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N 4 -Chloroacetylcytosine arabinoside
Names
IUPAC name
N -[1-(β-D -Arabinofuranosyl)-2-oxo-1,2-dihydropyrimidin-4-yl]-2-chloroacetamide
Systematic IUPAC name
2-Chloro-N -{1-[(2R ,3S ,4S ,5R )-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}acetamide
Identifiers
ChemSpider
InChI=1S/C11H14ClN3O6/c12-3-7(17)13-6-1-2-15(11(20)14-6)10-9(19)8(18)5(4-16)21-10/h1-2,5,8-10,16,18-19H,3-4H2,(H,13,14,17,20)/t5-,8-,9+,10-/m1/s1
Key: WEJWVQRPBCYTRE-STRWAFKBSA-N
InChI=1/C11H14ClN3O6/c12-3-7(17)13-6-1-2-15(11(20)14-6)10-9(19)8(18)5(4-16)21-10/h1-2,5,8-10,16,18-19H,3-4H2,(H,13,14,17,20)/t5-,8-,9+,10-/m1/s1
Key: WEJWVQRPBCYTRE-STRWAFKBBD
c1cn(c(=O)nc1NC(=O)CCl)[C@H]2[C@H]([C@@H]([C@H](O2)CO)O)O
Properties
C 11 H 14 Cl N 3 O 6
Molar mass
319.70 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
N 4 -Chloroacetylcytosine arabinoside is a GABA agonist [ 1] [dubious – discuss ] and might be a pro-drug for cytosine arabinoside , a chemotherapy medication.[ 2]
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