| Revision as of 00:56, 11 August 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{chembox}} (no changed fields - added verified revid - updated 'ChemSpiderID_Ref', 'DrugBank_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'StdInChI_Ref', 'StdInChIKey_Ref', 'ChEBI_Ref') per [[Misplaced Pages:WikiProject Chemicals/Chembox validati← Previous edit |
Latest revision as of 22:20, 10 February 2024 edit undoCitation bot (talk | contribs)Bots5,424,043 edits Altered issue. Added s2cid. Formatted dashes. | Use this bot. Report bugs. | Suggested by Abductive | Category:Macrolides | #UCB_Category 10/34 |
| (14 intermediate revisions by 11 users not shown) |
| Line 1: |
Line 1: |
|
{{chembox |
|
{{chembox |
|
|
| Verifiedfields = changed |
|
|
| Watchedfields = changed |
|
⚫ |
| verifiedrevid = 444171051 |
|
⚫ |
| ImageFile=Mitemcinal.png |
|
⚫ |
| ImageSize=200px |
|
⚫ |
| IUPACName=(1''R'',2''R'',3''S'',4''S'',5''R'',8''R'',9''R'',11''S'')-8-ethyl-4-oxy-2-oxan-2-yl]oxy-9-methoxy-1,3,5,9,11,13-hexamethyl-7,15-dioxabicyclopentadec-12-ene-6,10-dione |
|
⚫ |
| OtherNames=Mitemcinal, GM-611 |
|
⚫ |
|Section1={{Chembox Identifiers |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII_Ref = {{fdacite|correct|FDA}} |
|
| UNII = 6X5NRJ664L |
|
| UNII = 6X5NRJ664L |
|
|
| CASNo_Ref = {{cascite|correct|CAS}} |
| ⚫ |
| verifiedrevid = 437155010 |
|
|
⚫ |
| CASNo=154738-42-8 |
| ⚫ |
|ImageFile=Mitemcinal.png |
|
|
⚫ |
| PubChem=6918267 |
| ⚫ |
|ImageSize=200px |
|
|
⚫ |
| SMILES=C(C((OC)(C)(CC)OC2=O)=O)C1=C(C)C((O3()(O)(N(C)C(C)C)C(C)O3)((O4()O(C)(O)(OC)(C)C4)2C)C)(C)O1 |
| ⚫ |
|IUPACName=(1''R'',2''R'',3''S'',4''S'',5''R'',8''R'',9''R'',11''S'')-8-ethyl-4-oxy-2-oxan-2-yl]oxy-9-methoxy-1,3,5,9,11,13-hexamethyl-7,15-dioxabicyclopentadec-12-ene-6,10-dione |
|
|
|
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}} |
| ⚫ |
|OtherNames=Mitemcinal, GM-611 |
|
|
|
| ChemSpiderID = 5293473 |
| ⚫ |
|Section1={{Chembox Identifiers |
|
|
|
| InChI = 1/C40H69NO12/c1-16-28-40(12,47-15)33(43)23(6)31-21(4)18-39(11,53-31)35(52-37-30(42)27(17-22(5)48-37)41(13)20(2)3)24(7)32(25(8)36(45)50-28)51-29-19-38(10,46-14)34(44)26(9)49-29/h20,22-30,32,34-35,37,42,44H,16-19H2,1-15H3/t22-,23+,24+,25-,26+,27+,28-,29+,30-,32+,34+,35-,37+,38-,39-,40-/m1/s1 |
| ⚫ |
| CASNo=154802-96-7 |
|
|
|
| InChIKey = BELMMAAWNYFCGF-PZXAHSFZBB |
| ⚫ |
| PubChem=6918267 |
|
|
|
| StdInChI_Ref = {{stdinchicite|changed|chemspider}} |
| ⚫ |
| SMILES=C(C((OC)(C)(CC)OC2=O)=O)C1=C(C)C((O3()(O)(N(C)C(C)C)C(C)O3)((O4()O(C)(O)(OC)(C)C4)2C)C)(C)O1 |
|
|
|
| StdInChI = 1S/C40H69NO12/c1-16-28-40(12,47-15)33(43)23(6)31-21(4)18-39(11,53-31)35(52-37-30(42)27(17-22(5)48-37)41(13)20(2)3)24(7)32(25(8)36(45)50-28)51-29-19-38(10,46-14)34(44)26(9)49-29/h20,22-30,32,34-35,37,42,44H,16-19H2,1-15H3/t22-,23+,24+,25-,26+,27+,28-,29+,30-,32+,34+,35-,37+,38-,39-,40-/m1/s1 |
|
|
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}} |
|
|
| StdInChIKey = BELMMAAWNYFCGF-PZXAHSFZSA-N |
|
}} |
|
}} |
|
|Section2={{Chembox Properties |
|
|Section2={{Chembox Properties |
|
| Formula=C<sub>40</sub>H<sub>69</sub>NO<sub>12</sub> |
|
| Formula=C<sub>40</sub>H<sub>69</sub>NO<sub>12</sub> |
|
| MolarMass=755.98 g/mol |
|
| MolarMass=755.98 g/mol |
|
| Appearance= |
|
| Appearance= |
|
| Density= |
|
| Density= |
|
| MeltingPt= |
|
| MeltingPt= |
|
| BoilingPt= |
|
| BoilingPt= |
|
| Solubility= |
|
| Solubility= |
|
}} |
|
}} |
|
|Section3={{Chembox Hazards |
|
|Section3={{Chembox Hazards |
|
| MainHazards= |
|
| MainHazards= |
|
| FlashPt= |
|
| FlashPt= |
|
|
| AutoignitionPt = |
|
| Autoignition= |
|
|
}} |
|
}} |
|
}} |
|
}} |
|
|
|
|
|
'''Mitemcinal''' (GM-611 or 3'-N-dimethyl-11-deoxy-3'-N-isopropyl-12-O-methyl-11-oxo-8,9-didehydroerythromycin) is a ] ] derived from the ], ]. It was discovered in the labs of ]. Mitemcinal is orally administered and it is believed to have strong promotility (or prokinetic) effects. Promotility drugs relieve symptoms of reflux by speeding the clearance of acid from the oesophagus and stomach.<ref></ref> The parent compound, erythromycin, has these characteristics, but mitemcinal lacks the antibiotic properties of erythromycin.<ref>{{cite journal |author=Karamanolis G, Tack J |title=Promotility medications—now and in the future |journal=Dig Dis |volume=24 |issue=3-4 |pages=297–307 |year=2006 |pmid=16849857 |doi=10.1159/000092883 }}</ref> |
|
'''Mitemcinal''' (GM-611 or 3'-N-dimethyl-11-deoxy-3'-N-isopropyl-12-O-methyl-11-oxo-8,9-didehydroerythromycin) is a ] ] derived from the ], ]. It was discovered in the labs of ]. Mitemcinal is orally administered and it is believed to have strong promotility (or prokinetic) effects. Promotility drugs relieve symptoms of reflux by speeding the clearance of acid from the oesophagus and stomach.<ref></ref> The parent compound, erythromycin, has these characteristics, but mitemcinal lacks the antibiotic properties of erythromycin.<ref>{{cite journal |vauthors=Karamanolis G, Tack J |title=Promotility medications—now and in the future |journal=Dig Dis |volume=24 |issue=3–4 |pages=297–307 |year=2006 |pmid=16849857 |doi=10.1159/000092883 |doi-access=free }}</ref> |
|
|
|
|
|
Presently, erythromycin is commonly used off-label for gastric motility indications such as ]. If mitemcinal can be shown to be as effective a promotility agent, it would represent a significant advance in the GI field as treatment with this drug would not carry the risk of unintentional selection of antibiotic-resistant bacteria. This concept greatly intrigued Chugai, and the company pursued it as an ideal candidate for a long-term prokinetic agent to treat lower ] deficiencies including gastroparesis.<ref>{{cite journal |author=Ozaki K, Yogo K, Sudo H, ''et al.'' |title=Effects of mitemcinal (GM-611), an acid-resistant nonpeptide motilin receptor agonist, on the gastrointestinal contractile activity in conscious dogs |journal=Pharmacology |volume=79 |issue=4 |pages=223–35 |year=2007 |pmid=17426410 |doi=10.1159/000101537 }}</ref> |
|
Presently, erythromycin is commonly used off-label for gastric motility indications such as ]. If mitemcinal can be shown to be as effective a promotility agent, it would represent a significant advance in the GI field as treatment with this drug would not carry the risk of unintentional selection of antibiotic-resistant bacteria. This concept greatly intrigued Chugai, and the company pursued it as an ideal candidate for a long-term prokinetic agent to treat lower ] deficiencies including gastroparesis.<ref>{{cite journal |vauthors=Ozaki K, Yogo K, Sudo H, etal |title=Effects of mitemcinal (GM-611), an acid-resistant nonpeptide motilin receptor agonist, on the gastrointestinal contractile activity in conscious dogs |journal=Pharmacology |volume=79 |issue=4 |pages=223–35 |year=2007 |pmid=17426410 |doi=10.1159/000101537 |s2cid=30826969 }}</ref> |
|
|
|
|
|
The Phase II trials did not detect an increase in gastric emptying among the population of diabetic gastroparesis patients above placebo.<ref>{{cite journal |author=McCallum RW, Cynshi O |title=Clinical trial: effect of mitemcinal (a motilin agonist) on gastric emptying in patients with gastroparesis - a randomized, multicentre, placebo-controlled study |journal=Aliment Pharmacol Ther. |volume=26 |issue=8 |pages=1121–30 |year=2007 |month=Oct |pmid=17894654 |doi=10.1111/j.1365-2036.2007.03461.x }}</ref> Thus, although Chugai was able to demonstrate the required safety of the compound, development of this drug has stalled due to a lack of convincing efficacy data. |
|
The Phase II trials did not detect an increase in gastric emptying among the population of diabetic gastroparesis patients above placebo.<ref> The Conclusion of the cited reference does not indicate that there was no benefit. On the contrary, the study said there was an increase in gastric emptying. {{cite journal |vauthors=McCallum RW, Cynshi O |title=Clinical trial: effect of mitemcinal (a motilin agonist) on gastric emptying in patients with gastroparesis - a randomized, multicentre, placebo-controlled study |journal=Aliment. Pharmacol. Ther. |volume=26 |issue=8 |pages=1121–30 |date=Oct 2007 |pmid=17894654 |doi=10.1111/j.1365-2036.2007.03461.x |doi-access=free }}</ref> Thus, although Chugai was able to demonstrate the required safety of the compound, development of this drug has stalled due to a lack of convincing efficacy data. |
|
|
|
|
|
==Notes== |
|
==Notes and references== |
|
{{reflist}} |
|
{{reflist|2}} |
|
|
|
|
|
] |
|
] |