Otenzepad

{{short description|Drug}}

{{Drugbox

| image = 180px

| caption = Structure of Otenzepad

| CAS_number = 102394-31-0

| CAS_number_Ref = {{Cascite|correct|CAS}}

| PubChem = 107867

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

| UNII = OM7J0XAL0S

| ChEBI = 111174

| ChEMBL = 17045

| ChemSpiderID = 97004

| IUPHAR_ligand = 309

| IUPAC_name = 11-[2-[2-(diethylaminomethyl)piperidin-1-yl]acetyl]-5H-pyrido[2,3-b][1,4]benzodiazepin-6-one

| C=24 | H=31 | N=5 | O=2

| SMILES = CCN(CC)CC1CCCCN1CC(=O)N2C3=CC=CC=C3C(=O)NC4=C2N=CC=C4

| StdInChI=1S/C24H31N5O2/c1-3-27(4-2)16-18-10-7-8-15-28(18)17-22(30)29-21-13-6-5-11-19(21)24(31)26-20-12-9-14-25-23(20)29/h5-6,9,11-14,18H,3-4,7-8,10,15-17H2,1-2H3,(H,26,31)

| StdInChIKey = UBRKDAVQCKZSPO-UHFFFAOYSA-N

|bioavailability = 45% (oral){{cite web|url=https://drugs.ncats.io/substance/WW6A9TFL2C |website=National Centre for Advancing Translational Sciences |title=Otenzepad |access-date=10 June 2021}}

|routes_of_administration=oral

|elimination_half-life=2.5h}}

Otenzepad is a competitive muscarinic receptor antagonist that is relatively selective at the M2 receptor. It was investigated as a treatment for arrhythmia and bradycardia due to its cardioselectivity but research ceased after stage III clinical trials. The drug was originally developed by the German pharmaceutical company, Boehringer Ingelheim Pharma KG.

Pharmacodynamics

The (+)-enantiomer has 8 times greater potency at the M2 receptor than the (-)-enantiomer.

class="wikitable"

|+ Potency of Otenzepad at muscarinic receptor isoforms

! mAChR isoform

! Dissociation constant (Ki)

M1

| 537.0 - 1300nM{{cite journal | vauthors = Buckley NJ, Bonner TI, Buckley CM, Brann MR | title = Antagonist binding properties of five cloned muscarinic receptors expressed in CHO-K1 cells | journal = Mol. Pharmacol. | volume = 35 | issue = 4 | pages = 469–76 | year = 1989 | pmid = 2704370 }}

M2

| 81.0 - 186nM

M3

|838 - 2089.0nM

M4

|407.0 - 1800nM

M5

|2800nM

See also

References