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Details

Stereochemistry ACHIRAL
Molecular Formula C7H5NO3S
Molecular Weight 183.1859
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SACCHARIN

SMILES

c1ccc2c(c1)C(=NS2(=O)=O)O

InChI

InChIKey=CVHZOJJKTDOEJC-UHFFFAOYSA-N
InChI=1S/C7H5NO3S/c9-7-5-3-1-2-4-6(5)12(10,11)8-7/h1-4H,(H,8,9)

HIDE SMILES / InChI

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
Elevated expression of glucose transporter-1 in hypothalamic ependymal cells not involved in the formation of the brain-cerebrospinal fluid barrier.
2001
A role for kinesin in insulin-stimulated GLUT4 glucose transporter translocation in 3T3-L1 adipocytes.
2001 Apr 6
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
Characterization of EDTA-soluble polysaccharides from the scape of Musa paradisiaca (banana).
2001 Feb
Dietary effects of ortho-phenylphenol and sodium ortho-phenylphenate on rat urothelium.
2001 Feb
Negative-ion electrospray mass spectrometry of neutral underivatized oligosaccharides.
2001 Feb 1
Skeletal muscle and insulin sensitivity: pathophysiological alterations.
2001 Feb 1
Cysteine residues in the D-galactose-H+ symport protein of Escherichia coli: effects of mutagenesis on transport, reaction with N-ethylmaleimide and antibiotic binding.
2001 Feb 1
Golgi complex, endoplasmic reticulum exit sites, and microtubules in skeletal muscle fibers are organized by patterned activity.
2001 Feb 1
Glucans exhibit weak antioxidant activity, but stimulate macrophage free radical activity.
2001 Feb 15
Identification and characterization of neutral endopeptidase (EC 3. 4. 24. 11) from human prostasomes--localization in prostatic tissue and cell lines.
2001 Feb 15
Diabetes. Dialogue between muscle and fat.
2001 Feb 8
Further glucosides of lichens' acids from Central Asian lichens.
2001 Jan
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
What's the truth about the health risks of sugar substitutes such as saccharin and aspartame?
2001 Jan
Hypoxia-Induced increase in FDG uptake in MCF7 cells.
2001 Jan
The Schistosoma mansoni host-interactive tegument forms from vesicle eruptions of a cyton network.
2001 Jan
Changes of nasal function after temperature-controlled radiofrequency tissue volume reduction for the turbinate.
2001 Jan
The rate-limiting step for tumor [18F]fluoro-2-deoxy-D-glucose (FDG) incorporation.
2001 Jan
Placental glucose transport in gestational diabetes mellitus.
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
Saccharin activates cation conductance via inositol 1,4,5-trisphosphate production in a subset of isolated rod taste cells in the frog.
2001 Jan
Glut1 expression in T1 and T2 stage colorectal carcinomas: its relationship to clinicopathological features.
2001 Jan
Improved diabetic syndrome in C57BL/KsJ-db/db mice by oral administration of the Na(+)-glucose cotransporter inhibitor T-1095.
2001 Jan
Mechanism of amelioration of insulin resistance by beta3-adrenoceptor agonist AJ-9677 in the KK-Ay/Ta diabetic obese mouse model.
2001 Jan
Renal Na(+)-glucose cotransporters.
2001 Jan
Developmental reprogramming of rat GLUT-5 requires de novo mRNA and protein synthesis.
2001 Jan
Cellular responses of NG108-15 and SK-N-MC lines to sweet and bitter tastants as measured by extracellular acidification rates.
2001 Jan 1
Functional asymmetry of the sodium-D-glucose cotransporter expressed in yeast secretory vesicles.
2001 Jan 15
Polysaccharides of green Arabica and Robusta coffee beans.
2001 Jan 15
Compositional analysis of glycosaminoglycans by electrospray mass spectrometry.
2001 Jan 15
Direct inhibition of the hexose transporter GLUT1 by tyrosine kinase inhibitors.
2001 Jan 23
Engineering conformational flexibility in the lactose permease of Escherichia coli: use of glycine-scanning mutagenesis to rescue mutant Glu325-->Asp.
2001 Jan 23
Characteristics of endothelial cells derived from the blood-brain barrier and of astrocytes in culture.
2001 Jan 26
Identification of N- and O-linked oligosaccharides in human seminal vesicles.
2001 Jan-Feb
Effect of growth hormone on intestinal Na+/glucose cotransporter activity.
2001 Jan-Feb
Spatial compartmentalization of signal transduction in insulin action.
2001 Mar
Effects of excitotoxic brain lesions on taste-mediated odor learning in the rat.
2001 Mar
Genetic multiplicity of the human UDP-glucuronosyltransferases and regulation in the gastrointestinal tract.
2001 Mar
Hormonal regulation of chicken intestinal NHE and SGLT-1 activities.
2001 Mar
Effects of cellular ATP depletion on glucose transport and insulin signaling in 3T3-L1 adipocytes.
2001 Mar
Glucose metabolism in perfused mouse hearts overexpressing human GLUT-4 glucose transporter.
2001 Mar
Ceramide dissociates 3'-phosphoinositide production from pleckstrin homology domain translocation.
2001 Mar 1
GLUT4 vesicle trafficking in rat adipocytes after ethanol feeding: regulation by heterotrimeric G-proteins.
2001 Mar 1
Model of the 3-D structure of the GLUT3 glucose transporter and molecular dynamics simulation of glucose transport.
2001 Mar 1
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
Name Type Language
SACCHARIN
EP   FCC   HSDB   II   INCI   MART.   MI   USP-RS   VANDF   WHO-DD  
INCI  
Official Name English
SACCHARIN [EP MONOGRAPH]
Common Name English
SACCHARINUM [HPUS]
Common Name English
SACCHARIN [INCI]
Common Name English
INS-954(I)
Code English
SACCHARIN [II]
Common Name English
SACCHARIN [MI]
Common Name English
SACCHARIN [JAN]
Common Name English
SACCHARINUM
HPUS  
Common Name English
E-954(I)
Code English
1,2-BENZISOTHIAZOL-3(2H)-ONE, 1,1-DIOXIDE
Systematic Name English
SACCHARIN [IARC]
Common Name English
SACCHARIN [HSDB]
Common Name English
SACCHARIN [FCC]
Common Name English
1,2-BENZISOTHIAZOLIN-3-ONE 1,1-DIOXIDE
Systematic Name English
SACCHARIN [MART.]
Common Name English
NSC-5349
Code English
SACCHARIN [USP-RS]
Common Name English
SACCHARIN [WHO-DD]
Common Name English
INS NO.954(I)
Code English
SACCHARIN [VANDF]
Common Name English
Classification Tree Code System Code
JECFA EVALUATION INS-954(I)
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
CODEX ALIMENTARIUS (GSFA) INS-954(I)
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
NCI_THESAURUS C283
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
Code System Code Type Description
JECFA MONOGRAPH
INS-954(I)
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
PUBCHEM
5143
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
WIKIPEDIA
SACCHARIN
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
201-321-0
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
LACTMED
Saccharin
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL310671
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
USP_CATALOG
1607007
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY USP-RS
CAS
81-07-2
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
NCI_THESAURUS
C76515
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
DRUG BANK
DB12418
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
FDA UNII
FST467XS7D
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
HSDB
669
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
MERCK INDEX
M9715
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY Merck Index
EVMPD
SUB15170MIG
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
EPA CompTox
81-07-2
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
MESH
D012439
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY
RXCUI
9509
Created by admin on Fri Jun 25 21:18:22 UTC 2021 , Edited by admin on Fri Jun 25 21:18:22 UTC 2021
PRIMARY RxNorm