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Chemical compound
BW-A444
Legal status
2,2'-[1,4-phenylenebis[(1-oxo-2-propene-3,1-diyl)oxy-3,1-propanediyl]]bis[1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-[(3,4,5-trimethoxyphenyl)methyl]isoquinolinium] dichloride
CAS Number
ChemSpider
Formula C 62 H 78 Cl 2 N 2 O 14
Molar mass 1146 .21 g·mol−1 3D model (
JSmol )
[Cl-].[Cl-].O=C(OCCC[N+]2(C)C(c1cc(OC)c(OC)cc1CC2)Cc3cc(OC)c(OC)c(OC)c3)\C=C\c4ccc(cc4)\C=C\C(=O)OCCC[N+]6(C(c5c(cc(OC)c(OC)c5)CC6)Cc7cc(OC)c(OC)c(OC)c7)C
InChI=1S/C62H78N2O14.2ClH/c1-63(27-23-45-37-51(67-3)53(69-5)39-47(45)49(63)31-43-33-55(71-7)61(75-11)56(34-43)72-8)25-13-29-77-59(65)21-19-41-15-17-42(18-16-41)20-22-60(66)78-30-14-26-64(2)28-24-46-38-52(68-4)54(70-6)40-48(46)50(64)32-44-35-57(73-9)62(76-12)58(36-44)74-10;;/h15-22,33-40,49-50H,13-14,23-32H2,1-12H3;2*1H/q+2;;/p-2/b21-19+,22-20+;;
Key:UNQYVYCAHVEHIT-JXYRNBIZSA-L
BW A444U was an experimental
neuromuscular blocking drug or
skeletal muscle relaxant in the category of non-depolarizing
neuromuscular-blocking drugs , intended to be used adjunctively in surgical
anesthesia to facilitate endotracheal
intubation and to provide
skeletal muscle relaxation during
surgery or
mechanical ventilation . It was synthesized and developed in the early 1980s.
BW A444U represented the first-generation of
tetrahydroisoquinoline
neuromuscular-blocking drugs that are
nicotinic acetylcholine receptor
antagonists or
antinicotinics . It was an intermediate-duration
[1] non-depolarizing
neuromuscular-blocking drug or
skeletal muscle relaxant. It was synthesized by Mary M. Jackson and James C. Wisowaty, PhD (both chemists within the Chemical Development Laboratories at
Burroughs Wellcome Co. ,
Research Triangle Park, NC ) in collaboration with John J. Savarese MD (who at the time was an anesthesiologist in the Dept. of Anesthesia,
Harvard Medical School at the
Massachusetts General Hospital ,
Boston , MA).
The drug was tested clinically in the early 1980s,
[1] and quickly abandoned from further clinical development after a single clinical study, owing primarily to undesirable effects of histamine release when administered at clinically relevant doses.
References
^
a
b Savarese JJ, Ali HH, Basta SJ, Sunder N, Moss J, Gionfriddo MA, Lineberry CG, Wastila WB, El-Sayad HA, Montague D, Braswell L (1983).
"The clinical pharmacology of BW A444U. A nondepolarizing ester relaxant of intermediate duration" . Anesthesiology . 58 (4): 333–341.
doi :
10.1097/00000542-198304000-00006 .
PMID
6220623 .
S2CID
22212818 .
nAChRs Tooltip Nicotinic acetylcholine receptors
Agonists (and
PAMs Tooltip positive allosteric modulators )
5-HIAA
6-Chloronicotine
A-84,543
A-366,833
A-582,941
A-867,744
ABT-202
ABT-418
ABT-560
ABT-894
Acetylcholine
Altinicline
Anabasine
Anatabine
Anatoxin-a
AR-R17779
Bephenium hydroxynaphthoate
Butinoline
Butyrylcholine
Carbachol
Choline
Cotinine
Cytisine
Decamethonium
Desformylflustrabromine
Dianicline
Dimethylphenylpiperazinium
Epibatidine
Epiboxidine
Ethanol (alcohol)
Ethoxysebacylcholine
EVP-4473
EVP-6124
Galantamine
GTS-21
Ispronicline
Ivermectin
JNJ-39393406
Levamisole
Lobeline
MEM-63,908 (RG-3487)
Morantel
Nicotine (
tobacco )
NS-1738
PHA-543,613
PHA-709,829
PNU-120,596
PNU-282,987
Pozanicline
Pyrantel
Rivanicline
RJR-2429
Sazetidine A
SB-206553
Sebacylcholine
SIB-1508Y
SIB-1553A
SSR-180,711
Suberyldicholine
Suxamethonium (succinylcholine)
Suxethonium (succinyldicholine)
TC-1698
TC-1734
TC-1827
TC-2216
TC-5214
TC-5619
TC-6683
Tebanicline
Tribendimidine
Tropisetron
UB-165
Varenicline
WAY-317,538
XY-4083
Antagonists (and
NAMs Tooltip negative allosteric modulators )
Precursors (and
prodrugs )