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
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
Valproate-induced neural tube defects in folate-binding protein-2 (Folbp2) knockout mice.	2003 Dec	14745917
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
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
Arsenite-induced cytotoxicity in dorsal root ganglion explants.	2008 Apr 15	18226606
High dietary fat exacerbates arsenic-induced liver fibrosis in mice.	2008 Mar	18296743
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
Role of autophagy in arsenite-induced neurotoxicity: the involvement of α-synuclein.	2015 Mar 18	25639566

Patents

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:48:19 GMT 2023` Edited by `admin` on `Fri Dec 15 15:48:19 GMT 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