Ebrotidine - Misplaced Pages

Chemical compound

Pharmaceutical compound

Ebrotidine
Clinical data

Routes of administration	Oral
Identifiers
IUPAC name N-(4-bromophenyl)sulfonyl-N'-methylsulfanyl]ethyl]methanimidamide
CAS Number	100981-43-9
PubChem CID	65869
ChemSpider	59279
UNII	TMZ3IBW2OW
ChEMBL	ChEMBL1742471
CompTox Dashboard (EPA)	DTXSID80143601
Chemical and physical data
Formula	C₁₄H₁₇BrN₆O₂S₃
Molar mass	477.41 g·mol
3D model (JSmol)	Interactive image
SMILES Brc1ccc(cc1)S(=O)(=O)N/C=N/CCSCc2csc(n2)N=C(N)N
InChI InChI=1S/C14H17BrN6O2S3/c15-10-1-3-12(4-2-10)26(22,23)19-9-18-5-6-24-7-11-8-25-14(20-11)21-13(16)17/h1-4,8-9H,5-7H2,(H,18,19)(H4,16,17,20,21) Key:ZQHFZHPUZXNPMF-UHFFFAOYSA-N
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Ebrotidine is an H₂ receptor antagonist with gastroprotective activity against ethanol-, aspirin- or stress-induced gastric mucosal damage. The antisecretory properties of ebrotidine are similar to those of ranitidine, and approximately 10-fold greater than those of cimetidine. Ebrotidine has anti-Helicobacter pylori activity via inhibition of the urease enzyme and the proteolytic and mucolytic activities of the bacterium. However, its activity is synergistic with a number of antibacterial agents. Ebrotidine counteracts the inhibitory effects of H. pylori lipopolysaccharides. Ebrotidine was withdrawn from the market due to risks of hepatotoxicity.

Ebrotidine has been shown to be as effective as ranitidine for the treatment of gastric or duodenal ulcers or erosive reflux oesophagitis, with significantly better ulcer healing rates (albeit inexplicably) in those who smoke.

References

^ Patel SS, Wilde MI (June 1996). "Ebrotidine". Drugs. 51 (6): 974–80, discussion 981. doi:10.2165/00003495-199651060-00006. PMID 8736619. S2CID 264001739.

Histamine receptor modulators

H₁

Agonists

Antagonists

Others: Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, brilaroxazine, clozapine, iloperidone, olanzapine, paliperidone, quetiapine, risperidone, ziprasidone, zotepine)
Phenylpiperazine antidepressants (e.g., hydroxynefazodone, nefazodone, trazodone, triazoledione)
Tetracyclic antidepressants (e.g., amoxapine, loxapine, maprotiline, mianserin, mirtazapine, oxaprotiline)
Tricyclic antidepressants (e.g., amitriptyline, butriptyline, clomipramine, desipramine, dosulepin (dothiepin), doxepin, imipramine, iprindole, lofepramine, nortriptyline, protriptyline, trimipramine)
Typical antipsychotics (e.g., chlorpromazine, flupenthixol, fluphenazine, loxapine, perphenazine, prochlorperazine, thioridazine, thiothixene)

H₂

Agonists	Amthamine Betazole Dimaprit Histamine HTMT Impromidine L-Histidine UR-AK49
Antagonists	Bisfentidine Burimamide Cimetidine Dalcotidine Donetidine Ebrotidine Etintidine Famotidine Isolamtidine Lafutidine Lamtidine Lavoltidine (loxtidine) Lupitidine Metiamide Mifentidine Niperotidine Nizatidine Osutidine Oxmetidine Pibutidine Quisultazine (quisultidine) Ramixotidine Ranitidine Roxatidine Sufotidine Tiotidine Tuvatidine Venritidine Xaltidine Zolantidine

H₃

Agonists	α-Methylhistamine Cipralisant Histamine Imetit Immepip Immethridine L-Histidine Methimepip Proxyfan
Antagonists	A-349821 A-423579 ABT-239 ABT-652 AZD5213 Bavisant Betahistine Burimamide Ciproxifan Clobenpropit Conessine Enerisant GSK-189254 Impentamine Iodophenpropit Irdabisant JNJ-5207852 NNC 38-1049 PF-03654746 Pitolisant SCH-79687 Thioperamide VUF-5681

H₄

Agonists	4-Methylhistamine α-Methylhistamine Histamine L-Histidine OUP-16 VUF-8430
Antagonists	JNJ-7777120 Mianserin Seliforant Thioperamide Toreforant VUF-6002

See also: Receptor/signaling modulators; Monoamine metabolism modulators; Monoamine reuptake inhibitors

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