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Details

Stereochemistry ACHIRAL
Molecular Formula C7H4NO3S.Na.H2O
Molecular Weight 223.183
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SACCHARIN SODIUM MONOHYDRATE

SMILES

c1ccc2c(c1)C(=NS2(=O)=O)[O-].[Na+].O

InChI

InChIKey=ILJOYZVVZZFIKA-UHFFFAOYSA-M
InChI=1S/C7H5NO3S.Na.H2O/c9-7-5-3-1-2-4-6(5)12(10,11)8-7;;/h1-4H,(H,8,9);;1H2/q;+1;/p-1

HIDE SMILES / InChI

Molecular Formula C7H5NO3S
Molecular Weight 183.1859
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula HO
Molecular Weight 17.0073
Charge -1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: description was created based on several sources, including http://www.diabetes.co.uk/sweeteners/saccharin.html http://www.ukfoodguide.net/e954.htm

Saccharin is the most established of the artificial sweeteners on the market, this mixture of dextrose and saccharin has been in use for over a century and is found in diet versions of soft drinks. It is 300-500 times sweeter than sugar and contains zero calories. In 1977, the FDA tried to ban its use after evidence showed it caused cancer in rats. Extensive lobbying by the diet food industry allowed products to stay on the shelves as long as they carried warnings about the cancer risks in animals. This warning was removed in 2001 when the Calorie Control Council insisted the link between animal and human cancers could not automatically be made. Consumption of saccharin-sweetened products can benefit diabetics as the substance goes directly through the human digestive system without being digested. While saccharin has no food energy, it can trigger the release of insulin in humans due to its sweet taste. The T1R2/R3 sweet taste receptor exist on the surface of pancreatic beta cells. Saccharin is a unique in that it inhibits glucose-stimulated insulin secretion (GSIS) at submaximal and maximal glucose concentrations, with the other sweeteners having no effect. Investigation of saccharin’s dose-response characteristics showed that concentrations of 0.1 and 0.5 mM stimulated insulin secretion, while concentrations of 1 and 2.5 mM inhibited insulin secretion. Saccharin’s effect on insulin secretion was shown to be reversible in INS-1 832/13 clonal pancreatic beta cells after chronic exposure to 1 mM saccharin. Artificial sweeteners may affect insulin secretion via interaction with the sweet taste receptor, also saccharin may affect other cellular processes linked to insulin secretion, and that these effects are both time- and concentration-dependent

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q8TE23
Gene ID: 80834.0
Gene Symbol: TAS1R2
Target Organism: Homo sapiens (Human)
Target ID: Q7RTX0
Gene ID: 83756.0
Gene Symbol: TAS1R3
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
14 μg/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SACCHARIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
27 μg/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SACCHARIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5800 μg × min/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered: PROBENECID
SACCHARIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3700 μg × min/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
SACCHARIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
6500 μg × min/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SACCHARIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FED
6800 μg × min/mL
2 g single, oral
dose: 2 g
route of administration: Oral
experiment type: SINGLE
co-administered:
SACCHARIN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no (co-administration study)
Comment: coadministration with bupropion: had no effect on the CYP2B activity
no
no (co-administration study)
Comment: coadministration with bupropion: saccharin had no inhibitory effect on CYP2B activity in vivo
Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
PubMed

PubMed

TitleDatePubMed
Demonstration of conformational changes associated with activation of the maltose transport complex.
2001 Apr 13
A new type of endo-xyloglucan transferase devoted to xyloglucan hydrolysis in the cell wall of azuki bean epicotyls.
2001 Feb
Serial changes in 14C-deoxyglucose and 201Tl uptake in autoimmune myocarditis in rats.
2001 Feb
Negative-ion electrospray mass spectrometry of neutral underivatized oligosaccharides.
2001 Feb 1
Anti-tumor immunity provided by a synthetic multiple antigenic glycopeptide displaying a tri-Tn glycotope.
2001 Feb 15
Munc18c regulates insulin-stimulated glut4 translocation to the transverse tubules in skeletal muscle.
2001 Feb 9
Distinct long-term regulation of glycerol and non-esterified fatty acid release by insulin and TNF-alpha in 3T3-L1 adipocytes.
2001 Jan
Distinct differences in binding capacity to saccharide epitopes in supratentorial pilocytic astrocytomas, astrocytomas, anaplastic astrocytomas, and glioblastomas.
2001 Jan
Suppression of ethanol responding by centrally administered CTOP and naltrindole in AA and Wistar rats.
2001 Jan
The Schistosoma mansoni host-interactive tegument forms from vesicle eruptions of a cyton network.
2001 Jan
A saccharinate-iron(II) complex with a free saccharin molecule present, [Fe(phen)3]sac2.sacH.6H2O.
2001 Jan
Improved water solubility of neohesperidin dihydrochalcone in sweetener blends.
2001 Jan
Glut1 expression in T1 and T2 stage colorectal carcinomas: its relationship to clinicopathological features.
2001 Jan
Nasal mucociliary clearance in healthy children in a tropical country.
2001 Jan
Improved diabetic syndrome in C57BL/KsJ-db/db mice by oral administration of the Na(+)-glucose cotransporter inhibitor T-1095.
2001 Jan
Thiazolidinediones (PPARgamma agonists) but not PPARalpha agonists increase IRS-2 gene expression in 3T3-L1 and human adipocytes.
2001 Jan
Expression of auxilin or AP180 inhibits endocytosis by mislocalizing clathrin: evidence for formation of nascent pits containing AP1 or AP2 but not clathrin.
2001 Jan
Renal Na(+)-glucose cotransporters.
2001 Jan
Functional asymmetry of the sodium-D-glucose cotransporter expressed in yeast secretory vesicles.
2001 Jan 15
Compositional analysis of glycosaminoglycans by electrospray mass spectrometry.
2001 Jan 15
Neutralization of a conserved amino acid residue in the human Na+/glucose transporter (hSGLT1) generates a glucose-gated H+ channel.
2001 Jan 19
Interaction of quercetin glucosides with the intestinal sodium/glucose co-transporter (SGLT-1).
2001 Jan 26
Identification of N- and O-linked oligosaccharides in human seminal vesicles.
2001 Jan-Feb
Spatial compartmentalization of signal transduction in insulin action.
2001 Mar
Ceramide dissociates 3'-phosphoinositide production from pleckstrin homology domain translocation.
2001 Mar 1
Model of the 3-D structure of the GLUT3 glucose transporter and molecular dynamics simulation of glucose transport.
2001 Mar 1
Structure of a sialic acid-activating synthetase, CMP-acylneuraminate synthetase in the presence and absence of CDP.
2001 Mar 16
Characterization of the stromal cell-derived factor-1alpha-heparin complex.
2001 Mar 16
Arachidonic acid stimulates glucose uptake in 3T3-L1 adipocytes by increasing GLUT1 and GLUT4 levels at the plasma membrane. Evidence for involvement of lipoxygenase metabolites and peroxisome proliferator-activated receptor gamma.
2001 Mar 23
Lactose utilization by Saccharomyces cerevisiae strains expressing Kluyveromyces lactis LAC genes.
2001 Nov 30
Patents

Sample Use Guides

In Vivo Use Guide
no more than 80 to 3000 mg saccharin per kilogram or litre should be used
Route of Administration: Oral
In Vitro Use Guide
After assaying for prolactin (PRL) in saccharin-treated cultures, it was observed that this sweetener is also capable of stimulating PRL production two- to sixfold in a dose-dependent manner. Enhancement of PRL production can be observed at 0.5 mM saccharin, yet this is 10 times less than the saccharin concentration required to alter cell shape. These effects of saccharin on cell morphology and on PRL production are reversible in rat pituitary tumor cells (GH4C1). When added to cultures along with maximal concentrations of epidermal growth factor (EGF) or thyrotropin-releasing hormone (TRH), the effects of saccharin on PRL production are additive, suggesting that the actions of saccharin are mediated by a somewhat different pathway from that of the peptide hormones
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:05:57 UTC 2021
Edited
by admin
on Sat Jun 26 11:05:57 UTC 2021
Record UNII
A9CO00M9HV
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SACCHARIN SODIUM MONOHYDRATE
Common Name English
SODIUM SACCHARIN HYDRATE
Common Name English
1,2-BENZISOTHIAZOL-3(2H)-ONE, 1,1-DIOXIDE, SODIUM SALT, MONOHYDRATE
Systematic Name English
SODIUM SACCHARINATE MONOHYDRATE
Common Name English
Code System Code Type Description
FDA UNII
A9CO00M9HV
Created by admin on Sat Jun 26 11:05:57 UTC 2021 , Edited by admin on Sat Jun 26 11:05:57 UTC 2021
PRIMARY
CAS
171734-71-7
Created by admin on Sat Jun 26 11:05:57 UTC 2021 , Edited by admin on Sat Jun 26 11:05:57 UTC 2021
PRIMARY
EPA CompTox
82385-42-0
Created by admin on Sat Jun 26 11:05:57 UTC 2021 , Edited by admin on Sat Jun 26 11:05:57 UTC 2021
PRIMARY
EVMPD
SUB77955
Created by admin on Sat Jun 26 11:05:57 UTC 2021 , Edited by admin on Sat Jun 26 11:05:57 UTC 2021
PRIMARY
CAS
82385-42-0
Created by admin on Sat Jun 26 11:05:57 UTC 2021 , Edited by admin on Sat Jun 26 11:05:57 UTC 2021
NON-SPECIFIC STOICHIOMETRY
PUBCHEM
443755
Created by admin on Sat Jun 26 11:05:57 UTC 2021 , Edited by admin on Sat Jun 26 11:05:57 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE