Eletriptan and Timoprazole: Difference between pages

Line 1:

{{Drugbox

| Verifiedfields = changed

| Watchedfields = changed

| verifiedrevid = ~~443720637~~

| verifiedrevid = 459434734

| IUPAC_name = (''R'')-3-[(-1-methylpyrrolidin-2-yl)methyl]-5-(2-phenylsulfonylethyl)- 1H-indole

| IUPAC_name = 2-[(2-Pyridylmethyl)sulfinyl]-1''H''-benzimidazole

| image = Eletriptane Structural Formulae.png

| image = Timoprazole.svg

| tradename = Relpax

| Drugs.com = {{drugs.com|monograph|relpax}}

| MedlinePlus = a603029

| pregnancy_category =

| legal_status = Prescription (Rx)

| routes_of_administration = oral

| bioavailability = 50%

| protein_bound =

| metabolism = CYP3A4

| elimination_half-life = 4 hours

| excretion =

| ~~CASNo_Ref~~ = {{cascite|correct|~~CAS~~}}

| CAS_number_Ref = {{cascite|correct|}}

⚫

| CAS_number = 57237-97-5

| CAS_number_Ref = {{cascite|correct|??}}

⚫

| PubChem = 72171

⚫

| CAS_number = ~~143322~~-58-1

| ATC_prefix = N02

| ATC_suffix = CC06

| ATC_supplemental =

⚫

| PubChem = ~~77993~~

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB00216

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = ~~70379~~

| ChemSpiderID = 65144

| KEGG = D05900

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = ~~22QOO9B8KI~~

| UNII = 95H6S1X9CC

| KEGG_Ref = {{keggcite|changed|kegg}}

| KEGG =

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 50922

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 1510

| C=22 | H=26 | N=2 | O=2 | S=1

| C=13 | H=11 | N=3 | O=1 | S=1

| smiles = n1ccccc1CS(=O)c2[nH]c3ccccc3n2

| molecular_weight = 382.52

⚫

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| smiles = O=S(=O)(c1ccccc1)CCc4ccc2c(c(cn2)C[C@@H]3N(C)CCC3)c4

| StdInChI = 1S/C13H11N3OS/c17-18(9-10-5-3-4-8-14-10)13-15-11-6-1-2-7-12(11)16-13/h1-8H,9H2,(H,15,16)

| InChI = 1/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1

| InChIKey = PWVXXGRKLHYWKM-LJQANCHMBD

⚫

| StdInChI_Ref = {{stdinchicite|~~changed~~|chemspider}}

| StdInChI = 1S/C22H26N2O2S/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3/t19-/m1/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = ~~PWVXXGRKLHYWKM~~-~~LJQANCHMSA~~-N

| StdInChIKey = HBDKFZNDMVLSHM-UHFFFAOYSA-N

}}

'''Timoprazole''' is in a class of medications called [[proton pump inhibitor]]s (PPI) that inhibit [[gastric acid]] [[secretion]]. While it has never come to market, it was studied early on and is considered to be the "backbone" of the PPI class that succeeded it.<ref>{{cite book | vauthors = Snaeder W |year=1996 |title=Drug prototypes and their exploitation |publisher=Wiley |pages=414–5}}</ref><ref name="Hemenway 2007">{{cite book |doi=10.1007/978-0-387-49785-3_49 |chapter=Case Study: Omeprazole (Prilosec) |title=Prodrugs |series=Biotechnology: Pharmaceutical Aspects |year=2007 | vauthors = Hemenway JN |isbn=978-0-387-49782-2 |pages=1313–21}}</ref> This medication has high anti-[[secretion|secretory]] activity, which flared interest along with its simple structure.<ref name="Senn">{{cite book |doi=10.1002/3527608001.ch6 |chapter=The Development of a New Proton-Pump Inhibitor: The Case History of Pantoprazole |title=Analogue-based Drug Discovery |year=2006 | vauthors = Senn-Bilfinger J, Sturm E |isbn=978-3-527-60800-3 |pages=115–36}}</ref>

'''Eletriptan''' (also known as eletriptan hydrobromide) is a second generation [[triptan]] [[medication|drug]] marketed and manufactured by [[Pfizer|Pfizer Inc]] for the treatment of [[migraine]] [[headache]]s. It is sold in the US under the brand name '''Relpax'''.

⚫

== References ==

==Approval and availability==

Eletriptan was approved by the [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA) on December 26, 2002 for the acute treatment of migraine with or without [[Aura_(symptom)|aura]] in adults.<ref name=accessdata>FDA AccessData entry for [http://www.accessdata.fda.gov/scripts/cder/ob/docs/obdetail.cfm?Appl_No=020763&TABLE1=OB_Rx Eletriptan Hydrobromide], accessed March 10, 2010.</ref> It is available only by [[Medical prescription|prescription]] in the [[United States]] and [[Canada]]. It is not intended for the prophylactic therapy of migraine or for use in the management of hemiplegic or basilar migraine. It is available in 40 mg and 80 mg strengths.

Eletriptan is covered by {{US patent|5545644|U.S. Patent no. 5545644}}<ref>{{US patent|5545644|U.S. Patent no. 5545644}}, John E. Macor & Martin J. Wythes, ''Indole Derivatives'', August 13, 1996.</ref><ref name=accessdata/> and {{US patent|6110940|U.S. Patent no. 6110940}};<ref>{{US patent|6110940|U.S. Patent no. 6110940}}, Valerie Denise Harding, ''et al.'', ''Salts of an anti-migraine indole derivative'', August 29, 2000.</ref><ref name=accessdata/> the FDA lists the patents as scheduled for expiration on December 26, 2016 and August 29, 2017, respectively.<ref name=accessdata/>

==Mechanism of action==

Treatment with Eletriptan is believed to reduce swelling of the blood vessels surrounding the brain. This swelling is associated with the head pain of a migraine attack. Eletriptan blocks the release of substances from nerve endings that cause more pain and other symptoms like nausea, and sensitivity to light and sound. It is thought that these actions contribute to relief of symptoms by Eletriptan.

Eletriptan is a [[serotonin]] [[agonist]]. Specifically, it is a selective [[5-hydroxytryptamine]] 1B/1D ([[5-HT1B|5-HT1B]]) receptor [[agonist]].

Eletriptan binds with high affinity to the [[5-HT1B|5-HT[1B]], [[5-HT1D|1D]], [[5-HT1F|1F]]] receptors.

It has a modest affinity to the [[5-HT1A|5-HT[1A]], [[5-HT1E|1E]], [[5-HT2B receptor|2B]], [[5-HT7|7]]] receptors.

And little to no affinity at the [[5-HT2A|5-HT[2A]], [[5-HT2C receptor|2C]], [[5-HT3|3]], [[5-HT4|4]], [[5-HT5A|5A]], [[5-HT6|6]]] receptors.

Eletriptan has no significant affinity or pharmacological activity at adrenergic alpha1, alpha2, or beta; dopaminergic D1 or D2; muscarinic; or opioid receptors. Eletriptan could be efficiently co-administrated with nitric oxide synthase (NOS's) inhibitors for the treatment of NOS-dependent diseases (US patent US 2007/0254940)

Two theories have been proposed to explain the efficacy of 5-HT receptor agonists in migraine. One theory suggests that activation of 5-HT1 receptors located on intracranial blood vessels, including those on the arteriovenous anastomoses, leads to vasoconstriction, which is correlated with the relief of migraine headache. The other hypothesis suggests that activation of 5-HT1 receptors on sensory nerve endings in the trigeminal system results in the inhibition of pro-inflammatory neuropeptide release.

==Additional Chemical Names==

* [[Merck Index]]: 3-[[(2''R'')-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole

* 5-[2-(benzenesulfonyl)ethyl]-3-(1-methylpyrrolidin-2(''R'')-ylmethyl)-1H-indole

* (''R'')-5-[2-(phenylsulfonyl)ethyl]-3-[(1-methyl-2-pyrrolidinyl)methyl]-1H-indole

⚫

==References==

==External links==

* [http://129.128.185.122/drugbank2/drugs/DB00216/fda_labels/990 FDA label] (December 2002)

* [[Physicians' Desk Reference]] entry for [http://www.pdrhealth.com/drugs/rx/rx-mono.aspx?contentFileName=rel1663.html&contentName=Relpax&contentId=649 ''Relpax'']

* [[Medline]] Plus Drug Information for [http://www.nlm.nih.gov/medlineplus/druginfo/meds/a603029.html Eletriptan]

* Pfizer [http://www.relpax.com Relpax site]

[[Category:~~Triptans~~]]

[[Category:Proton-pump inhibitors]]

[[Category:~~Pfizer~~]]

[[Category:Abandoned drugs]]

[[Category:Pyrrolidines]]

[[Category:Sulfones]]

[[de:Eletriptan]]

[[es:Eletriptán]]

[[it:Eletriptan]]