Identification

Name
Theobromine
Accession Number
DB01412
Type
Small Molecule
Groups
Approved, Investigational
Description

3,7-Dimethylxanthine. The principle alkaloid in Theobroma cacao (the cacao bean) and other plants. A xanthine alkaloid that is used as a bronchodilator and as a vasodilator. It has a weaker diuretic activity than theophylline and is also a less powerful stimulant of smooth muscle. It has practically no stimulant effect on the central nervous system. It was formerly used as a diuretic and in the treatment of angina pectoris and hypertension. (From Martindale, The Extra Pharmacopoeia, 30th ed, pp1318-9)

Structure
Thumb
Synonyms
  • 3,7-dihydro-3,7-Dimethyl-1H-purine-2,6-dione
  • 3,7-Dimethylpurine-2,6-dione
  • 3,7-Dimethylxanthine
  • Theobromin
  • Theobromine
External IDs
FEMA NO. 3591 / NSC-5039 / SC-15090
Categories
UNII
OBD445WZ5P
CAS number
83-67-0
Weight
Average: 180.164
Monoisotopic: 180.06472552
Chemical Formula
C7H8N4O2
InChI Key
YAPQBXQYLJRXSA-UHFFFAOYSA-N
InChI
InChI=1S/C7H8N4O2/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2/h3H,1-2H3,(H,9,12,13)
IUPAC Name
3,7-dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione
SMILES
CN1C=NC2=C1C(=O)NC(=O)N2C

Pharmacology

Indication

theobromine is used as a vasodilator, a diuretic, and heart stimulant. And similar to caffeine, it may be useful in management of fatigue and orthostatic hypotension.

Structured Indications
Not Available
Pharmacodynamics

Theobromine, a xanthine derivative like caffeine and the bronchodilator theophylline, is used as a CNS stimulant, mild diuretic, and respiratory stimulant (in neonates with apnea of prematurity).

Mechanism of action

Theobromine stimulates medullary, vagal, vasomotor, and respiratory centers, promoting bradycardia, vasoconstriction, and increased respiratory rate. This action was previously believed to be due primarily to increased intracellular cyclic 3′,5′-adenosine monophosphate (cyclic AMP) following inhibition of phosphodiesterase, the enzyme that degrades cyclic AMP. It is now thought that xanthines such as caffeine and theobromine act as antagonist at adenosine-receptors within the plasma membrane of virtually every cell. As adenosine acts as an autocoid, inhibiting the release of neurotransmitters from presynaptic sites but augmenting the actions of norepinephrine or angiotensin, antagonism of adenosine receptors promotes neurotransmitter release. This explains the stimulatory effects of xanthine derivatives such as theobromine and caffeine. Blockade of the adenosine A1 receptor in the heart leads to the accelerated, pronounced "pounding" of the heart upon caffeine intake.

TargetActionsOrganism
AAdenosine receptor A1
antagonist
Human
AAdenosine receptor A2a
antagonist
Human
UcAMP-specific 3',5'-cyclic phosphodiesterase 4B
inhibitor
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Caffeine MetabolismMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AbirateroneThe serum concentration of Theobromine can be increased when it is combined with Abiraterone.Approved
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Theobromine.Approved, Illicit
AlphacetylmethadolThe risk or severity of adverse effects can be increased when Alphacetylmethadol is combined with Theobromine.Experimental, Illicit
AlphaprodineThe risk or severity of adverse effects can be increased when Alphaprodine is combined with Theobromine.Illicit
AzithromycinThe metabolism of Theobromine can be decreased when combined with Azithromycin.Approved
BezitramideThe risk or severity of adverse effects can be increased when Bezitramide is combined with Theobromine.Experimental, Illicit, Withdrawn
BortezomibThe metabolism of Theobromine can be decreased when combined with Bortezomib.Approved, Investigational
BuprenorphineThe risk or severity of adverse effects can be increased when Buprenorphine is combined with Theobromine.Approved, Illicit, Investigational, Vet Approved
ButorphanolThe risk or severity of adverse effects can be increased when Butorphanol is combined with Theobromine.Approved, Illicit, Vet Approved
CaffeineThe metabolism of Theobromine can be decreased when combined with Caffeine.Approved
CarfentanilThe risk or severity of adverse effects can be increased when Carfentanil is combined with Theobromine.Illicit, Investigational, Vet Approved
CitalopramThe metabolism of Theobromine can be decreased when combined with Citalopram.Approved
ClotrimazoleThe metabolism of Theobromine can be decreased when combined with Clotrimazole.Approved, Vet Approved
CodeineThe risk or severity of adverse effects can be increased when Codeine is combined with Theobromine.Approved, Illicit
Cyproterone acetateThe serum concentration of Theobromine can be decreased when it is combined with Cyproterone acetate.Approved, Investigational
DeferasiroxThe serum concentration of Theobromine can be increased when it is combined with Deferasirox.Approved, Investigational
DextromoramideThe risk or severity of adverse effects can be increased when Dextromoramide is combined with Theobromine.Experimental, Illicit
DextropropoxypheneThe risk or severity of adverse effects can be increased when Dextropropoxyphene is combined with Theobromine.Approved, Illicit, Investigational, Withdrawn
DezocineThe risk or severity of adverse effects can be increased when Dezocine is combined with Theobromine.Approved, Investigational
DihydrocodeineThe risk or severity of adverse effects can be increased when Dihydrocodeine is combined with Theobromine.Approved, Illicit
DihydroetorphineThe risk or severity of adverse effects can be increased when Dihydroetorphine is combined with Theobromine.Experimental, Illicit
DihydromorphineThe risk or severity of adverse effects can be increased when Dihydromorphine is combined with Theobromine.Experimental, Illicit
DiphenoxylateThe risk or severity of adverse effects can be increased when Diphenoxylate is combined with Theobromine.Approved, Illicit
DosulepinThe metabolism of Theobromine can be decreased when combined with Dosulepin.Approved
DPDPEThe risk or severity of adverse effects can be increased when DPDPE is combined with Theobromine.Investigational
EthylmorphineThe risk or severity of adverse effects can be increased when Ethylmorphine is combined with Theobromine.Approved, Illicit
EtorphineThe risk or severity of adverse effects can be increased when Etorphine is combined with Theobromine.Illicit, Vet Approved
FentanylThe risk or severity of adverse effects can be increased when Fentanyl is combined with Theobromine.Approved, Illicit, Investigational, Vet Approved
FluvoxamineThe metabolism of Theobromine can be decreased when combined with Fluvoxamine.Approved, Investigational
HeroinThe risk or severity of adverse effects can be increased when Heroin is combined with Theobromine.Approved, Illicit, Investigational
HydrocodoneThe risk or severity of adverse effects can be increased when Hydrocodone is combined with Theobromine.Approved, Illicit
HydromorphoneThe risk or severity of adverse effects can be increased when Hydromorphone is combined with Theobromine.Approved, Illicit
IsoniazidThe metabolism of Theobromine can be decreased when combined with Isoniazid.Approved
KetobemidoneThe risk or severity of adverse effects can be increased when Ketobemidone is combined with Theobromine.Approved, Investigational
Levomethadyl AcetateThe risk or severity of adverse effects can be increased when Levomethadyl Acetate is combined with Theobromine.Approved, Investigational
LevorphanolThe risk or severity of adverse effects can be increased when Levorphanol is combined with Theobromine.Approved
LidocaineThe metabolism of Theobromine can be decreased when combined with Lidocaine.Approved, Vet Approved
LobeglitazoneThe metabolism of Theobromine can be decreased when combined with Lobeglitazone.Approved, Investigational
LofentanilThe risk or severity of adverse effects can be increased when Lofentanil is combined with Theobromine.Illicit
MeptazinolThe risk or severity of adverse effects can be increased when Meptazinol is combined with Theobromine.Experimental
MethadoneThe risk or severity of adverse effects can be increased when Methadone is combined with Theobromine.Approved
Methadyl AcetateThe risk or severity of adverse effects can be increased when Methadyl Acetate is combined with Theobromine.Approved, Illicit
MexiletineThe metabolism of Theobromine can be decreased when combined with Mexiletine.Approved
MidostaurinThe metabolism of Theobromine can be decreased when combined with Midostaurin.Approved
MorphineThe risk or severity of adverse effects can be increased when Morphine is combined with Theobromine.Approved, Investigational
NalbuphineThe risk or severity of adverse effects can be increased when Nalbuphine is combined with Theobromine.Approved
NevirapineThe metabolism of Theobromine can be decreased when combined with Nevirapine.Approved
NicomorphineThe risk or severity of adverse effects can be increased when Nicomorphine is combined with Theobromine.Experimental
NicotineThe metabolism of Theobromine can be decreased when combined with Nicotine.Approved
NormethadoneThe risk or severity of adverse effects can be increased when Normethadone is combined with Theobromine.Approved, Illicit
OpiumThe risk or severity of adverse effects can be increased when Opium is combined with Theobromine.Approved, Illicit
OsimertinibThe serum concentration of Theobromine can be decreased when it is combined with Osimertinib.Approved
OxycodoneThe risk or severity of adverse effects can be increased when Oxycodone is combined with Theobromine.Approved, Illicit, Investigational
OxymorphoneThe risk or severity of adverse effects can be increased when Oxymorphone is combined with Theobromine.Approved, Investigational, Vet Approved
Peginterferon alfa-2bThe serum concentration of Theobromine can be increased when it is combined with Peginterferon alfa-2b.Approved
PentazocineThe risk or severity of adverse effects can be increased when Pentazocine is combined with Theobromine.Approved, Vet Approved
PethidineThe risk or severity of adverse effects can be increased when Pethidine is combined with Theobromine.Approved
PhenazocineThe risk or severity of adverse effects can be increased when Phenazocine is combined with Theobromine.Experimental
PhenoperidineThe risk or severity of adverse effects can be increased when Phenoperidine is combined with Theobromine.Experimental
PiritramideThe risk or severity of adverse effects can be increased when Piritramide is combined with Theobromine.Investigational
RemifentanilThe risk or severity of adverse effects can be increased when Remifentanil is combined with Theobromine.Approved
RopiniroleThe metabolism of Theobromine can be decreased when combined with Ropinirole.Approved, Investigational
SimeprevirThe metabolism of Theobromine can be decreased when combined with Simeprevir.Approved
Sodium phosphateTheobromine may increase the nephrotoxic activities of Sodium phosphate.Approved
SufentanilThe risk or severity of adverse effects can be increased when Sufentanil is combined with Theobromine.Approved, Investigational
TapentadolThe risk or severity of adverse effects can be increased when Tapentadol is combined with Theobromine.Approved
Tenofovir disoproxilThe metabolism of Theobromine can be decreased when combined with Tenofovir disoproxil.Approved, Investigational
TeriflunomideThe serum concentration of Theobromine can be decreased when it is combined with Teriflunomide.Approved
TheophyllineThe metabolism of Theobromine can be decreased when combined with Theophylline.Approved
TiclopidineThe metabolism of Theobromine can be decreased when combined with Ticlopidine.Approved
TilidineThe risk or severity of adverse effects can be increased when Tilidine is combined with Theobromine.Experimental
TramadolThe risk or severity of adverse effects can be increased when Tramadol is combined with Theobromine.Approved, Investigational
VemurafenibThe serum concentration of Theobromine can be increased when it is combined with Vemurafenib.Approved
ZucapsaicinThe metabolism of Theobromine can be decreased when combined with Zucapsaicin.Approved
Food Interactions
Not Available

References

Synthesis Reference

Misako Mizuno, Hiroshi Ashihara, Kouichi Mizuno, Tatsuhito Fujimura, "CAMELLIA SINENSIS GENE ENCODING A CAFFEINE SYNTHESIS ASSOCIATED N-METHYL TRANSFERASE WITH 7-METHYLXANTHINE N3 METHYL TRANSFERASE, THEOBROMINE N1 METHYL TRANSFERASE, AND PARAXANTHINE N3 METHYL TRANSFERASE ACTIVITIES AND USE THEREOF." U.S. Patent US06930227, issued August 16, 2005.

US06930227
General References
  1. Usmani OS, Belvisi MG, Patel HJ, Crispino N, Birrell MA, Korbonits M, Korbonits D, Barnes PJ: Theobromine inhibits sensory nerve activation and cough. FASEB J. 2005 Feb;19(2):231-3. Epub 2004 Nov 17. [PubMed:15548587]
  2. Slattery ML, West DW: Smoking, alcohol, coffee, tea, caffeine, and theobromine: risk of prostate cancer in Utah (United States). Cancer Causes Control. 1993 Nov;4(6):559-63. [PubMed:8280834]
External Links
Human Metabolome Database
HMDB02825
KEGG Compound
C07480
PubChem Compound
5429
PubChem Substance
46508574
ChemSpider
5236
BindingDB
50014260
ChEBI
28946
ChEMBL
CHEMBL1114
PharmGKB
PA451646
HET
37T
Wikipedia
Theobromine
ATC Codes
R03DA20 — Combinations of xanthinesR03DA07 — TheobromineR03DA57 — Theobromine, combinationsC03BD01 — Theobromine
PDB Entries
2efj
MSDS
Download (74.2 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAcute Tracheobronchitis1
3CompletedTreatmentCoughing1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)357 °CPhysProp
water solubility330 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP-0.78HANSCH,C ET AL. (1995)
pKa9.9KORTUM,G ET AL (1961)
Predicted Properties
PropertyValueSource
Water Solubility9.74 mg/mLALOGPS
logP-0.46ALOGPS
logP-0.77ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.91ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area67.23 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity44.93 m3·mol-1ChemAxon
Polarizability16.85 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9902
Caco-2 permeable+0.6172
P-glycoprotein substrateNon-substrate0.7281
P-glycoprotein inhibitor INon-inhibitor0.8939
P-glycoprotein inhibitor IINon-inhibitor0.911
Renal organic cation transporterNon-inhibitor0.8807
CYP450 2C9 substrateNon-substrate0.7738
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateNon-substrate0.5974
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9933
CYP450 2D6 inhibitorNon-inhibitor0.9827
CYP450 2C19 inhibitorNon-inhibitor0.9895
CYP450 3A4 inhibitorNon-inhibitor0.9616
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9956
Ames testNon AMES toxic0.9132
CarcinogenicityNon-carcinogens0.9447
BiodegradationReady biodegradable0.5942
Rat acute toxicity2.7898 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8819
hERG inhibition (predictor II)Non-inhibitor0.8927
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
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Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (1 TMS)GC-MSsplash10-0079-7980000000-efb14ee11aad17b6b4d2
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-001i-6900000000-7d44855bbf11e559d96e
GC-MS Spectrum - GC-MSGC-MSsplash10-0079-7980000000-efb14ee11aad17b6b4d2
Mass Spectrum (Electron Ionization)MSsplash10-001i-9700000000-770b2dc556ada7d97cae
MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)LC-MS/MSsplash10-001i-0900000000-8d639c53ad9b2b8f508e
MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)LC-MS/MSsplash10-014i-9300000000-0d20b5fe9b93b113a29e
MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)LC-MS/MSsplash10-014l-9000000000-55968ca3e94ce5a05cfe
MS/MS Spectrum - EI-B (Unknown) , PositiveLC-MS/MSsplash10-001i-6900000000-7d44855bbf11e559d96e
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, PositiveLC-MS/MSsplash10-001i-1900000000-1932568f11357ae32f55
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, PositiveLC-MS/MSsplash10-001i-2900000000-3918185c5a4afb18f11a
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, PositiveLC-MS/MSsplash10-0910-5900000000-b590772083f824ea0fc6
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, PositiveLC-MS/MSsplash10-014i-9400000000-c06ac99fd6e0c84d9653
LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, PositiveLC-MS/MSsplash10-014i-9100000000-3802e577174b5a4acced
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , negativeLC-MS/MSsplash10-004j-7900000000-54365e34320abc3c8f2e
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-1900000000-599d34de0bc963388dc0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-001i-2900000000-8a0fd0cd87c35684d19f
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0910-5900000000-b590772083f824ea0fc6
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9400000000-c06ac99fd6e0c84d9653
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-9100000000-3802e577174b5a4acced
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-b1202b5f491f2aaaf542
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01qi-0900000000-d58a783853c528b7d126
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01b9-8900000000-d9e4a4411ab0ed3620a0
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-9200000000-3e4c74d70eb361d592a2
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-014i-9000000000-b8b687b3b9ae3c76bc63
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-001i-0900000000-9969958696e82ec648a8
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-01p9-0900000000-9b6882138a54379ed1f8
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-1900000000-7a6ca221466a7b3d83d5
MS/MS Spectrum - , positiveLC-MS/MSsplash10-001i-0900000000-79f9d425a871d43d6a4d
1H NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Xanthine / 6-oxopurine / Purinone / Alkaloid or derivatives / Pyrimidone / N-substituted imidazole / Pyrimidine / Azole / Imidazole / Heteroaromatic compound
show 12 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dimethylxanthine (CHEBI:28946) / Purine alkaloids (C07480) / a small molecule (3-7-DIMETHYLXANTHINE)

Targets

Kind
Protein
Organism
Human
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. Chou CC, Vickroy TW: Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. Am J Vet Res. 2003 Feb;64(2):216-24. [PubMed:12602592]
  2. 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. [PubMed:16702031]
  3. 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. [PubMed:17372967]
  4. 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. [PubMed:17126319]
  5. 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. [PubMed:17162470]
  6. 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. [PubMed:17085856]
  7. Fisone G, Borgkvist A, Usiello A: Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72. [PubMed:15095008]
  8. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607]
Kind
Protein
Organism
Human
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. Chou CC, Vickroy TW: Antagonism of adenosine receptors by caffeine and caffeine metabolites in equine forebrain tissues. Am J Vet Res. 2003 Feb;64(2):216-24. [PubMed:12602592]
  2. 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. [PubMed:17558310]
  3. 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. [PubMed:17577101]
  4. 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. [PubMed:17616786]
  5. Fisone G, Borgkvist A, Usiello A: Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72. [PubMed:15095008]
  6. Daly JW, Jacobson KA, Ukena D: Adenosine receptors: development of selective agonists and antagonists. Prog Clin Biol Res. 1987;230:41-63. [PubMed:3588607]
Kind
Protein
Organism
Human
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. Essayan DM: Cyclic nucleotide phosphodiesterases. J Allergy Clin Immunol. 2001 Nov;108(5):671-80. [PubMed:11692087]
  2. Fisone G, Borgkvist A, Usiello A: Caffeine as a psychomotor stimulant: mechanism of action. Cell Mol Life Sci. 2004 Apr;61(7-8):857-72. [PubMed:15095008]
  3. Daly JW: Caffeine analogs: biomedical impact. Cell Mol Life Sci. 2007 Aug;64(16):2153-69. [PubMed:17514358]
  4. Deree J, Martins JO, Melbostad H, Loomis WH, Coimbra R: Insights into the regulation of TNF-alpha production in human mononuclear cells: the effects of non-specific phosphodiesterase inhibition. Clinics (Sao Paulo). 2008 Jun;63(3):321-8. [PubMed:18568240]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
  2. Gates S, Miners JO: Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism. Br J Clin Pharmacol. 1999 Mar;47(3):299-305. [PubMed:10215755]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on July 17, 2007 06:41 / Updated on November 09, 2017 02:59