mg single, intramuscular
ATROPINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
4.1 h
1.67 mg single, intramuscular
ATROPINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
82%
1.67 mg single, intramuscular
ATROPINE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

PubMed

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
Record UNII
7C0697DR9I
Record Status Validated (UNII)
Record Version