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

CHEMBL113

CAFFEINE
💊 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
Cn1c(=O)c2c(ncn2C)n(C)c1=O

Basic Information

ChEMBL ID CHEMBL113
Name CAFFEINE
Phase Approved
Structure Type MOL
InChI Key RYYVLZVUVIJVGH-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Anhydrous caffeine Caffeine Caffeine anhydrous Caffeine component of anoquan Caffeine component of cafergot Caffeine component of darvon compound Caffeine component of dhc plus Caffeine component of esgic Caffeine component of excedrin Caffeine component of femcet Caffeine component of fioricet Caffeine component of fiorinal +18 more
25
Targets
230
Activities
4
Assay Types
30
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

194.2
MW (Da)
-1.03
ALogP
6
HBA
0
HBD
61.8
PSA (Ų)
0.54
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1948
Availability OTC
Chirality Achiral

Routes of Administration

Oral Parenteral Topical

Flags

Natural Product

Extended Properties

Molecular Formula C8H10N4O2
MW 194.19
Aromatic Rings 2
Heavy Atoms 14
NP-Likeness -1.09

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Adenosine receptor antagonist ANTAGONIST Adenosine receptor

Indications

Apnea Attention Deficit Disorder with Hyperactivity Migraine Disorders Pain Alzheimer Disease Atrial Fibrillation Back Pain Bronchopulmonary Dysplasia Common Cold Coronary Disease Dysmenorrhea Headache Hypoxia Intermittent Claudication Low Back Pain Migraine with Aura Migraine without Aura Multiple Sclerosis, Relapsing-Remitting Neck Pain Obesity

ATC Classification

D11AX26
caffeine
Level 1: DERMATOLOGICALS
Level 2: OTHER DERMATOLOGICAL PREPARATIONS
N06BC01
caffeine
Level 1: NERVOUS SYSTEM
Level 2: PSYCHOANALEPTICS

Activity Summary

Ki 159 meas. best 5.61
IC50 62 meas. best 5.14
Kd 5 meas. best 6.16
EC50 4 meas. best 4.34

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NAD-dependent protein deacetylase sirtuin-3, mitochondrial
CHEMBL4461
Kd 6.16 6.16 690.0 1
Adenosine receptor A2a
CHEMBL251
Ki 5.61 4.7271 2480.0 21
Adenosine receptor A2a
CHEMBL251
Kd 5.26 4.93 5510.0 2
Acetylcholinesterase
CHEMBL220
IC50 5.14 5.12 7250.0 2
Nuclear receptor subfamily 2 group E member 1
CHEMBL1961788
IC50 5.1 5.1 7943.3 1
Adenosine receptor A2a
CHEMBL302
Ki 5.03 4.5141 9400.0 22
Adenosine receptor A2a
CHEMBL251
IC50 5.02 4.855 9600.0 2
Adenosine receptor A2b
CHEMBL255
Ki 5.0 4.6163 10000.0 19
Guanine deaminase
CHEMBL3129
Ki 5.0 4.995 10000.0 2
Adenosine receptor A2b
CHEMBL255
IC50 4.98 4.98 10400.0 1
Adenosine receptor A1
CHEMBL226
IC50 4.97 4.97 10700.0 1
Adenosine receptor A1
CHEMBL226
Ki 4.97 4.476 10700.0 15
Adenosine receptor A3
CHEMBL256
Ki 4.9 4.8822 12589.2 9
Adenosine receptor A3
CHEMBL256
IC50 4.88 4.88 13300.0 1
Adenosine receptor
CHEMBL2111386
Ki 4.82 4.452 15000.0 5
Adenosine receptor A1
CHEMBL318
Ki 4.77 4.4494 17000.0 36
Palmitoleoyl-protein carboxylesterase NOTUM
CHEMBL3714531
IC50 4.73 4.4833 18600.0 3
Adenosine receptor A2b
CHEMBL2237
Ki 4.64 4.64 23000.0 1
Adenosine A2 receptor
CHEMBL2094117
Ki 4.57 4.4467 27000.0 12
Adenosine receptor A1
CHEMBL4975
Ki 4.54 4.54 29000.0 1
Adenosine receptor A2b
CHEMBL2592
Ki 4.52 4.52 30000.0 1
Adenosine A2 receptor
CHEMBL2094257
Ki 4.52 4.52 30000.0 1
Adenosine receptor A1
CHEMBL226
Kd 4.35 4.35 45000.0 1
Palmitoleoyl-protein carboxylesterase NOTUM
CHEMBL3714531
EC50 4.34 4.34 45800.0 2
Adenosine receptor A2a
CHEMBL2605
Ki 4.3 4.25 50000.0 4
Unchecked
CHEMBL612545
Ki 4.3 4.15 50000.0 2
Transient receptor potential cation channel subfamily A member 1
CHEMBL1075310
EC50 4.21 4.21 61800.0 1
Adenosine A2 receptor
CHEMBL2094117
IC50 4.2 4.2 63000.0 1
Phosphodiesterase 1
CHEMBL2111322
IC50 4.16 4.16 70000.0 1
Glycogen phosphorylase, muscle form
CHEMBL4696
IC50 4.13 4.095 74900.0 6
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
CHEMBL3130
IC50 4.12 4.12 75000.0 1
Palmitoleoyl-protein carboxylesterase NOTUM
CHEMBL3714531
Kd 4.07 4.07 85000.0 1
Unchecked
CHEMBL612545
IC50 4.04 4.0133 92000.0 3
Transient receptor potential cation channel subfamily A member 1
CHEMBL5160
EC50 4.02 4.02 95900.0 1
Adenosine receptor A1
CHEMBL2304404
Ki 4.0 4.0 100000.0 4

Pharmacokinetic Data

Parameter Value Units Species
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 2.6 mL.min-1.kg-1 Canis lupus familiaris
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 1.4 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 2.1 mL.min-1.kg-1 Canis lupus familiaris
CL 3.1 mL.min-1.kg-1 Macaca
CL 13.0 mL.min-1.kg-1 Rattus norvegicus
CL 3.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL - - Homo sapiens
CL 2.79 mL.min-1.kg-1 Homo sapiens
CL 3.09 uL.min-1.(10^6cells)-1 Homo sapiens
CL 6.3 uL.min-1.(10^6cells)-1 Homo sapiens
CL 1.67 mL.min-1.kg-1 Homo sapiens
CL - - Homo sapiens
CL 4.0 mL.min-1.g-1 Homo sapiens
CL 2.0 mL.min-1.g-1 Homo sapiens
F 80.0 % Homo sapiens
F 100.0 % Homo sapiens
F 98.0 % Homo sapiens
F 100.0 % Homo sapiens
Fu 0.64 - -
Fu 0.543 - -
Fu 0.64 - Homo sapiens
Fu 0.64 - Homo sapiens
Fu 0.64 - Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NAD-dependent protein deacetylase sirtuin-3, mitochondrial Kd = 690.0 nM 6.16 Binding affinity to human SIRT3 assessed as dissociation constant by SPR analysi... 38261767
Adenosine receptor A2a Ki = 2480.0 nM 5.61 Competitive binding affinity to human adenosine A2A receptor expressed in HEK293... 23200243
Adenosine receptor A2a Ki = 5011.87 nM 5.3 Displacement of [3H]ZM241385 from stabilized human adenosine receptor A2a expres... 21661720
Adenosine receptor A2a Kd = 5510.0 nM 5.26 Binding affinity to human wild type adenosine A2A receptor expressed in Expi293F... 35859869
Acetylcholinesterase IC50 = 7250.0 nM 5.14 Inhibition of human AChE using acetylthiocholine iodide as substrate treated 5 m... 23791077
Acetylcholinesterase IC50 = 7943.28 nM 5.1 Inhibition of Acetylcholinesterase (unknown origin) 34019396
Nuclear receptor subfamily 2 group E member 1 IC50 = 7943.28 nM 5.1 Inhibition of tlx (unknown origin) 34019396
Adenosine receptor A2a Ki = 9400.0 nM 5.03 Displacement of [3H]CGS21680 from adenosine A2A receptor in rat brain striatal m... 9514015
Adenosine receptor A2a IC50 = 9600.0 nM 5.02 Inhibition of human A2a adenosine receptor 34019396
Adenosine receptor A2a Ki = 9560.0 nM 5.02 Displacement of [3H]CGS21680 from human adenosine A2A receptor expressed in HEK2... 23200243
Guanine deaminase Ki = 10000.0 nM 5.0 Inhibition of guanine deaminase (unknown origin) 34019396
Adenosine receptor A2b Ki = 10000.0 nM 5.0 Inhibition of human A2B adenosine receptor 30576906
Guanine deaminase Ki = 10200.0 nM 4.99 Inhibition of GDA by colorimetric assay 20716488
Adenosine receptor A2b Ki = 10400.0 nM 4.98 Binding affinity at human Adenosine A2B receptor expressed in HEK293 cells, usin... 12014951
Adenosine receptor A2b IC50 = 10400.0 nM 4.98 Inhibition of human A2b adenosine receptor 34019396
Adenosine receptor A2b Ki = 10400.0 nM 4.98 Antagonist activity against human adenosine A2B receptor 20537438
Adenosine receptor A2b Ki = 10400.0 nM 4.98 Displacement of [125I]I-ABOPX from human recombinant adenosine A2B receptor expr... 19569717
Adenosine receptor A1 Ki = 10700.0 nM 4.97 Displacement of [3H]CCPA from human adenosine receptor A1 expressed in CHO cell ... 31780082
Adenosine receptor A1 Ki = 10700.0 nM 4.97 Binding affinity to human adenosine A1 receptor by radioligand displacement assa... 30108984
Adenosine receptor A1 Ki = 10700.0 nM 4.97 Antagonist activity at adenosine A1 receptor (unknown origin) 34695776

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885861 Rattus norvegicus 1377
- 10.6019/CHEMBL3885881 Rattus norvegicus 455
35168113 10.1016/j.ejmech.2022.114158 ADMET 36
1501234 10.1021/jm00094a022 Rattus norvegicus 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
8355252 10.1021/jm00069a009 Mus musculus 13
8355252 10.1021/jm00069a009 Rattus norvegicus 10
22319196 10.1124/jpet.111.189902 Transient receptor potential cation channel subfamily A member 1 10
21661720 10.1021/jm2003798 Adenosine receptor A2a 9
20004571 10.1016/j.bmcl.2009.11.017 Unchecked 9
15920768 10.1002/jps.20373 ADMET 8
17533133 10.1016/j.bmc.2007.05.025 Vibrio harveyi 8
16789751 10.1021/jm060230+ ADMET 8
20070106 10.1021/jm901371v Homo sapiens 8
34019396 10.1021/acs.jmedchem.1c00261 Unchecked 7
7265121 10.1021/jm00135a020 Mus musculus 7
19022538 10.1016/j.ejmech.2008.10.010 Unchecked 6
6279840 10.1021/jm00345a001 Adenosine receptor 6
12061889 10.1021/jm0200409 ADMET 5
6716406 10.1021/jm00371a023 Mus musculus 5

Data from ChEMBL 36 via Core Engine