CAFFEINE


Synonyms	Anhydrous caffeine Cafcit Caffeine Caffeine anhydrous Caffeine melting point standard Caffeinum Coffeine Coffeinum Durvitan FEMA NO. 2224 Guaranine Methyltheobromine NSC-5036 Nodoz Nodoz caplets and chewable tablets
Status
Molecule Category	Free-form
ATC	D11AX26 N06BC01
UNII	3G6A5W338E
EPA CompTox	DTXSID0020232


Active Pharmaceutical Ingredients Bioactive chemicals	Exact Similarity SubStructure	Threshold (%) >= 70

Structure


InChI Key	RYYVLZVUVIJVGH-UHFFFAOYSA-N
Smiles	Cn1c(=O)c2c(ncn2C)n(C)c1=O
InChI	InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3

Physicochemical Descriptors

Property Name	Value
Molecular Formula	C8H10N4O2
Molecular Weight	194.19
AlogP	-1.03
Hydrogen Bond Acceptor	6.0
Hydrogen Bond Donor	0.0
Number of Rotational Bond	0.0
Polar Surface Area	61.82
Molecular species	NEUTRAL
Aromatic Rings	2.0
Heavy Atoms	14.0

Pharmacology

Mechanism of Action	Action	Reference
Adenosine receptor antagonist	ANTAGONIST	FDA PubMed Wikipedia

Targets	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Enzyme Oxidoreductase	-	-	-	-	16-33
Ion channel Voltage-gated ion channel Voltage-gated sodium channel	-	-	-	-	9.7
Membrane receptor Family A G protein-coupled receptor Small molecule receptor (family A GPCR) Nucleotide-like receptor (family A GPCR) Adenosine receptor	-	-	-	-	9-58
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides	-	-	-	-	-1.8-103.59
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters	-	-	-	-

	EC50(nM)	IC50(nM)	Kd(nM)	Ki(nM)	Inhibition(%)
Cavia porcellus	-	-	-	-	9.7
Cricetulus griseus	-	-	-	-	90.35-103.59
Homo sapiens	-	-	-	-	-1.8-33
Rattus norvegicus	-	-	-	-	14-80

Target Conservation

Related Entries

Cross References

Resources	Reference
ChEBI	27732
ChEMBL	CHEMBL113
DrugBank	DB00201
DrugCentral	463
FDA SRS	3G6A5W338E
Human Metabolome Database	HMDB0001847
Guide to Pharmacology	407
KEGG	C07481
PDB	CFF
PharmGKB	PA448710
PubChem	2519
SureChEMBL	SCHEMBL5671
ZINC	ZINC000000001084

CONTENTS


PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains. Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).

PREMIER has received funding from the Innovative Medicines Initiative 2 Joint Undertaking (JU) under grant agreement No 875508. The JU receives support from the EU’s Horizon 2020 research and innovation programme and the European Federation of Pharmaceutical Industries and Associations (EFPIA). The views reflect only the authors’ perspective and the JU is not responsible for any use that may be made of the information this manuscript contains.

Elements of the website have been developed under projects PREMIER and the Biocenter Finland Drug Discovery and Chemical Biology network. CSC-IT is thanked for providing computational resources. Content of the website is provided without guarantee for correctness. Data has been collected and integrated from multiple public sources, for the largest: FDA, HUGO Gene Nomenclature Committee, ChEMBL, IUPHAR/BPS guide to pharmacology, Reactome, UniProt, and Ensembl. Credit is given to Ensembl for collecting species images (provided under public domain licences such as Wikimedia and NHGRI).