Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H10N4O2 |
Molecular Weight | 194.1909 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cn1cnc2c1c(=O)n(C)c(=O)n2C
InChI
InChIKey=RYYVLZVUVIJVGH-UHFFFAOYSA-N
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
DescriptionSources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C328Curator's Comment:: description was created based on several sources, including
http://www.webmd.com/vitamins-supplements/ingredientmono-979-caffeine.aspx?activeingredientid=979
Sources: https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&code=C328
Curator's Comment:: description was created based on several sources, including
http://www.webmd.com/vitamins-supplements/ingredientmono-979-caffeine.aspx?activeingredientid=979
Caffeine is a methylxanthine alkaloid found in the seeds, nuts, or leaves of a number of plants native to South America and East Asia that is structurally related to adenosine and acts primarily as an adenosine receptor antagonist with psychotropic and anti-inflammatory activities. Upon ingestion, caffeine binds to adenosine receptors in the central nervous system (CNS), which inhibits adenosine binding. This inhibits the adenosine-mediated downregulation of CNS activity; thus, stimulating the activity of the medullary, vagal, vasomotor, and respiratory centers in the brain. The anti-inflammatory effects of caffeine are due the nonselective competitive inhibition of phosphodiesterases.
Caffeine is used by mouth or rectally in combination with painkillers (such as aspirin and acetaminophen) and a chemical called ergotamine for treating migraineheadaches. It is also used with painkillers for simple headaches and preventing and treating headaches after epidural anesthesia. Caffeine creams are applied to the skin to reduce redness and itching in dermatitis. Healthcare providers sometimes give caffeine intravenously (by IV) for headache after epidural anesthesia, breathing problems in newborns, and to increase urine flow. In foods, caffeine is used as an ingredient in soft drinks, energy drinks, and other beverages.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL251 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164628 |
23.4 µM [Ki] | ||
Target ID: CHEMBL255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164628 |
20.5 µM [Ki] | ||
Target ID: CHEMBL226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24164628 |
44.9 µM [Ki] | ||
Target ID: CHEMBL2111322 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2374150 |
70.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.drugs.com/pro/cafergot.html |
Primary | CAFERGOT Approved UseErgotamine is an alpha adrenergic blocking agent with a direct stimulating effect on the smooth muscle of peripheral and cranial blood vessels and produces depression of central vasomotor centers. The compound also has the properties of serotonin antagonism. In comparison to hydrogenated ergotamine, the adrenergic blocking actions are less pronounced and vasoconstrictive actions are greater. Caffeine, also a cranial vasoconstrictor, is added to further enhance the vasoconstrictive effect without the necessity of increasing ergotamine dosage. Launch Date-6.6579838E11 |
||
Primary | CAFCIT Approved UseCaffeine Citrate injection USP is indicated for the short-term treatment of apnea of prematurity in infants between 28 and <33 weeks gestational age. Launch Date9.3778562E11 |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3.35 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28561231 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAFFEINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
65.64 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28561231 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAFFEINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
|
43000 nM*h Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01361217 |
100 mg single, oral dose: 100 mg route of administration: oral experiment type: single co-administered: |
CAFFEINE plasma | Homo sapiens population: healthy age: adults sex: food status: |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.19 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/28561231 |
200 mg single, oral dose: 200 mg route of administration: Oral experiment type: SINGLE co-administered: |
CAFFEINE unknown | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
12.4 g single, oral Overdose |
unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: |
Other AEs: Nausea, Vomiting... |
50 g single, oral Overdose |
unknown, 27 years n = 1 Health Status: unknown Age Group: 27 years Sex: F Population Size: 1 Sources: |
Other AEs: Tachycardia, Seizure... Other AEs: Tachycardia (1 patient) Sources: Seizure (1 patient) |
5000 mg single, oral (total) Overdose |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
Other AEs: Malaise, Anxiety... Other AEs: Malaise (1 patient) Sources: Anxiety (1 patient) Dizziness (1 patient) Nausea (1 patient) |
4000 mg single, oral Overdose |
pregnant, 33 years n = 1 Health Status: pregnant Age Group: 33 years Sex: F Population Size: 1 Sources: |
Other AEs: Nausea, Vomiting... |
1.6 g single, oral Overdose |
healthy, 44 years n = 1 Health Status: healthy Age Group: 44 years Sex: M Population Size: 1 Sources: |
Other AEs: Atrial fibrillation... |
800 mg multiple, oral (total) Highest studied dose |
healthy, adult n = 12 Health Status: healthy Age Group: adult Population Size: 12 Sources: |
|
24 g single, oral Overdose |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: M Population Size: 1 Sources: |
Other AEs: Rhabdomyolysis, Acute renal failure... Other AEs: Rhabdomyolysis (1 patient) Sources: Acute renal failure (1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Nausea | 1 patient | 12.4 g single, oral Overdose |
unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: |
Vomiting | 1 patient | 12.4 g single, oral Overdose |
unknown, 14 years n = 1 Health Status: unknown Age Group: 14 years Sex: F Population Size: 1 Sources: |
Seizure | 1 patient | 50 g single, oral Overdose |
unknown, 27 years n = 1 Health Status: unknown Age Group: 27 years Sex: F Population Size: 1 Sources: |
Tachycardia | 1 patient | 50 g single, oral Overdose |
unknown, 27 years n = 1 Health Status: unknown Age Group: 27 years Sex: F Population Size: 1 Sources: |
Anxiety | 1 patient | 5000 mg single, oral (total) Overdose |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
Dizziness | 1 patient | 5000 mg single, oral (total) Overdose |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
Malaise | 1 patient | 5000 mg single, oral (total) Overdose |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
Nausea | 1 patient | 5000 mg single, oral (total) Overdose |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: F Population Size: 1 Sources: |
Nausea | 1 patient | 4000 mg single, oral Overdose |
pregnant, 33 years n = 1 Health Status: pregnant Age Group: 33 years Sex: F Population Size: 1 Sources: |
Vomiting | 1 patient | 4000 mg single, oral Overdose |
pregnant, 33 years n = 1 Health Status: pregnant Age Group: 33 years Sex: F Population Size: 1 Sources: |
Atrial fibrillation | 1 patient | 1.6 g single, oral Overdose |
healthy, 44 years n = 1 Health Status: healthy Age Group: 44 years Sex: M Population Size: 1 Sources: |
Acute renal failure | 1 patient | 24 g single, oral Overdose |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: M Population Size: 1 Sources: |
Rhabdomyolysis | 1 patient | 24 g single, oral Overdose |
unknown, adult n = 1 Health Status: unknown Age Group: adult Sex: M Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
no | weak (co-administration study) Comment: When caffeine was coadministered the Cmax of melatonin was increased on average by 137% and AUC by 120% |
|||
Sources: https://pubmed.ncbi.nlm.nih.gov/8723732/ |
yes | |||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 7.0 |
major | likely (co-administration study) Comment: lower doses of caffeine may be needed following coadministration of drugs which are reported to decrease caffeine elimination (e.g., cimetidine and ketoconazole) and higher caffeine doses may be needed following coadministration of drugs that increase caffeine elimination (e.g., phenobarbital and phenytoin) Page: 7.0 |
||
yes | ||||
yes | ||||
yes | ||||
Sources: https://pubmed.ncbi.nlm.nih.gov/8204093/ Page: 9.0 |
yes | |||
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
Epileptogenic action of caffeine during anoxia in the neonatal rat hippocampus. | 1999 Jul |
|
The effect of caffeine in animal models of learning and memory. | 1999 Jun 4 |
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Actions of adenosine A2A receptor antagonist KW-6002 on drug-induced catalepsy and hypokinesia caused by reserpine or MPTP. | 1999 Nov |
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Coffee, caffeine and blood pressure: a critical review. | 1999 Nov |
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Caffeine abolishes the mammalian G(2)/M DNA damage checkpoint by inhibiting ataxia-telangiectasia-mutated kinase activity. | 2000 Apr 7 |
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Caffeine augments proteinuria in puromycin-aminonucleoside nephrotic rats. | 2000 Mar |
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Treatment of pentobarbitol sodium (Nembutal) hyperactivity: a new approach. | 2000 Mar |
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Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects. | 2001 |
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Regulation of in vitro penetration of frozen-thawed boar spermatozoa by caffeine and adenosine. | 2001 Apr |
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Excitation-contraction coupling in pulmonary vascular smooth muscle involves tyrosine kinase and Rho kinase. | 2001 Apr |
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Contribution of ryanodine receptor subtype 3 to ca2+ responses in Ca2+-overloaded cultured rat portal vein myocytes. | 2001 Apr 6 |
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Combined effects of red pepper and caffeine consumption on 24 h energy balance in subjects given free access to foods. | 2001 Feb |
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Ionomycin and 2,5'-di(tertbutyl)-1,4,-benzohydroquinone elicit Ca2+-induced Ca2+ release from intracellular pools in Physarum polycephalum. | 2001 Feb |
|
Age, fatigue, and excitation-contraction coupling in masseter muscles of rats. | 2001 Feb |
|
Caffeine stores and dopamine differentially require Ca(2+) channels in goldfish somatotropes. | 2001 Feb |
|
BK channel activation by NS-1619 is partially mediated by intracellular Ca2+ release in smooth muscle cells of porcine coronary artery. | 2001 Feb |
|
Protection against cellular damage in the rat heart by iodoacetate. | 2001 Feb |
|
Intravenous nicotine and caffeine: subjective and physiological effects in cocaine abusers. | 2001 Feb |
|
Selected contribution: effect of the aldehyde acrolein on acetylcholine-induced membrane current in airway smooth muscle cells. | 2001 Feb |
|
Adenoviral SERCA1a gene transfer to adult rat ventricular myocytes induces physiological changes in calcium handling. | 2001 Feb 1 |
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Effects of alprazolam, caffeine, and zolpidem in humans trained to discriminate triazolam from placebo. | 2001 Feb 1 |
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Predetermined recruitment of calcium release sites underlies excitation-contraction coupling in rat atrial myocytes. | 2001 Feb 1 |
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The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones. | 2001 Feb 1 |
|
The role of the D(2) dopamine receptor (D(2)R) in A(2A) adenosine receptor (A(2A)R)-mediated behavioral and cellular responses as revealed by A(2A) and D(2) receptor knockout mice. | 2001 Feb 13 |
|
Mechanisms of hydrogen peroxide-induced relaxation in rabbit mesenteric small artery. | 2001 Feb 2 |
|
Caffeine increases paragigantocellularis neuronal firing rate and induces withdrawal signs in morphine-dependent rats. | 2001 Feb 2 |
|
Mitochondrial calcium oscillations in C2C12 myotubes. | 2001 Feb 9 |
|
Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
|
Health tips. Caffeine. | 2001 Jan |
|
Characterization of an intense bitter-tasting 1H,4H-quinolizinium-7-olate by application of the taste dilution analysis, a novel bioassay for the screening and identification of taste-active compounds in foods. | 2001 Jan |
|
Calculation of the dimensions of dosage forms with release controlled by diffusion for in vivo use. | 2001 Jan |
|
Relationships between use of television during meals and children's food consumption patterns. | 2001 Jan |
|
Hypothesized treatment for migraines using low doses of tryptophan, niacin, calcium, caffeine, and acetylsalicylic acid. | 2001 Jan |
|
PROP (6-n-Propylthiouracil) tasting and sensory responses to caffeine,sucrose, neohesperidin dihydrochalcone and chocolate. | 2001 Jan |
|
[Ca(2+)](i) signaling in renal arterial smooth muscle cells of pregnant rat is enhanced during inhibition of NOS. | 2001 Jan |
|
Caffeine dissociates complexes between DNA and intercalating dyes: application for bleaching fluorochrome-stained cells for their subsequent restaining and analysis by laser scanning cytometry. | 2001 Jan 1 |
|
Sorption and desorption studies on chitin gels. | 2001 Jan 10 |
|
The effects of phosphodiesterase inhibition on cyclic GMP and cyclic AMP accumulation in the hippocampus of the rat. | 2001 Jan 12 |
|
Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder. | 2001 Jan 15 |
|
Selectively suppressed Ca2+-induced Ca2+ release activity of alpha-ryanodine receptor (alpha-RyR) in frog skeletal muscle sarcoplasmic reticulum: potential distinct modes in Ca2+ release between alpha- and beta-RyR. | 2001 Jan 26 |
|
Functional analysis of the Neurospora crassa PZL-1 protein phosphatase by expression in budding and fission yeast. | 2001 Jan 30 |
|
Adenosine induces initial hypoxic-ischemic depression of synaptic transmission in the rat hippocampus in vivo. | 2001 Mar |
|
Regulation of slow wave frequency by IP(3)-sensitive calcium release in the murine small intestine. | 2001 Mar |
|
Binding of urate and caffeine to haemocyanin analysed by isothermal titration calorimetry. | 2001 Mar |
|
Dopaminergic role in stimulant-induced wakefulness. | 2001 Mar 1 |
|
7-Methylxanthine methyltransferase of coffee plants. Gene isolation and enzymatic properties. | 2001 Mar 16 |
|
Study of the cytolethal distending toxin (CDT)-activated cell cycle checkpoint. Involvement of the CHK2 kinase. | 2001 Mar 2 |
|
Ca2+-induced Ca2+ release from the endoplasmic reticulum amplifies the Ca2+ signal mediated by activation of voltage-gated L-type Ca2+ channels in pancreatic beta-cells. | 2001 Mar 30 |
|
Escape deficits induced by inescapable shock and metabolic stress are reversed by adenosine receptor antagonists. | 2001 May |
Patents
Sample Use Guides
Caffeine is used by mouth in combination with painkillers (such as aspirin and acetaminophen) for treating headaches. Maximum oral dose of excedrin is 2 tablets a day (each tablet of excedrin contains 65 mg of caffeine). Caffeine creams are applied to the skin to reduce redness and itching in dermatitis. Healthcare providers sometimes give caffeine intravenously (by IV) for headache after epidural anesthesia, breathing problems in newborns, and to increase urine flow. In foods, caffeine is used as an ingredient in soft drinks, energy drinks, and other beverages.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/6309393
Binding of caffeine to adrenergic receptors was measured using [3H]N6-Cyclohexyladenosine as a radioligand. Nonspecificbinding was less than 10% of total binding as defined with 10 uM 2-chloroadenosine. Membranes were incubated with 10-6 - 10-3 M caffeine.
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Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
WHO-VATC |
QV04CG30
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NDF-RT |
N0000175729
Created by
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CFR |
21 CFR 340.10
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NDF-RT |
N0000175790
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WHO-VATC |
QN06BC01
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NCI_THESAURUS |
C54060
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NCI_THESAURUS |
C47795
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NDF-RT |
N0000175739
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IARC | Caffeine | ||
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NDF-RT |
N0000008118
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NDF-RT |
N0000008118
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DSLD |
367 (Number of products:3156)
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FDA ORPHAN DRUG |
367512
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EPA PESTICIDE CODE |
660
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WHO-ATC |
V04CG30
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FDA ORPHAN DRUG |
31288
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WHO-ATC |
N06BC01
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LIVERTOX |
137
Created by
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CFR |
21 CFR 340.50
Created by
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Code System | Code | Type | Description | ||
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Caffeine
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PRIMARY | |||
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D002110
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PRIMARY | |||
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1886
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PRIMARY | RxNorm | ||
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407
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PRIMARY | |||
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CAFFEINE
Created by
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PRIMARY | Description: Silky, colourless crystals or a white, crystalline powder; odourless. Solubility: Soluble in 60 parts of water and in 100 parts of ethanol (~750 g/l) TS; slightly soluble in ether R. Category: Central nervous stimulant. Storage: Caffeine should be kept in a well-closed container. Labelling: The designation on the container of Caffeine should state whether the substance is the monohydrate or is in the anhydrous form. Additional information: Caffeine monohydrate is efflorescent in air. Definition: Caffeine contains not less than 98.5% and not more than 101.0% of C8H10N4O2, calculated with reference to the dried substance. | ||
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463
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PRIMARY | |||
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DB00201
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PRIMARY | |||
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CHEMBL113
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PRIMARY | |||
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35
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PRIMARY | |||
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1085003
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PRIMARY | USP-RS | ||
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2519
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PRIMARY | |||
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CAFFEINE
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PRIMARY | |||
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C328
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PRIMARY | |||
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1086006
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PRIMARY | USP-RS | ||
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58-08-2
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PRIMARY | |||
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SUB26077
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PRIMARY | |||
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200-362-1
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PRIMARY | |||
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SUB13146MIG
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PRIMARY | |||
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58-08-2
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PRIMARY | |||
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M2909
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PRIMARY | Merck Index | ||
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3G6A5W338E
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PRIMARY |
ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE ACTIVE (PARENT)
METABOLITE ACTIVE (PARENT)
PARENT (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)