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    Chemistry

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    Also known as: 58-08-2, Guaranine, 1,3,7-trimethylxanthine, Methyltheobromine, Theine, Thein
    Molecular Formula
    C8H10N4O2
    Molecular Weight
    194.19  g/mol
    InChI Key
    RYYVLZVUVIJVGH-UHFFFAOYSA-N
    FDA UNII
    3G6A5W338E
    Caffeine
    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.
    Caffeine is a Central Nervous System Stimulant and Methylxanthine. The physiologic effect of caffeine is by means of Central Nervous System Stimulation.
    1 2D Structure

    Caffeine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1,3,7-trimethylpurine-2,6-dione
    2.1.2 InChI
    InChI=1S/C8H10N4O2/c1-10-4-9-6-5(10)7(13)12(3)8(14)11(6)2/h4H,1-3H3
    2.1.3 InChI Key
    RYYVLZVUVIJVGH-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CN1C=NC2=C1C(=O)N(C(=O)N2C)C
    2.2 Other Identifiers
    2.2.1 UNII
    3G6A5W338E
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 1,3,7-trimethylxanthine

    2. Caffedrine

    3. Coffeinum N

    4. Coffeinum Purrum

    5. Dexitac

    6. Durvitan

    7. No Doz

    8. Percoffedrinol N

    9. Percutafine

    10. Quick Pep

    11. Quick-pep

    12. Quickpep

    13. Vivarin

    2.3.2 Depositor-Supplied Synonyms

    1. 58-08-2

    2. Guaranine

    3. 1,3,7-trimethylxanthine

    4. Methyltheobromine

    5. Theine

    6. Thein

    7. Cafeina

    8. Koffein

    9. Mateina

    10. Alert-pep

    11. Caffein

    12. Cafipel

    13. Coffeine

    14. Refresh'n

    15. Caffedrine

    16. Vivarin

    17. Anhydrous Caffeine

    18. Stim

    19. Cafamil

    20. Cafecon

    21. Caffine

    22. Dexitac

    23. Nodaca

    24. No-doz

    25. Eldiatric C

    26. 7-methyltheophylline

    27. Durvitan

    28. Hycomine

    29. Organex

    30. Nix Nap

    31. Methyltheobromide

    32. Coffeinum

    33. Coffein

    34. Phensal

    35. 1,3,7-trimethylpurine-2,6-dione

    36. 3,7-dihydro-1,3,7-trimethyl-1h-purine-2,6-dione

    37. Caffeine, Synthetic

    38. Quick-pep

    39. Synalgos

    40. Tirend

    41. 1,3,7-trimethyl-2,6-dioxopurine

    42. Theophylline, 7-methyl

    43. Dhcplus

    44. Tri-aqua

    45. 1h-purine-2,6-dione, 3,7-dihydro-1,3,7-trimethyl-

    46. Kofein

    47. Miudol

    48. Caffeine, Anhydrous

    49. Theobromine, 1-methyl-

    50. Propoxyphene Compound 65

    51. 1,3,7-trimethyl-3,7-dihydro-1h-purine-2,6-dione

    52. Kofein [czech]

    53. Coffein [german]

    54. Koffein [german]

    55. 1-methyltheobromine

    56. Caffeine (natural)

    57. Xanthine, 1,3,7-trimethyl

    58. Caffeina [italian]

    59. Theophylline Me

    60. Methylxanthine Theophylline

    61. Theobromine Me

    62. Nci-c02733

    63. Sk-65 Compound

    64. Anacin

    65. Anacin Maximum Strength

    66. Caffeine Anhydrous

    67. Fema No. 2224

    68. P-a-c Analgesic Tablets

    69. C8h10n4o2

    70. Hsdb 36

    71. Caffeinum

    72. Brn 0017705

    73. 1,3,7-trimethyl-2,3,6,7-tetrahydro-1h-purine-2,6-dione

    74. Nsc 5036

    75. A.s.a. And Codeine Compound

    76. 1,3,7-trimethyl-1h-purine-2,6(3h,7h)-dione

    77. Ai3-20154

    78. Nsc-5036

    79. Chembl113

    80. Caffeine Melting Point Standard

    81. Cff

    82. Chebi:27732

    83. 3g6a5w338e

    84. Mfcd00005758

    85. Caffenium

    86. Sk 65 Compound

    87. Caffeina

    88. Dsstox_cid_232

    89. Caffeine [ban:jan]

    90. Caffeine-d3

    91. Dsstox_rid_75448

    92. Dsstox_gsid_20232

    93. Cafeine

    94. Teina

    95. Cas-58-08-2

    96. Caffeine (usp)

    97. Smr000326667

    98. Ccris 1314

    99. Sr-01000075187

    100. Anhydrous Caffeine (tn)

    101. Einecs 200-362-1

    102. Monomethyl Derivative Of Theophylline

    103. Caffeine [usp:ban:jan]

    104. Anhydrous Caffeine (jp15)

    105. Unii-3g6a5w338e

    106. Caffeine Hydrous

    107. 1gfz

    108. Caffeine, Bioxtra

    109. Tnp00310

    110. Monohydrate Caffeine

    111. Respia (tn)

    112. 1-methyl-theobromine

    113. 7-methyl Theophylline

    114. Cafergot (salt/mix)

    115. 1,7-trimethylxanthine

    116. Spectrum_001301

    117. 1l5q

    118. 1l7x

    119. 2a3b

    120. 3g6m

    121. 3,7-dihydro-1,3,7-trimethyl-1h-purine

    122. Caffeine [fhfi]

    123. Caffeine [hsdb]

    124. Caffeine [iarc]

    125. Caffeine [inci]

    126. Caffeine [fcc]

    127. Xanthine,3,7-trimethyl

    128. Caffeine [ii]

    129. Caffeine [mi]

    130. Theine, Methyltheobromine

    131. Caffeine [vandf]

    132. Caffeinum [hpus]

    133. 1,3,7-trimethylxantine

    134. Spectrum2_001261

    135. Spectrum3_000321

    136. Spectrum4_001782

    137. Spectrum5_000423

    138. Lopac-c-0750

    139. Caffeine [mart.]

    140. Bmse000206

    141. Caffeine [usp-rs]

    142. Caffeine [who-dd]

    143. Caffeine [who-ip]

    144. Molmap_000054

    145. Probes1_000150

    146. Probes2_000128

    147. C 0750

    148. Ec 200-362-1

    149. Schembl5671

    150. Anhydrous Caffeine (jp17)

    151. Nciopen2_008255

    152. Bidd:pxr0172

    153. Lopac0_000228

    154. 1, 3, 7-trimethylxanthine

    155. Bspbio_001921

    156. Gtpl407

    157. Kbiogr_002325

    158. Kbioss_001781

    159. 1,3,7-trimethyl-1,3,7-trihydropurine-2,6-dione

    160. 5-26-13-00558 (beilstein Handbook Reference)

    161. 95789-13-2

    162. Mls001055341

    163. Mls001056714

    164. Mls001066409

    165. Bidd:er0554

    166. Bidd:gt0632

    167. Divk1c_000730

    168. Spectrum1500155

    169. Cu-01000012617-3

    170. Spbio_001222

    171. Caffeine [orange Book]

    172. Esgic Component Caffeine

    173. Triad Component Caffeine

    174. Megxp0_001350

    175. Zinc1084

    176. Caffeine [ep Monograph]

    177. Dimenhydrinate Impurity C

    178. Femcet Component Caffeine

    179. Trezix Component Caffeine

    180. 1,3,7-trimethyl-2,6-dioxo-1,2,3,6-tetrahydropurine

    181. Anhydrous Caffeine [jan]

    182. Caffeine [usp Monograph]

    183. Component Of Dilone (salt/mix)

    184. Dtxsid0020232

    185. 1,7-trimethyl-2,6-dioxopurine

    186. Acon1_000085

    187. Anoquan Component Caffeine

    188. Bdbm10849

    189. Hms502e12

    190. Kbio1_000730

    191. Kbio2_001781

    192. Kbio2_004349

    193. Kbio2_006917

    194. Kbio3_001141

    195. Caffeine 1.0 Mg/ml In Methanol

    196. Coffeinum [who-ip Latin]

    197. Nsc5036

    198. Cafergot Component Caffeine

    199. Caffeine, Powder, Reagentplus(r)

    200. Component Of Percodan (salt/mix)

    201. Excedrin Component Caffeine

    202. Fioricet Component Caffeine

    203. Fiorinal Component Caffeine

    204. Migergot Component Caffeine

    205. Ninds_000730

    206. Norgesic Component Caffeine

    207. Wigraine Component Caffeine

    208. Bio1_000473

    209. Bio1_000962

    210. Bio1_001451

    211. Caffeine Component Of Esgic

    212. Caffeine Component Of Triad

    213. Dhc Plus Component Caffeine

    214. Hms1920i09

    215. Hms2091o11

    216. Hms2232m13

    217. Hms3260n17

    218. Hms3372j18

    219. Hms3435f10

    220. Hms3715d13

    221. Pharmakon1600-01500155

    222. Invagesic Component Caffeine

    223. Lanorinal Component Caffeine

    224. Nodoz Caplets And Chewable Tablets

    225. Caffeine 10 Microg/ml In Methanol

    226. Caffeine Anhydrous [who-ip]

    227. Caffeine Component Of Femcet

    228. Cs-m0795

    229. Caffeine Component Of Anoquan

    230. Tox21_201685

    231. Tox21_300010

    232. Tox21_500228

    233. Caffeine (1,3,7-trimethylxanthine)

    234. Caffeine 100 Microg/ml In Methanol

    235. Ccg-38825

    236. Nsc755917

    237. Orphengesic Component Caffeine

    238. Pdsp1_001016

    239. Pdsp1_001235

    240. Pdsp2_001000

    241. Pdsp2_001219

    242. Stk177283

    243. Caffeine Component Of Cafergot

    244. Caffeine Component Of Dhc Plus

    245. Caffeine Component Of Excedrin

    246. Caffeine Component Of Fioricet

    247. Caffeine Component Of Fiorinal

    248. Caffeine Component Of Migergot

    249. Caffeine Component Of Norgesic

    250. Caffeine Component Of Wigraine

    251. Propoxyphene Compound 65 (salt/mix)

    252. Synalgos-dc Component Caffeine

    253. Akos000121334

    254. Caffeine Component Of Invagesic

    255. Caffeine Component Of Lanorinal

    256. 5-26-13-00558 (beilstein)

    257. Bayer Select Headache Pain (salt/mix)

    258. Caffeine, Anhydrous, 99%, Fcc, Fg

    259. Db00201

    260. Lp00228

    261. Nsc-755917

    262. Sdccgmls-0064595.p001

    263. Sdccgmls-0064595.p002

    264. Sdccgsbi-0050216.p005

    265. Caffeine Component Of Orphengesic

    266. Idi1_000730

    267. Medigesic Plus Component Caffeine

    268. Synalgos-dc-a Component Caffeine

    269. 3,3,7-trimethyl-1h-purine-2,6-dione

    270. Caffeine Component Of Synalgos-dc

    271. Darvon Compound Component Caffeine

    272. Invagesic Forte Component Caffeine

    273. Ncgc00015208-01

    274. Ncgc00015208-02

    275. Ncgc00015208-03

    276. Ncgc00015208-04

    277. Ncgc00015208-05

    278. Ncgc00015208-06

    279. Ncgc00015208-07

    280. Ncgc00015208-08

    281. Ncgc00015208-10

    282. Ncgc00015208-11

    283. Ncgc00015208-12

    284. Ncgc00015208-13

    285. Ncgc00015208-14

    286. Ncgc00015208-15

    287. Ncgc00015208-16

    288. Ncgc00015208-17

    289. Ncgc00015208-18

    290. Ncgc00015208-20

    291. Ncgc00015208-29

    292. Ncgc00090699-01

    293. Ncgc00090699-02

    294. Ncgc00090699-03

    295. Ncgc00090699-04

    296. Ncgc00090699-05

    297. Ncgc00090699-06

    298. Ncgc00090699-07

    299. Ncgc00090699-08

    300. Ncgc00090699-09

    301. Ncgc00168808-01

    302. Ncgc00168808-02

    303. Ncgc00254057-01

    304. Ncgc00259234-01

    305. Ncgc00260913-01

    306. Ac-12774

    307. As-15340

    308. Caffeine, Saj Special Grade, >=98.5%

    309. Component Of P-a-c Compound (salt/mix)

    310. Caffeine Component Of Synalgos-dc-a

    311. Component Of A.s.a. Compound (salt/mix)

    312. Orphengesic Forte Component Caffeine

    313. Sbi-0050216.p004

    314. Caffeine Component Of Medigesic Plus

    315. Db-023002

    316. Wln: T56 Bn Dn Fnvnvj B1 F1 H1

    317. Caffeine Component Of Darvon Compound

    318. Caffeine Component Of Invagesic Forte

    319. Eu-0100228

    320. Ft-0664195

    321. N1379

    322. N2379

    323. Theophylline Impurity A [ep Impurity]

    324. Caffeine Component Of Orphengesic Forte

    325. Bim-0050216.0001

    326. C07481

    327. D00528

    328. Dimenhydrinate Impurity C [ep Impurity]

    329. Pentoxifylline Impurity F [ep Impurity]

    330. Q60235

    331. 1,3,7-trimethyl-3,7-dihydropurine-2,6-dione

    332. 1h-purine-2, 3,7-dihydro-1,3,7-trimethyl-

    333. Ab00051930-09

    334. Ab00051930_10

    335. Caffeine, Purum, Anhydrous, >=99.0% (hplc)

    336. 3,7-dihydro-1,3,7-trimethyl-1h-purine (9ci)

    337. Caffeine, Anhydrous, Tested According To Ph.eur.

    338. L000155

    339. 3,7-dihydro-1,3,7-trimethyl-1h-purin-2,6-dion

    340. Caffeine, Sigma Reference Standard, Vial Of 250 Mg

    341. Sr-01000075187-1

    342. Sr-01000075187-4

    343. Sr-01000075187-7

    344. Sr-01000075187-8

    345. Brd-k02404261-001-02-7

    346. Brd-k02404261-001-03-5

    347. Brd-k02404261-001-07-6

    348. Caffeine, Certified Reference Material, Tracecert(r)

    349. Caffeine, Meets Usp Testing Specifications, Anhydrous

    350. Melting Point Standard 235-237c, Analytical Standard

    351. 1,3,7-trimethyl-3,7-dihydro-1h-purine-2,6-dione #

    352. Caffeine, British Pharmacopoeia (bp) Reference Standard

    353. Caffeine, European Pharmacopoeia (ep) Reference Standard

    354. F3371-0262

    355. Theophylline Monohydrate Impurity A [ep Impurity]

    356. Z112207564

    357. Caffeine 2000 Microg/ml In Water:methanol (81:19 G/g)

    358. 07e4fb58-fd79-4175-8e3d-05bf96954522

    359. 3,7-dihydro-1,3,7-trimethyl-1h-purin-2,6-dion (coffein)

    360. Caffeine Solution, Analytical Standard, 1.0 Mg/ml In Methanol

    361. Caffeine, United States Pharmacopeia (usp) Reference Standard

    362. Caffeine, Pharmaceutical Secondary Standard; Certified Reference Material

    363. Caffeine For System Suitability, European Pharmacopoeia (ep) Reference Standard

    364. Caffeine Melting Point Standard, United States Pharmacopeia (usp) Reference Standard

    365. Caffeine Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    366. 114303-55-8

    367. Caffeine Melting Point Standard, Pharmaceutical Secondary Standard; Certified Reference Material

    368. Caffeine, Pharmagrade, Ep, Manufactured Under Appropriate Gmp Controls For Pharma Or Biopharmaceutical Production

    369. Mettler-toledo Calibration Substance Me 18872, Caffeine, Analytical Standard, For The Calibration Of The Thermosystem 900, Traceable To Primary Standards (lgc)

    2.3.3 Other Synonyms

    1. Caffeine Mixture With Ergotamine

    2. Ergotamine Mixture With Caffeine

    3. Cafergamine

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 194.19 g/mol
    Molecular Formula C8H10N4O2
    XLogP3-0.1
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count0
    Exact Mass194.08037557 g/mol
    Monoisotopic Mass194.08037557 g/mol
    Topological Polar Surface Area58.4 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity293
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameCafcit
    PubMed HealthCaffeine Citrate (By mouth)
    Drug ClassesStimulant, Respiratory
    Active IngredientCaffeine citrate
    Dosage FormSolution
    RouteIntravenous; Oral
    Strengtheq 30mg base/3ml (eq 10mg base/ml)
    Market StatusPrescription
    CompanyEurohlth Intl

    2 of 6  
    Drug NameLanorinal
    PubMed HealthAspirin/Caffeine/Dihydrocodeine (By mouth)
    Drug ClassesAnalgesic, Opioid/Salicylate, Aspirin Combination
    Active Ingredientbutalbital; caffeine; Aspirin
    Dosage FormCapsule
    RouteOral
    Strength50mg; 325mg; 40mg
    Market StatusPrescription
    CompanyLannett

    3 of 6  
    Drug NameSynalgos-dc
    Active Ingredientdihydrocodeine bitartrate; caffeine; Aspirin
    Dosage FormCapsule
    RouteOral
    Strength30mg; 356.4mg; 16mg
    Market StatusPrescription
    CompanyCaraco

    4 of 6  
    Drug NameCafcit
    PubMed HealthCaffeine Citrate (By mouth)
    Drug ClassesStimulant, Respiratory
    Active IngredientCaffeine citrate
    Dosage FormSolution
    RouteIntravenous; Oral
    Strengtheq 30mg base/3ml (eq 10mg base/ml)
    Market StatusPrescription
    CompanyEurohlth Intl

    5 of 6  
    Drug NameLanorinal
    PubMed HealthAspirin/Caffeine/Dihydrocodeine (By mouth)
    Drug ClassesAnalgesic, Opioid/Salicylate, Aspirin Combination
    Active Ingredientbutalbital; caffeine; Aspirin
    Dosage FormCapsule
    RouteOral
    Strength50mg; 325mg; 40mg
    Market StatusPrescription
    CompanyLannett

    6 of 6  
    Drug NameSynalgos-dc
    Active Ingredientdihydrocodeine bitartrate; caffeine; Aspirin
    Dosage FormCapsule
    RouteOral
    Strength30mg; 356.4mg; 16mg
    Market StatusPrescription
    CompanyCaraco

    4.2 Therapeutic Uses

    Central Nervous System Stimulants; Phosphodiesterase Inhibitors; Purinergic P1 Receptor Antagonists

    National Library of Medicine's Medical Subject Headings. Caffeine. Online file (MeSH, 2014). Available from, as of January 30, 2014: https://www.nlm.nih.gov/mesh/2014/mesh_browser/MBrowser.html

    Caffeine is used orally as a mild CNS stimulant to aid in staying awake and to restore mental alertness in fatigued patients.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2567

    Apnea of prematurity. Caffeine citrate is used iv or orally in the short-term (10-12 days) treatment of apnea of prematurity in neonates who are between 28 and less than 33 weeks of gestational age. Caffeine is designated an orphan drug by the US Food and Drug Administration (FDA) for use in apnea in premature neonates.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2567

    Caffeine is used in combination with ergotamine tartrate to abort vascular headaches such as migraine and cluster headaches (histamine cephalalgia).

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2567

    For more Therapeutic Uses (Complete) data for CAFFEINE (11 total), please visit the HSDB record page.

    4.3 Drug Warning

    Because it has been suggested that caffeine may promote gastric ulceration, the drug should be used cautiously in patients with a history of peptic ulcer. Because of its suspected arrhythmogenic potential, it is generally recommended that caffeine be avoided in patients with symptomatic cardiac arrhythmias and/or palpitations and during the first several days to weeks after an acute myocardial infarction

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2568

    Prior to initiation of caffeine citrate therapy, baseline serum concentrations of caffeine should be measured in neonates previously treated with theophylline, since preterm neonates metabolize theophylline to caffeine. Similarly, baseline serum concentrations of caffeine should be measured in infants born to mothers who consumed caffeine prior to delivery since caffeine readily crosses the placenta. Serious toxicity has been reported when serum caffeine concentrations exceed 50 ug/mL. /Caffeine citrate/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2568

    In clinical trials reported in the literature, cases of hypoglycemia and hyperglycemia have been reported in patients receiving caffeine; therefore, blood glucose concentration may need to be monitored periodically in neonates receiving caffeine citrate. /Caffeine citrate/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2568

    During the placebo-controlled trial of caffeine citrate establishing efficacy in the US for apnea of prematurity, 6 cases of necrotizing enterocolitis developed among the 85 neonates studied, 3 cases of which were fatal. Five of the 6 neonates had been randomized to treatment with or had been exposed to caffeine citrate. Reports in the literature have raised the possibility of an association betwen the use of methylxanthines and the development of necrotizing enterocolitis, although a causal relationship between methylxanthine use and the development of necrotizing enterocolitis have not been established. Therefore, as with all premature neonates, patients being treated with caffeine citrate should be monitored carefully for the development of necrotizing enterocolitis. /Caffeine citrate/

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2568

    For more Drug Warnings (Complete) data for CAFFEINE (25 total), please visit the HSDB record page.

    4.4 Minimum/Potential Fatal Human Dose

    In adults, iv doses of 57 mg/kg and oral doses of 18-50 g have been fatal.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    In one 5-year-old patient, death occurred following oral ingestion of approximately 3 g of caffeine.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    4.5 Drug Indication

    Caffeine is indicated for the short term treatment of apnea of prematurity in infants and off label for the prevention and treatment of bronchopulmonary dysplasia caused by premature birth. In addition, it is indicated in combination with sodium benzoate to treat respiratory depression resulting from an overdose with CNS depressant drugs. Caffeine has a broad range of over the counter uses, and is found in energy supplements, athletic enhancement products, pain relief products, as well as cosmetic products.

    FDA Label

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Caffeine stimulates the central nervous system (CNS), heightening alertness, and sometimes causing restlessness and agitation. It relaxes smooth muscle, stimulates the contraction of cardiac muscle, and enhances athletic performance. Caffeine promotes gastric acid secretion and increases gastrointestinal motility. It is often combined in products with analgesics and ergot alkaloids, relieving the symptoms of migraine and other types of headaches. Finally, caffeine acts as a mild diuretic.

    5.2 MeSH Pharmacological Classification

    Phosphodiesterase Inhibitors

    Compounds which inhibit or antagonize the biosynthesis or actions of phosphodiesterases. (See all compounds classified as Phosphodiesterase Inhibitors.)

    Purinergic P1 Receptor Antagonists

    Compounds that bind to and block the stimulation of PURINERGIC P1 RECEPTORS. (See all compounds classified as Purinergic P1 Receptor Antagonists.)

    Central Nervous System Stimulants

    A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CAFFEINE
    5.3.2 FDA UNII
    3G6A5W338E
    5.3.3 Pharmacological Classes
    Central Nervous System Stimulation [PE]; Methylxanthine [EPC]; Xanthines [CS]; Central Nervous System Stimulant [EPC]
    5.4 ATC Code

    N06BC01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    D - Dermatologicals

    D11 - Other dermatological preparations

    D11A - Other dermatological preparations

    D11AX - Other dermatologicals

    D11AX26 - Caffeine

    N - Nervous system

    N06 - Psychoanaleptics

    N06B - Psychostimulants, agents used for adhd and nootropics

    N06BC - Xanthine derivatives

    N06BC01 - Caffeine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Caffeine is rapidly absorbed after oral or parenteral administration, reaching peak plasma concentration within 30 minutes to 2 hours after administration. After oral administration, onset of action takes place within 45 to 1 hour. Food may delay caffeine absorption. The peak plasma level for caffeine ranges from 6-10mg/L. The absolute bioavailability is unavailable in neonates, but reaches about 100% in adults.

    Route of Elimination

    The major metabolites of caffeine can be found excreted in the urine. About 0.5% to 2% of a caffeine dose is found excreted in urine, as it because it is heavily absorbed in the renal tubules.

    Volume of Distribution

    Caffeine has the ability to rapidly cross the blood-brain barrier. It is water and fat soluble and distributes throughout the body. Caffeine concentrations in the cerebrospinal fluid of preterm newborns are similar to the concentrations found in the plasma. The mean volume of distribution of caffeine in infants is 0.8-0.9 L/kg and 0.6 L/kg in the adult population.

    Clearance

    The clearance of caffeine varies, but on average, is about 0.078L/kg/h (1.3mL/min/kg).

    World-wide, many fetuses and infants are exposed to methylxanthines via maternal consumption of coffee and other beverages containing these substances. Methylxanthines (caffeine, theophylline and aminophylline) are also commonly used as a medication for apnea of prematurity. ... Methylxanthines readily passes the placenta barrier and enters all tissues and thus may affect the fetus/newborn at any time during pregnancy or postnatal life, given that the effector systems are mature. ...

    PMID:20859804 Aden U; Handb Exp Pharmacol (200): 373-89 (2011)

    Caffeine and citrated caffeine are well absorbed following oral administration. Absorption of caffeine following oral administration may be more rapid than that following IM injection of caffeine and sodium benzoate. Absorption following rectal administration of caffeine in suppositories may be slow and erratic. ... Following oral administration of 100 mg of caffeine (as coffee), peak plasma concentrations of about 1.5-1.8 ug/mL are reached after 50-75 minutes.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    After oral administration of 10 mg caffeine base/kg to preterm neonates, the peak plasma concentration for caffeine ranged from 6-10 mg/L and the mean time to reach peak concentration /Tmax/ ranged from 30 minutes to 2 hours. The /Tmax/ was not affected by formula feeding.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    Caffeine is rapidly distributed into body tissues, readily crossing the placenta and blood-brain barrier. Caffeine concentration in the CSF fluid of preterm neonates approximates the plasma concentration. The mean volume of distribution of caffeine in infants (0.8-0.9 L/kg) is slightly higher than that in adults (0.6 L/kg). ... Caffeine has been shown to distribute into milk in a milk-to-serum concentration ratio of 0.5-0.76.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    For more Absorption, Distribution and Excretion (Complete) data for CAFFEINE (11 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    Caffeine metabolism occurs mainly in the liver via the cytochrome CYP1A2 enzyme. The products of caffeine metabolism include paraxanthine, theobromine, and theophylline. The first step of caffeine metabolism is demethylation, yielding paraxanthine (a major metabolite), followed by theobromine, and theophylline, which are both minor metabolites. They are then excreted in urine as urates after additional metabolism. The enzymes xanthine oxidase and N-acetyltransferase 2 (NAT2) also participate in the metabolism of caffeine.

    Caffeine is metabolized by the cytochrome P-450 (CYP) enzyme system, principally by isoenzyme 1A2. Therefore, caffeine has the potential to interact with drugs that are metabolized by CYP1A2 or with drugs that induce or inhibit this isoenzyme.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    In adults, the drug is rapidly metabolized in the liver to 1-methyluric acid, 1-methylxanthine, and 7-methylxanthine.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    Interconversion between caffeine and theophylline has been reported in preterm neonates...

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    In-vivo and in-vitro experiments showed a progressive increase in the activity of the hepatic microsomal enzymes that metabolize caffeine during neonatal development. In beagle puppies, change in caffeine clearance was determined by the rate of maturation of caffeine-7-demethylase. Caffeine is eliminated in animals by biotransformation in the liver to dimethylxanthines, dimethyl- and monomethyluric acids and uracil derivatives; important quantitative differences have been demonstrated in the formation and elimination of metabolites in rats, mice and Chinese hamsters. These differences are even more important in monkeys, where caffeine is almost completely metabolized to theophylline. ... Some species-dependent metabolites have been identified. Trimethylallantoin was first reported in rats. A ... derivative of paraxanthine was found in mice and identified as the 3-beta-D-glucuronide of paraxanthine. Methylated ureas and sulfur-containing derivatives found in urine in trace amounts are produced by the intestinal flora. In contrast, the acetylated uracil derivative, 5-acetylamino-6-formylamino-3-methyluracil, one of the most important caffeine metabolites in humans, has not been identified in rodents or other animal species. Other uracil derivatives produced from caffeine, theobromine and paraxanthine in rats were found in human urine. In rats, the hepatic demethylation of caffeine shows an age-related decline, resulting in a greatly increased elimination half-time in older adult rats.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 322 (1991)

    Caffeine metabolism is qualitatively relatively similar in animals and humans ... . The main metabolic pathways are: demethylation and hydroxylation of the 8-position leading to the formation of the respective uracil and uric acid derivatives. There are, however, some quantitative differences in the metabolic profile. Humans are characterized by the importance of 3-methyl demethylation leading to the formation of paraxanthine and especially metabolites thereof through subsequent metabolic steps. The main urinary metabolites in humans are 1-methyluric acid, 1-methylxanthine, 5-acetylamino-6-formylamino-3- methyluracil (not found in rats and mice), 1,7-dimethyluric acid and paraxanthin. In rats and mice, the metabolism of caffeine is predominantly via theobromine and theophylline. The main urinary metabolites are 1,3-dimethyluracil, paraxanthine, trimethyluric acid, theophylline, and theobromine. Caffeine metabolism decreases during pregnancy, resulting in higher serum concentrations.

    OECD SIDS for Caffeine (CAS 58-08-2); Available from, as of January 9, 2014: https://www.inchem.org/documents/sids/sids/CAFEINE.pdf

    Caffeine has known human metabolites that include 1,3,7-Trimethyluric acid, Theobromine, paraxanthine, and theophylline.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Biological Half-Life

    In an average-sized adult or child above the age of 9, the half-life of caffeine is approximately 5 hours. Various characteristics and conditions can alter caffeine half-life. It can be reduced by up to 50% in smokers. Pregnant women show an increased half-life of 15 hours or higher, especially in the third trimester. The half-life in newborns is prolonged to about 8 hours at full-term and 100 hours in premature infants, likely due to reduced ability to metabolize it. Liver disease or drugs that inhibit CYP1A2 can increase caffeine half-life.

    Elimination 1/2 life in adults = 2.5-4.5 hours; [Reference #1]

    Caffeine has a plasma half-life (t1/2) of 3 to 5 hours in adults. In one study, when administered to pregnant women prior to delivery, caffeine had a prolonged mean half-life of 80 hours in neonates after delivery.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    Mean half-life /T 1/2/ and fraction excreted unchanged in urine of caffeine in infants have been shown to be inversely related to gestational/postconceptual age. In neonates, the /T 1/2/ is approximately 3-4 days...

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    The half-time for caffeine is 0.7-1.0 hr in rats and mice, 1-1.6 hr in rabbits, 3-5 hr in monkeys, 4-4.3 hr in dogs and 11-12 hr in baboons.

    IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V51 321 (1991)

    /The authors/ studied 17 preterm infants receiving caffeine, and measured their plasma levels of caffeine and the theophylline metabolite by high-pressure liquid chromatography. The half-life was calculated by computer analysis using the least-square method. The mean gestational age of our patients was 29.7 +/- 1.9 weeks (mean +/- SD) and they were studied at 20.7 +/- 6.6 days (mean +/- SD) postnatal age. The caffeine half-life was 52.03 +/- 23.87 hr (means +/- SD) and the theophylline half-life was 77.04 +/- 65.01 hr (mean +/- SD).

    PMID:2714159 Pearlman SA et al; Dev Pharmacol Ther 12 (2): 65-9 (1989)

    5.8 Mechanism of Action

    The mechanism of action of caffeine is complex, as it impacts several body systems, which are listed below. The effects as they relate to various body systems are described as follows: **General and cellular actions** Caffeine exerts several actions on cells, but the clinical relevance is poorly understood. One probable mechanism is the inhibition of nucleotide phosphodiesterase enzymes, adenosine receptors, regulation of calcium handling in cells, and participates in adenosine receptor antagonism. Phosphodiesterase enzymes regulate cell function via actions on second messengers cAMP and cGMP. This causes lipolysis through activation of hormone-sensitive lipases, releasing fatty acids and glycerol. **Respiratory** The exact mechanism of action of caffeine in treating apnea related to prematurity is unknown, however, there are several proposed mechanisms, including respiratory center stimulation in the central nervous system, a reduced threshold to hypercapnia with increased response, and increased consumption of oxygen, among others. The blocking of the adenosine receptors enhances respiratory drive via an increase in brain medullary response to carbon dioxide, stimulating ventilation and respiratory drive, while increasing contractility of the diaphragm. **Central nervous system** Caffeine demonstrates antagonism of all 4 adenosine receptor subtypes (A1, A2a, A2b, A3) in the central nervous system. Caffeine's effects on alertness and combatting drowsiness are specifically related to the antagonism of the A2a receptor. **Renal system** Caffeine has diuretic effects due to is stimulatory effects on renal blood flow, increase in glomerular filtration, and increase in sodium excretion. **Cardiovascular system** Adenosine receptor antagonism at the A1 receptor by caffeine stimulates inotropic effects in the heart. Blocking of adenosine receptors promotes catecholamine release, leading to stimulatory effects occurring in the heart and the rest of the body. In the blood vessels, caffeine exerts direct antagonism of adenosine receptors, causing vasodilation. It stimulates the endothelial cells in the blood vessel wall to release nitric oxide, potentiating blood vessel relaxation. Catecholamine release, however, antagonizes this and exerts inotropic and chronotropic effects on the heart, ultimately leading to vasoconstriction. Finally, caffeine is shown to raise systolic blood pressure measurements by 5 to 10 mmHg when it is not taken regularly, versus no effect in those who consume it regularly. The vasoconstricting effects of caffeine are beneficial in migraines and other types of headache, which are normally caused by vasodilation in the brain.

    Caffeine competitively inhibits phosphodiesterase, the enzyme that degrades cyclic 3',5'-adenosine monophosphate (AMP). Increased levels of intracellular cyclic AMP mediate most of caffeine's pharmacologic actions.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    Caffeine stimulates all levels of the CNS... Caffeine's cortical effects are milder and of shorter duration than those of amphetamines. In slightly larger doses, caffeine stimulates medullary, vagal, vasomotor, and respiratory centers, promoting bradycardia, vasoconstriction, and increased respiratory rate.

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

    Caffeine constricts cerebral vasculature. In contrast, the drug directly dilates peripheral blood vessels...

    American Society of Health-System Pharmacists 2013; Drug Information 2013. Bethesda, MD. 2013, p. 2569

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    04-Jan-2021
    30-Nov-2024
    KGS
    overview
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    Average Price (USD/KGS)

    Number of Transactions

    Total Quantity (KGS)

    Total Value (USD)

    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DRUG PRODUCT COMPOSITIONS

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    DOSAGE - CAPSULE;ORAL - 356.4MG;30MG;16MG

    USFDA APPLICATION NUMBER - 11483

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    USFDA APPLICATION NUMBER - 19429

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    USFDA APPLICATION NUMBER - 20232

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    DOSAGE - TABLET;ORAL - 250MG;250MG;65MG

    USFDA APPLICATION NUMBER - 20802

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    DOSAGE - TABLET;ORAL - 100MG;1MG

    USFDA APPLICATION NUMBER - 84294

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    DOSAGE - TABLET;ORAL - 325MG;50MG;40MG

    USFDA APPLICATION NUMBER - 86162

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    DOSAGE - TABLET;ORAL - 325MG;50MG;40MG

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