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Details

Stereochemistry ACHIRAL
Molecular Formula C7H7N4O2.C6H11O7.Ca
Molecular Weight 414.381
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of THEOBROMINE CALCIUM GLUCONATE

SMILES

[Ca++].CN1C=NC2=C1C(=O)[N-]C(=O)N2C.OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O

InChI

InChIKey=YUMGBTPDXDOEGH-PVBYDLIKSA-L
InChI=1S/C7H8N4O2.C6H12O7.Ca/c1-10-3-8-5-4(10)6(12)9-7(13)11(5)2;7-1-2(8)3(9)4(10)5(11)6(12)13;/h3H,1-2H3,(H,9,12,13);2-5,7-11H,1H2,(H,12,13);/q;;+2/p-2/t;2-,3-,4+,5-;/m.1./s1

HIDE SMILES / InChI
Molecular Formula Ca
Molecular Weight 40.078
Charge 2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C6H10O7
Molecular Weight 194.1394
Charge -2
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula C7H8N4O2
Molecular Weight 180.164
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

CNS Activity

CNS Active
3,913

Originator

Woskresensky, A.
9

Approval Year

1921
1,467

Targets

Primary TargetPharmacologyConditionPotency
Adenosine receptor A2a
15
Antagonist
2,778
 250.0 µM [IC50]
Adenosine A1 receptor
50
Antagonist
2,778
 120.0 µM [Ki]
Cytochrome P450 1A2
72
Substrate
661
Cytochrome P450 2E1
25
Substrate
661

Conditions

ConditionModalityTargetsHighest PhaseProduct
Hypertension
567
 Primary
Approved
8,429
Thesodate
Acute bronchitis
10
 Palliative
Phase III
656
Unknown
Angina pectoris
106
 Primary
Approved
8,429
Thesodate

Cmax

ValueDoseCo-administeredAnalytePopulation
8.38 μg/mL
4 mg/kg bw single, intravenous
 THEOBROMINE plasma
Equus caballus

AUC

ValueDoseCo-administeredAnalytePopulation
92 μg × h/mL
4 mg/kg bw single, intravenous
 THEOBROMINE plasma
Equus caballus
13351 mg × min/L
50 mg/kg bw single, oral
 THEOBROMINE plasma
Rattus norvegicus

T1/2

ValueDoseCo-administeredAnalytePopulation
15.7 h
4 mg/kg bw single, intravenous
 THEOBROMINE plasma
Equus caballus
4.23 h
50 mg/kg bw single, oral
 THEOBROMINE plasma
Rattus norvegicus

Funbound

ValueDoseCo-administeredAnalytePopulation
88%
50 mg/kg bw single, oral
 THEOBROMINE plasma
Rattus norvegicus

Overview

CYP3A4CYP2C9CYP2D6hERG
inhibitor
1,612

OverviewOther

Other InhibitorOther SubstrateOther Inducer
CYP2E1
667

CYP1A2
1,054

Drug as victim

Tox targets

PubMed

Patents

04737502
9
05780476
9
05801182
9
05866576
9
06616955
10
JP2002071628A
9
JP2002544218A
14
JP2003137786A
9
JP2003535111A
9
JP2004520359A
14
JP2006151878A
9
JP2008031146A
9
JP2009531466A
75
JP2011217706A
9
JPH09302034A
9
JPS5436291A
9
JPS5492990A
9
JPS56156280A
10
JPS5711981A
10
JPS57131790A
9
JPS5724385A
9
JPS5724386A
9
JPS574989A
9
JPS58148819A
9
JPS5826886A
9
JPS5838284A
9
JPS6452718A
9

Sample Use Guides

In Vivo Use Guide
1 tablet (500 mg of theobromide sodium acetate) 3–4 times daily
Route of Administration: Oral
In Vitro Use Guide
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
Record UNII
C8T5Q6L2DE
Record Status Validated (UNII)
Record Version
NIH
NCATS
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