From Wikipedia, the free encyclopedia
Lesogaberan
Names
Preferred IUPAC name
[(2R )-3-Amino-2-fluoropropyl]phosphinic acid
Other names
AZD-3355
Identifiers
ChEMBL
ChemSpider
ECHA InfoCard
100.133.162
UNII
InChI=1S/C3H9FNO2P/c4-3(1-5)2-8(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m1/s1
N Key: LJNUIEQATDYXJH-GSVOUGTGSA-N
N InChI=1/C3H9FNO2P/c4-3(1-5)2-8(6)7/h3,8H,1-2,5H2,(H,6,7)/t3-/m1/s1
Key: LJNUIEQATDYXJH-GSVOUGTGBQ
Properties
C 3 H 9 F N O 2 P
Molar mass
141.082 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
Lesogaberan (AZD-3355 ) was
[1] an experimental drug candidate developed by
AstraZeneca for the treatment of
gastroesophageal reflux disease (GERD).
[2] As a
GABAB receptor
agonist ,
[3] it has the same
mechanism of action as
baclofen , but is anticipated to have fewer of the
central nervous system side effects that limit the clinical use of baclofen for the treatment of GERD.
[4]
References
^ AstraZeneca.
"AZD3355" . Retrieved 30 December 2011 .
^ Bredenoord, Albert J. (2009). "Lesogaberan, a GABAB agonist for the potential treatment of gastroesophageal reflux disease". IDrugs . 12 (9): 576–584.
PMID
19697277 .
^ Alstermark; Amin, K; Dinn, SR; et al. (2008). "Synthesis and Pharmacological Evaluation of Novel γ-Aminobutyric Acid Type B (GABAB) Receptor Agonists as Gastroesophageal Reflux Inhibitors". Journal of Medicinal Chemistry . 51 (14): 4315–4320.
doi :
10.1021/jm701425k .
PMID
18578471 .
^ Brian E. Lacy; Robert Chehade; Michael D. Crowell (2010). "Lesogaberan". Drugs of the Future . 35 (12): 987–992.
doi :
10.1358/dof.2010.035.012.1540661 .
S2CID
258021903 .
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see
here for a full list):
α-EMTBL
Alcohols (e.g.,
drinking alcohol ,
2M2B )
Anabolic steroids
Avermectins (e.g.,
ivermectin )
Barbiturates (e.g.,
phenobarbital )
Benzodiazepines (e.g.,
diazepam )
Bromide compounds (e.g.,
potassium bromide )
Carbamates (e.g.,
meprobamate )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,
ergoloid (dihydroergotoxine) )
Etazepine
Etifoxine
Fenamates (e.g.,
mefenamic acid )
Flavonoids (e.g.,
apigenin ,
hispidulin )
Fluoxetine
Flupirtine
Imidazoles (e.g.,
etomidate )
Kava constituents (e.g.,
kavain )
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,
allopregnanolone ,
cholesterol ,
THDOC )
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,
β-carbolines (e.g.,
abecarnil ),
cyclopyrrolones (e.g.,
zopiclone ),
imidazopyridines (e.g.,
zolpidem ),
pyrazolopyrimidines (e.g.,
zaleplon ))
Norfluoxetine
Petrichloral
Phenols (e.g.,
propofol )
Phenytoin
Piperidinediones (e.g.,
glutethimide )
Propanidid
Pyrazolopyridines (e.g.,
etazolate )
Quinazolinones (e.g.,
methaqualone )
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,
baicalin )
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) )
Topiramate
Valerian constituents (e.g.,
valerenic acid )
Volatiles /
gases (e.g.,
chloral hydrate ,
chloroform ,
diethyl ether ,
paraldehyde ,
sevoflurane )
Negative modulators:
1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g.,
penicillins ,
cephalosporins ,
carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (
TBPS ,
TBPO ,
IPTBO )
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g.,
fipronil )
Flavonoids (e.g.,
amentoflavone ,
oroxylin A )
Flumazenil
Fluoroquinolones (e.g.,
ciprofloxacin )
Flurothyl
Furosemide
Golexanolone
Iomazenil (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g.,
apalutamide ,
bicalutamide ,
enzalutamide ,
flutamide ,
nilutamide )
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e.,
picrotin ,
picrotoxinin and
dihydropicrotoxinin )
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor