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Details

Stereochemistry ACHIRAL
Molecular Formula C7H8N4O2.C7H4O3.2Na.H2O
Molecular Weight 380.2637
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOBROMINE SODIUM SALICYLATE MONOHYDRATE

SMILES

O.[Na+].[Na+].[O-]C(=O)C1=C([O-])C=CC=C1.CN2C=NC3=C2C(=O)NC(=O)N3C

InChI

InChIKey=MWKXONJZCRBEBM-UHFFFAOYSA-L
InChI=1S/C7H8N4O2.C7H6O3.2Na.H2O/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;8-6-4-2-1-3-5(6)7(9)10;;;/h3H,1-2H3,(H,9,12,13);1-4,8H,(H,9,10);;;1H2/q;;2*+1;/p-2

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H8N4O2
Molecular Weight 180.164
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C7H5O3
Molecular Weight 137.1128
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Theobromine is the primary alkaloid present in the cocoa and chocolate. Theobromine is found in the shells and beans of the cacao plant and it is extracted from the husks of the bean and used for the synthesis of caffeine. Theobromine is an adenosine A1 and A2a receptor antagonist. Thesodate 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. The symptomatic adverse reactions produced by theobromine are more or less tolerable and if they become severe, they can be treated symptomatically, these include anxiety, restlessness, tremors, sleeplessness, nausea and vomiting, loss of appetite. Theobromine is currently not in use as a medicinal drug.

Originator

Sources: DOI: 10.1002/jlac.18420410117

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P30543
Gene ID: 25369.0
Gene Symbol: Adora2a
Target Organism: Rattus norvegicus (Rat)
250.0 µM [IC50]
120.0 µM [Ki]
Target ID: P05177
Gene ID: 1544.0
Gene Symbol: CYP1A2
Target Organism: Homo sapiens (Human)
Target ID: P05181
Gene ID: 1571.0
Gene Symbol: CYP2E1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Thesodate

Approved Use

Theobromine was used as a diuretic and in the treatment of angina pectoris and hypertension.
Palliative
Unknown

Approved Use

Unknown
Primary
Thesodate

Approved Use

Theobromine used as a diuretic and in the treatment of angina pectoris and hypertension
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
8.38 μg/mL
4 mg/kg bw single, intravenous
dose: 4 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THEOBROMINE plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
92 μg × h/mL
4 mg/kg bw single, intravenous
dose: 4 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THEOBROMINE plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
13351 mg × min/L
50 mg/kg bw single, oral
dose: 50 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
THEOBROMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
15.7 h
4 mg/kg bw single, intravenous
dose: 4 mg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
THEOBROMINE plasma
Equus caballus
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.23 h
50 mg/kg bw single, oral
dose: 50 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
THEOBROMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
88%
50 mg/kg bw single, oral
dose: 50 mg/kg bw
route of administration: Oral
experiment type: SINGLE
co-administered:
THEOBROMINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer


Drug as victimTox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Identification and quantification of drugs in human amniotic fluid.
1975 Nov
Biotransformation of caffeine, paraxanthine, theobromine and theophylline by cDNA-expressed human CYP1A2 and CYP2E1.
1992 Apr
Cytochrome P450 isoform selectivity in human hepatic theobromine metabolism.
1999 Mar
Flavin monooxygenase 3 (FMO3) polymorphism in a white population: allele frequencies, mutation linkage, and functional effects on clozapine and caffeine metabolism.
1999 Oct
Effects of caffeine and its reactive metabolites theophylline and theobromine on the differentiating testis.
2001
Medicinal and ethnoveterinary remedies of hunters in Trinidad.
2001
Rat ventral prostate xanthine oxidase bioactivation of ethanol to acetaldehyde and 1-hydroxyethyl free radicals: analysis of its potential role in heavy alcohol drinking tumor-promoting effects.
2001
Suppressive effect of coffee on lipopolysaccharide-induced hepatitis in D-galactosamine-sensitized rats.
2001 Aug
Continuous measurement of caffeine and two metabolites in blood and skeletal muscle of unrestrained adult horses by semi-automated in vivo microdialysis.
2001 Dec
Adenosine modulates Mg(2+) uptake in distal convoluted tubule cells via A(1) and A(2) purinoceptors.
2001 Dec
Efferent arteriole tubuloglomerular feedback in the renal nephron.
2001 Jan
Uncertainty factors for chemical risk assessment. human variability in the pharmacokinetics of CYP1A2 probe substrates.
2001 Jul
Uncertainty factors for chemical risk assessment: interspecies differences in the in vivo pharmacokinetics and metabolism of human CYP1A2 substrates.
2001 Jul
Seizure activity and unresponsiveness after hydroxycut ingestion.
2001 May
In vivo effects of adenosine A(2) receptor agonist and antagonist on neuronal and astrocytic intermediary metabolism studied with ex vivo (13)C MR spectroscopy.
2001 Nov
Effects of phenothiazine neuroleptics on the rate of caffeine demethylation and hydroxylation in the rat liver.
2001 Nov-Dec
A TLC visualisation reagent for dimethylamphetamine and other abused tertiary amines.
2001 Oct-Dec
Effects of adenosine receptor agonists and antagonists in a genetic animal model of primary paroxysmal dystonia.
2001 Sep
Determination of theophylline by HPLC and GC-IDMS, the effect of chemically similar xanthine derivatives on the specificity of the method and the possibility of paracetamol as interfering substance.
2002
Caffeine potentiates the discriminative-stimulus effects of nicotine in rats.
2002 Aug
Platinum complexes of oxopurines: cis-bis(theophyllinato-N7)bis(triphenylphosphine)platinum(II) and cis-chloro(theobrominato-N1)bis(triphenylphosphine)platinum(II) ethanol hemisolvate.
2002 Feb
Activation of adenosine A2a receptor pathway reduces leukocyte infiltration but enhances edema formation in rat caerulein pancreatitis.
2002 Jan
Inhibition of vaccinia virus replication by adenosine in BSC-40 cells: involvement of A(2) receptor-mediated PKA activation.
2002 Jul
Study of catechin and xanthine tea profiles as geographical tracers.
2002 Mar 27
Spinal noradrenergic activation mediates allodynia reduction from an allosteric adenosine modulator in a rat model of neuropathic pain.
2002 May
Adenosine acts through an A3 receptor to prevent the induction of murine anti-CD3-activated killer T cells.
2002 May 20
Value assignment of nutrient concentrations in standard reference material 2384 baking chocolate.
2002 Nov 20
Isolation of a new dual-functional caffeine synthase gene encoding an enzyme for the conversion of 7-methylxanthine to caffeine from coffee (Coffea arabica L.).
2003 Jan 16
Antioxidant and prooxidant properties of caffeine, theobromine and xanthine.
2003 Sep
Patents

Sample Use Guides

1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily
Route of Administration: Oral
Alkaline phosphatase activity, a marker of early to mid-stage osteogenesis, was elevated in cultures of Human Mesenchymal Stem Cells that received 25 uM theobromine and reached a maximal level of stimulation at 50–100 uM theobromine.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:07:11 GMT 2023
Edited
by admin
on Fri Dec 15 15:07:11 GMT 2023
Record UNII
P6VR6P4A5V
Record Status Validated (UNII)
Record Version
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Name Type Language
THEOBROMINE SODIUM SALICYLATE MONOHYDRATE
Systematic Name English
THEOBROMINE SODIUM SALICYLATE [JAN]
Common Name English
THEOBROMINE SODIUM SALICYLATE
JAN   MI   WHO-DD  
Systematic Name English
Theobromine sodium salicylate [WHO-DD]
Common Name English
DIURETIN
Brand Name English
EQUIMOLAR MIXTURE OF SODIUM THEOBROMINE, SODIUM SALICYLATE AND WATER
Common Name English
THEOBROMINE SODIUM SALICYLATE [MI]
Common Name English
Code System Code Type Description
FDA UNII
P6VR6P4A5V
Created by admin on Fri Dec 15 15:07:11 GMT 2023 , Edited by admin on Fri Dec 15 15:07:11 GMT 2023
PRIMARY
EVMPD
SUB15514MIG
Created by admin on Fri Dec 15 15:07:11 GMT 2023 , Edited by admin on Fri Dec 15 15:07:11 GMT 2023
PRIMARY
SMS_ID
100000076967
Created by admin on Fri Dec 15 15:07:11 GMT 2023 , Edited by admin on Fri Dec 15 15:07:11 GMT 2023
PRIMARY
PUBCHEM
54712690
Created by admin on Fri Dec 15 15:07:11 GMT 2023 , Edited by admin on Fri Dec 15 15:07:11 GMT 2023
PRIMARY
ChEMBL
CHEMBL1114
Created by admin on Fri Dec 15 15:07:11 GMT 2023 , Edited by admin on Fri Dec 15 15:07:11 GMT 2023
PRIMARY
MERCK INDEX
m10703
Created by admin on Fri Dec 15 15:07:11 GMT 2023 , Edited by admin on Fri Dec 15 15:07:11 GMT 2023
PRIMARY Merck Index
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
ANHYDROUS->SOLVATE
Related Record Type Details
ACTIVE MOIETY