Quinine arsenate

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	ABSOLUTE
Molecular Formula	3C20H24N2O2.2AsH3O4
Molecular Weight	1257.1363
Optical Activity	UNSPECIFIED
Defined Stereocenters	12 / 12
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[As](O)(O)=O.O[As](O)(O)=O.COC1=CC2=C(C=C1)N=CC=C2[C@@H](O)[C@@H]3C[C@@H]4CCN3C[C@@H]4C=C.COC5=CC6=C(C=C5)N=CC=C6[C@@H](O)[C@@H]7C[C@@H]8CCN7C[C@@H]8C=C.COC9=CC%10=C(C=C9)N=CC=C%10[C@@H](O)[C@@H]%11C[C@@H]%12CCN%11C[C@@H]%12C=C

InChI

InChIKey=CDTYBBCOIQJQRO-INGJVHGESA-N

InChI=1S/3C20H24N2O2.2AsH3O4/c3*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*2-1(3,4)5/h3*3-6,8,11,13-14,19-20,23H,1,7,9-10,12H2,2H3;2*(H3,2,3,4,5)/t3*13-,14-,19-,20+;;/m000../s1

HIDE SMILES / InChI

Molecular Formula	C20H24N2O2
Molecular Weight	324.4168
Charge	0
Count

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

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

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
Role of autophagy in arsenite-induced neurotoxicity: the involvement of α-synuclein.	2015-03-18	25639566
Monomethylarsenic diglutathione transport by the human multidrug resistance protein 1 (MRP1/ABCC1).	2011-12	21918036
Fast, quantitative in situ hybridization of rare mRNAs using 14C-standards and phosphorus imaging.	2009-12-15	19761793
Effects of different inorganic arsenic species in Cyprinus carpio (Cyprinidae) tissues after short-time exposure: bioaccumulation, biotransformation and biological responses.	2009-12	19632019
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.	2009-10	19691357
Glutathione-supported arsenate reduction coupled to arsenolysis catalyzed by ornithine carbamoyl transferase.	2009-09-01	19248796
Mechanism of thiol-supported arsenate reduction mediated by phosphorolytic-arsenolytic enzymes: II. Enzymatic formation of arsenylated products susceptible for reduction to arsenite by thiols.	2009-08	19478237
Inorganic arsenic modulates the expression of selenoproteins in mouse embryonic stem cell.	2009-06-01	19429247
Effects of inorganic arsenic on the rat and mouse urinary bladder.	2008-12	18728046
Effects of endogenous hydrogen peroxide and glutathione on the stability of arsenic metabolites in rat bile.	2008-10-01	18619986
Arsenite-induced cytotoxicity in dorsal root ganglion explants.	2008-04-15	18226606
High dietary fat exacerbates arsenic-induced liver fibrosis in mice.	2008-03	18296743
Glutathione-dependent reduction of arsenate by glycogen phosphorylase a reaction coupled to glycogenolysis.	2007-11	17693425
Glutathione-dependent reduction of arsenate by glycogen phosphorylase responsiveness to endogenous and xenobiotic inhibitors.	2007-11	17693424
Redox regulation of RhoA.	2006-12-05	17128987
Glutathione-S-transferase-omega [MMA(V) reductase] knockout mice: enzyme and arsenic species concentrations in tissues after arsenate administration.	2006-11-01	16930657
Organic anion transporting polypeptide-C mediates arsenic uptake in HEK-293 cells.	2006-07	16479312
Developmentally restricted genetic determinants of human arsenic metabolism: association between urinary methylated arsenic and CYT19 polymorphisms in children.	2005-06	15929903
Glutathione modulates recombinant rat arsenic (+3 oxidation state) methyltransferase-catalyzed formation of trimethylarsine oxide and trimethylarsine.	2004-12	15606138
Regulation of cytoplasmic stress granules by apoptosis-inducing factor.	2004-09-01	15316071
Human 3'-phosphoadenosine 5'-phosphosulfate synthetase (isoform 1, brain): kinetic properties of the adenosine triphosphate sulfurylase and adenosine 5'-phosphosulfate kinase domains.	2004-04-13	15065880
Arsenic induced inhibition of delta-aminolevulinate dehydratase activity in rat blood and its response to meso 2,3-dimercaptosuccinic acid and monoisoamyl DMSA.	2004-03	15202869
Valproate-induced neural tube defects in folate-binding protein-2 (Folbp2) knockout mice.	2003-12	14745917
Arsenite and arsenate activate extracellular signal-regulated kinases 1/2 by an epidermal growth factor receptor-mediated pathway in normal human keratinocytes.	2003-12	14674888
Genetic variation in genes associated with arsenic metabolism: glutathione S-transferase omega 1-1 and purine nucleoside phosphorylase polymorphisms in European and indigenous Americans.	2003-08	12928150
Purine nucleoside phosphorylase as a cytosolic arsenate reductase.	2002-11	12388830
Enhanced transcription factor DNA binding and gene expression induced by arsenite or arsenate in renal slices.	1999-07	10445758
Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms.	1998-04	9548797
Arsenic-induced neural tube defects in mice: alterations in cell cycle gene expression.	1996-11-01	8946558
Screening for reproductive toxicity in Fundulus heteroclitus by genetic expression profiling.	1996	23888923
Pharmacological characterization of multidrug resistant MRP-transfected human tumor cells.	1994-11-15	7954421

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:09:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:09:14 GMT 2025`
Record UNII	8C15XFK30P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHININUM ARSENICICUM

Preferred Name

English

Quinine arsenate

Common Name

English

Cinchonan-9-ol, 6?-methoxy-, (8?,9R)-, arsenate (3:2) (salt)

Systematic Name

English

Quinine arsenate [WHO-DD]

Common Name

English

CHININUM ARSENICICUM [HPUS]

Common Name

English

Arsenic acid (H<sub>3</sub>AsO<sub>4</sub>), compd. with (8?,9R)-6?-methoxycinchonan-9-ol (2:3)

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547