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.[H][C@]1(C[C@@H]2CCN1C[C@@H]2C=C)[C@H](O)C3=C4C=C(OC)C=CC4=NC=C3.[H][C@]5(C[C@@H]6CCN5C[C@@H]6C=C)[C@H](O)C7=C8C=C(OC)C=CC8=NC=C7.[H][C@]9(C[C@@H]%10CCN9C[C@@H]%10C=C)[C@H](O)C%11=C%12C=C(OC)C=CC%12=NC=C%11

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	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	324.4168
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
Inorganic and methylated arsenic compounds induce cell death in murine macrophages via different mechanisms.	1998 Apr	9548797
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
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
Inorganic arsenic modulates the expression of selenoproteins in mouse embryonic stem cell.	2009 Jun 1	19429247

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:19 UTC 2023` Edited by `admin` on `Fri Dec 15 15:48:19 UTC 2023`
Record UNII	8C15XFK30P
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Quinine arsenate

Common Name

English

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

Systematic Name

English

Quinine arsenate [WHO-DD]

Common Name

English

CHININUM ARSENICICUM [HPUS]

Common Name

English

CHININUM ARSENICICUM

Common Name

English

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

Systematic Name

English

Classification Tree Code System Code

CFR

21 CFR 310.547