QUININE ARSENATE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C20H24N2O2.8H2O.AsH3O4
Molecular Weight	934.9004
Optical Activity	UNSPECIFIED
Defined Stereocenters	8 / 8
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C=C[C@@]1([H])CN2CC[C@@]1([H])C[C@@]2([H])[C@@]([H])(c3ccnc4ccc(cc34)OC)O.C=C[C@@]1([H])CN2CC[C@@]1([H])C[C@@]2([H])[C@@]([H])(c3ccnc4ccc(cc34)OC)O.[As](=O)(O)(O)O.O.O.O.O.O.O.O.O

InChI

InChIKey=CDTWVNODIPITIB-QLOUZFAJSA-N

InChI=1S/2C20H24N2O2.AsH3O4.8H2O/c2*1-3-13-12-22-9-7-14(13)10-19(22)20(23)16-6-8-21-18-5-4-15(24-2)11-17(16)18;2-1(3,4)5;;;;;;;;/h2*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;(H3,2,3,4,5);8*1H2/t2*13-,14-,19-,20+;;;;;;;;;/m00........./s1

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	AsH3O4
Molecular Weight	141.943
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C20H24N2O2
Molecular Weight	324.4175
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://link.springer.com/chapter/10.1007/978-1-4684-6168-8_3 | https://www.nj.gov/health/eoh/rtkweb/documents/fs/0086.pdf

Ammonium dihydrogen arsenate is an inorganic compound that has been considered a potential electro-optic material and has been explored by a number of investigators for modulation purposes. Ammonium arsenate is a cancerogenic substance.

Approval Year

PubMed

Title	Date	PubMed
Pharmacological characterization of multidrug resistant MRP-transfected human tumor cells.	1994 Nov 15	7954421
Screening for reproductive toxicity in Fundulus heteroclitus by genetic expression profiling.	1996	23888923
Arsenic-induced neural tube defects in mice: alterations in cell cycle gene expression.	1996 Nov-Dec	8946558
Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms.	1998 Apr	9548797
Enhanced transcription factor DNA binding and gene expression induced by arsenite or arsenate in renal slices.	1999 Jul	10445758
Purine nucleoside phosphorylase as a cytosolic arsenate reductase.	2002 Nov	12388830
Genetic variation in genes associated with arsenic metabolism: glutathione S-transferase omega 1-1 and purine nucleoside phosphorylase polymorphisms in European and indigenous Americans.	2003 Aug	12928150
Valproate-induced neural tube defects in folate-binding protein-2 (Folbp2) knockout mice.	2003 Dec	14745917
Arsenite and arsenate activate extracellular signal-regulated kinases 1/2 by an epidermal growth factor receptor-mediated pathway in normal human keratinocytes.	2003 Dec	14674888
Human 3'-phosphoadenosine 5'-phosphosulfate synthetase (isoform 1, brain): kinetic properties of the adenosine triphosphate sulfurylase and adenosine 5'-phosphosulfate kinase domains.	2004 Apr 13	15065880
Glutathione modulates recombinant rat arsenic (+3 oxidation state) methyltransferase-catalyzed formation of trimethylarsine oxide and trimethylarsine.	2004 Dec	15606138
Arsenic induced inhibition of delta-aminolevulinate dehydratase activity in rat blood and its response to meso 2,3-dimercaptosuccinic acid and monoisoamyl DMSA.	2004 Mar	15202869
Regulation of cytoplasmic stress granules by apoptosis-inducing factor.	2004 Sep 1	15316071
Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children.	2005 Jun	15929903
Redox regulation of RhoA.	2006 Dec 5	17128987
Organic anion transporting polypeptide-C mediates arsenic uptake in HEK-293 cells.	2006 Jul	16479312
Glutathione-S-transferase-omega [MMA(V) reductase] knockout mice: enzyme and arsenic species concentrations in tissues after arsenate administration.	2006 Nov 1	16930657
Glutathione-dependent reduction of arsenate by glycogen phosphorylase a reaction coupled to glycogenolysis.	2007 Nov	17693425
Glutathione-dependent reduction of arsenate by glycogen phosphorylase responsiveness to endogenous and xenobiotic inhibitors.	2007 Nov	17693424
Arsenite-induced cytotoxicity in dorsal root ganglion explants.	2008 Apr 15	18226606
Effects of inorganic arsenic on the rat and mouse urinary bladder.	2008 Dec	18728046
High dietary fat exacerbates arsenic-induced liver fibrosis in mice.	2008 Mar	18296743
Effects of endogenous hydrogen peroxide and glutathione on the stability of arsenic metabolites in rat bile.	2008 Oct 1	18619986
Mechanism of thiol-supported arsenate reduction mediated by phosphorolytic-arsenolytic enzymes: II. Enzymatic formation of arsenylated products susceptible for reduction to arsenite by thiols.	2009 Aug	19478237
Effects of different inorganic arsenic species in Cyprinus carpio (Cyprinidae) tissues after short-time exposure: bioaccumulation, biotransformation and biological responses.	2009 Dec	19632019
Fast, quantitative in situ hybridization of rare mRNAs using 14C-standards and phosphorus imaging.	2009 Dec 15	19761793
Inorganic arsenic modulates the expression of selenoproteins in mouse embryonic stem cell.	2009 Jun 1	19429247
Disruption of the arsenic (+3 oxidation state) methyltransferase gene in the mouse alters the phenotype for methylation of arsenic and affects distribution and retention of orally administered arsenate.	2009 Oct	19691357
Glutathione-supported arsenate reduction coupled to arsenolysis catalyzed by ornithine carbamoyl transferase.	2009 Sep 1	19248796
Monomethylarsenic diglutathione transport by the human multidrug resistance protein 1 (MRP1/ABCC1).	2011 Dec	21918036
Role of autophagy in arsenite-induced neurotoxicity: the involvement of α-synuclein.	2015 Mar 18	25639566

Patents

Substance Class	Chemical Created by `admin` on `Sat Jun 26 15:08:14 UTC 2021` Edited by `admin` on `Sat Jun 26 15:08:14 UTC 2021`
Record UNII	8C15XFK30P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

QUININE ARSENATE

Common Name

English

QUININE ARSENATE [WHO-DD]

Common Name

English

CINCHONAN-9-OL, 6'-METHOXY-, (8.ALPHA.,9R)-, ARSENATE (3:2) (SALT)

Common Name

English

CHININUM ARSENICICUM [HPUS]

Common Name

English

CHININUM ARSENICICUM

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547