Skip to main content
Free research Free research Free compound review with research home and workspace preview
Quick search ChEMBL 36
Compound Detail

CHEMBL30

CIMETIDINE
💊 Approved Drug
Enter ChEMBL ID:
Free Research Context This compound will appear in recent viewed items on the research home for this browser.
Research home View demo workspace
💊 Approved Drug
CN/C(=N\CCSCc1nc[nH]c1C)NC#N
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL30
Name CIMETIDINE
Phase Approved
Structure Type MOL
InChI Key AQIXAKUUQRKLND-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Acid-eze Aciloc Acinil Acitak 200 Acitak 400 Acitak 800 Brumetadina Brumetidina Cimal Cimetidina Cimetidine Cimetidinum +18 more
17
Targets
64
Activities
3
Assay Types
18
PK Parameters
20
Publications
30
Known Names
17
Indications
1
Mechanisms

Molecular Properties

252.3
MW (Da)
0.60
ALogP
4
HBA
3
HBD
88.9
PSA (Ų)
0.23
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1977
Availability OTC
Chirality Achiral

Routes of Administration

Oral Parenteral

Flags

Natural Product
USAN Stem -tidine
USAN Year 1975

Extended Properties

Molecular Formula C10H16N6S
MW 252.35
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness -1.18

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Histamine H2 receptor antagonist ANTAGONIST Histamine H2 receptor ✓ ✓

Indications

Duodenal Ulcer Gastroesophageal Reflux Heartburn Peptic Ulcer Dermatitis, Atopic Gastrointestinal Hemorrhage Hemorrhage Ulcer Breast Carcinoma In Situ Breast Neoplasms Breast Neoplasms Endometrial Neoplasms Protoporphyria, Erythropoietic Amyotrophic Lateral Sclerosis Anxiety Disorders Infections Pulmonary Disease, Chronic Obstructive

ATC Classification

A02BA01
cimetidine
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS
A02BA51
cimetidine, combinations
Level 1: ALIMENTARY TRACT AND METABOLISM
Level 2: DRUGS FOR ACID RELATED DISORDERS

Activity Summary

IC50 32 meas. best 6.85
Ki 25 meas. best 7.16
Kd 7 meas. best 6.6

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Histamine H2 receptor
CHEMBL1941
 Ki 7.16 6.5157 70.0 7
Histamine H2 receptor
CHEMBL1941
 IC50 6.85 6.2356 140.0 9
Histamine H2 receptor
CHEMBL4654
 Kd 6.6 6.6 251.2 2
Histamine H2 receptor
CHEMBL2882
 Kd 6.58 6.286 263.0 5
Histamine H2 receptor
CHEMBL2882
 Ki 6.52 6.3733 302.0 3
Solute carrier family 22 member 1
CHEMBL2073664
 IC50 6.23 6.23 590.0 1
Potassium-transporting ATPase
CHEMBL2095173
 IC50 6.09 6.09 820.0 1
Histamine H2 receptor
CHEMBL2882
 IC50 5.99 5.99 1020.0 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
 IC50 5.92 5.6067 1200.0 3
Solute carrier family 22 member 1
CHEMBL2073670
 Ki 5.24 5.24 5700.0 1
Solute carrier family 22 member 2
CHEMBL2073662
 IC50 5.1 5.1 8000.0 1
Solute carrier family 22 member 2
CHEMBL1770032
 Ki 5.03 5.03 9400.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.9 4.72 12589.2 2
Cytochrome P450 3A4
CHEMBL340
 IC50 4.82 4.82 15000.0 1
Unchecked
CHEMBL612545
 IC50 4.7 4.7 20000.0 1
Solute carrier family 22 member 2
CHEMBL1743122
 IC50 4.64 4.64 23000.0 1
Multidrug and toxin extrusion protein 2
CHEMBL1743127
 IC50 4.41 4.41 39000.0 1
Organic anion transporter 3
CHEMBL2073666
 Ki 4.33 4.33 46800.0 1
Organic anion transporter 3
CHEMBL1641348
 Ki 4.28 4.28 53000.0 1
Solute carrier family 22 member 2
CHEMBL1743122
 Ki 4.24 4.24 57000.0 1
Cytochrome P450 2D6
CHEMBL289
 Ki 4.11 4.11 77000.0 1
Organic anion transporter 3
CHEMBL1641348
 IC50 4.03 4.03 92400.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 8.1 mL.min-1.kg-1 Homo sapiens
CL 8.1 mL.min-1.kg-1 Homo sapiens
CL 0.2 mL.min-1.kg-1 Homo sapiens
CL 8.1 mL.min-1.kg-1 Homo sapiens
Cmax 11900.0 nM Homo sapiens
F 79.0 % Homo sapiens
F 60.0 % Homo sapiens
F 60.0 % Homo sapiens
Fu 0.81 - -
Fu 0.374 - -
Fu 0.81 - Homo sapiens
Fu 0.78 - Homo sapiens
Fu 0.78 - Homo sapiens
Fu 1.0 - Homo sapiens
Fu 0.76 - Rattus norvegicus
MRT 2.5 hr Homo sapiens
T1/2 2.2 hr Homo sapiens
Vd 2.3 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Histamine H2 receptor Ki = 70.0 nM 7.16 Displacement of [3H]Cimetidine from histamine H2 receptor (unknown origin) 24365159
Histamine H2 receptor Ki = 70.79 nM 7.15 Displacement of [3H]Cimetidine from histamine H2 receptor (unknown origin) 24365159
Histamine H2 receptor Ki = 140.0 nM 6.85 Binding affinity to human histamine H2 receptor by radioligand displacement assa... 23466604
Histamine H2 receptor IC50 = 140.0 nM 6.85 Binding affinity to human histamine H2 receptor by radioligand displacement assa... 23466604
Histamine H2 receptor Ki = 170.0 nM 6.77 Displacement of radiolabeled cimetidine from human histamine H2 receptor 18983139
Histamine H2 receptor IC50 = 180.0 nM 6.75 Displacement of radiolabeled cimetidine from human histamine H2 receptor 18983139
Histamine H2 receptor Kd = 251.19 nM 6.6 Antagonistic activity by inhibition histamine H2 receptor from rats. -
Histamine H2 receptor Kd = 251.19 nM 6.6 Antagonistic activity for inhibition of histamine H2 receptor from anesthetized ... -
Histamine H2 receptor Kd = 263.03 nM 6.58 In vitro inhibitory activity against histamine H2-receptor in isolated Guinea pi... 1352351
Histamine H2 receptor IC50 = 270.0 nM 6.57 Binding affinity to human histamine H2 receptor by radioligand displacement assa... 23582449
Histamine H2 receptor Ki = 302.0 nM 6.52 Inhibition of [125I]APT binding to H2 receptors in guinea pig cerebral membranes... 1613748
Histamine H2 receptor Kd = 371.54 nM 6.43 Antagonistic activity against Histamine H2 receptor expressed as the charge of r... 3806596
Histamine H2 receptor Kd = 398.11 nM 6.4 Antagonistic activity against Histamine H2 receptor expressed as the charge of r... 3806596
Histamine H2 receptor Ki = 490.0 nM 6.31 Displacement of [125I]APT from human recombinant histamine H2 receptor expressed... 27997171
Histamine H2 receptor IC50 = 500.0 nM 6.3 Displacement of [125I]APT from human recombinant histamine H2 receptor expressed... 27997171
Histamine H2 receptor Ki = 501.19 nM 6.3 Evaluated in vitro for Histamine H2 receptor inhibition using the dimaprit stimu... 6131129
Histamine H2 receptor Ki = 501.19 nM 6.3 In vitro inhibition of Histamine H2 receptor by measuring its ability to block t... 6121913
Histamine H2 receptor IC50 = 530.0 nM 6.28 Inhibition of H2 receptor (unknown origin) 28849908
Solute carrier family 22 member 1 IC50 = 590.0 nM 6.23 TP_TRANSPORTER: inhibition of MPP+ uptake (MPP+: 1 uM) in Xenopus laevis oocytes 12176030
Histamine H2 receptor IC50 = 781.0 nM 6.11 Inhibition of histamine H2 receptor 18588282

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1430
- 10.6019/CHEMBL3885881 Rattus norvegicus 467
- 10.5281/zenodo.13943903 ADMET 89
31158845 10.1038/s41586-019-1291-3 ADMET 55
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
12699389 10.1021/jm021012t ATP-dependent translocase ABCB1 13
21212239 10.1124/dmd.110.036780 ADMET 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
21051535 10.1124/dmd.110.034629 ADMET 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20070106 10.1021/jm901371v Homo sapiens 8
- 10.1007/s00044-004-0012-z Rattus norvegicus 8
6834386 10.1021/jm00358a015 Canis familiaris 6
3681897 10.1021/jm00395a015 Rattus norvegicus 5
11602674 - ATP-dependent translocase ABCB1 5
21599003 10.1021/jm2001629 ADMET 5
12061889 10.1021/jm0200409 ADMET 5
15658873 10.1021/jm049711o ADMET 5
18426954 10.1124/dmd.108.020479 ADMET 4
6131126 10.1021/jm00355a001 No relevant target 4

Data from ChEMBL 36 via Core Engine