Caffeine

Identification

Summary

Caffeine is a stimulant present in tea, coffee, cola beverages, analgesic drugs, and agents used to increase alertness. It is also used in to prevent and treat pulmonary complications of premature birth.

Brand Names
Anacin, Arthriten Inflammatory Pain, Ascomp, Bc Arthritis, Bc Original Formula, Diurex, Dvorah, Esgic, Exaprin, Excedrin, Excedrin Tension Headache, Fioricet, Fioricet With Codeine, Fiorinal, Goody's Extra Strength, Goody's Headache Relief Shot, Goody's PM, Midol Complete, Midol Cramps & Bodyaches, Migergot, Norgesic, Norgesic Forte, Orbivan, Orphengesic, Pamprin Max Formula, Peyona, Stanback Headache Powder Reformulated Jan 2011, Trezix, Trianal, Trianal C, Triatec, Triatec-8, Vanatol, Vanatol S, Vanquish, Vivarin
Generic Name
Caffeine
DrugBank Accession Number
DB00201
Background

Caffeine is a drug of the methylxanthine class used for a variety of purposes, including certain respiratory conditions of the premature newborn, pain relief, and to combat drowsiness. Caffeine is similar in chemical structure to Theophylline and Theobromine.4,16 It can be sourced from coffee beans, but also occurs naturally in various teas and cacao beans, which are different than coffee beans.12 Caffeine is also used in a variety of cosmetic products and can be administered topically, orally, by inhalation, or by injection.12

The caffeine citrate injection, used for apnea of the premature newborn, was initially approved by the FDA in 1999.19 According to an article from 2017, more than 15 million babies are born prematurely worldwide. This correlates to about 1 in 10 births. Premature birth can lead to apnea and bronchopulmonary dysplasia, a condition that interferes with lung development and may eventually cause asthma or early onset emphysema in those born prematurely.5 Caffeine is beneficial in preventing and treating apnea and bronchopulmonary dysplasia in newborns, improving the quality of life of premature infants.12

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 194.1906
Monoisotopic: 194.080375584
Chemical Formula
C8H10N4O2
Synonyms
  • 1-methyltheobromine
  • 1,3,7-trimethyl-2,6-dioxopurine
  • 1,3,7-trimethylpurine-2,6-dione
  • 1,3,7-trimethylxanthine
  • 3,7-Dihydro-1,3,7-trimethyl-1H-purin-2,6-dion
  • 7-methyltheophylline
  • Anhydrous caffeine
  • Cafeína
  • Caféine
  • Caffeine
  • Caffeinum
  • Coffein
  • Coffeinum
  • Guaranine
  • Koffein
  • Mateína
  • Methyltheobromine
  • Teína
  • Thein
  • Theine
External IDs
  • Fema no. 2224
  • NSC-5036

Pharmacology

Indication

Caffeine is indicated for the short term treatment of apnea of prematurity in infants and off label for the prevention and treatment of bronchopulmonary dysplasia caused by premature birth.12,16 In addition, it is indicated in combination with sodium benzoate to treat respiratory depression resulting from an overdose with CNS depressant drugs.23 Caffeine has a broad range of over the counter uses, and is found in energy supplements, athletic enhancement products, pain relief products, as well as cosmetic products.12,17,21

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofApnea of prematurity••••••••••••••••••••
Treatment ofBronchopulmonary dysplasia (bpd)••• •••••
Prevention ofBronchopulmonary dysplasia (bpd)••• •••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Acetaminophen (DB00316), Carbaspirin calcium (DB13612)••• •••••••••
Used in combination for symptomatic treatment ofCommon coldCombination Product in combination with: Phenylephrine (DB00388), Acetaminophen (DB00316), Desloratadine (DB00967)•••••••••••••••••••• •••••••• ••••••
Associated Therapies
Contraindications & Blackbox Warnings
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Pharmacodynamics

Caffeine stimulates the central nervous system (CNS), heightening alertness, and sometimes causing restlessness and agitation. It relaxes smooth muscle, stimulates the contraction of cardiac muscle, and enhances athletic performance.1,12,18 Caffeine promotes gastric acid secretion and increases gastrointestinal motility. It is often combined in products with analgesics and ergot alkaloids, relieving the symptoms of migraine and other types of headaches. Finally, caffeine acts as a mild diuretic.12

Mechanism of action

The mechanism of action of caffeine is complex, as it impacts several body systems, which are listed below. The effects as they relate to various body systems are described as follows:

General and cellular actions

Caffeine exerts several actions on cells, but the clinical relevance is poorly understood. One probable mechanism is the inhibition of nucleotide phosphodiesterase enzymes, adenosine receptors, regulation of calcium handling in cells, and participates in adenosine receptor antagonism.8,18 Phosphodiesterase enzymes regulate cell function via actions on second messengers cAMP and cGMP.9 This causes lipolysis through activation of hormone-sensitive lipases, releasing fatty acids and glycerol.14

Respiratory

The exact mechanism of action of caffeine in treating apnea related to prematurity is unknown, however, there are several proposed mechanisms, including respiratory center stimulation in the central nervous system, a reduced threshold to hypercapnia with increased response, and increased consumption of oxygen, among others.16 The blocking of the adenosine receptors enhances respiratory drive via an increase in brain medullary response to carbon dioxide, stimulating ventilation and respiratory drive, while increasing contractility of the diaphragm.12

Central nervous system

Caffeine demonstrates antagonism of all 4 adenosine receptor subtypes (A1, A2a, A2b, A3) in the central nervous system.12,16 Caffeine's effects on alertness and combatting drowsiness are specifically related to the antagonism of the A2a receptor.12

Renal system

Caffeine has diuretic effects due to is stimulatory effects on renal blood flow, increase in glomerular filtration, and increase in sodium excretion.12

Cardiovascular system

Adenosine receptor antagonism at the A1 receptor by caffeine stimulates inotropic effects in the heart. Blocking of adenosine receptors promotes catecholamine release, leading to stimulatory effects occurring in the heart and the rest of the body. In the blood vessels, caffeine exerts direct antagonism of adenosine receptors, causing vasodilation. It stimulates the endothelial cells in the blood vessel wall to release nitric oxide, potentiating blood vessel relaxation. Catecholamine release, however, antagonizes this and exerts inotropic and chronotropic effects on the heart, ultimately leading to vasoconstriction. Finally, caffeine is shown to raise systolic blood pressure measurements by 5 to 10 mmHg when it is not taken regularly, versus no effect in those who consume it regularly.12 The vasoconstricting effects of caffeine are beneficial in migraines and other types of headache, which are normally caused by vasodilation in the brain.6,21

TargetActionsOrganism
AAdenosine receptor A1
antagonist
Humans
AAdenosine receptor A2a
antagonist
Humans
AAdenosine receptor A2b
antagonist
Humans
AAdenosine receptor A3
antagonist
Humans
APhosphodiesterase enzymes
inhibitor
Humans
UcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Humans
URyanodine receptor 1Not AvailableHumans
UCyclic nucleotide phosphodiesterase
inhibitor
Humans
UDNA-dependent protein kinase catalytic subunit
inhibitor
Humans
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
inhibitor
Humans
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
inhibitor
Humans
UPhosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
inhibitor
Humans
UInositol 1,4,5-trisphosphate receptor
inhibitor
Humans
USerine-protein kinase ATM
inhibitor
Humans
Absorption

Caffeine is rapidly absorbed after oral or parenteral administration, reaching peak plasma concentration within 30 minutes to 2 hours after administration.10 After oral administration, onset of action takes place within 45 to 1 hour.15 Food may delay caffeine absorption. The peak plasma level for caffeine ranges from 6-10mg/L.16 The absolute bioavailability is unavailable in neonates16, but reaches about 100% in adults.12

Volume of distribution

Caffeine has the ability to rapidly cross the blood-brain barrier. It is water and fat soluble and distributes throughout the body.12,14,16 Caffeine concentrations in the cerebrospinal fluid of preterm newborns are similar to the concentrations found in the plasma. The mean volume of distribution of caffeine in infants is 0.8-0.9 L/kg and 0.6 L/kg in the adult population.16

Protein binding

Plasma protein binding of caffeine has not been determined for neonates or infants. In vitro studies indicate a protein binding of about 10%-36%. Caffeine is reversibly bound to plasma proteins.14,16

Metabolism

Caffeine metabolism occurs mainly in the liver via the cytochrome CYP1A2 enzyme.10 The products of caffeine metabolism include paraxanthine, theobromine, and theophylline. The first step of caffeine metabolism is demethylation, yielding paraxanthine (a major metabolite), followed by theobromine, and theophylline, which are both minor metabolites. They are then excreted in urine as urates after additional metabolism.10,12,16 The enzymes xanthine oxidase and N-acetyltransferase 2 (NAT2) also participate in the metabolism of caffeine.10

Hover over products below to view reaction partners

Route of elimination

The major metabolites of caffeine can be found excreted in the urine.12 About 0.5% to 2% of a caffeine dose is found excreted in urine, as it because it is heavily absorbed in the renal tubules.14,10

Half-life

In an average-sized adult or child above the age of 9, the half-life of caffeine is approximately 5 hours. Various characteristics and conditions can alter caffeine half-life. It can be reduced by up to 50% in smokers. Pregnant women show an increased half-life of 15 hours or higher, especially in the third trimester. The half-life in newborns is prolonged to about 8 hours at full-term and 100 hours in premature infants, likely due to reduced ability to metabolize it. Liver disease or drugs that inhibit CYP1A2 can increase caffeine half-life.12,14

Clearance

The clearance of caffeine varies, but on average, is about 0.078 L/kg/h (1.3 mL/min/kg).10,14

Adverse Effects
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Toxicity

The oral LD50 of caffeine in rats is 192 mg/kg.MSDS An acute fatal overdose of caffeine in humans is about 10–14 grams (equivalent to 150–200 mg/kg of body weight).14

Caffeine overdose

In the case of caffeine overdose, seizures may occur, as caffeine is a central nervous system stimulant. It should be used with extreme caution in those with epilepsy or other seizure disorders.16 Symptoms of overdose may include nausea, vomiting, diarrhea, and gastrointestinal upset. Intoxication with caffeine is included in the World Health Organization’s International Classification of Diseases (ICD-10). Agitation, anxiety, restlessness, insomnia, tachycardia, tremors, tachycardia, psychomotor agitation, and, in some cases, death can occur, depending on the amount of caffeine consumed. Overdose is more likely to occur in individuals who do not consume caffeine regularly but consume energy drinks.8

Overdose management

For a mild caffeine overdose, offer symptomatic treatment. In the case of a severe overdose, intubation for airway protection from changes in mental status or vomiting may be needed. Activated charcoal and hemodialysis can prevent further complications of an overdose and prevent absorption and metabolism. Benzodiazepine drugs can be administered to prevent or treat seizures. IV fluids and vasopressors may be necessary to combat hypotension associated with caffeine overdose. In addition, magnesium and beta blocking drugs can be used to treat arrhythmias that may occur, with defibrillation and resuscitation if the arrhythmias are lethal. Follow local ACLS protocols.12

Pathways
PathwayCategory
Caffeine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Interacting Gene/EnzymeAllele nameGenotype(s)Defining Change(s)Type(s)DescriptionDetails
Cytochrome P450 1A2---(C;C) / (A;C)C alleleADR Directly StudiedPatients with this genotype have increased risk of a non-fatal myocardial infarction with caffeineDetails

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe therapeutic efficacy of 1,2-Benzodiazepine can be decreased when used in combination with Caffeine.
AbametapirThe serum concentration of Caffeine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Caffeine can be increased when combined with Abatacept.
AbemaciclibCaffeine may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AbirateroneThe serum concentration of Caffeine can be increased when it is combined with Abiraterone.
Food Interactions
No interactions found.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Caffeine citrateU26EO4675Q69-22-7RCQXSQPPHJPGOF-UHFFFAOYSA-N
Product Images
International/Other Brands
Caffedrine / Dexitac / Durvitan / Enerjets / No-Doz / Pep-Back / Quick Pep / Wake-Up
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CafcitInjection20 mg/1mLIntravenousBedford Pharmaceuticals2008-11-042016-04-30US flag
CafcitSolution20 mg/1mLOralBedford Pharmaceuticals2008-11-042016-05-29US flag
Caffeine and Sodium BenzoateInjection, solution125 mg/1mLIntramuscular; IntravenousAMERICAN REGENT, INC.1993-02-01Not applicableUS flag
Caffeine CitrateInjection20 mg/1mLIntravenousHikma Pharmaceuticals USA Inc.2024-01-11Not applicableUS flag
Caffeine CitrateInjection20 mg/1mLIntravenousHikma Pharmaceuticals USA Inc.2008-11-04Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Caffeine CitrateSolution20 mg/1mLOralRemedy Repack2013-10-312014-10-31US flag
Caffeine CitrateSolution60 mg/3mLOralMicro Labs Limited2020-02-01Not applicableUS flag
Caffeine CitrateInjection20 mg/1mLIntravenousPaddock Laboratories, Inc.2006-09-212015-08-31US flag
Caffeine CitrateSolution20 mg/1mLOralExela Pharma Sciences, LLC2006-09-21Not applicableUS flag
Caffeine CitrateInjection20 mg/1mLIntravenousSun Pharmaceutical Industries Ltd2009-10-01Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
357 Super MagnumTablet, multilayer200 1/1OralKing Richard Promotions Dba Dbi2016-05-19Not applicableUS flag
AlertTablet, film coated200 mg/1OralTime Cap Labs, Inc2011-11-30Not applicableUS flag
AlertTablet200 mg/1OralDOLGENCORP, LLC1996-11-21Not applicableUS flag
Alert AidTablet200 mg/1OralAmerisource Bergen1996-11-21Not applicableUS flag
Alert Aid Caffeine Capsules 175mgCapsule175 mg / capOralSun Products Corporation1991-12-312004-03-11Canada flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
(extra Strength) Acetaminophen, Caffeine & 8mg Codeine Phosphate CapletsCaffeine (15 mg) + Acetaminophen (500 mg) + Codeine phosphate (8 mg)TabletOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.1998-07-222002-07-31Canada flag
217Caffeine citrate (30 mg / tab) + Acetylsalicylic acid (325 mg / tab)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1910-12-311998-04-21Canada flag
217 Strong TabCaffeine citrate (30 mg / tab) + Acetylsalicylic acid (500 mg / tab)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1973-12-311998-04-21Canada flag
222 TabletsCaffeine citrate (30 mg) + Acetylsalicylic acid (375 mg) + Codeine phosphate (8 mg)TabletOralMcneil Consumer Healthcare Division Of Johnson & Johnson Inc1951-12-312015-08-17Canada flag
282 Mep TabCaffeine citrate (30 mg) + Acetylsalicylic acid (350 mg) + Codeine phosphate (15 mg) + Meprobamate (200 mg)TabletOralMerck Frosst Canada & Cie, Merck Frosst Canada & Co.1959-12-311998-08-14Canada flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
4229 First Aid KitCaffeine (32.4 mg/1) + Acetaminophen (110 mg/1) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Isopropyl alcohol (0.7 mL/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1)KitOral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4248 First Aid KitCaffeine (32.4 mg/1) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Hydrocortisone acetate (1 g/100g) + Hydrocortisone acetate (1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Menthol (0.33 g/100g) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmic; Oral; Respiratory (inhalation); TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
4346 First Aid KitCaffeine (32.4 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Calcium carbonate (420 mg/1) + Lidocaine hydrochloride (24.64 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Water (98.6 mL/100mL)Kit; Liquid; Ointment; Spray; TabletOphthalmic; Oral; TopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUS flag
Caffeine and Sodium BenzoateCaffeine (125 mg/1mL)Injection, solutionIntramuscular; IntravenousAMERICAN REGENT, INC.1993-02-01Not applicableUS flag
Cl LightCaffeine (0.63 g/100mL) + Garcinia gummi-gutta fruit (0.04 g/100mL)CreamTopicalPowerful X2018-08-30Not applicableUS flag

Categories

ATC Codes
D11AX26 — CaffeineR03DA20 — Combinations of xanthinesV04CG30 — Caffeine and sodium benzoateN06BC01 — Caffeine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as xanthines. These are purine derivatives with a ketone group conjugated at carbons 2 and 6 of the purine moiety.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Imidazopyrimidines
Sub Class
Purines and purine derivatives
Direct Parent
Xanthines
Alternative Parents
6-oxopurines / Alkaloids and derivatives / Pyrimidones / N-substituted imidazoles / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
6-oxopurine / Alkaloid or derivatives / Aromatic heteropolycyclic compound / Azacycle / Azole / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Lactam / N-substituted imidazole
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
purine alkaloid, trimethylxanthine (CHEBI:27732) / Purine alkaloids (C07481) / a small molecule (1-3-7-TRIMETHYLXANTHINE)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
3G6A5W338E
CAS number
58-08-2
InChI Key
RYYVLZVUVIJVGH-UHFFFAOYSA-N
InChI
InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
IUPAC Name
1,3,7-trimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CN1C=NC2=C1C(=O)N(C)C(=O)N2C

References

Synthesis Reference

Kaspar Bott, "Preparation of caffeine." U.S. Patent US4380631, issued December, 1976.

US4380631
General References
  1. Nehlig A, Daval JL, Debry G: Caffeine and the central nervous system: mechanisms of action, biochemical, metabolic and psychostimulant effects. Brain Res Brain Res Rev. 1992 May-Aug;17(2):139-70. [Article]
  2. Ding R, Shi J, Pabon K, Scotto KW: Xanthines down-regulate the drug transporter ABCG2 and reverse multidrug resistance. Mol Pharmacol. 2012 Mar;81(3):328-37. doi: 10.1124/mol.111.075556. Epub 2011 Nov 23. [Article]
  3. Kole J, Barnhill A: Caffeine Content Labeling: A Missed Opportunity for Promoting Personal and Public Health. J Caffeine Res. 2013 Sep;3(3):108-113. doi: 10.1089/jcr.2013.0017. [Article]
  4. Michael Z, Spyropoulos F, Ghanta S, Christou H: Bronchopulmonary Dysplasia: An Update of Current Pharmacologic Therapies and New Approaches. Clin Med Insights Pediatr. 2018 Dec 11;12:1179556518817322. doi: 10.1177/1179556518817322. eCollection 2018. [Article]
  5. Collins JJP, Tibboel D, de Kleer IM, Reiss IKM, Rottier RJ: The Future of Bronchopulmonary Dysplasia: Emerging Pathophysiological Concepts and Potential New Avenues of Treatment. Front Med (Lausanne). 2017 May 22;4:61. doi: 10.3389/fmed.2017.00061. eCollection 2017. [Article]
  6. Lipton RB, Diener HC, Robbins MS, Garas SY, Patel K: Caffeine in the management of patients with headache. J Headache Pain. 2017 Oct 24;18(1):107. doi: 10.1186/s10194-017-0806-2. [Article]
  7. Schneider E, Freundlieb S, Tapio S, Boos W: Molecular characterization of the MalT-dependent periplasmic alpha-amylase of Escherichia coli encoded by malS. J Biol Chem. 1992 Mar 15;267(8):5148-54. [Article]
  8. Cappelletti S, Piacentino D, Sani G, Aromatario M: Caffeine: cognitive and physical performance enhancer or psychoactive drug? Curr Neuropharmacol. 2015 Jan;13(1):71-88. doi: 10.2174/1570159X13666141210215655. [Article]
  9. Boswell-Smith V, Spina D, Page CP: Phosphodiesterase inhibitors. Br J Pharmacol. 2006 Jan;147 Suppl 1:S252-7. doi: 10.1038/sj.bjp.0706495. [Article]
  10. White JR Jr, Padowski JM, Zhong Y, Chen G, Luo S, Lazarus P, Layton ME, McPherson S: Pharmacokinetic analysis and comparison of caffeine administered rapidly or slowly in coffee chilled or hot versus chilled energy drink in healthy young adults. Clin Toxicol (Phila). 2016;54(4):308-12. doi: 10.3109/15563650.2016.1146740. [Article]
  11. Mandel HG: Update on caffeine consumption, disposition and action. Food Chem Toxicol. 2002 Sep;40(9):1231-4. doi: 10.1016/s0278-6915(02)00093-5. [Article]
  12. Justin Evans; Amanda S. Battisti (2019). Caffeine. Stat Pearls Publishing.
  13. IARC Working Group on the Evaluation of Carcinogenic Risk to Humans (1991). Coffee, Tea, Mate, Methylxanthines and Methylglyoxal. International Agency for Research on Cancer.
  14. Institute of Medicine (US) Committee on Military Nutrition Research. (2001). Caffeine for the Sustainment of Mental Task Performance: Formulations for Military Operations.. National Academic Press.
  15. Highly Concentrated Caffeine in Dietary Supplements: Guidance for Industry [Link]
  16. Caffeine citrate injection FDA label [Link]
  17. DailyMed Search: Caffeine [Link]
  18. PDB reference [Link]
  19. FDA approval [Link]
  20. Alcohol and Drug Foundation, Australia [Link]
  21. Migergot, DailyMed [Link]
  22. Caffeine pathway: Pharm GKB [Link]
  23. Caffeine and sodium benzoate injection [Link]
  24. FDA Approved Drug Products: SYNALGOS®-DC (aspirin, caffeine, and dihydrocodeine bitartrate) capsules, for oral use, CIII (Jan 2024) [Link]
Human Metabolome Database
HMDB0001847
KEGG Drug
D00528
KEGG Compound
C07481
PubChem Compound
2519
PubChem Substance
46506408
ChemSpider
2424
BindingDB
10849
RxNav
1886
ChEBI
27732
ChEMBL
CHEMBL113
ZINC
ZINC000000001084
Therapeutic Targets Database
DAP000099
PharmGKB
PA448710
Guide to Pharmacology
GtP Drug Page
PDBe Ligand
CFF
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Caffeine
PDB Entries
1c8l / 1gfz / 1l5q / 1l7x / 2a3b / 3dd1 / 3dds / 3ddw / 3g6m / 3rfm
show 44 more
FDA label
Download (37.7 KB)
MSDS
Download (46.9 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingPreventionChronic Lung Disease of Prematurity / Hemodynamics Instability / Intubation / Primary apnea of premature newborns1
4CompletedBasic ScienceAdult Population1
4CompletedBasic ScienceAnxiety1
4CompletedBasic SciencePlacebo Effect1
4CompletedBasic ScienceTransplanted Organ Rejection1

Pharmacoeconomics

Manufacturers
  • Mead johnson and co
  • App pharmaceuticals llc
  • Luitpold pharmaceuticals inc
  • Paddock laboratories inc
  • Sun pharmaceutical industries ltd
Packagers
  • Actavis Group
  • Aidarex Pharmacuticals LLC
  • Alphagen Laboratories Inc.
  • American Regent
  • Amerisource Health Services Corp.
  • Amneal Pharmaceuticals
  • Apotheca Inc.
  • APP Pharmaceuticals
  • A-S Medication Solutions LLC
  • Athlon Pharmaceuticals Inc.
  • Atley Pharmaceuticals
  • Bedford Labs
  • Ben Venue Laboratories Inc.
  • Bioniche Pharma
  • Blansett Pharmacal Co. Inc.
  • Blenheim Pharmacal
  • Brighton Pharmaceuticals
  • Bristol-Myers Squibb Co.
  • Bryant Ranch Prepack
  • Cardinal Health
  • Carlisle Laboratories Inc.
  • Comprehensive Consultant Services Inc.
  • Concord Labs
  • Corepharma LLC
  • CVS Pharmacy
  • D.M. Graham Laboratories Inc.
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Everett Laboratories Inc.
  • Forest Pharmaceuticals
  • G & W Labs
  • Gilbert Laboratories
  • GlaxoSmithKline Inc.
  • Goldline Laboratories Inc.
  • Heartland Repack Services LLC
  • Hope Pharmaceuticals
  • Hospira Inc.
  • Innoviant Pharmacy Inc.
  • J T Baker
  • Kaiser Foundation Hospital
  • Keene Pharmaceuticals Inc.
  • Keltman Pharmaceuticals Inc.
  • Lannett Co. Inc.
  • Liberty Pharmaceuticals
  • Luitpold Pharmaceuticals Inc.
  • Lunsco Inc.
  • Major Pharmaceuticals
  • Mallinckrodt Inc.
  • Marlex Pharmaceuticals
  • Marnel Pharmaceuticals Inc.
  • MCR American Pharmaceuticals Inc.
  • Mikart Inc.
  • Murfreesboro Pharmaceutical Nursing Supply
  • Nexgen Pharma Inc.
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Palmetto Pharmaceuticals Inc.
  • Patient First Corp.
  • PCA LLC
  • PD-Rx Pharmaceuticals Inc.
  • Perrigo Co.
  • Pharmaceutical Utilization Management Program VA Inc.
  • Physicians Total Care Inc.
  • Poly Pharmaceuticals Inc.
  • Preferred Pharmaceuticals Inc.
  • Prepackage Specialists
  • Prepak Systems Inc.
  • Prescript Pharmaceuticals
  • Prometic Pharma Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Redpharm Drug
  • Resource Optimization and Innovation LLC
  • Rising Pharmaceuticals
  • Rite Aid Corp.
  • Sandhills Packaging Inc.
  • Sciele Pharma Inc.
  • Seatrace Pharmaceuticals Inc.
  • Southwood Pharmaceuticals
  • Stat Rx Usa
  • Talbert Medical Management Corp.
  • Teva Pharmaceutical Industries Ltd.
  • US Pharmaceutical Corp.
  • Va Cmop Dallas
  • Victory Pharma
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
  • West-Ward Pharmaceuticals
  • Xanodyne Pharmaceuticals Inc.
Dosage Forms
FormRouteStrength
TabletOral
Tablet, multilayerOral200 1/1
KitOral; Respiratory (inhalation); Topical
KitOphthalmic; Oral; Respiratory (inhalation); Topical
Kit; liquid; ointment; spray; tabletOphthalmic; Oral; Topical
TabletOral250 mg
TabletOral4.000 mg
SyrupOral
Tablet, film coatedOral200 mg/1
CapsuleOral175 mg / cap
TabletOral175 mg
TabletOral100 mg / tab
Tablet, coatedOral200 mg/1
TabletOral500.00 mg
Tablet, coatedOral
Tablet, effervescentOral
CapsuleOral
SuppositoryRectal
Tablet, multilayerOral200 mg/200mg
Injection, solutionIntramuscular; Intravenous125 mg/1mL
InjectionIntravenous20 mg/1mL
InjectionIntravenous60 mg/3mL
Injection, solutionIntramuscular; Intravenous60 mg/3mL
Injection, solutionIntravenous20 mg/1mL
SolutionIntravenous20 mg/1mL
SolutionOral20 mg/1mL
SolutionOral60 mg/3mL
SolutionIntravenous20 mg / mL
SolutionOral20 mg / mL
TabletOral100 mg
SolutionIntravenous; Oral60 mg
TabletOral100 mg
Tablet, sugar coatedOral15 mg
CapsuleOral30 mg
TabletOral4.00 mg
TabletOral200 mg
Suppository
Tablet
TabletOral200 mg / tab
Tablet, film coatedOral100 mg/1
LiquidTopical
Tablet, coated
Kit; tablet, film coatedOral
KitOral
Tablet, film coatedOral
Capsule, gelatin coatedOral
Granule, for solutionOral
TabletOral500.000 mg
SolutionOral
CapsuleOral15 mg
GranuleOral
Injection, solution10 mg/ml
Injection, solutionOral10 MG/ML
Capsule, coatedOral
Tablet, film coatedTopical
PowderOral
TabletOral15 mg
TabletOral325.000 mg
Tablet, coatedOral100 mg/1
Capsule, liquid filledOral200 mg/1
Injection, solutionIntravenous20 mg/ml
CapsuleOral25 mg
Capsule, liquid filledOral
CreamTopical
CreamTopical5.0 mg/1000mL
Tablet, sugar coatedOral
Capsule, coatedOral500 mg
Tablet, multilayerOral
Tablet, effervescentOral65 mg
Injection, solutionOral
Injection, solution; solutionIntravenous; Oral20 mg/ml
SolutionIntravenous; Oral20 mg / mL
SolutionIntravenous; Oral20 mg/1ml
InjectionParenteral20 mg/ml
SolutionIntravenous; Oral10 mg
CapsuleOral100 mg
TabletOral300.000 mg
PowderTopical
LiquidOral
Tablet, coatedTopical
InjectionParenteral
InjectionIntravenous
LozengeOral50 mg/1
TabletOral12.5 mg
WaferOral60 mg / piece
Tablet, film coatedOral150 mg
LiquidOral50 mg / bottle
Granule, effervescentOral
SolutionIntravenous; Oral20 mg
Tablet, delayed releaseOral
Powder, for solutionOral
TabletOral30 mg
TabletOral200 mg/1
TabletOral65 mg
Tablet, sugar coatedOral30 mg
Prices
Unit descriptionCostUnit
Migergot 12 2-100 mg Suppository Box105.43USD box
Cafcit 20 mg/ml oral soln16.4USD ml
Cafcit 20 mg/ml vial16.4USD ml
Caffeine cit 20 mg/ml oral sol15.21USD ml
Caffeine citrate 20 mg/ml vial12.8USD ml
Migergot suppository7.39USD suppository
Esgic tablet2.5USD tablet
Esgic 50-325-40 mg tablet2.27USD tablet
Darvon-n 100 mg tablet1.95USD tablet
Esgic-plus 50-500-40 mg tablet1.95USD tablet
Cafergot 1-100 mg tablet1.9USD tablet
Darvon 65 mg pulvule1.49USD each
Fioricet 50-325-40 mg tablet1.24USD tablet
Butalb-apap-caff 50-500-40 tablet1.2USD tablet
Butalb-apap-caff 50-325-40 tablet0.44USD tablet
Caffeine citrate powder0.36USD g
Propoxyphene hcl 65 mg capsule0.33USD capsule
Vivarin 200 mg caplet0.17USD caplet
Vivarin 200 mg tablet0.17USD tablet
No doz 200 mg caplet0.16USD caplet
Caffeine citrated powder purif0.13USD g
Stay awake 200 mg tablet0.1USD tablet
CVS Pharmacy caffeine 200 mg tablet0.09USD tablet
Ra stay awake 100 mg tablet0.09USD tablet
Caffeine powder0.07USD g
Caffeine 200 mg tablet0.01USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US5972916No1999-10-262017-07-14US flag

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)235-237https://www.sigmaaldrich.com/catalog/product/sial/41019?lang=en®ion=US
boiling point (°C)178http://www.inchem.org/documents/icsc/icsc/eics0405.htm
water solubility2.17 g/100mLhttp://www.inchem.org/documents/icsc/icsc/eics0405.htm
logP-0.07http://www.inchem.org/documents/icsc/icsc/eics0405.htm
logS-0.97https://pubchem.ncbi.nlm.nih.gov/compound/Caffeine
Caco2 permeability-4.41https://pubs.acs.org/doi/full/10.1021/ci049884m?src=recsys
pKa14https://www.sigmaaldrich.com/content/dam/sigma-aldrich/docs/Sigma-Aldrich/Product_Information_Sheet/c0750pis.pdf
Predicted Properties
PropertyValueSource
Water Solubility11.0 mg/mLALOGPS
logP-0.24ALOGPS
logP-0.55Chemaxon
logS-1.2ALOGPS
pKa (Strongest Basic)-1.2Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count3Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area58.44 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity49.83 m3·mol-1Chemaxon
Polarizability18.95 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9974
Blood Brain Barrier+0.9935
Caco-2 permeable+0.633
P-glycoprotein substrateNon-substrate0.7572
P-glycoprotein inhibitor INon-inhibitor0.8086
P-glycoprotein inhibitor IINon-inhibitor0.8471
Renal organic cation transporterNon-inhibitor0.8872
CYP450 2C9 substrateNon-substrate0.7484
CYP450 2D6 substrateNon-substrate0.5869
CYP450 3A4 substrateNon-substrate0.5305
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9906
CYP450 2D6 inhibitorNon-inhibitor0.9836
CYP450 2C19 inhibitorNon-inhibitor0.9927
CYP450 3A4 inhibitorNon-inhibitor0.9618
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9924
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9359
BiodegradationReady biodegradable0.6696
Rat acute toxicity2.9741 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8925
hERG inhibition (predictor II)Non-inhibitor0.8702
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.61 KB)
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)GC-MSsplash10-0536-3900000000-a9e112713ffae6dabdaa
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (0 TMS)GC-MSsplash10-0536-2900000000-8cdcd005b2e7622a02a3
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-052f-0900000000-f1084acfddb240696073
GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies)GC-MSsplash10-05nf-6900000000-8670a644cee5d9de78d4
GC-MS Spectrum - GC-MSGC-MSsplash10-0536-3900000000-4430852b279a72e34822
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-052r-0900000000-41f36d541d34d2088964
GC-MS Spectrum - EI-BGC-MSsplash10-0006-0900000000-51898e93480e848d7da1
GC-MS Spectrum - CI-BGC-MSsplash10-0002-0900000000-2aed5d425b6a95add5db
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-4900000000-3ff72dace6687d242f1f
GC-MS Spectrum - EI-BGC-MSsplash10-0006-1900000000-2ba1fae6e27c7b836984
GC-MS Spectrum - CI-BGC-MSsplash10-0002-0900000000-fd859aeb416e320d6379
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0536-3900000000-a9e112713ffae6dabdaa
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-0536-2900000000-8cdcd005b2e7622a02a3
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-052f-0900000000-f1084acfddb240696073
GC-MS Spectrum - GC-EI-TOFGC-MSsplash10-05nf-6900000000-8670a644cee5d9de78d4
GC-MS Spectrum - GC-MSGC-MSsplash10-0536-3900000000-4430852b279a72e34822
Mass Spectrum (Electron Ionization)MSsplash10-052f-8900000000-68b5e9aa3404fb3d8d3a
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-0006-0900000000-447fc72b2c709e2e18a9
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-000i-1900000000-5e3b29de16ad91c79fe0
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-0006-9100000000-d6f6c52ac36c8f25a500
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-0006-0900000000-cddd24399d942b1ac97c
MS/MS Spectrum - CI-B (Unknown) , PositiveLC-MS/MSsplash10-0002-0900000000-2aed5d425b6a95add5db
MS/MS Spectrum - EI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-0a4l-4900000000-3ff72dace6687d242f1f
MS/MS Spectrum - EI-B (HITACHI M-68) , PositiveLC-MS/MSsplash10-0006-1900000000-2ba1fae6e27c7b836984
MS/MS Spectrum - CI-B (HITACHI M-60) , PositiveLC-MS/MSsplash10-0002-0900000000-63b9ef42a3e8d59e9997
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-0002-0900000000-185b3d97d8857a0f269d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-0002-0900000000-f8a0c0dd9f5c4a272eaf
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-000i-1900000000-dd8e35226d0704aa657d
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-01x9-9800000000-70e3b0eb52481c39d191
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-001l-9100000000-6d428a5571beb0e3fed4
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , PositiveLC-MS/MSsplash10-0002-0900000000-98bec16f898808c3de68
LC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 30V, PositiveLC-MS/MSsplash10-0002-0900000000-b112e4e059e1ecf98c5f
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSsplash10-00dr-0900000000-42c6f8fc7b924e9c64f3
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-000i-4900000000-a60a480f1340558740a2
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-695d910d49fc0beb1d54
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-094879886a2e72bf0c56
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-fa38c865089a3a05f287
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000b-0900000000-0e82732a924c974dd0c8
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-bfc94c8091471847482b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-1900000000-c8fcf16986c494898203
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-3900000000-9569e0552abb7ebd145a
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-3a924abd44877050c1c9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-c6803f746febffe7ab6b
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-0002-0900000000-66e04d2c507b4751e506
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-9af60e39c843cb715435
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-1900000000-f858247f1e9a9dc03988
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-3900000000-73043667076aaf483c6e
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-2175b91e18c95954cc54
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-013ba6bf69c2800dafeb
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000b-0900000000-1ad354a17e0fd85a18db
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-f751c01e71d548d07cfa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01w0-0900000000-88cd919e5f37c53adf12
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-807dd2315cef11dedba7
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-2900000000-87822a5f5a6be99a2eaa
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-5900000000-6f909aa0d652aca47648
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0006-9500000000-e06eca9e3e2ab56477d0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-0900000000-1c1dcfab5dc129669de4
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0002-0900000000-fe8fd0aa7989e70bba69
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-000i-1900000000-dd8e35226d0704aa657d
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-01x9-9800000000-9e04f1fb471150acc039
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001l-9100000000-6d428a5571beb0e3fed4
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-000i-0900000000-c32a8e70a7c0e7c6b19b
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-98bec16f898808c3de68
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-b112e4e059e1ecf98c5f
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000j-0900000000-fb4fdea2278a980eebd9
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-d625aea76a3256436c31
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-6cd84afa1441c734413d
LC-MS/MS Spectrum - LC-ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-bc9f9a43b0fd465d435c
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0900000000-413259091ba7edc46b87
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-000i-0900000000-b8ca373712477994b200
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00di-0900000000-5e7721bcb84a3ae2c1eb
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-64da1f31ba17e532a3c6
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-6f74190396d61622726f
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-000i-0900000000-238b01405bce15c86f0d
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-4900000000-a60a480f1340558740a2
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0900000000-3b056c4352ea9d7dcd81
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000j-0900000000-409abf86df5de9a03860
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0900000000-f236794b68cee8f6798c
MS/MS Spectrum - ESI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-3d4e16572c9b12ac6836
MS/MS Spectrum - APCI-ITFT , positiveLC-MS/MSsplash10-000i-0900000000-ac06ecf59a06be305ff0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-379b84bcfaca54a7dfda
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-addead61d4054b3441a8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-5f50a455b1080c1567a8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-3900000000-f2f619c6f46110349f8d
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001l-9200000000-1e2e3ad36f08671d7555
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9700000000-173bbed7bcb1994af424
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-379b84bcfaca54a7dfda
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-0900000000-addead61d4054b3441a8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-3900000000-f2f619c6f46110349f8d
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0002-0900000000-5f50a455b1080c1567a8
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-9700000000-173bbed7bcb1994af424
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-001l-9200000000-1e2e3ad36f08671d7555
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,1H] 2D NMR Spectrum2D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-143.751083
predicted
DarkChem Lite v0.1.0
[M-H]-143.435283
predicted
DarkChem Lite v0.1.0
[M-H]-143.531983
predicted
DarkChem Lite v0.1.0
[M-H]-143.410983
predicted
DarkChem Lite v0.1.0
[M-H]-137.65517
predicted
DeepCCS 1.0 (2019)
[M-H]-143.751083
predicted
DarkChem Lite v0.1.0
[M-H]-143.435283
predicted
DarkChem Lite v0.1.0
[M-H]-143.531983
predicted
DarkChem Lite v0.1.0
[M-H]-143.410983
predicted
DarkChem Lite v0.1.0
[M-H]-137.65517
predicted
DeepCCS 1.0 (2019)
[M+H]+144.370883
predicted
DarkChem Lite v0.1.0
[M+H]+144.198983
predicted
DarkChem Lite v0.1.0
[M+H]+144.265983
predicted
DarkChem Lite v0.1.0
[M+H]+144.457783
predicted
DarkChem Lite v0.1.0
[M+H]+139.96652
predicted
DeepCCS 1.0 (2019)
[M+H]+144.370883
predicted
DarkChem Lite v0.1.0
[M+H]+144.198983
predicted
DarkChem Lite v0.1.0
[M+H]+144.265983
predicted
DarkChem Lite v0.1.0
[M+H]+144.457783
predicted
DarkChem Lite v0.1.0
[M+H]+139.96652
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.331583
predicted
DarkChem Lite v0.1.0
[M+Na]+144.207783
predicted
DarkChem Lite v0.1.0
[M+Na]+144.069383
predicted
DarkChem Lite v0.1.0
[M+Na]+144.316883
predicted
DarkChem Lite v0.1.0
[M+Na]+146.58247
predicted
DeepCCS 1.0 (2019)
[M+Na]+144.331583
predicted
DarkChem Lite v0.1.0
[M+Na]+144.207783
predicted
DarkChem Lite v0.1.0
[M+Na]+144.069383
predicted
DarkChem Lite v0.1.0
[M+Na]+144.316883
predicted
DarkChem Lite v0.1.0
[M+Na]+146.58247
predicted
DeepCCS 1.0 (2019)

Targets

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Details
1. Adenosine receptor A1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Purine nucleoside binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibit adenylyl cyclase.
Gene Name
ADORA1
Uniprot ID
P30542
Uniprot Name
Adenosine receptor A1
Molecular Weight
36511.325 Da
References
  1. Gaytan SP, Saadani-Makki F, Bodineau L, Frugiere A, Larnicol N, Pasaro R: Effect of postnatal exposure to caffeine on the pattern of adenosine A1 receptor distribution in respiration-related nuclei of the rat brainstem. Auton Neurosci. 2006 Jun 30;126-127:339-46. Epub 2006 May 15. [Article]
  2. Wang SJ: Caffeine facilitation of glutamate release from rat cerebral cortex nerve terminals (synaptosomes) through activation protein kinase C pathway: an interaction with presynaptic adenosine A1 receptors. Synapse. 2007 Jun;61(6):401-11. [Article]
  3. Rieg T, Schnermann J, Vallon V: Adenosine A1 receptors determine effects of caffeine on total fluid intake but not caffeine appetite. Eur J Pharmacol. 2007 Jan 26;555(2-3):174-7. Epub 2006 Oct 25. [Article]
  4. Mustafa S, Venkatesh P, Pasha K, Mullangi R, Srinivas NR: Altered intravenous pharmacokinetics of topotecan in rats with acute renal failure (ARF) induced by uranyl nitrate: do adenosine A1 antagonists (selective/non-selective) normalize the altered topotecan kinetics in ARF? Xenobiotica. 2006 Dec;36(12):1239-58. [Article]
  5. Listos J, Malec D, Fidecka S: Adenosine receptor antagonists intensify the benzodiazepine withdrawal signs in mice. Pharmacol Rep. 2006 Sep-Oct;58(5):643-51. [Article]
  6. Caffeine citrate injection FDA label [Link]
Details
2. Adenosine receptor A2a
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Identical protein binding
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2A
Uniprot ID
P29274
Uniprot Name
Adenosine receptor A2a
Molecular Weight
44706.925 Da
References
  1. Riksen NP, Franke B, van den Broek P, Smits P, Rongen GA: The 1976C>T polymorphism in the adenosine A2A receptor gene does not affect the vasodilator response to adenosine in humans in vivo. Pharmacogenet Genomics. 2007 Jul;17(7):551-4. [Article]
  2. Zhao G, Messina E, Xu X, Ochoa M, Sun HL, Leung K, Shryock J, Belardinelli L, Hintze TH: Caffeine attenuates the duration of coronary vasodilation and changes in hemodynamics induced by regadenoson (CVT-3146), a novel adenosine A2A receptor agonist. J Cardiovasc Pharmacol. 2007 Jun;49(6):369-75. [Article]
  3. Cornelis MC, El-Sohemy A, Campos H: Genetic polymorphism of the adenosine A2A receptor is associated with habitual caffeine consumption. Am J Clin Nutr. 2007 Jul;86(1):240-4. [Article]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which activate adenylyl cyclase.
Gene Name
ADORA2B
Uniprot ID
P29275
Uniprot Name
Adenosine receptor A2b
Molecular Weight
36332.655 Da
References
  1. Ribeiro JA, Sebastiao AM: Caffeine and adenosine. J Alzheimers Dis. 2010;20 Suppl 1:S3-15. doi: 10.3233/JAD-2010-1379. [Article]
  2. Justin Evans; Amanda S. Battisti (2019). Caffeine. Stat Pearls Publishing.
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
G-protein coupled adenosine receptor activity
Specific Function
Receptor for adenosine. The activity of this receptor is mediated by G proteins which inhibits adenylyl cyclase. Possible role in reproduction.
Gene Name
ADORA3
Uniprot ID
P0DMS8
Uniprot Name
Adenosine receptor A3
Molecular Weight
36184.175 Da
References
  1. Ribeiro JA, Sebastiao AM: Caffeine and adenosine. J Alzheimers Dis. 2010;20 Suppl 1:S3-15. doi: 10.3233/JAD-2010-1379. [Article]
  2. Justin Evans; Amanda S. Battisti (2019). Caffeine. Stat Pearls Publishing.
Kind
Protein group
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
Curator comments
Caffeine is a nonselective phosphodiesterase inhibitor.
General Function
Metal ion binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a preference for cGMP as...

Components:
References
  1. Boswell-Smith V, Spina D, Page CP: Phosphodiesterase inhibitors. Br J Pharmacol. 2006 Jan;147 Suppl 1:S252-7. doi: 10.1038/sj.bjp.0706495. [Article]
  2. Howell LL: Comparative effects of caffeine and selective phosphodiesterase inhibitors on respiration and behavior in rhesus monkeys. J Pharmacol Exp Ther. 1993 Aug;266(2):894-903. [Article]
  3. Caffeine citrate injection FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Hydrolyzes the second messenger cAMP, which is a key regulator of many important physiological processes. May be involved in mediating central nervous system effects of therapeutic agents ranging f...
Gene Name
PDE4B
Uniprot ID
Q07343
Uniprot Name
cAMP-specific 3',5'-cyclic phosphodiesterase 4B
Molecular Weight
83342.695 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
  3. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Voltage-gated calcium channel activity
Specific Function
Calcium channel that mediates the release of Ca(2+) from the sarcoplasmic reticulum into the cytoplasm and thereby plays a key role in triggering muscle contraction following depolarization of T-tu...
Gene Name
RYR1
Uniprot ID
P21817
Uniprot Name
Ryanodine receptor 1
Molecular Weight
565170.715 Da
References
  1. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Metal ion binding
Specific Function
Cyclic nucleotide phosphodiesterase with a dual-specificity for the second messengers cAMP and cGMP, which are key regulators of many important physiological processes. Has a higher affinity for cG...

Components:
References
  1. Ribeiro JA, Sebastiao AM: Caffeine and adenosine. J Alzheimers Dis. 2010;20 Suppl 1:S3-15. doi: 10.3233/JAD-2010-1379. [Article]
  2. Essayan DM: Cyclic nucleotide phosphodiesterases. J Allergy Clin Immunol. 2001 Nov;108(5):671-80. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transcription factor binding
Specific Function
Serine/threonine-protein kinase that acts as a molecular sensor for DNA damage. Involved in DNA non-homologous end joining (NHEJ) required for double-strand break (DSB) repair and V(D)J recombinati...
Gene Name
PRKDC
Uniprot ID
P78527
Uniprot Name
DNA-dependent protein kinase catalytic subunit
Molecular Weight
469084.155 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol-4,5-bisphosphate 3-kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PftdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate phosphatidylinositol 3,4,5-trisphosphate (PIP3). PIP3 plays a key role by rec...
Gene Name
PIK3CD
Uniprot ID
O00329
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform
Molecular Weight
119478.065 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein serine/threonine kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns (Phosphatidylinositol), PtdIns4P (Phosphatidylinositol 4-phosphate) and PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate...
Gene Name
PIK3CA
Uniprot ID
P42336
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit alpha isoform
Molecular Weight
124283.025 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol-4,5-bisphosphate 3-kinase activity
Specific Function
Phosphoinositide-3-kinase (PI3K) that phosphorylates PtdIns (Phosphatidylinositol), PtdIns4P (Phosphatidylinositol 4-phosphate) and PtdIns(4,5)P2 (Phosphatidylinositol 4,5-bisphosphate) to generate...
Gene Name
PIK3CB
Uniprot ID
P42338
Uniprot Name
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit beta isoform
Molecular Weight
122761.225 Da
References
  1. Foukas LC, Daniele N, Ktori C, Anderson KE, Jensen J, Shepherd PR: Direct effects of caffeine and theophylline on p110 delta and other phosphoinositide 3-kinases. Differential effects on lipid kinase and protein kinase activities. J Biol Chem. 2002 Oct 4;277(40):37124-30. Epub 2002 Jul 26. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Phosphatidylinositol binding
Specific Function
Intracellular channel that mediates calcium release from the endoplasmic reticulum following stimulation by inositol 1,4,5-trisphosphate. Involved in the regulation of epithelial secretion of elect...

Components:
References
  1. Parker I, Ivorra I: Caffeine inhibits inositol trisphosphate-mediated liberation of intracellular calcium in Xenopus oocytes. J Physiol. 1991 Feb;433:229-40. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Protein serine/threonine kinase activity
Specific Function
Serine/threonine protein kinase which activates checkpoint signaling upon double strand breaks (DSBs), apoptosis and genotoxic stresses such as ionizing ultraviolet A light (UVA), thereby acting as...
Gene Name
ATM
Uniprot ID
Q13315
Uniprot Name
Serine-protein kinase ATM
Molecular Weight
350684.105 Da
References
  1. Sarkaria JN, Busby EC, Tibbetts RS, Roos P, Taya Y, Karnitz LM, Abraham RT: Inhibition of ATM and ATR kinase activities by the radiosensitizing agent, caffeine. Cancer Res. 1999 Sep 1;59(17):4375-82. [Article]
  2. Blasina A, Price BD, Turenne GA, McGowan CH: Caffeine inhibits the checkpoint kinase ATM. Curr Biol. 1999 Oct 7;9(19):1135-8. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inhibitor
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A2
Uniprot ID
P05177
Uniprot Name
Cytochrome P450 1A2
Molecular Weight
58293.76 Da
References
  1. Brosen K: Drug interactions and the cytochrome P450 system. The role of cytochrome P450 1A2. Clin Pharmacokinet. 1995;29 Suppl 1:20-5. [Article]
  2. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  3. Hickman D, Wang JP, Wang Y, Unadkat JD: Evaluation of the selectivity of In vitro probes and suitability of organic solvents for the measurement of human cytochrome P450 monooxygenase activities. Drug Metab Dispos. 1998 Mar;26(3):207-15. [Article]
  4. Hartter S, Nordmark A, Rose DM, Bertilsson L, Tybring G, Laine K: Effects of caffeine intake on the pharmacokinetics of melatonin, a probe drug for CYP1A2 activity. Br J Clin Pharmacol. 2003 Dec;56(6):679-82. [Article]
  5. Gu L, Gonzalez FJ, Kalow W, Tang BK: Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. Pharmacogenetics. 1992 Apr;2(2):73-7. [Article]
  6. Flockhart Table of Drug Interactions [Link]
  7. Caffeine citrate injection FDA label [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Kot M, Daniel WA: Effect of cytochrome P450 (CYP) inducers on caffeine metabolism in the rat. Pharmacol Rep. 2007 May-Jun;59(3):296-305. [Article]
  2. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Collom SL, Jamakhandi AP, Tackett AJ, Radominska-Pandya A, Miller GP: CYP2E1 active site residues in substrate recognition sequence 5 identified by photoaffinity labeling and homology modeling. Arch Biochem Biophys. 2007 Mar 1;459(1):59-69. doi: 10.1016/j.abb.2006.10.028. Epub 2006 Nov 2. [Article]
  2. Fuhr U, Rost KL, Engelhardt R, Sachs M, Liermann D, Belloc C, Beaune P, Janezic S, Grant D, Meyer UA, Staib AH: Evaluation of caffeine as a test drug for CYP1A2, NAT2 and CYP2E1 phenotyping in man by in vivo versus in vitro correlations. Pharmacogenetics. 1996 Apr;6(2):159-76. [Article]
  3. Gu L, Gonzalez FJ, Kalow W, Tang BK: Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1. Pharmacogenetics. 1992 Apr;2(2):73-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Thorn CF, Aklillu E, McDonagh EM, Klein TE, Altman RB: PharmGKB summary: caffeine pathway. Pharmacogenet Genomics. 2012 May;22(5):389-95. doi: 10.1097/FPC.0b013e3283505d5e. [Article]
  2. Kot M, Daniel WA: The relative contribution of human cytochrome P450 isoforms to the four caffeine oxidation pathways: an in vitro comparative study with cDNA-expressed P450s including CYP2C isoforms. Biochem Pharmacol. 2008 Aug 15;76(4):543-51. doi: 10.1016/j.bcp.2008.05.025. Epub 2008 Jul 9. [Article]
  3. Kot M, Daniel WA: Caffeine as a marker substrate for testing cytochrome P450 activity in human and rat. Pharmacol Rep. 2008 Nov-Dec;60(6):789-97. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C9
Uniprot ID
P11712
Uniprot Name
Cytochrome P450 2C9
Molecular Weight
55627.365 Da
References
  1. Zhou SF, Zhou ZW, Yang LP, Cai JP: Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675. Epub 2009 Sep 1. [Article]
  2. Utoh M, Murayama N, Uno Y, Onose Y, Hosaka S, Fujino H, Shimizu M, Iwasaki K, Yamazaki H: Monkey liver cytochrome P450 2C9 is involved in caffeine 7-N-demethylation to form theophylline. Xenobiotica. 2013 Dec;43(12):1037-42. doi: 10.3109/00498254.2013.793874. Epub 2013 May 16. [Article]
  3. Kot M, Daniel WA: The relative contribution of human cytochrome P450 isoforms to the four caffeine oxidation pathways: an in vitro comparative study with cDNA-expressed P450s including CYP2C isoforms. Biochem Pharmacol. 2008 Aug 15;76(4):543-51. doi: 10.1016/j.bcp.2008.05.025. Epub 2008 Jul 9. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d 24-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1A1
Uniprot ID
P04798
Uniprot Name
Cytochrome P450 1A1
Molecular Weight
58164.815 Da
References
  1. Tassaneeyakul W, Birkett DJ, Veronese ME, McManus ME, Tukey RH, Quattrochi LC, Gelboin HV, Miners JO: Specificity of substrate and inhibitor probes for human cytochromes P450 1A1 and 1A2. J Pharmacol Exp Ther. 1993 Apr;265(1):401-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP1B1
Uniprot ID
Q16678
Uniprot Name
Cytochrome P450 1B1
Molecular Weight
60845.33 Da
References
  1. Shimada T, Gillam EM, Sutter TR, Strickland PT, Guengerich FP, Yamazaki H: Oxidation of xenobiotics by recombinant human cytochrome P450 1B1. Drug Metab Dispos. 1997 May;25(5):617-22. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Ha HR, Chen J, Krahenbuhl S, Follath F: Biotransformation of caffeine by cDNA-expressed human cytochromes P-450. Eur J Clin Pharmacol. 1996;49(4):309-15. doi: 10.1007/bf00226333. [Article]
  2. Ozdemir V, Naranjo CA, Shulman RW, Herrmann N, Sellers EM, Reed K, Kalow W: Determinants of interindividual variability and extent of CYP2D6 and CYP1A2 inhibition by paroxetine and fluvoxamine in vivo. J Clin Psychopharmacol. 1998 Jun;18(3):198-207. [Article]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Ding R, Shi J, Pabon K, Scotto KW: Xanthines down-regulate the drug transporter ABCG2 and reverse multidrug resistance. Mol Pharmacol. 2012 Mar;81(3):328-37. doi: 10.1124/mol.111.075556. Epub 2011 Nov 23. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48