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    Chemistry

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    Also known as: 51481-61-9, Tagamet, Acinil, Ulcedin, Eureceptor, Gastromet
    Molecular Formula
    C10H16N6S
    Molecular Weight
    252.34  g/mol
    InChI Key
    AQIXAKUUQRKLND-UHFFFAOYSA-N
    FDA UNII
    80061L1WGD
    Cimetidine
    A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.
    Cimetidine is a Histamine-2 Receptor Antagonist. The mechanism of action of cimetidine is as a Histamine H2 Receptor Antagonist.
    1 2D Structure

    Cimetidine

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine
    2.1.2 InChI
    InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)
    2.1.3 InChI Key
    AQIXAKUUQRKLND-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC1=C(N=CN1)CSCCNC(=NC)NC#N
    2.2 Other Identifiers
    2.2.1 UNII
    80061L1WGD
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Altramet

    2. Biomet

    3. Biomet400

    4. Cimetidine Hcl

    5. Cimetidine Hydrochloride

    6. Eureceptor

    7. Hcl, Cimetidine

    8. Histodil

    9. Hydrochloride, Cimetidine

    10. N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)guanidine

    11. Sk And F 92334

    12. Sk And F-92334

    13. Sk And F92334

    14. Skf 92334

    15. Skf-92334

    16. Skf92334

    17. Tagamet

    2.3.2 Depositor-Supplied Synonyms

    1. 51481-61-9

    2. Tagamet

    3. Acinil

    4. Ulcedin

    5. Eureceptor

    6. Gastromet

    7. Dyspamet

    8. Tametin

    9. Ulcimet

    10. Cimal

    11. Ulcedine

    12. Ulcomedina

    13. Cimetag

    14. Tratul

    15. Skf-92334

    16. Acibilin

    17. Cimetum

    18. Edalene

    19. Ulcomet

    20. Ulhys

    21. Tagamet Hb

    22. Tagamet Hb 200

    23. Cimetidina

    24. Cimetidinum

    25. Valmagen

    26. Brumetidina

    27. N-cyano-n'-methyl-n''-[2-[[(4-methyl-1h-imidazol-5-yl)methyl]thio]ethyl]guanidine

    28. Skf 92334

    29. 1-cyano-2-methyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

    30. Stomedine

    31. Aciloc

    32. 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine

    33. 1-cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine

    34. Nsc-335308

    35. Chebi:3699

    36. N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)guanidine

    37. Chembl30

    38. Metracin

    39. Brumetadina

    40. 2-cyano-1-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

    41. Mls000069791

    42. 76181-71-0

    43. Gastrobitan

    44. Ulcestop

    45. Ulcofalk

    46. Evicer

    47. Peptol

    48. 80061l1wgd

    49. 51481-61-9 (free)

    50. Guanidine, N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)-

    51. Guanidine, N-cyano-n'-methyl-n''-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-

    52. Guanidine, N-cyano-n'-methyl-n''-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-, (z)-

    53. Nsc 335308

    54. 2984-61-4

    55. Ncgc00015240-06

    56. Smr000038895

    57. Cimetidine 100 Microg/ml In Acetonitrile

    58. Dsstox_cid_329

    59. 2-cyano-1-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

    60. Dsstox_rid_75517

    61. Guanidine, N''-cyano-n-methyl-n'-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)-

    62. N''-cyano-n-methyl-n'-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

    63. N-cyano-n'-methyl-n''-(2-([(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine

    64. Cimetidinum [inn-latin]

    65. Dsstox_gsid_20329

    66. Cimetidina [inn-spanish]

    67. Drg-0150

    68. (e)-2-cyano-1-methyl-3-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)guanidine

    69. (z)-3-cyano-1-methyl-2-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

    70. 1-cyano-2-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

    71. 2-cyano-1-methyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

    72. Guanidine, N''-cyano-n-methyl-n'-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-

    73. Tagamet (tn)

    74. Ccris 3247

    75. Equaline Acid Reducer

    76. Hsdb 3917

    77. Topcare Heartburn Relief

    78. Sr-01000075260

    79. Sr-05000001434

    80. Fpf 1002

    81. Einecs 257-232-2

    82. Mfcd00133296

    83. Cemitidine

    84. Metidine

    85. Unii-80061l1wgd

    86. 1-cyano-2-methyl-3-(2-((5-methyl-1h-imidazol-4-yl)methylthio)ethyl)guanidine

    87. 1-cyano-2-methyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylthio]ethyl]guanidine

    88. Cimetidine,(s)

    89. Prestwick_65

    90. Cimetidine (tagamet)

    91. Cimetidine [usan:usp:inn:ban:jan]

    92. Cimetidine A

    93. Spectrum_000495

    94. Tocris-0902

    95. Cimetidine [mi]

    96. Opera_id_314

    97. Cimetidine [inn]

    98. Cimetidine [jan]

    99. Prestwick3_000026

    100. Spectrum2_000782

    101. Spectrum3_001389

    102. Spectrum4_000812

    103. Spectrum5_001541

    104. Cimetidine [hsdb]

    105. Cimetidine [iarc]

    106. Cimetidine [usan]

    107. Lopac-c-4522

    108. Cimetidine [vandf]

    109. Upcmld-dp029

    110. 2-cyano-1-methyl-3-[2-(5-methyl-1h-imidazol-4-yl-methylthio)ethyl]guanidine

    111. C 4522

    112. Cimetidine [mart.]

    113. Schembl1093

    114. Schembl1094

    115. Skf-92334; Tagamet

    116. Cimetidine [usp-rs]

    117. Cimetidine [who-dd]

    118. Cimetidine [who-ip]

    119. Guanidine, N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio) Ethyl)-

    120. Lopac0_000293

    121. Bspbio_000091

    122. Bspbio_002978

    123. Kbiogr_001323

    124. Kbioss_000975

    125. Us9138393, Cimetidine

    126. Us9144538, Cimetidine

    127. Mls001148596

    128. Mls002153265

    129. Mls002154178

    130. Divk1c_000166

    131. Spectrum1500684

    132. Spbio_000884

    133. Bpbio1_000101

    134. Cimetidine (jp17/usp/inn)

    135. Gtpl1231

    136. Cimetidine [orange Book]

    137. Dtxsid4020329

    138. Schembl11282982

    139. Upcmld-dp029:001

    140. Bdbm22889

    141. Cimetidine For System Suitability

    142. Hms500i08

    143. Kbio1_000166

    144. Kbio2_000975

    145. Kbio2_003543

    146. Kbio2_006111

    147. Kbio3_002198

    148. Cimetidine [ep Monograph]

    149. Cimetidine For Peak Identification

    150. Ninds_000166

    151. Bdbm181119

    152. Cimetidine [usp Monograph]

    153. Hms1921c14

    154. Hms2089o03

    155. Hms2092i14

    156. Hms2095e13

    157. Hms2232f16

    158. Hms3259m15

    159. Hms3260l08

    160. Hms3267a03

    161. Hms3369l10

    162. Hms3414i17

    163. Hms3651e21

    164. Hms3678i17

    165. Hms3712e13

    166. Hms3750i05

    167. Hms3884i12

    168. Pharmakon1600-01500684

    169. Cimetidine 1.0 Mg/ml In Methanol

    170. Cimetidinum [who-ip Latin]

    171. Ex-a1088

    172. Tox21_110106

    173. Tox21_201160

    174. Tox21_500293

    175. Bdbm50103595

    176. Bdbm50403559

    177. Ccg-40160

    178. Nsc335308

    179. Nsc757428

    180. S1845

    181. Stk528249

    182. Zinc18115268

    183. 1-cyano-2-methyl-3-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]guanidine

    184. Akos005460997

    185. Akos015900557

    186. Akos015951369

    187. Akos016003398

    188. Akos016340377

    189. Akos026749950

    190. Akos032949548

    191. Tox21_110106_1

    192. Ab03708

    193. Ac-8100

    194. Ccg-204388

    195. Ccg-220026

    196. Ccg-221597

    197. Db00501

    198. Ks-5087

    199. Lp00293

    200. Nc00501

    201. Nsc 757428

    202. Nsc-757428

    203. Sdccgsbi-0050281.p005

    204. Idi1_000166

    205. N''-cyano-n-methyl-n'-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

    206. N''-cyano-n-methyl-n'-[2-[(5-methyl-1h-imidazol-4-yl)methylthio]ethyl]guanidine

    207. N-cyano-n'-methyl-[2-[[[5-methyl-1h-imidazol-4-yl]methyl]thio]ethyl]guanidine

    208. Ncgc00015240-01

    209. Ncgc00015240-02

    210. Ncgc00015240-03

    211. Ncgc00015240-04

    212. Ncgc00015240-05

    213. Ncgc00015240-07

    214. Ncgc00024859-01

    215. Ncgc00024859-02

    216. Ncgc00024859-03

    217. Ncgc00024859-04

    218. Ncgc00024859-05

    219. Ncgc00091439-01

    220. Ncgc00091439-02

    221. Ncgc00091439-03

    222. Ncgc00091439-04

    223. Ncgc00091439-05

    224. Ncgc00091439-07

    225. Ncgc00091439-10

    226. Ncgc00185989-01

    227. Ncgc00188961-01

    228. Ncgc00258712-01

    229. Ncgc00260978-01

    230. Hy-14289

    231. Nci60_002936

    232. Sbi-0050281.p004

    233. Db-051971

    234. Eu-0100293

    235. Ft-0602955

    236. Sw196380-2

    237. C06952

    238. D00295

    239. F16651

    240. Ab00052157-03

    241. Ab00052157_04

    242. Ab00052157_05

    243. 481c619

    244. A828616

    245. L000186

    246. L003827

    247. L013434

    248. Q409492

    249. Sr-05000001750

    250. Q-200855

    251. Q-200856

    252. Sr-01000075260-1

    253. Sr-01000075260-3

    254. Sr-05000001434-1

    255. Sr-05000001434-2

    256. Sr-05000001750-1

    257. Brd-k18618618-001-01-6

    258. Brd-k34157611-001-04-6

    259. Brd-k34157611-001-07-9

    260. Z1259192068

    261. Cimetidine, European Pharmacopoeia (ep) Reference Standard

    262. Cimetidine, United States Pharmacopeia (usp) Reference Standard

    263. 1-ethyl-2,3-dimethylimidazolium Tosylate, 98% [edimim] [tos]

    264. 1-cyan-2-methyl-3-(2-{[(5-methylimidazol-4-yl)methyl]thio}ethyl)guanidin

    265. Cimetidine, Pharmaceutical Secondary Standard; Certified Reference Material

    266. N"-cyano-n-methyl-n'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]-guanidine

    267. N"-cyano-n-methyl-n'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine

    268. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine

    269. N-cyano-n'-methyl-n"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine

    270. N-cyano-n'-methyl-n"-[2-(5-methyl-4-imidazolylmethylthio)ethyl]guanidine

    271. (z)-1-cyano-2-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

    272. (z)-n''-cyano-n-methyl-n'-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

    273. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)-benzenesulfonamide(cimetidine)

    274. 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)-guanidine

    275. 2-methyl-8-phenethyl-imidazo[1,2-a]pyridine-3-carboxylic Acid Methyl Ester(cimetidine)

    276. 2-methylamino-2-[2-(4-methyl-1h-5-imidazolylmethylsulfanyl)ethylamino]-(e)-1-imino Cyanide

    277. 3-cyano-2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

    278. 4-(((2-(((cyanoamino)(methylamino)methylene)amino)ethyl)thio)methyl)-5-methyl-1h-imidazole

    279. Cimetidine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

    280. Cimetidine For System Suitability, European Pharmacopoeia (ep) Reference Standard

    281. Guanidine, N-cyano-n'-methyl-n''-[2-[[5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-

    282. N''-cyano-n-methyl-n'-(2-((5-methyl-1h-imidazol-4-yl)-methylthio)ethyl)guanidine

    283. N-cyano-n'-methyl-n"- [2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine

    284. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl) Methylthio)ethyl]guanidine

    285. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)- Methylthio)ethyl]guanidine

    286. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine

    287. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)methyl-thio)ethyl]guanidine

    288. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl) Guanidine

    289. N-cyano-n'-methyl-n"-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]guanidine

    290. N-cyano-n'-methyl-n"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-guanidine

    291. N-cyano-n'-methyl-n"-[2-{(5-methyl-1h-imidazol-4-yl)methylthio}ethyl]guanidine

    292. N-cyano-n'-methyl-n''-(2-([(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine #

    293. N-cyano-n'-methyl-n''-[2-[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]guanidine

    294. N-cyano-n'-methyl-n''-[2-[[(5-methylimidazol-4-yl]methyl]thio]ethyl)guanidine

    295. N-cyano-n'-methyl-n-"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine

    296. N-methyl-n'-{2-[(5-methylimidazol-4-yl)-methylthio]-ethyl}-n"-cyanoguanidine

    297. N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]-1-cyanoiminomethanediamine

    298. N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]imino(-n-cyano)methanediaminem

    299. N-tert-butyl-n''''''''-[4-(1h-imidazol-4-yl)-phenyl]-formamidine(cimetidine)

    300. (cimetidine) N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine,cyanide

    301. (cimetidine) N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]cyanoiminomethanediamine

    302. (cimetidine)n-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]cyanomethyliminomethanediamine

    303. 2-methylamino-2-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethylamino]-(z)-1-imino Cyanide(cimetidine)

    304. Guanidine,n-cyano-n'-methyl-n''-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-,(z)-

    305. N''''''''''''''''''''''''''''''''-cyano-n-methyl-n''''''''''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

    306. N''''''''''''''''-cyano-n-methyl-n''''''''-({[(5-methyl-1h-imidazol-4-yl)methyl]thio}methyl)guanidine(cimetidine)

    307. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]-lambda~4~-sulfanyl}ethyl)guanidine

    308. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

    309. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine (cimetidine)

    310. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine(cimetidine)

    311. N-cyano-n''''''''-methyl-n''''''''''''''''-(2-(((5-methyl-1h-imidazol-4-yl) Methyl)thio)ethyl)guanidine(cimetidine)

    312. N-cyanomethyl-n''''''''-methyl-n''''''''''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine ( Cimetidine)

    313. N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-cyanoguanidine(cimetidine)

    314. N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-n''''''''''''''''-cyano-guanidine

    315. N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-n''''''''''''''''-cyano-guanidine(cimetidine)

    316. N-methyl-n''''''''-cyano-n''''''''''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine

    317. N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]cyanoiminomethanediamine (cimetidine)

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 252.34 g/mol
    Molecular Formula C10H16N6S
    XLogP30.4
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count4
    Rotatable Bond Count7
    Exact Mass252.11571571 g/mol
    Monoisotopic Mass252.11571571 g/mol
    Topological Polar Surface Area114 Ų
    Heavy Atom Count17
    Formal Charge0
    Complexity296
    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 4  
    Drug NameCimetidine
    PubMed HealthCimetidine
    Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
    Drug LabelCimetidine is a histamine H2-receptor antagonist. Chemically it is N"-cyano-N-methyl-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]-ethyl]guanidine. Its structural formula is:Cimetidine contains an imidazole ring, and is chemically related to h
    Active IngredientCimetidine
    Dosage FormTablet
    RouteOral
    Strength300mg; 200mg; 100mg; 800mg; 400mg
    Market StatusOver the Counter; Prescription
    CompanyIvax Sub Teva Pharms; Teva; Apotex; Perrigo; Contract Pharmacal; Pliva; Mylan; Dava Pharms

    2 of 4  
    Drug NameTagamet hb
    Active IngredientCimetidine
    Dosage FormTablet
    RouteOral
    Strength200mg
    Market StatusOver the Counter
    CompanyMedtech Prods

    3 of 4  
    Drug NameCimetidine
    PubMed HealthCimetidine
    Drug ClassesAntiulcer, Gastric Acid Secretion Inhibitor
    Drug LabelCimetidine is a histamine H2-receptor antagonist. Chemically it is N"-cyano-N-methyl-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]-ethyl]guanidine. Its structural formula is:Cimetidine contains an imidazole ring, and is chemically related to h
    Active IngredientCimetidine
    Dosage FormTablet
    RouteOral
    Strength300mg; 200mg; 100mg; 800mg; 400mg
    Market StatusOver the Counter; Prescription
    CompanyIvax Sub Teva Pharms; Teva; Apotex; Perrigo; Contract Pharmacal; Pliva; Mylan; Dava Pharms

    4 of 4  
    Drug NameTagamet hb
    Active IngredientCimetidine
    Dosage FormTablet
    RouteOral
    Strength200mg
    Market StatusOver the Counter
    CompanyMedtech Prods

    4.2 Therapeutic Uses

    Adjuvants, Immunologic; Analgesics, Non-Narcotic; Anti-Ulcer Agents; Enzyme Inhibitors; Histamine H2 Antagonists

    National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

    IN MAN, A SINGLE DOSE (300 MG) WILL INHIBIT BASAL (FASTING) SECRETION AND ALSO SECRETION INDUCED BY SOLID, LIQ, OR PEPTONE MEALS, SHAM FEEDING, FUNDIC DISTENTION, PENTAGASTRIN, BETHANECHOL, INSULIN, AND CAFFEINE, AS WELL AS THE PHYSIOLOGICAL STIMULUS PROVIDED BY EATING. ... THIS SPECTRUM INCL THE CEPHALIC OR VAGAL PHASE.

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 631

    CIMETIDINE IS THE PREFERRED ALTERNATIVE FOR MANY PATIENTS WHO CANNOT OR WILL NOT TOLERATE AN INTENSIVE, PROLONGED ANTACID REGIMEN.

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 899

    Cimetidine is a useful alternative to antacids in preventing aspiration pneumonitis during childbirth and elective surgical procedures. It is less useful than antacids during emergency surgery because of its slow onset of action. This drug had been given to prevent alkalosis in patients subjected to prolonged nasogastric aspiration, especially those secreting large amounts of acid, and to decrease ileostomy/jejunostomy output in the short bowel syndrome.

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 899

    For more Therapeutic Uses (Complete) data for CIMETIDINE (21 total), please visit the HSDB record page.

    4.3 Drug Warning

    DESPITE POOR PENETRATION TO THE CNS, NEURAL DYSFUNCTION HAS BEEN ENCOUNTERED, PARTICULARLY WITH HIGH DOSES IN ELDERLY PATIENTS AND IN ASSOCIATION WITH IMPAIRED RENAL EXCRETION. THE EFFECTS INCL CONFUSION, SLURRED SPEECH, DELIRIUM, HALLUCINATIONS, AND COMA.

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 631

    IN SOME INSTANCES, WITHDRAWAL OF CIMETIDINE AFTER A PERIOD OF TREATMENT HAS BEEN FOLLOWED BY RELAPSES IN THE SYMPTOMS OF ULCER AND EVEN BY PERFORATION OF DUODENAL, ESOPHAGEAL, OR GASTRIC ULCERS.

    Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 632

    ... CIMETIDINE IS INEFFECTIVE IN ACUTE OR ALCOHOLIC PANCREATITIS AND IT MAY ACTUALLY INCR AND PROLONG HYPERAMYLASEMIA.

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 899

    ... CLIN EXPERIENCE IN CHILDREN IS EXTREMELY LIMITED, AND THE BENEFIT/RISK RATIO SHOULD BE CONSIDERED CAREFULLY.

    American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 771

    For more Drug Warnings (Complete) data for CIMETIDINE (15 total), please visit the HSDB record page.

    4.4 Drug Indication

    Cimetidine is indicated to reduce gastric acid secretion and to treat the following disease states: duodenal ulcers, non-malignant gastric ulcers, gastroesophageal reflux disease, and pathological hypersecretion associated with Zollinger-Ellison Syndrome, systemic mastocytosis, and multiple endocrine adenomas. It is indicated for prophylaxis of recurrent gastric or duodenal ulcers, as adjunctive therapy in the management of cystic fibrosis in children, and to treat NSAID induced lesions and gastrointestinal symptoms.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Cimetidine is a histamine H2-receptor antagonist. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin. It is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Cimetidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Cimetidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.

    5.2 MeSH Pharmacological Classification

    Cytochrome P-450 CYP1A2 Inhibitors

    Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)

    Histamine H2 Antagonists

    Drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of histamine. Their clinically most important action is the inhibition of acid secretion in the treatment of gastrointestinal ulcers. Smooth muscle may also be affected. Some drugs in this class have strong effects in the central nervous system, but these actions are not well understood. (See all compounds classified as Histamine H2 Antagonists.)

    Anti-Ulcer Agents

    Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    CIMETIDINE
    5.3.2 FDA UNII
    80061L1WGD
    5.3.3 Pharmacological Classes
    Histamine-2 Receptor Antagonist [EPC]; Histamine H2 Receptor Antagonists [MoA]
    5.4 ATC Code

    A - Alimentary tract and metabolism

    A02 - Drugs for acid related disorders

    A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

    A02BA - H2-receptor antagonists

    A02BA01 - Cimetidine

    5.5 Absorption, Distribution and Excretion

    Absorption

    Two peak plasma concentrations are often observed after oral administration of cimetidine, likely as a result of discontinuous absorption in the gastrointestinal tract. In healthy patients, the absolute bioavailability of cimetidine is approximately 60%; however, the bioavailability can be as high as 70% in patients with peptic ulcer disease. Overall, rates of bioavailability are much more variable in patients with peptic ulcer disease.

    Route of Elimination

    Cimetidine is excreted primarily in the urine.

    Volume of Distribution

    The volume of distribution of cimetidine is reported to be 1 L/kg.

    Clearance

    Cimetidine's reported systemic clearance value is approximately 500-600 ml/min.

    About 15% of cimetidine is metabolized in the liver. Seventy percent is excreted unchanged in the urine, with fecal losses accounting for approximately 10%.

    Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 434

    Given orally, cimetidine and ranitidine are almost completely absorbed. Because of first-pass metabolism in the liver, the bioavailability is 50-60%. Both drugs are little bound to plasma proteins (10-20%).

    Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 824

    Both drugs are mainly excreted in urine - cimetidine up to 90% within 24 hr (50-75% unchanged) and ranitidine up to 60% within 24 hr (about 40% unchanged). The apparent volume of distribution is quite large, in the range of 1.5 l/kg bw, demonstrating that nearly all drug exists outside the intravascular space.

    Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 824

    Cimetidine is widely distributed throughout the body and is 15-20% bound to plasma proteins. Animal studies indicate that the drug crosses the placenta. Cimetidine is distributed into milk.

    McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2140

    For more Absorption, Distribution and Excretion (Complete) data for CIMETIDINE (14 total), please visit the HSDB record page.

    5.6 Metabolism/Metabolites

    After intravenous administration of cimetidine, the majority of the parent drug (58-77%) is eliminated unchanged in the urine. Cimetidines primary metabolite is cimetidine sulfoxide and represents an estimated 10-15% of total elimination. Researchers have also identified a minor cimetidine metabolite with a hydroxylated methyl group on the imidazole ring which represents only 4% of total elimination. Both cytochrome P450 enzymes and flavin-containing monooxygenases are implicated in the metabolism of cimetidine, although it is unclear which specific enzymes are involved. Cimetidine is a well known enzyme inhibitor and may impair the metabolism of certain co-administered medications.

    About 50% to 80% of an intravenous dose is excreted as unchanged drug; 40% of an oral dose is excreted unchanged in the urine in patients with peptic ulcer disease. Most of the remainder of the drug appears in the urine as 5-hydroxymethyl or sulfoxide metabolites.

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 900

    Cimetidine is metabolized in the liver to sulfoxide and 5-hydroxymethyl derivatives, and possibly guanylurea, although this latter compound may result from in vitro degradation.

    McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2140

    5.7 Biological Half-Life

    Cimetidine's half-life is estimated to be around 2 hours.

    ELEVEN PATIENTS WITH ASCITIC CIRRHOSIS & ELEVEN PATIENTS WITHOUT LIVER DISEASE RECEIVED 200 MG OF CIMETIDINE ORALLY AND IV. NO DIFFERENCES WERE OBSERVED IN CIMETIDINE T/2 BETWEEN THE 2 GROUPS. CIMETIDINE CLEARANCE WAS DIMINISHED IN CIRRHOTIC PATIENTS (0.426 + OR - 0.138 VERSUS 0.649 + OR - 0.163 L/HR/KG).

    PMID:6852412 ALBIN H ET AL; GASTROENTEROL CLIN BIOL 7 (3): 251-5 (1983)

    The elimination half-life in man is 1.9 to 2.2 hours.

    Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 434

    The plasma elimination half-life is about 2 hours.

    American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 900

    The half-time for elimination of cimetidine ... is 2 to 3 hours ... .

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 900

    5.8 Mechanism of Action

    Cimetidine binds to an H2-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity.

    H2 antagonists inhibit gastric acid secretion elicited by histamine & other H2 agonists in a dose-dependent, competitive manner; the degree of inhibition parallels the concentration of the drug in plasma over a wide range. The H2 antagonists also inhibit acid secretion elicited by gastrin &, to a lesser extent, by muscarinic agonists. Importantly, these drugs inhibit basal (fasting) & nocturnal acid secretion & that stimulated by food, sham feeding, fundic distention, & various pharmacological agents; this property reflects the vital role of histamine in mediating the effects of diverse stimuli. The H2 antagonists reduce both the volume of gastric juice secreted & its H+ concentration. The output of pepsin, which is secreted by the chief cells of gastric glands (mainly under cholinergic control), generally falls in parallel with the reduction in volume of gastric juice. /H2 antagonists/

    Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 899

    Cimetidine blocks H2-receptors, which in part are responsible for the inflammatory response, in the cutaneous blood vessels of humans.

    USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1612

    The effects of cimetidine, omeprazole and atropine sulfate on the healing of acetic acid-induced gastric ulcers in rats with limited food intake time (9:00-10:00 am and 5:00-6:00 pm) were evaluated 15 days after the acid injection. Oral repeated admin of cimetidine (25-100 mg/kg twice daily) or omeprazole (10-50 mg/kg once daily) dose dependently accelerated ulcer healing. ... A single oral admin of omeprazole (50 mg/kg) or cimetidine (100 mg/kg) resulted in potent and long-lasting anti-acid secretory and gastrin-releasing actions. The degree and duration of anti-acid secretion by atropine sulfate were equal to those of cimetidine, but the elevation of gastrin release by atropine sulfate was weak and temporary. These results indicate that the gastric ulcers of rats with a limited food intake time are useful for evaluating the healing effects of cimetidine and omeprazole on gastric ulcers. In addition, the effects of both drugs may be related to the incr gastrin release rather than to the reduced acid secretion.

    PMID:7843261 Ito M et al; Eur J Pharmacol 263 (3): 245-51 (1994)

    Both KB-5492, a new anti-ulcer agent, and cimetidine, admin po at 25-200 mg/kg, dose-dependently prevented cysteamine (400 mg/kg, sc)-induced duodenal ulcers in rats with ED50 values of 63 and 40 mg/kg, respectively. Anti-ulcer doses of cimetidine, but not KB-5492, inhibited gastric acid hypersecretion induced by cysteamine (400 mg/kg, sc). In contrast, anti-ulcer doses of KB-5492, but not cimetidine, incr duodenal HC03- secretion in normal anesthetized rats. These findings suggest that KB-5492 prevents cysteamine-induced duodenal ulcers by stimulating duodenal HC03- secretion, whereas cimetidine does so by inhibiting cysteamine-induced gastric acid hypersecretion.

    PMID:8022123 Morimoto Y et al; Jpn J Pharmacol 64 (3): 221-4 (1994)

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    Registration Number : 217MF10539

    Registrant's Address : Zhoutie Town, Yixing City, Jiangsu Province, P. R. of China

    Initial Date of Registration : 2005-09-09

    Latest Date of Registration : --

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    Registrant Name : Yuhanmedica Co., Ltd.

    Registration Date : 2012-10-11

    Registration Number : 20050831-27-B-63-01(15)

    Manufacturer Name : Wuxi Kaili Pharmaceutical Co., Ltd

    Manufacturer Address : Zhoutie Town, Yixing City, Jiangsu Province, PR China

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    11-Jan-2021
    08-Oct-2024
    KGS
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    Average Price (USD/KGS)

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

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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