From Wikipedia, the free encyclopedia
Muscarinic acetylcholine receptor antagonist
BIBN 99
Names
IUPAC name
N -[3-[1-[2-(8-chloro-6-oxo-5H-pyrido[2,3-b][1,4]benzodiazepin-11-yl)-2-oxoethyl]piperidin-4-yl]propyl]-N-ethyl-2,2-dimethylpentanamide
Identifiers
ChEMBL
ChemSpider
Key: LUPAFPUKESJDMZ-UHFFFAOYSA-N
InChI=1S/C31H42ClN5O3/c1-5-15-31(3,4)30(40)36(6-2)17-8-9-22-13-18-35(19-14-22)21-27(38)37-26-12-11-23(32)20-24(26)29(39)34-25-10-7-16-33-28(25)37/h7,10-12,16,20,22H,5-6,8-9,13-15,17-19,21H2,1-4H3,(H,34,39)
CCCC(C)(C)C(=O)N(CC)CCCC1CCN(CC1)CC(=O)N2C3=C(C=C(C=C3)Cl)C(=O)NC4=C2N=CC=C4
Properties
C 31 H 42 Cl N 5 O 3
Molar mass
568.16 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
BIBN 99 is an antagonist of mACh receptors . Specifically, it is selective for the M2 type.[ 1]
During research, it was observed that BIBN 99 was able to diminish the cognitive deficits caused by injury.[ 2] Another also came to the conclusion that the compound could provide cognitive improvements.[ 3] The cognitive effects could possibly be caused by the increased release of acetylcholine , a neurotransmitter.[ 4]
^ Doods, H.; Entzeroth, M.; Ziegler, H.; Schiavi, G.; Engel, W.; Mihm, G.; Rudolf, K.; Eberlein, W. (1993-09-21). "Characterization of BIBN 99: a lipophilic and selective muscarinic M2 receptor antagonist" . European Journal of Pharmacology . 242 (1): 23– 30. doi :10.1016/0014-2999(93)90005-3 . ISSN 0014-2999 . PMID 8223934 .
^ Pike, B. R.; Hamm, R. J. (1995-07-17). "Post-injury administration of BIBN 99, a selective muscarinic M2 receptor antagonist, improves cognitive performance following traumatic brain injury in rats" . Brain Research . 686 (1): 37– 43. doi :10.1016/0006-8993(95)00448-y . ISSN 0006-8993 . PMID 7583269 .
^ Rowe, W. B.; O'Donnell, J.-P.; Pearson, D.; Rose, G. M.; Meaney, M. J.; Quirion, R. (2003-10-17). "Long-term effects of BIBN-99, a selective muscarinic M2 receptor antagonist, on improving spatial memory performance in aged cognitively impaired rats" . Behavioural Brain Research . 145 (1– 2): 171– 178. doi :10.1016/s0166-4328(03)00116-5 . ISSN 0166-4328 . PMID 14529815 .
^ Quirion, R.; Wilson, A.; Rowe, W.; Aubert, I.; Richard, J.; Doods, H.; Parent, A.; White, N.; Meaney, M. J. (February 1995). "Facilitation of acetylcholine release and cognitive performance by an M(2)-muscarinic receptor antagonist in aged memory-impaired" . The Journal of Neuroscience: The Official Journal of the Society for Neuroscience . 15 (2): 1455– 1462. doi :10.1523/JNEUROSCI.15-02-01455.1995 . ISSN 0270-6474 . PMC 6577836 . PMID 7869110 .
mAChRs Tooltip Muscarinic acetylcholine receptors
Agonists Antagonists
3-Quinuclidinyl benzilate
4-DAMP
Aclidinium bromide (+formoterol )
Abediterol
AF-DX 250
AF-DX 384
Ambutonium bromide
Anisodamine
Anisodine
Antihistamines (first-generation) (e.g., brompheniramine , buclizine , captodiame , chlorphenamine (chlorpheniramine) , cinnarizine , clemastine , cyproheptadine , dimenhydrinate , dimetindene , diphenhydramine , doxylamine , meclizine , mequitazine , perlapine , phenindamine , pheniramine , phenyltoloxamine , promethazine , propiomazine , triprolidine )
AQ-RA 741
Atropine
Atropine methonitrate
Atypical antipsychotics (e.g., clozapine , fluperlapine , olanzapine (+fluoxetine ), rilapine , quetiapine , tenilapine , zotepine )
Benactyzine
Benzatropine (benztropine)
Benzilone
Benzilylcholine mustard
Benzydamine
Bevonium
BIBN 99
Biperiden
Bornaprine
Camylofin
CAR-226,086
CAR-301,060
CAR-302,196
CAR-302,282
CAR-302,368
CAR-302,537
CAR-302,668
Caramiphen
Cimetropium bromide
Clidinium bromide
Cloperastine
CS-27349
Cyclobenzaprine
Cyclopentolate
Darifenacin
DAU-5884
Desfesoterodine
Dexetimide
DIBD
Dicycloverine (dicyclomine)
Dihexyverine
Difemerine
Diphemanil metilsulfate
Ditran
Drofenine
EA-3167
EA-3443
EA-3580
EA-3834
Emepronium bromide
Etanautine
Etybenzatropine (ethybenztropine)
Fenpiverinium
Fentonium bromide
Fesoterodine
Flavoxate
Glycopyrronium bromide (+beclometasone/formoterol , +indacaterol , +neostigmine )
Hexahydrodifenidol
Hexahydrosiladifenidol
Hexbutinol
Hexocyclium
Himbacine
HL-031,120
Homatropine
Imidafenacin
Ipratropium bromide (+salbutamol )
Isopropamide
J-104,129
Hyoscyamine
Mamba toxin 3
Mamba toxin 7
Mazaticol
Mebeverine
Meladrazine
Mepenzolate
Methantheline
Methoctramine
Methylatropine
Methylhomatropine
Methylscopolamine
Metixene
Muscarinic toxin 7
N-Ethyl-3-piperidyl benzilate
N-Methyl-3-piperidyl benzilate
Nefopam
Octatropine methylbromide (anisotropine methylbromide)
Orphenadrine
Otenzepad (AF-DX 116)
Otilonium bromide
Oxapium iodide
Oxitropium bromide
Oxybutynin
Oxyphencyclimine
Oxyphenonium bromide
PBID
PD-102,807
PD-0298029
Penthienate
Pethidine
pFHHSiD
Phenglutarimide
Phenyltoloxamine
Pipenzolate bromide
Piperidolate
Pirenzepine
Piroheptine
Pizotifen
Poldine
Pridinol
Prifinium bromide
Procyclidine
Profenamine (ethopropazine)
Propantheline bromide
Propiverine
Quinidine
3-Quinuclidinyl thiochromane-4-carboxylate
Revefenacin
Rociverine
RU-47,213
SCH-57,790
SCH-72,788
SCH-217,443
Scopolamine (hyoscine)
Scopolamine butylbromide (hyoscine butylbromide)
Silahexacyclium
Sofpironium bromide
Solifenacin
SSRIs Tooltip Selective serotonin reuptake inhibitors (e.g., femoxetine , paroxetine )
Telenzepine
Terodiline
Tetracyclic antidepressants (e.g., amoxapine , maprotiline , mianserin , mirtazapine )
Tiemonium iodide
Timepidium bromide
Tiotropium bromide
Tiquizium bromide
Tofenacin
Tolterodine
Tricyclic antidepressants (e.g., amitriptyline (+perphenazine ), amitriptylinoxide , butriptyline , cidoxepin , clomipramine , desipramine , desmethyldesipramine , dibenzepin , dosulepin (dothiepin) , doxepin , imipramine , lofepramine , nitroxazepine , northiaden (desmethyldosulepin) , nortriptyline , protriptyline , quinupramine , trimipramine )
Tridihexethyl
Trihexyphenidyl
Trimebutine
Tripitamine (tripitramine)
Tropacine
Tropatepine
Tropicamide
Tropine benzilate
Trospium chloride
Typical antipsychotics (e.g., chlorpromazine , chlorprothixene , cyamemazine (cyamepromazine) , loxapine , mesoridazine , thioridazine )
Umeclidinium bromide (+vilanterol )
WIN-2299
Xanomeline
Zamifenacin
Precursors (and prodrugs )