caffeine indications/contra

Stem definitionDrug idCAS RN
463 58-08-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • anhydrous caffeine
  • peyona
  • caffeine
  • 1,3,7-trimethyl-2,6-dioxopurine
  • 7-methyltheophylline
  • cafalgine
  • cafeina
  • durvitan
  • guaranine
  • thein
  • caffeine citrate
  • caffeine, citrated
  • nymusa
A methylxanthine naturally occurring in some beverages and also used as a pharmacological agent. Caffeine's most notable pharmacological effect is as a central nervous system stimulant, increasing alertness and producing agitation. It also relaxes SMOOTH MUSCLE, stimulates CARDIAC MUSCLE, stimulates DIURESIS, and appears to be useful in the treatment of some types of headache. Several cellular actions of caffeine have been observed, but it is not entirely clear how each contributes to its pharmacological profile. Among the most important are inhibition of cyclic nucleotide PHOSPHODIESTERASES, antagonism of ADENOSINE RECEPTORS, and modulation of intracellular calcium handling.
  • Molecular weight: 194.19
  • Formula: C8H10N4O2
  • CLOGP: -0.04
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 0
  • TPSA: 58.44
  • ALOGS: -1.25
  • ROTB: 0

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P

Approvals:

DateAgencyCompanyOrphan
Nov. 26, 1948 FDA NOVARTIS

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Overdose 945.18 32.10 300 3061 33678 3348820
Completed suicide 865.65 32.10 275 3086 30839 3351659
Toxicity to various agents 788.07 32.10 284 3077 46770 3335728
Foetal exposure during pregnancy 576.78 32.10 172 3189 15379 3367119
Drug dependence 567.86 32.10 131 3230 4245 3378253
Accidental overdose 533.84 32.10 137 3224 6981 3375517
Death 519.15 32.10 303 3058 152021 3230477
Drug ineffective 450.57 32.10 252 3109 115838 3266660
Drug withdrawal syndrome neonatal 443.83 32.10 95 3266 2155 3380343
Nicotine dependence 383.85 32.10 60 3301 191 3382307
Drug abuse 328.17 32.10 117 3244 18213 3364285
Cardio-respiratory arrest 320.25 32.10 110 3251 15330 3367168
Incorrect drug administration duration 297.97 32.10 74 3287 3267 3379231
Drug hypersensitivity 290.93 32.10 129 3232 35551 3346947
Maternal exposure during breast feeding 251.91 32.10 54 3307 1226 3381272
Intentional product misuse 249.65 32.10 87 3274 12614 3369884
Ergot poisoning 235.28 32.10 34 3327 50 3382448
Nausea 205.99 32.10 162 3199 129483 3253015
Drug interaction 202.74 32.10 110 3251 46702 3335796
Cardiac arrest 178.96 32.10 85 3276 27234 3355264
Respiratory arrest 163.90 32.10 62 3299 11306 3371192
Headache 158.79 32.10 121 3240 91859 3290639
Intentional overdose 156.42 32.10 65 3296 15160 3367338
Premature baby 155.18 32.10 53 3308 7200 3375298
Palpitations 145.46 32.10 66 3295 19017 3363481
Vomiting 141.85 32.10 112 3249 89419 3293079
Myocardial stunning 141.14 32.10 20 3341 23 3382475
Dizziness 119.50 32.10 95 3266 76417 3306081
Pulmonary oedema 112.72 32.10 48 3313 11863 3370635
Drug screen positive 110.10 32.10 30 3331 1898 3380600

Pharmacologic Action:

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SourceCodeDescription
ATC N06BC01 NERVOUS SYSTEM
PSYCHOANALEPTICS
PSYCHOSTIMULANTS, AGENTS USED FOR ADHD AND NOOTROPICS
Xanthine derivatives
ATC V04CG30 VARIOUS
DIAGNOSTIC AGENTS
OTHER DIAGNOSTIC AGENTS
Tests for gastric secretion
CHEBI has role CHEBI:35471 psychotropic drug
CHEBI has role CHEBI:35498 diuretic
CHEBI has role CHEBI:64047 food additive
CHEBI has role CHEBI:60809 adjuvant
CHEBI has role CHEBI:35337 central nervous system stimulant
FDA PE N0000175729 Central Nervous System Stimulation
FDA EPC N0000175790 Methylxanthine
FDA Chemical/Ingredient N0000008118 Xanthines
MeSH PA D002491 Central Nervous System Agents
MeSH PA D000697 Central Nervous System Stimulants
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018377 Neurotransmitter Agents
MeSH PA D010726 Phosphodiesterase Inhibitors
MeSH PA D058905 Purinergic Agents
MeSH PA D058914 Purinergic Antagonists
MeSH PA D058915 Purinergic P1 Receptor Antagonists

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Sinus headache indication 4969004
Apnea in the newborn indication 13094009
Pain indication 22253000
Migraine indication 37796009 DOID:6364
Joint pain indication 57676002
Allergic rhinitis indication 61582004
Nasal discharge indication 64531003
Nasal congestion indication 68235000
Common cold indication 82272006 DOID:10459
Vascular headache indication 128187005
Backache indication 161891005
Cluster headache syndrome indication 193031009
Spasticity indication 221360009
Headache disorder indication 230461009
Dysmenorrhea indication 266599000
Influenza-like symptoms indication 315642008
Tension-type headache indication 398057008
Cluster Headache Prevention indication
Brain damage contraindication 2470005
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005 DOID:8677
Ocular hypertension contraindication 4210003 DOID:9282
Gastritis contraindication 4556007 DOID:4029
Hypophosphatemia contraindication 4996001
Tachyarrhythmia contraindication 6285003
Suicidal thoughts contraindication 6471006
Dependent drug abuse contraindication 6525002
Urinary tract obstruction contraindication 7163005 DOID:5200
Alcoholism contraindication 7200002
Alcohol withdrawal delirium contraindication 8635005
Hyperammonemia contraindication 9360008
Peptic ulcer contraindication 13200003 DOID:750
Chronic obstructive lung disease contraindication 13645005 DOID:3083
Asthenia contraindication 13791008
Hepatic encephalopathy contraindication 13920009 DOID:13413
Hyperkalemia contraindication 14140009
Severe chronic ulcerative colitis contraindication 14311001
Constipation contraindication 14760008 DOID:2089
Chronic disease of respiratory system contraindication 17097001
Mood swings contraindication 18963009
Myocardial infarction contraindication 22298006 DOID:5844
Glaucoma contraindication 23986001 DOID:1686
Inflammatory bowel disease contraindication 24526004 DOID:0050589
Ventricular tachycardia contraindication 25569003
Alcohol intoxication contraindication 25702006
Complete atrioventricular block contraindication 27885002
Shock contraindication 27942005
Toxic megacolon contraindication 28536002 DOID:1770
Hypovolemia contraindication 28560003
Orthostatic hypotension contraindication 28651003
Acute cerebrovascular insufficiency contraindication 29322000
Atony of colon contraindication 29479008
Hypercapnia contraindication 29596007
Dehydration contraindication 34095006
Hyperthyroidism contraindication 34486009 DOID:7998
Depressive disorder contraindication 35489007 DOID:2848
Acute hepatitis contraindication 37871000
Hypertensive disorder contraindication 38341003 DOID:10763
Disorder of gallbladder contraindication 39621005 DOID:0060262
Gastrointestinal ulcer contraindication 40845000
Hypothyroidism contraindication 40930008 DOID:1459
Complete trisomy 21 syndrome contraindication 41040004 DOID:14250
Hypokalemia contraindication 43339004
Body fluid retention contraindication 43498006
Hyperactive behavior contraindication 44548000
Fecal impaction contraindication 44635007
Conduction disorder of the heart contraindication 44808001
Low blood pressure contraindication 45007003
Achalasia of esophagus contraindication 45564002 DOID:9164
Chronic heart failure contraindication 48447003
Bradycardia contraindication 48867003
Retroperitoneal fibrosis contraindication 49120005
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Acidosis contraindication 51387008
Fibrosis of lung contraindication 51615001 DOID:3770
Gastrointestinal perforation contraindication 51875005
Vitamin K deficiency contraindication 52675005 DOID:11249
Nasal polyp contraindication 52756005
Gastrectomy contraindication 53442002
Paralytic ileus contraindication 55525008 DOID:8442
Peptic reflux disease contraindication 57643001 DOID:13976
Congenital myotonia, autosomal dominant form contraindication 57938005
Acute nephropathy contraindication 58574008
Leber's optic atrophy contraindication 58610003 DOID:705
Hepatic failure contraindication 59927004
Diarrhea contraindication 62315008
Thrombophlebitis contraindication 64156001 DOID:3875
Ulcerative colitis contraindication 64766004 DOID:8577
Blood coagulation disorder contraindication 64779008 DOID:1247
Arterial thrombosis contraindication 65198009
Drug AND/OR toxin-induced diarrhea contraindication 65979008
Substance abuse contraindication 66214007
Hypermagnesemia contraindication 66978005
Benign intracranial hypertension contraindication 68267002 DOID:11459
Hemorrhoids contraindication 70153002 DOID:9746
Poisoning by acetaminophen contraindication 70273001
Agoraphobia contraindication 70691001 DOID:593
Arteriosclerotic vascular disease contraindication 72092001 DOID:2349
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050848
Factor II deficiency contraindication 73975000
Reye's syndrome contraindication 74351001 DOID:14525
Gastrointestinal hemorrhage contraindication 74474003
Urethral stricture contraindication 76618002
Thrombotic thrombocytopenic purpura contraindication 78129009 DOID:10772
Spastic paralysis contraindication 78403003
Disturbance of salivary secretion contraindication 78948009
Decreased respiratory function contraindication 80954004
Injury of head contraindication 82271004
Chronic idiopathic constipation contraindication 82934008
Cor pulmonale contraindication 83291003 DOID:8515
Hiatal hernia contraindication 84089009 DOID:12642
Atrophic gastritis contraindication 84568007 DOID:8929
Epilepsy contraindication 84757009 DOID:1826
Pulmonary emphysema contraindication 87433001
Gout contraindication 90560007 DOID:13189
Chronic renal failure syndrome contraindication 90688005 DOID:784
Kidney disease contraindication 90708001 DOID:2527
Thyrotoxicosis contraindication 90739004 DOID:7997
Hemophilia contraindication 90935002
Myasthenia gravis contraindication 91637004 DOID:437
Obstruction of duodenum contraindication 95532008 DOID:3558
Disorder of biliary tract contraindication 105997008 DOID:9741
Anemia due to enzyme deficiency contraindication 111577008
Prolonged QT interval contraindication 111975006
Acute abdominal pain contraindication 116290004
Procedure on urinary system contraindication 118677009
Gastrointestinal obstruction contraindication 126765001
Neoplasm of brain contraindication 126952004 DOID:1319
von Willebrand disorder contraindication 128105004 DOID:12531
Seizure disorder contraindication 128613002 DOID:1826
Autonomic dysreflexia contraindication 129618003
Bleeding contraindication 131148009
Prolonged PR interval contraindication 164947007
Drug-induced psychosis contraindication 191483003 DOID:1742
Obsessive-compulsive disorder contraindication 191736004 DOID:10933
Insomnia contraindication 193462001
Partial atrioventricular block contraindication 195039008
Decompensated cardiac failure contraindication 195111005
Acute pancreatitis contraindication 197456007 DOID:2913
Impaired renal function disorder contraindication 197663003
Coronary artery bypass graft contraindication 232717009
Myocardial dysfunction contraindication 233928007
Peripheral ischemia contraindication 233958001
Gastroesophageal reflux disease contraindication 235595009 DOID:8534
Gastroparesis contraindication 235675006 DOID:11914
Disease of liver contraindication 235856003 DOID:409
Chronic diarrhea contraindication 236071009
Hyporeninemic hypoaldosteronism contraindication 236464008
Aluminum intoxication contraindication 236546003
Bladder outflow obstruction contraindication 236645006
Morbid obesity contraindication 238136002 DOID:11981
Sepsis syndrome contraindication 238150007
Pyloric obstruction contraindication 244815007 DOID:3122
Sleep automatism contraindication 247962006
Raynaud's phenomenon contraindication 266261006
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Drowsy contraindication 271782001
Exacerbation of asthma contraindication 281239006
Cerebral ischemia contraindication 287731003
Pregnancy, function contraindication 289908002
Lesion of brain contraindication 301766008
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Neutropenic disorder contraindication 303011007 DOID:1227
Familial hyperkalemic periodic paralysis contraindication 304737009 DOID:14451
Panic disorder contraindication 371631005 DOID:594
Coma contraindication 371632003
Primary adrenocortical insufficiency contraindication 373662000 DOID:13774
Operation on gastrointestinal tract contraindication 386621005
Hypoxia contraindication 389086002
Angle-closure glaucoma contraindication 392291006 DOID:13550
Cardiovascular event risk contraindication 395112001
Pseudomembranous enterocolitis contraindication 397683000 DOID:0060185
Gastric ulcer contraindication 397825006 DOID:10808
Peripheral vascular disease contraindication 400047006
Respiratory insufficiency contraindication 409623005
Breastfeeding (mother) contraindication 413712001
Chronic lung disease contraindication 413839001
Chronic myocardial ischemia contraindication 413844008 DOID:3393
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Myocardial infarction in recovery phase contraindication 418044006
Central nervous system depression contraindication 418072004
Porphyria contraindication 418470004 DOID:13268
Ultrarapid metabolizer due to cytochrome p450 CYP2D6 variant contraindication 422681000
Dysfunction of sphincter of Oddi contraindication 430887001
Fibrosis of pleura contraindication 442110002
Congenital long QT syndrome contraindication 442917000
Hypertensive urgency contraindication 443482000
Acute erosive gastritis contraindication 444926003
Smokes tobacco daily contraindication 449868002
Severe dehydration contraindication 450316000
Acute exacerbation of asthma contraindication 708038006
Ergot Alkaloid Toxicity contraindication
Acute Thromboembolic Stroke contraindication
Organic Cardiac Disease contraindication
Severe Pruritus contraindication
Fatigue off-label use 84229001
Urinary incontinence off-label use 165232002
Obesity off-label use 414916001 DOID:9970

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 1.86 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Adenosine receptor A2b GPCR ANTAGONIST Ki 4.77 WOMBAT-PK CHEMBL
Adenosine receptor A1 GPCR ANTAGONIST Ki 4.97 IUPHAR CHEMBL
Adenosine receptor A2a GPCR ANTAGONIST Ki 5.61 CHEMBL CHEMBL
Acetylcholinesterase Enzyme IC50 5.14 CHEMBL
Potassium voltage-gated channel subfamily H member 2 Ion channel IC50 5.31 CHEMBL
Adenosine receptor A3 GPCR ANTAGONIST Ki 4.33 WOMBAT-PK
Phosphatidylinositol 4,5-bisphosphate 3-kinase catalytic subunit delta isoform Kinase IC50 4.12 CHEMBL
Guanine deaminase Enzyme Ki 4.99 CHEMBL
Adenosine receptor A1 GPCR Ki 4.54 CHEMBL
Adenosine receptor A1 GPCR Ki 4.77 CHEMBL
Adenosine A2a receptor Unclassified Ki 4.10 CHEMBL
Adenosine receptor A2a GPCR Ki 5.03 CHEMBL
Adenosine A2 receptor GPCR Ki 4.57 CHEMBL
Glycogen phosphorylase, muscle form Enzyme IC50 4.13 CHEMBL
Adenosine receptor A1 GPCR Ki 4 CHEMBL
Adenosine receptor GPCR Ki 4.22 CHEMBL
Adenosine receptor A2b Unclassified ANTAGONIST Ki 4.89 IUPHAR

External reference:

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IDSource
CHEBI:27732 CHEBI
DB00201 DRUGBANK_ID
407 IUPHAR_LIGAND_ID
4017537 VUID
N0000145919 NUI
C0006644 UMLSCUI
D00528 KEGG_DRUG
CHEMBL113 ChEMBL_ID
3G6A5W338E UNII
2519 PUBCHEM_CID
4017537 VANDF
N0000006506 NDFRT
N0000145919 NDFRT
000600 NDDF
4939 MMSL
1886 RXNORM
255641001 SNOMEDCT_US
91107009 SNOMEDCT_US
4318 MMSL
d00801 MMSL
CHEMBL1200569 ChEMBL_ID
D002110 MESH_DESCRIPTOR_UI
69-22-7 SECONDARY_CAS_RN
C026189 MESH_SUPPLEMENTAL_RECORD_UI
CFF PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Fiorinal with Codeine HUMAN PRESCRIPTION DRUG LABEL 4 0023-6010 CAPSULE 40 mg ORAL NDA 20 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2000 TABLET, FILM COATED 65 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2021 TABLET, COATED 65 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-2035 TABLET, COATED 65 mg ORAL NDA 10 sections
EXCEDRIN HUMAN OTC DRUG LABEL 3 0067-2039 TABLET, FILM COATED 65 mg ORAL NDA 9 sections
NoDoz HUMAN OTC DRUG LABEL 1 0067-2070 TABLET, COATED 200 mg ORAL OTC monograph final 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-8103 TABLET, FILM COATED 65 mg ORAL ANDA 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-8104 TABLET, FILM COATED 65 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 2 0067-8119 TABLET, FILM COATED 65 mg ORAL OTC monograph not final 9 sections
Excedrin HUMAN OTC DRUG LABEL 2 0067-8139 TABLET, FILM COATED 65 mg ORAL OTC monograph not final 9 sections
Excedrin PM Triple Action Caplets and Excedrin Tension Headache HUMAN OTC DRUG LABEL 5 0067-8147 KIT 65 mg None OTC monograph not final 9 sections
good sense migraine formula HUMAN OTC DRUG LABEL 3 0113-0374 TABLET, FILM COATED 65 mg ORAL ANDA 9 sections
good sense stay awake HUMAN OTC DRUG LABEL 1 0113-0409 TABLET 200 mg ORAL OTC monograph final 9 sections
PANADOL HUMAN OTC DRUG LABEL 2 0135-0620 TABLET, FILM COATED 65 mg ORAL OTC monograph not final 9 sections
Butalbital, Acetaminophen, and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0143-0170 CAPSULE 40 mg ORAL ANDA 14 sections
Butalbital, Aspirin and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0143-1785 TABLET 40 mg ORAL ANDA 11 sections
Butalbital, Acetaminophen and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0143-1787 TABLET 40 mg ORAL ANDA 13 sections
ERGOTAMINE HUMAN PRESCRIPTION DRUG LABEL 2 0143-2120 TABLET, FILM COATED 100 mg ORAL ANDA 14 sections
CAFERGOT HUMAN PRESCRIPTION DRUG LABEL 2 0179-0089 TABLET 100 mg ORAL ANDA 19 sections
Butalbital, Acetaminophen and Caffeine HUMAN PRESCRIPTION DRUG LABEL 3 0179-0137 TABLET 40 mg ORAL ANDA 14 sections
Bayer Back and Body HUMAN OTC DRUG LABEL 2 0280-2150 TABLET 35.50 mg ORAL OTC monograph not final 15 sections
Bayer HUMAN OTC DRUG LABEL 2 0280-2635 CAPSULE 32.50 mg ORAL OTC MONOGRAPH FINAL 9 sections
Midol Complete HUMAN OTC DRUG LABEL 3 0280-8005 TABLET 60 mg ORAL OTC monograph not final 9 sections
Midol Complete HUMAN OTC DRUG LABEL 3 0280-8015 TABLET, COATED 60 mg ORAL OTC monograph not final 16 sections
Extra Strength Headache Relief HUMAN OTC DRUG LABEL 3 0363-0021 CAPSULE 65 mg ORAL OTC monograph not final 9 sections
Headache Relief HUMAN OTC DRUG LABEL 3 0363-0159 TABLET, FILM COATED 65 mg ORAL OTC MONOGRAPH NOT FINAL 9 sections
Regular Strength Aspirin HUMAN OTC DRUG LABEL 2 0363-0164 TABLET, FILM COATED 32 mg ORAL OTC MONOGRAPH NOT FINAL 9 sections
Stay Awake HUMAN OTC DRUG LABEL 1 0363-0226 TABLET 200 mg ORAL OTC MONOGRAPH FINAL 9 sections
Headache Relief HUMAN OTC DRUG LABEL 3 0363-0247 TABLET 65 mg ORAL OTC MONOGRAPH NOT FINAL 9 sections
Menstrual Relief HUMAN OTC DRUG LABEL 3 0363-0252 TABLET 60 mg ORAL OTC MONOGRAPH NOT FINAL 9 sections