Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C8H10N4O2.C6H8O7 |
| Molecular Weight | 386.3141 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)CC(O)(CC(O)=O)C(O)=O.CN1C=NC2=C1C(=O)N(C)C(=O)N2C
InChI
InChIKey=RCQXSQPPHJPGOF-UHFFFAOYSA-N
InChI=1S/C8H10N4O2.C6H8O7/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2;7-3(8)1-6(13,5(11)12)2-4(9)10/h4H,1-3H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
DescriptionCurator's Comment: description was created based on several sources, including
http://www.webmd.com/vitamins-supplements/ingredientmono-979-caffeine.aspx?activeingredientid=979
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 |
23.4 µM [Ki] | ||
Target ID: CHEMBL255 |
20.5 µM [Ki] | ||
Target ID: CHEMBL226 |
44.9 µM [Ki] | ||
Target ID: CHEMBL2111322 |
70.0 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| 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 Date1948 |
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| 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 Date1999 |
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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 |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
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% |
|||
| yes | ||||
| yes |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| 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 | ||||
Page: 9.0 |
yes | |||
| yes |
Tox targets
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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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| Caffeine citrate: a review of its use in apnoea of prematurity. | 2001 |
|
| Effect of caffeine on the genotoxic effects of gamma radiation and 4-NQO in diploid yeast. | 2001 |
|
| Excitation-contraction coupling in pulmonary vascular smooth muscle involves tyrosine kinase and Rho kinase. | 2001 Apr |
|
| Combined effects of red pepper and caffeine consumption on 24 h energy balance in subjects given free access to foods. | 2001 Feb |
|
| Ionomycin and 2,5'-di(tertbutyl)-1,4,-benzohydroquinone elicit Ca2+-induced Ca2+ release from intracellular pools in Physarum polycephalum. | 2001 Feb |
|
| Caffeine and intraocular pressure in a Nigerian population. | 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 |
|
| Calcium homeostasis and cell death in Sol8 dystrophin-deficient cell line in culture. | 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 |
|
| Regional differences in mechanisms of cerebral circulatory response to neuronal activation. | 2001 Feb |
|
| Uric acid inhibits liver phosphorylase a activity under simulated in vivo conditions. | 2001 Feb |
|
| Adenoviral SERCA1a gene transfer to adult rat ventricular myocytes induces physiological changes in calcium handling. | 2001 Feb 1 |
|
| Effects of alprazolam, caffeine, and zolpidem in humans trained to discriminate triazolam from placebo. | 2001 Feb 1 |
|
| Predetermined recruitment of calcium release sites underlies excitation-contraction coupling in rat atrial myocytes. | 2001 Feb 1 |
|
| The effects of intracellular pH changes on resting cytosolic calcium in voltage-clamped snail neurones. | 2001 Feb 1 |
|
| Evidence for glutamate receptor mediated transmission at mechanoreceptors in the skin. | 2001 Feb 12 |
|
| 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 |
|
| Coordinated control of cell Ca(2+) loading and triggered release from the sarcoplasmic reticulum underlies the rapid inotropic response to increased L-type Ca(2+) current. | 2001 Feb 2 |
|
| Overexpression of FK506-binding protein FKBP12.6 in cardiomyocytes reduces ryanodine receptor-mediated Ca(2+) leak from the sarcoplasmic reticulum and increases contractility. | 2001 Feb 2 |
|
| [Cerebral infarction in a patient consuming MaHuang extract and guarana]. | 2001 Feb 3 |
|
| Caffeine metabolism in a group of 67 patients with primary biliary cirrhosis. | 2001 Jan |
|
| Health tips. Caffeine. | 2001 Jan |
|
| Is the combination of ibuprofen and caffeine effective for the treatment of a tension-type headache? | 2001 Jan |
|
| Clinical correlations in infants in the neonatal intensive care unit with varying severity of gastroesophageal reflux. | 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 |
|
| A preferred amplitude of calcium sparks in skeletal muscle. | 2001 Jan |
|
| Risk factors for sleep bruxism in the general population. | 2001 Jan |
|
| Calculation of the dimensions of dosage forms with release controlled by diffusion for in vivo use. | 2001 Jan |
|
| Sorption and desorption studies on chitin gels. | 2001 Jan 10 |
|
| Characterization of the ryanodine receptor-Ca2+ release channel from the thoracic tissues of the lepidopteran insect Heliothis virescens. | 2001 Jan 15 |
|
| Origin and propagation of spontaneous excitation in smooth muscle of the guinea-pig urinary bladder. | 2001 Jan 15 |
|
| Suspected caffeine and ephedrine toxicosis resulting from ingestion of an herbal supplement containing guarana and ma huang in dogs: 47 cases (1997-1999). | 2001 Jan 15 |
|
| Functional analysis of the Neurospora crassa PZL-1 protein phosphatase by expression in budding and fission yeast. | 2001 Jan 30 |
|
| Acute but not chronic caffeine impairs functional responses to ischaemia-reperfusion in rat isolated perfused heart. | 2001 Jan-Feb |
|
| Signalling mechanisms underlying the myogenic response in human subcutaneous resistance arteries. | 2001 Mar |
|
| Low-dose ramipril treatment improves relaxation and calcium cycling after established cardiac hypertrophy. | 2001 Mar |
|
| 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 |
|
| Multiple effects of caffeine on Ca2+ release and influx in human B lymphocytes. | 2001 Mar |
|
| Dopaminergic role in stimulant-induced wakefulness. | 2001 Mar 1 |
|
| Study of the cytolethal distending toxin (CDT)-activated cell cycle checkpoint. Involvement of the CHK2 kinase. | 2001 Mar 2 |
|
| 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:
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| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
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EU-Orphan Drug |
EU/3/03/132
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EMA ASSESSMENT REPORTS |
PEYONA (AUTHORIZED: APNEA)
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NCI_THESAURUS |
C47795
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WHO-ESSENTIAL MEDICINES LIST |
29
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20033
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CHEMBL113
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SUB13151MIG
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C1033
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U26EO4675Q
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m2909
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C026189
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CAFFEINE CITRATE
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U26EO4675Q
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DBSALT000866
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6241
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100000091411
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69-22-7
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DTXSID5046938
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ACTIVE MOIETY
PARENT (SALT/SOLVATE)
SUBSTANCE RECORD
