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Compound Detail

CHEMBL517712

ATROPINE
💊 Approved Drug
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💊 Approved Drug
CN1[C@@H]2CC[C@H]1C[C@@H](OC(=O)C(CO)c1ccccc1)C2

Basic Information

ChEMBL ID CHEMBL517712
Name ATROPINE
Phase Approved
Structure Type MOL
InChI Key RKUNBYITZUJHSG-SPUOUPEWSA-N
Therapeutic ✓ Yes

Known Names

Atroject Atropen Atrophate Atropine Atropine (autoinjector) Atropine component of atnaa Atropine component of duodote Atropinum Dl-hyoscyamine
26
Targets
141
Activities
4
Assay Types
13
PK Parameters
20
Publications
9
Known Names
20
Indications
3
Mechanisms

Molecular Properties

289.4
MW (Da)
1.93
ALogP
4
HBA
1
HBD
49.8
PSA (Ų)
0.86
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1960
Availability Prescription
Chirality Racemic

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product
USAN Stem -trop-

Extended Properties

Molecular Formula C17H23NO3
MW 289.38
Aromatic Rings 1
Heavy Atoms 21
NP-Likeness 0.79

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Muscarinic acetylcholine receptor M3 antagonist ANTAGONIST Muscarinic acetylcholine receptor M3
Muscarinic acetylcholine receptor M1 antagonist ANTAGONIST Muscarinic acetylcholine receptor M1
Muscarinic acetylcholine receptor M2 antagonist ANTAGONIST Muscarinic acetylcholine receptor M2

Indications

Digestive System Diseases Mydriasis Poisoning Amblyopia Anisometropia Dwarfism, Pituitary Headache Myopia Myopia, Degenerative Pain Strabismus Amyotrophic Lateral Sclerosis Blood Coagulation Disorders Bradycardia Breast Neoplasms Heart Arrest Hemorrhage Hypospadias Organophosphate Poisoning Pneumonia, Ventilator-Associated

ATC Classification

A03BA01
atropine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR FUNCTIONAL GASTROINTESTINAL DISORDERS
S01FA01
atropine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 94 meas. best 9.98
Kd 29 meas. best 9.2
IC50 17 meas. best 9.32
EC50 1 meas. best 9.01

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 9.98 9.1367 0.1 6
Unchecked
CHEMBL612545
Ki 9.92 8.5763 0.1 8
Muscarinic acetylcholine receptor M3
CHEMBL320
Ki 9.92 9.51 0.1 2
Muscarinic acetylcholine receptor M1
CHEMBL2672
Ki 9.7 9.16 0.2 2
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 9.68 9.2257 0.2 7
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 9.6 9.2556 0.2 9
Muscarinic acetylcholine receptor M1
CHEMBL276
Ki 9.59 9.215 0.3 6
Muscarinic acetylcholine receptor
CHEMBL1907609
Ki 9.52 9.3629 0.3 7
Muscarinic acetylcholine receptor
CHEMBL2094109
Ki 9.49 9.005 0.3 6
Acetylcholinesterase
CHEMBL3198
Ki 9.46 9.305 0.3 2
Muscarinic acetylcholine receptor M2
CHEMBL3197
Ki 9.46 9.305 0.3 2
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 9.46 8.61 0.3 16
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 9.36 9.13 0.4 5
Muscarinic acetylcholine receptor
CHEMBL1907609
IC50 9.32 8.84 0.5 3
Muscarinic acetylcholine receptor M4
CHEMBL317
Ki 9.28 9.28 0.5 2
Muscarinic acetylcholine receptor M3
CHEMBL320
Kd 9.2 9.2 0.6 1
Muscarinic acetylcholine receptors; M1 & M2
CHEMBL2095219
Ki 9.17 9.17 0.7 1
Muscarinic acetylcholine receptor M2
CHEMBL309
Ki 9.15 8.8583 0.7 6
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 9.13 9.13 0.7 1
Muscarinic acetylcholine receptor M3
CHEMBL5498
Kd 9.11 8.98 0.8 4
Muscarinic acetylcholine receptor M5
CHEMBL277
Ki 9.07 9.07 0.9 1
Cavia porcellus
CHEMBL369
Kd 9.05 8.932 0.9 5
Muscarinic acetylcholine receptor
CHEMBL2094109
Kd 9.05 8.95 0.9 6
Muscarinic acetylcholine receptor M5
CHEMBL2035
IC50 9.04 9.04 0.9 1
Trachea
CHEMBL4296542
EC50 9.01 9.01 1.0 1
Unchecked
CHEMBL612545
Kd 8.98 8.98 1.0 1
Muscarinic acetylcholine receptor
CHEMBL1907609
Kd 8.89 8.8325 1.3 4
Rattus norvegicus
CHEMBL376
Kd 8.89 8.81 1.3 2
Muscarinic acetylcholine receptor M1
CHEMBL276
Kd 8.89 8.89 1.3 1
Muscarinic acetylcholine receptor M2
CHEMBL211
Kd 8.87 8.785 1.3 2
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 8.82 8.82 1.5 1
Ileum
CHEMBL613680
Kd 8.69 8.545 2.0 2
Muscarinic acetylcholine receptor M3
CHEMBL245
IC50 8.68 8.585 2.1 2
Muscarinic acetylcholine receptor M2
CHEMBL309
Kd 8.57 8.57 2.7 1
Muscarinic acetylcholine receptor M2
CHEMBL211
IC50 8.43 7.765 3.7 4
Rattus norvegicus
CHEMBL376
IC50 7.29 7.29 51.0 1
Unchecked
CHEMBL612545
IC50 6.33 6.33 470.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 6.28 6.28 530.0 1
Alpha-1D adrenergic receptor
CHEMBL223
Ki 6.18 6.18 666.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 6.0 6.0 1012.0 1
Alpha-1D adrenergic receptor
CHEMBL223
IC50 5.87 5.87 1354.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 4.91 4.91 12200.0 1
Nicotinic acetylcholine receptor alpha 5 subunit
CHEMBL2366408
Ki 4.49 4.49 32500.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 7.6 mL.min-1.kg-1 Homo sapiens
CL 3.3 mL.min-1.kg-1 Homo sapiens
CL 7.6 mL.min-1.kg-1 Homo sapiens
CL 7.6 mL.min-1.kg-1 Homo sapiens
F 79.0 % Homo sapiens
Fu 0.82 - -
Fu 0.171 - -
Fu 0.82 - Homo sapiens
Fu 0.61 - Homo sapiens
Fu 0.61 - Homo sapiens
KA 167000000.0 M-1 Canis lupus familiaris
MRT 7.2 hr Homo sapiens
T1/2 4.1 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor M4 Ki = 0.104 nM 9.98 DRUGMATRIX: Muscarinic M4 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Muscarinic acetylcholine receptor M3 Ki = 0.12 nM 9.92 Ability to displace [3H]N-methylscopolamine (NMS) from M3 receptor in rat submax... 8464039
Unchecked Ki = 0.12 nM 9.92 Inhibition of muscarinic acetylcholine receptor in rat cortex 23523385
Muscarinic acetylcholine receptor M1 Ki = 0.2 nM 9.7 Binding affinity against Muscarinic acetylcholine receptor M1 by displacement of... 3385735
Muscarinic acetylcholine receptor M5 Ki = 0.21 nM 9.68 Activation of human muscarinic M5 receptor expressed in CHO cells coexpressing G... 19438238
Muscarinic acetylcholine receptor M1 Ki = 0.25 nM 9.6 Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells ... 11831911
Muscarinic acetylcholine receptor M1 Ki = 0.26 nM 9.59 Ability to displace [3H]pirenzepine (PZ) from M1 receptor in rat cortex homogena... 8464039
Muscarinic acetylcholine receptor M1 Ki = 0.26 nM 9.59 Displacement of [3H]pirenzepine from muscarinic acetylcholine receptor M1 in rat... 1920350
Muscarinic acetylcholine receptor Ki = 0.3 nM 9.52 The compound was tested for inhibition of [3H]NMS binding against muscarinic ace... 1956033
Muscarinic acetylcholine receptor M1 Ki = 0.3 nM 9.52 Displacement of [3H]pirenzepine from muscarinic M1 receptor 8496700
Muscarinic acetylcholine receptor Ki = 0.32 nM 9.49 Ability of compound to displace (-)-[3H]3-Quinuclidinyl benzilate (-)-[3H]-QNB f... 9371246
Muscarinic acetylcholine receptor M1 Ki = 0.329 nM 9.48 Inhibition of [3H]QNB binding to CHO cells bearing transfected muscarinic acetyl... 2016720
Muscarinic acetylcholine receptor Ki = 0.337 nM 9.47 Inhibition of [3H]QNB binding against muscarinic acetylcholine receptor in rat b... 1956033
Muscarinic acetylcholine receptor Ki = 0.337 nM 9.47 Inhibition of [3H]QNB binding to muscarinic acetylcholine receptor of rat heart ... 1613746
Muscarinic acetylcholine receptor M4 Ki = 0.34 nM 9.47 Binding affinity (Ki) against binding of [3H]NMS using membranes from CHO cells ... 11831911
Muscarinic acetylcholine receptor M2 Ki = 0.35 nM 9.46 Ability to displace [3H]oxotremorine ([3H]-OXO-M) from mouse cerebral cortex 1507203
Acetylcholinesterase Ki = 0.35 nM 9.46 Compound was evaluated for the binding affinity by displacing [3H]oxotremorine f... 1552502
Muscarinic acetylcholine receptor M2 Ki = 0.344 nM 9.46 muscarinic acetylcholine receptor M1 2016720
Muscarinic acetylcholine receptor M1 Ki = 0.366 nM 9.44 DRUGMATRIX: Muscarinic M1 radioligand binding (ligand: [3H] N-Methylscopolamine) -
Unchecked Ki = 0.371 nM 9.43 Inhibition of [3H]QNB binding towards muscarinic acetylcholine receptor in rat h... 2016720

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 432
31158845 10.1038/s41586-019-1291-3 ADMET 55
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
32233403 10.1021/acs.jmedchem.9b02172 Muscarinic acetylcholine receptor M2 8
20070106 10.1021/jm901371v Homo sapiens 8
- 10.6019/CHEMBL5058564 HEK-293T 8
11831902 10.1021/jm010196t Muscarinic acetylcholine receptor 5
12061889 10.1021/jm0200409 ADMET 5
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 5
28388054 10.1021/acs.jmedchem.6b01892 Muscarinic acetylcholine receptor M2 5
19397318 10.1021/jm9003945 No relevant target 4
9544563 10.1021/np9703712 Rattus norvegicus 4
18426954 10.1124/dmd.108.020479 ADMET 4
3806623 10.1021/jm00385a028 Rattus norvegicus 4
- 10.6019/CHEMBL5058564 U2OS 4
9371246 10.1021/jm970346t Muscarinic acetylcholine receptor 4
3411598 10.1021/jm00117a006 Muscarinic acetylcholine receptor 4
2016720 10.1021/jm00108a030 Unchecked 3
1548680 10.1021/jm00083a016 Muscarinic acetylcholine receptor 3
3806594 10.1021/jm00384a034 Unchecked 3

Data from ChEMBL 36 via Core Engine