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Compound Detail

CHEMBL569713

SCOPOLAMINE
💊 Approved Drug
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💊 Approved Drug
CN1[C@@H]2C[C@@H](OC(=O)[C@H](CO)c3ccccc3)C[C@H]1[C@@H]1O[C@@H]12

Basic Information

ChEMBL ID CHEMBL569713
Name SCOPOLAMINE
Phase Approved
Structure Type MOL
InChI Key STECJAGHUSJQJN-FWXGHANASA-N
Therapeutic ✓ Yes

Known Names

Scopolamine Transderm scop
12
Targets
31
Activities
3
Assay Types
7
PK Parameters
20
Publications
2
Known Names
13
Indications
1
Mechanisms

Molecular Properties

303.4
MW (Da)
0.92
ALogP
5
HBA
1
HBD
62.3
PSA (Ų)
0.66
QED
0
Ro5 Violations
4
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1979
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Topical

Flags

Natural Product

Extended Properties

Molecular Formula C17H21NO4
MW 303.36
Aromatic Rings 1
Heavy Atoms 22
NP-Likeness 1.36

Mechanism of Action

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

Indications

Motion Sickness Nausea Postoperative Nausea and Vomiting Postoperative Nausea and Vomiting Amyotrophic Lateral Sclerosis Bipolar Disorder Depressive Disorder Depressive Disorder, Major Pain Alzheimer Disease Dementia Phobia, Social Renal Colic

ATC Classification

A04AD01
scopolamine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIEMETICS AND ANTINAUSEANTS
A04AD51
scopolamine, combinations
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: ANTIEMETICS AND ANTINAUSEANTS
N05CM05
scopolamine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOLEPTICS
S01FA02
scopolamine
Level 1: SENSORY ORGANS
Level 2: OPHTHALMOLOGICALS

Activity Summary

Ki 16 meas. best 10.1
IC50 11 meas. best 8.89
Kd 4 meas. best 9.19

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Muscarinic acetylcholine receptor
CHEMBL1907609
Ki 10.1 10.1 0.1 1
Muscarinic acetylcholine receptor M1
CHEMBL2672
Ki 9.39 9.39 0.4 1
Muscarinic acetylcholine receptor M1
CHEMBL276
Ki 9.28 9.28 0.5 1
Muscarinic acetylcholine receptor M3
CHEMBL320
Kd 9.19 9.19 0.7 1
Muscarinic acetylcholine receptor M1
CHEMBL276
Kd 9.12 9.12 0.8 1
Unchecked
CHEMBL612545
Ki 8.95 8.95 1.1 1
Muscarinic acetylcholine receptor M5
CHEMBL2035
Ki 8.89 8.32 1.3 2
Muscarinic acetylcholine receptor M4
CHEMBL1821
IC50 8.89 8.5767 1.3 3
Muscarinic acetylcholine receptor M1
CHEMBL216
IC50 8.76 8.5825 1.7 4
Muscarinic acetylcholine receptor M2
CHEMBL211
Ki 8.52 8.2483 3.0 6
Muscarinic acetylcholine receptor M2
CHEMBL309
Kd 8.52 8.52 3.0 1
Muscarinic acetylcholine receptor
CHEMBL1907609
IC50 8.4 8.2667 4.0 3
Muscarinic acetylcholine receptor M2
CHEMBL309
Ki 8.34 8.34 4.6 1
Muscarinic acetylcholine receptor M3
CHEMBL245
Ki 8.19 8.19 6.5 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Ki 8.12 8.12 7.5 1
Rattus norvegicus
CHEMBL376
IC50 8.05 8.05 8.9 1
Muscarinic acetylcholine receptor M4
CHEMBL1821
Ki 7.43 7.43 36.9 1
Muscarinic acetylcholine receptor M1
CHEMBL216
Kd 4.23 4.23 59160.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 15.0 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
CL 16.0 mL.min-1.kg-1 Homo sapiens
F 49.0 % Homo sapiens
KA 135000000.0 M-1 Canis lupus familiaris
MRT 3.2 hr Homo sapiens
T1/2 4.5 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Muscarinic acetylcholine receptor Ki = 0.08 nM 10.1 Inhibition of [3H]pirenzepine binding to muscarinic receptor in rat cortical hom... -
Muscarinic acetylcholine receptor M1 Ki = 0.41 nM 9.39 Binding affinity towards Muscarinic acetylcholine receptor M1 was determined in ... 9016336
Muscarinic acetylcholine receptor M1 Ki = 0.53 nM 9.28 Binding affinity towards rat Muscarinic acetylcholine receptor M1 was determined 9016336
Muscarinic acetylcholine receptor M3 Kd = 0.65 nM 9.19 In vitro receptor binding against Muscarinic acetylcholine receptor M3 in rat su... 2374141
Muscarinic acetylcholine receptor M1 Kd = 0.75 nM 9.12 In vitro receptor binding against Muscarinic acetylcholine receptor M1 in rat ce... 2374141
Unchecked Ki = 1.122 nM 8.95 Antagonist activity at muscarinic receptor 19419864
Muscarinic acetylcholine receptor M4 IC50 = 1.288 nM 8.89 Antagonist activity at human M4 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor M5 Ki = 1.288 nM 8.89 Displacement of [3H]-NMS from wild-type human muscarinic M5 receptor expressed i... 25051097
Muscarinic acetylcholine receptor M1 IC50 = 1.738 nM 8.76 Antagonist activity at human M1 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor M1 IC50 = 1.85 nM 8.73 Antagonist activity at human muscarinic M1 receptor expressed in CHO cells incub... 38354305
Muscarinic acetylcholine receptor M2 Kd = 3.0 nM 8.52 In vitro receptor binding against Muscarinic acetylcholine receptor M2 in rat he... 2374141
Muscarinic acetylcholine receptor M2 Ki = 3.02 nM 8.52 Displacement of [3H]-NMS from wild-type human muscarinic M2 receptor expressed i... 25051097
Muscarinic acetylcholine receptor M1 IC50 = 3.311 nM 8.48 Antagonist activity at human M1 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor M2 Ki = 3.311 nM 8.48 Displacement of [3H]-NMS from human muscarinic M2 Y177Q mutant expressed in Flp-... 25051097
Muscarinic acetylcholine receptor M2 Ki = 3.311 nM 8.48 Displacement of [3H]-NMS from human muscarinic M2 W422A mutant expressed in Flp-... 25051097
Muscarinic acetylcholine receptor M2 Ki = 3.548 nM 8.45 Displacement of [3H]-NMS from human muscarinic M2 Y177Q/T423H mutant expressed i... 25051097
Muscarinic acetylcholine receptor M4 IC50 = 3.802 nM 8.42 Antagonist activity at human M4 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor M4 IC50 = 3.802 nM 8.42 Antagonist activity at human M4 receptor expressed in HEK293T cells assessed as ... 25275964
Muscarinic acetylcholine receptor IC50 = 4.0 nM 8.4 Inhibition of [3H]quinuclidinyl benzilate (QNB) binding from rat forebrain membr... 8558529
Muscarinic acetylcholine receptor IC50 = 4.0 nM 8.4 Inhibition of [3H]quinuclidinyl benzilate (QNB) binding from rat forebrain membr... 8558529

Literature References

PubMed DOI Target Context # Activities
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
20070106 10.1021/jm901371v Homo sapiens 8
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 7
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M2 7
25275964 10.1021/jm501173q Muscarinic acetylcholine receptor M1 6
8277504 10.1021/jm00078a011 Rattus norvegicus 6
25275964 10.1021/jm501173q Muscarinic acetylcholine receptor M4 6
25051097 10.1021/jm500790x Muscarinic acetylcholine receptor M2 5
38354305 10.1021/acs.jmedchem.3c01970 Mus musculus 5
23379472 10.1021/jm301774u Muscarinic acetylcholine receptor M5 5
10821709 10.1021/jm991170t Mus musculus 4
11087574 10.1021/jm000972h Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4
7265121 10.1021/jm00135a020 Mus musculus 4
- 10.6019/CHEMBL4651402 SARS-CoV-2 4
19397318 10.1021/jm9003945 No relevant target 4
12824022 10.1016/s0960-894x(03)00437-2 Mus musculus 4
592326 10.1021/jm00222a015 Mus musculus 3
6644747 10.1021/jm00366a023 Mus musculus 3
8558529 10.1021/jm9506433 Muscarinic acetylcholine receptor 3

Data from ChEMBL 36 via Core Engine