caffeine Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.40 g O
0.40 g P

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 21.50 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 1 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 51.77 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 98 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.63 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.40 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.64 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 4.90 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
Nov. 26, 1948 FDA NOVARTIS

FDA Adverse Event Reporting System (Female)

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
Completed suicide 11901.26 39.95 2686 8289 18348 2328762
Toxicity to various agents 11409.04 39.95 2820 8155 29934 2317176
Overdose 3588.97 39.95 1038 9937 18869 2328241
Death 2402.64 39.95 1115 9860 80353 2266757
Intentional overdose 1965.15 39.95 576 10399 10745 2336365
Intentional product misuse 1896.68 39.95 539 10436 8950 2338160
Acute hepatic failure 1538.88 39.95 353 10622 2289 2344821
Metabolic acidosis 1333.93 39.95 371 10604 5627 2341483
Cardio-respiratory arrest 1310.26 39.95 402 10573 8744 2338366
Cardiac arrest 1173.72 39.95 417 10558 14513 2332597
Respiratory arrest 1106.93 39.95 323 10652 5855 2341255
Drug abuse 1087.40 39.95 373 10602 11653 2335457
Suicide attempt 973.36 39.95 338 10637 10944 2336166
Coma 908.89 39.95 304 10671 8752 2338358
Hepatic failure 881.57 39.95 266 10709 5423 2341687
Hepatotoxicity 873.21 39.95 237 10738 3244 2343866
Poisoning 777.83 39.95 207 10768 2613 2344497
Hypotension 640.88 39.95 342 10633 32094 2315016
Coagulopathy 577.57 39.95 165 10810 2744 2344366
Alanine aminotransferase increased 559.35 39.95 240 10735 13792 2333318
Aspartate aminotransferase increased 550.17 39.95 230 10745 12382 2334728
Depressed level of consciousness 549.27 39.95 200 10775 7404 2339706
Liver injury 498.84 39.95 140 10835 2174 2344936
Medication error 486.79 39.95 173 10802 5958 2341152
Accidental overdose 436.34 39.95 143 10832 3829 2343281
Vomiting 431.59 39.95 360 10615 71242 2275868
Drug hypersensitivity 406.22 39.95 292 10683 46351 2300759
Hepatic necrosis 385.72 39.95 98 10877 1012 2346098
Somnolence 381.40 39.95 218 10757 23267 2323843
International normalised ratio increased 367.95 39.95 148 10827 7188 2339922
Exposure via ingestion 366.86 39.95 88 10887 700 2346410
Anion gap 358.99 39.95 64 10911 71 2347039
Tachycardia 357.16 39.95 185 10790 16224 2330886
Acute kidney injury 350.07 39.95 220 10755 27902 2319208
Exposure during pregnancy 313.03 39.95 197 10778 25022 2322088
Drug ineffective 301.94 39.95 347 10628 101277 2245833
Respiratory depression 274.45 39.95 87 10888 2083 2345027
Hepatitis 273.97 39.95 115 10860 6222 2340888
Acidosis 243.36 39.95 74 10901 1536 2345574
Brain oedema 240.83 39.95 80 10895 2230 2344880
Pyroglutamate increased 236.64 39.95 40 10935 22 2347088
Drug-induced liver injury 225.42 39.95 86 10889 3613 2343497
Encephalopathy 225.04 39.95 91 10884 4470 2342640
Nausea 215.73 39.95 309 10666 111880 2235230
Substance abuse 203.20 39.95 51 10924 498 2346612
Prothrombin time prolonged 194.64 39.95 63 10912 1614 2345496
Loss of consciousness 187.19 39.95 128 10847 18639 2328471
Transaminases increased 184.10 39.95 79 10896 4508 2342602
Acute lung injury 179.98 39.95 38 10937 154 2346956
Confusional state 178.95 39.95 138 10837 24206 2322904
Analgesic drug level increased 174.80 39.95 40 10935 252 2346858
Renal failure 172.22 39.95 118 10857 17231 2329879
Blood bilirubin increased 166.24 39.95 77 10898 5268 2341842
Drug interaction 165.18 39.95 142 10833 29021 2318089
Liver function test abnormal 164.28 39.95 85 10890 7405 2339705
Unresponsive to stimuli 163.45 39.95 74 10901 4802 2342308
Multiple organ dysfunction syndrome 159.82 39.95 84 10891 7557 2339553
Drug screen positive 159.41 39.95 47 10928 873 2346237
Abdominal pain 158.42 39.95 149 10826 34225 2312885
Hepatic encephalopathy 153.01 39.95 52 10923 1555 2345555
Pyrexia 151.31 39.95 179 10796 53529 2293581
Agitation 148.64 39.95 91 10884 10960 2336150
Liver transplant 147.06 39.95 40 10935 547 2346563
Lethargy 146.62 39.95 83 10892 8647 2338463
Sinus tachycardia 145.82 39.95 61 10914 3264 2343846
Hepatic function abnormal 144.80 39.95 73 10902 6019 2341091
Blood pH decreased 139.71 39.95 37 10938 454 2346656
Bradycardia 138.87 39.95 84 10891 9897 2337213
Thrombocytopenia 137.35 39.95 107 10868 19024 2328086
Poisoning deliberate 135.18 39.95 44 10931 1147 2345963
Hypothermia 134.65 39.95 51 10924 2097 2345013
Hypoglycaemia 133.32 39.95 77 10898 8330 2338780
Heart rate increased 128.16 39.95 83 10892 11022 2336088
Rhabdomyolysis 126.97 39.95 69 10906 6635 2340475
Seizure 124.18 39.95 112 10863 24354 2322756
Acute respiratory distress syndrome 120.02 39.95 53 10922 3239 2343871
Hepatic enzyme increased 119.88 39.95 76 10899 9726 2337384
Toxic epidermal necrolysis 119.10 39.95 52 10923 3092 2344018
Asphyxia 117.64 39.95 38 10937 966 2346144
Arteriosclerosis coronary artery 115.78 39.95 39 10936 1134 2345976
Drug dependence 114.17 39.95 50 10925 2995 2344115
Brain death 111.50 39.95 32 10943 538 2346572
Product administration error 110.87 39.95 53 10922 3890 2343220
Pain 109.06 39.95 164 10811 61693 2285417
Headache 102.73 39.95 184 10791 79995 2267115
Stevens-Johnson syndrome 101.09 39.95 51 10924 4208 2342902
Mental status changes 96.20 39.95 54 10921 5528 2341582
Haemolysis 95.89 39.95 33 10942 1025 2346085
Abdominal pain upper 94.48 39.95 92 10883 22008 2325102
Blood creatine phosphokinase increased 89.36 39.95 50 10925 5086 2342024
Hepatocellular injury 88.81 39.95 46 10929 4009 2343101
Pulmonary oedema 87.30 39.95 56 10919 7307 2339803
Blood lactic acid increased 86.78 39.95 29 10946 822 2346288
Rheumatoid arthritis 86.18 39.95 82 10893 19058 2328052
Drug level increased 86.16 39.95 40 10935 2747 2344363
Intentional self-injury 85.20 39.95 45 10930 4082 2343028
Anion gap increased 83.74 39.95 22 10953 261 2346849
Hypertension 83.23 39.95 95 10880 27266 2319844
Electrocardiogram QRS complex prolonged 83.18 39.95 30 10945 1072 2346038
Leukocytosis 82.46 39.95 42 10933 3534 2343576
Condition aggravated 80.78 39.95 101 10874 31878 2315232
Rash 80.46 39.95 140 10835 59418 2287692
Analgesic drug level above therapeutic 79.51 39.95 15 10960 28 2347082
Visual impairment 78.40 39.95 63 10912 11692 2335418
Gamma-glutamyltransferase increased 77.81 39.95 47 10928 5515 2341595
Body temperature increased 75.32 39.95 38 10937 3133 2343977
Generalised tonic-clonic seizure 71.57 39.95 44 10931 5328 2341782
Photophobia 71.21 39.95 33 10942 2256 2344854
Ventricular arrhythmia 70.84 39.95 23 10952 594 2346516
Body temperature decreased 70.77 39.95 28 10947 1295 2345815
Electrocardiogram QT prolonged 70.09 39.95 50 10925 7764 2339346
Pruritus 69.37 39.95 110 10865 43230 2303880
Blood creatinine increased 69.28 39.95 56 10919 10477 2336633
Renal impairment 69.24 39.95 55 10920 10037 2337073
Respiratory failure 68.70 39.95 62 10913 13466 2333644
Gastrointestinal haemorrhage 67.14 39.95 59 10916 12376 2334734
Blood alkaline phosphatase increased 66.00 39.95 45 10930 6500 2340610
Mydriasis 65.96 39.95 31 10944 2188 2344922
Toxicologic test abnormal 65.81 39.95 16 10959 135 2346975
Jaundice 65.55 39.95 42 10933 5466 2341644
Peripheral swelling 65.52 39.95 68 10907 17529 2329581
Drug abuser 64.52 39.95 24 10951 937 2346173
Premature labour 64.39 39.95 30 10945 2076 2345034
Haemoglobin decreased 63.77 39.95 68 10907 18083 2329027
Premature baby 63.49 39.95 34 10941 3170 2343940
Self-medication 63.42 39.95 21 10954 578 2346532
Accidental death 62.80 39.95 18 10957 301 2346809
Product use issue 62.24 39.95 56 10919 12113 2334997
Maternal exposure during pregnancy 61.85 39.95 61 10914 14802 2332308
Shock 61.65 39.95 36 10939 3968 2343142
Joint swelling 60.84 39.95 64 10911 16755 2330355
Drug reaction with eosinophilia and systemic symptoms 60.58 39.95 40 10935 5478 2341632
Gastrointestinal sounds abnormal 60.24 39.95 20 10955 555 2346555
Oliguria 59.83 39.95 25 10950 1332 2345778
Alcohol use 59.56 39.95 19 10956 463 2346647
Blood bicarbonate decreased 58.77 39.95 19 10956 484 2346626
Cholestasis 58.74 39.95 34 10941 3687 2343423
Pneumonia aspiration 58.56 39.95 34 10941 3708 2343402
Synovial fluid analysis 58.49 39.95 11 10964 20 2347090
Respiratory distress 58.30 39.95 38 10937 5091 2342019
Renal papillary necrosis 58.21 39.95 12 10963 42 2347068
Night sweats 57.97 39.95 33 10942 3467 2343643
Dilatation intrahepatic duct acquired 57.77 39.95 13 10962 75 2347035
Hepatitis fulminant 57.63 39.95 20 10955 637 2346473
Loss of personal independence in daily activities 57.10 39.95 38 10937 5273 2341837
Respiratory rate increased 57.10 39.95 25 10950 1495 2345615
Urticaria 57.08 39.95 74 10901 24187 2322923
Respiratory alkalosis 56.84 39.95 17 10958 332 2346778
Suicidal ideation 56.65 39.95 51 10924 11036 2336074
Incorrect dose administered 56.37 39.95 48 10927 9647 2337463
Brain herniation 55.89 39.95 19 10956 568 2346542
Muscle spasticity 55.08 39.95 25 10950 1628 2345482
Insomnia 55.05 39.95 75 10900 25712 2321398
Ammonia increased 54.81 39.95 20 10955 739 2346371
Bursitis 54.70 39.95 26 10949 1882 2345228
Drug intolerance 54.68 39.95 55 10920 13662 2333448
Activated partial thromboplastin time prolonged 54.40 39.95 23 10952 1262 2345848
White blood cell count increased 53.81 39.95 41 10934 7037 2340073
Blood sodium decreased 53.43 39.95 30 10945 3070 2344040
Bradypnoea 53.19 39.95 17 10958 417 2346693
Agranulocytosis 52.80 39.95 31 10944 3451 2343659
Asthenia 52.79 39.95 102 10873 46824 2300286
Hyperthermia 51.45 39.95 23 10952 1445 2345665
Contraindicated product administered 51.43 39.95 29 10946 2992 2344118
Pancreatitis 51.11 39.95 42 10933 8037 2339073
Tachypnoea 50.86 39.95 26 10949 2203 2344907
Dyspnoea 50.53 39.95 137 10838 78596 2268514
Migraine 50.52 39.95 47 10928 10606 2336504
Hepatitis cholestatic 49.95 39.95 21 10954 1136 2345974
Antidepressant drug level above therapeutic 49.88 39.95 11 10964 57 2347053
Fatigue 49.86 39.95 143 10832 84730 2262380
Lower respiratory tract infection 49.31 39.95 35 10940 5389 2341721
Conjunctivitis 49.12 39.95 26 10949 2367 2344743
Malaise 48.67 39.95 109 10866 55476 2291634
Foetal death 48.61 39.95 24 10951 1888 2345222
Pancreatitis acute 47.39 39.95 30 10945 3823 2343287
Coma hepatic 47.36 39.95 13 10962 184 2346926
Tenosynovitis stenosans 47.26 39.95 12 10963 123 2346987
Pneumonia 46.94 39.95 100 10875 49196 2297914
Product use in unapproved indication 46.65 39.95 46 10929 11154 2335956
Drug level above therapeutic 46.24 39.95 16 10959 505 2346605
Ulcer 46.03 39.95 23 10952 1857 2345253
Foetal exposure during pregnancy 45.70 39.95 33 10942 5219 2341891
Lactic acidosis 45.26 39.95 33 10942 5297 2341813
Hallucination 44.65 39.95 39 10936 8109 2339001
Serotonin syndrome 44.63 39.95 28 10947 3512 2343598
Blood pressure decreased 44.28 39.95 41 10934 9195 2337915
Disorientation 44.28 39.95 35 10940 6337 2340773
Renal tubular necrosis 43.55 39.95 21 10954 1569 2345541
Accidental exposure to product 43.23 39.95 39 10936 8458 2338652
Inflammation 42.90 39.95 34 10941 6179 2340931
PCO2 decreased 42.58 39.95 13 10962 273 2346837
Crepitations 42.40 39.95 16 10959 650 2346460
Back pain 42.10 39.95 74 10901 31585 2315525
Face oedema 41.84 39.95 28 10947 3920 2343190
Scleritis 41.63 39.95 13 10962 295 2346815
Respiratory disorder 41.48 39.95 28 10947 3976 2343134
Blood glucose increased 41.32 39.95 45 10930 12245 2334865
Emphysema 41.25 39.95 18 10957 1067 2346043
Hyperbilirubinaemia 41.04 39.95 20 10955 1529 2345581
Hypoxia 40.70 39.95 33 10942 6194 2340916
Anaphylactic reaction 40.67 39.95 40 10935 9665 2337445
Alcohol poisoning 40.21 39.95 13 10962 331 2346779

FDA Adverse Event Reporting System (Male)

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
Toxicity to various agents 5648.69 46.31 1549 4563 27592 1713077
Completed suicide 5232.48 46.31 1300 4812 15012 1725657
Overdose 2018.23 46.31 627 5485 16074 1724595
Intentional product misuse 1129.46 46.31 334 5778 7024 1733645
Drug abuse 940.78 46.31 338 5774 13351 1727318
Intentional overdose 931.53 46.31 291 5821 7379 1733290
Death 915.54 46.31 587 5525 86856 1653813
Cardio-respiratory arrest 836.59 46.31 281 5831 9012 1731657
Acute hepatic failure 744.87 46.31 184 5928 1859 1738810
Respiratory arrest 577.96 46.31 190 5922 5649 1735020
Cardiac arrest 547.80 46.31 239 5873 15691 1724978
Accidental overdose 462.54 46.31 148 5964 4016 1736653
Metabolic acidosis 459.75 46.31 157 5955 5245 1735424
Hepatotoxicity 453.81 46.31 136 5976 2948 1737721
Coma 382.01 46.31 148 5964 7114 1733555
Suicide attempt 358.51 46.31 142 5970 7239 1733430
Hypotension 342.26 46.31 214 5898 29440 1711229
Coagulopathy 329.87 46.31 104 6008 2677 1737992
Poisoning 318.31 46.31 99 6013 2433 1738236
Hepatic failure 309.18 46.31 120 5992 5783 1734886
Alanine aminotransferase increased 265.34 46.31 134 5978 12144 1728525
Medication error 264.64 46.31 101 6011 4642 1736027
Aspartate aminotransferase increased 260.90 46.31 127 5985 10629 1730040
Depressed level of consciousness 258.95 46.31 109 6003 6483 1734186
International normalised ratio increased 256.89 46.31 116 5996 8183 1732486
Substance abuse 245.99 46.31 66 6046 937 1739732
Liver injury 225.62 46.31 71 6041 1811 1738858
Hepatic necrosis 221.23 46.31 57 6055 684 1739985
Acute kidney injury 217.31 46.31 173 5939 34771 1705898
Toxic epidermal necrolysis 197.76 46.31 68 6044 2303 1738366
Anion gap 193.07 46.31 35 6077 53 1740616
Respiratory depression 177.94 46.31 62 6050 2185 1738484
Exposure via ingestion 167.89 46.31 45 6067 635 1740034
Vomiting 161.46 46.31 152 5960 38163 1702506
Stevens-Johnson syndrome 153.70 46.31 62 6050 3295 1737374
Drug interaction 151.62 46.31 128 5984 27830 1712839
Rhabdomyolysis 137.32 46.31 84 6028 11006 1729663
Tachycardia 137.14 46.31 88 6024 12540 1728129
Transaminases increased 128.18 46.31 57 6055 3860 1736809
Brain oedema 126.79 46.31 48 6064 2148 1738521
Multiple organ dysfunction syndrome 119.51 46.31 72 6040 9170 1731499
Prothrombin time prolonged 117.89 46.31 42 6070 1579 1739090
Agitation 112.70 46.31 74 6038 10952 1729717
Pulmonary oedema 111.03 46.31 61 6051 6525 1734144
Unresponsive to stimuli 110.02 46.31 54 6058 4575 1736094
Pulmonary congestion 109.81 46.31 41 6071 1764 1738905
Somnolence 106.03 46.31 84 6028 16655 1724014
Acidosis 105.89 46.31 38 6074 1459 1739210
Renal failure 100.91 46.31 88 6024 19929 1720740
Hepatic encephalopathy 100.30 46.31 41 6071 2251 1738418
Hepatic function abnormal 98.97 46.31 58 6054 7016 1733653
Lethargy 98.13 46.31 58 6054 7126 1733543
Hepatitis 95.00 46.31 50 6062 4905 1735764
Blood pH decreased 91.49 46.31 26 6086 460 1740209
Encephalopathy 91.29 46.31 47 6065 4405 1736264
Brain death 91.02 46.31 26 6086 469 1740200
Mental status changes 88.12 46.31 51 6061 6024 1734645
Liver function test abnormal 85.53 46.31 49 6063 5677 1734992
Seizure 83.71 46.31 80 6032 20361 1720308
Drug screen positive 82.99 46.31 29 6083 1028 1739641
Drug hypersensitivity 81.22 46.31 69 6043 15066 1725603
Thrombocytopenia 79.22 46.31 79 6033 21170 1719499
Pneumonia aspiration 78.47 46.31 45 6067 5221 1735448
Blood creatinine increased 75.68 46.31 64 6048 13882 1726787
Drug level increased 73.84 46.31 35 6077 2742 1737927
Cholestasis 73.14 46.31 38 6074 3627 1737042
Confusional state 70.05 46.31 74 6038 21204 1719465
Pyrexia 69.40 46.31 109 6003 46291 1694378
Ammonia increased 69.24 46.31 24 6088 830 1739839
Liver transplant 68.99 46.31 22 6090 584 1740085
Hepatocellular injury 68.80 46.31 35 6077 3196 1737473
Anion gap increased 67.32 46.31 18 6094 251 1740418
Methaemoglobinaemia 66.39 46.31 19 6093 345 1740324
Leukocytosis 65.85 46.31 35 6077 3498 1737171
Jaundice 65.10 46.31 42 6070 6020 1734649
Loss of consciousness 64.25 46.31 60 6052 14815 1725854
Hepatic enzyme increased 64.11 46.31 43 6069 6578 1734091
Abdominal pain 62.46 46.31 70 6042 21420 1719249
Incorrect dose administered 62.04 46.31 44 6068 7365 1733304
Bradycardia 60.56 46.31 50 6062 10484 1730185
Drug-induced liver injury 60.14 46.31 32 6080 3205 1737464
Heart rate increased 59.98 46.31 41 6071 6469 1734200
Shock 57.85 46.31 34 6078 4127 1736542
Blood bilirubin increased 56.95 46.31 39 6073 6171 1734498
Hypoglycaemia 56.92 46.31 44 6068 8394 1732275
Hypothermia 55.74 46.31 25 6087 1723 1738946
Blood bicarbonate decreased 54.97 46.31 17 6095 407 1740262
Alcohol use 54.20 46.31 20 6092 831 1739838
Brain injury 53.99 46.31 21 6091 1010 1739659
Arteriosclerosis coronary artery 53.85 46.31 25 6087 1867 1738802
Environmental exposure 52.34 46.31 11 6101 48 1740621
Electrocardiogram QRS complex prolonged 52.27 46.31 19 6093 756 1739913
Analgesic drug level increased 51.25 46.31 12 6100 93 1740576
Anaphylactic reaction 50.47 46.31 36 6076 6077 1734592
Drug abuser 50.19 46.31 22 6090 1435 1739234
Hepatitis acute 49.96 46.31 21 6091 1236 1739433
Aggression 49.75 46.31 40 6072 8075 1732594
Haemodialysis 48.98 46.31 26 6086 2590 1738079
Blood alkaline phosphatase increased 48.52 46.31 33 6079 5162 1735507
Gastrointestinal haemorrhage 47.58 46.31 50 6062 14217 1726452

Pharmacologic Action:

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
FDA PE N0000175729 Central Nervous System Stimulation
FDA EPC N0000175790 Methylxanthine
FDA Chemical/Ingredient N0000008118 Xanthines
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
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 D058914 Purinergic Antagonists
MeSH PA D058915 Purinergic P1 Receptor Antagonists

Drug Use (View source of the data)

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
Fatigue off-label use 84229001
Urinary incontinence off-label use 165232002
Obesity off-label use 414916001 DOID:9970
Brain damage contraindication 2470005
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
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
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
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
Hepatic coma contraindication 72836002 DOID:12550
Diabetes mellitus contraindication 73211009 DOID:9351
Sleep apnea contraindication 73430006 DOID:0050847
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
Kidney disease contraindication 90708001 DOID:557
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
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
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
Sleep automatism contraindication 247962006
Raynaud's phenomenon contraindication 266261006
Benign prostatic hyperplasia contraindication 266569009
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
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
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
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

Acid dissociation constants calculated using MoKa v3.0.0

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:

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:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Fiorinal with Codeine HUMAN PRESCRIPTION DRUG LABEL 4 0023-6010 CAPSULE 40 mg ORAL NDA 20 sections
Fiorinal HUMAN PRESCRIPTION DRUG LABEL 3 0023-6146 CAPSULE 40 mg ORAL NDA 12 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 0067-2001 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
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
Excedrin PM Triple Action Caplets and Excedrin Extra Strength Pain Reliever HUMAN OTC DRUG LABEL 6 0067-8148 KIT 65 mg None OTC monograph not final 9 sections
Excedrin Extra Strength and Excedrin Tension Headache HUMAN OTC DRUG LABEL 5 0067-8151 KIT 65 mg None OTC monograph not final 9 sections
Excedrin Extra Strength and Excedrin Tension Headache HUMAN OTC DRUG LABEL 5 0067-8151 KIT 65 mg None OTC monograph not final 9 sections
EXCEDRIN HUMAN OTC DRUG LABEL 3 0067-8201 TABLET, FILM COATED 65 mg ORAL NDA 9 sections
Excedrin HUMAN OTC DRUG LABEL 3 0067-8202 TABLET, FILM COATED 65 mg ORAL 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
basic care migraine relief HUMAN OTC DRUG LABEL 3 0113-7374 TABLET, FILM COATED 65 mg ORAL ANDA 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, 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
Bayer Back and Body HUMAN OTC DRUG LABEL 2 0280-2150 TABLET 35.50 mg ORAL OTC monograph not final 15 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
Stay Awake HUMAN OTC DRUG LABEL 1 0363-0226 TABLET 200 mg ORAL OTC MONOGRAPH FINAL 9 sections
Menstrual Relief HUMAN OTC DRUG LABEL 3 0363-0252 TABLET 60 mg ORAL OTC MONOGRAPH NOT FINAL 9 sections
migraine relief HUMAN OTC DRUG LABEL 3 0363-0374 TABLET, FILM COATED 65 mg ORAL ANDA 9 sections
Tension Headache Relief HUMAN OTC DRUG LABEL 2 0363-0428 TABLET, FILM COATED 65 mg ORAL OTC MONOGRAPH NOT FINAL 9 sections