Basic information
- CAS
517-43-1- Standard SMILES
O=C(O)c1cc(O)c2c(c1)C(C1c3cc(C(=O)O)cc(O)c3C(=O)c3c(OC4OC(CO)C(O)C(O)C4O)cccc31)c1cccc(OC3OC(CO)C(O)C(O)C3O)c1C2=O- InChIKey
IPQVTOJGNYVQEO-UHFFFAOYSA-N- Molecular formula
- C42H38O20
- Average molar mass
- 862.7 g/mol
- Monoisotopic mass
- 862.1956436
Overview
Sennosides (also known as senna glycoside or senna) is a medication used to treat constipation and empty the large intestine before surgery. The medication is taken by mouth or via the rectum. It typically begins working in minutes when given by rectum and within twelve hours when given by mouth. It is a weaker laxative than bisacodyl or castor oil. Sennoside A, one of the sennosides present in the laxative medication, has recently proven effective in inhibiting the ribonuclease H (RNase H) activity of human immunodeficiency virus (HIV) reverse transcriptase.
Names & identifiers
- Preferred name
- Sennosides
- IUPAC
- 9-[2-carboxy-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid
- English name
- Senna, Cassia obovata, ext.
- Molecular formula
- C42H38O20
- Molecular weight
- 0
Names & synonyms
SennosidesGlysennidLaxativeColonormNytilaxSankaijoExchange selectDocuset SodiumLaxative PillsLaxative SennaSenna GlycosideColistat Plus
Show more names
Ccris 7490SENNA EXTRACT 8%Einecs 285-393-9Senna extract CRSCassiaobovata ext.Cassia obovata extractExtracts of Sennae FoliumSenna, Cassia obovata, ext.Senna extract (Cassia obovata)9-[2-carboxy-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracen-9-yl]-4-hydroxy-10-oxo-5-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-9H-anthracene-2-carboxylic acid
Gentle NatureSenna LiquidColon DetoxGeri-kotSenna PlusSenna-TabsNature's RemedySenna Lax
Database identifiers
- CAS
517-43-1、62211-03-4、66575-30-2、81-27-6、85085-71-8
Properties
Computed structural properties
- XLogP
- 1.2
- Topological polar surface area
- 348 Ų
- Hydrogen bond donors
- 12
- Hydrogen bond acceptors
- 20
- Rotatable bonds
- 9
- Heavy atoms
- 62
- Formal charge
- 0
- Complexity
- 1,550
Experimental & physicochemical properties
Drugs
Pharmaceuticals
Pharmaceuticals -> Used in Switzerland
CosmeticsSkin conditioning
Physicochemical properties
- Cosmetics Ingredients Functions
- SKIN CONDITIONING
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Danger
H317 (100%): May cause an allergic skin reaction [Warning Sensitization, Skin]
P233, P260, P261, P271, P272, P280, P284, P302+P352, P304+P340, P321, P333+P317, P342+P316, P362+P364, P403, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 78 reports by companies from 1 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
This chemical does not meet GHS hazard criteria for 66.7% (2 of 3) of all reports.
Warning
Hazard information
Hazard Classes and Categories
Skin Sens. 1 (100%)
Acute Tox. 4 (33.3%)
Chemistry & industry
Pharmacology
ATC Code
A - Alimentary tract and metabolism
QA - Alimentary tract and metabolism
Protein BindingBecause sennosides are ingested and their action occurs in the gut, it is generally not thought to be protein bound.
PharmacodynamicsSenna stimulates peristalsis and increases fecal water content to increase motility of feces through the large intestine.
Mechanism of Action
Sennoside A and B, the components of senna, are metabolized by gut bacteria into the active metabolite rheinanthrone [DB13175]. Rheinanthrone [DB13175] appears to increase cyclooxegenase 2 (COX2) expression in macrophage cells leading to an increase in prostaglandin E2 (PGE2). This increase in PGE2 is associated with a decrease in aquaporin 3 expression in mucosal epithelial cells of the large intestine. A decrease in aquaporin 3 expression likely produces the laxative effect by restricting water reabsorption by the large intestine thereby increasing fecal water content. The exact mechanism by which rheinanthrone increases COX2 expression is unknown. Rheinanthrone [DB13175] also stimulates peristalsis in the large intestine although the mechanism behind this effect is unknown. Rhein [DB13174], another active metabolite is thought to excite submucosal acetylcholinergic neurons resulting in increased chloride and prostaglandin secretion. The movement of chloride ions into the large intestine would also help to draw water into the lumen.
Biological Half-LifeThe half life of radiolabelled intravenous sennoside B in rats was 8.568±0.651h.
Metabolism/Metabolites
Sennosides A and B are metabolised to sennidins A and B by gut bacteria. Sennidins A and B are further metabolized to rheinanthrone [DB13175] by gut bacteria using beta-glucosidase. Rheinanthrone [DB13175] is absorbed into systemic circulation where 2.6% is metabolized to rhein [DB13174] and sennidins A and B via oxidation. Rheinanthrone [DB13175] is the major active metabolite of sennosides A and B which produces the laxative effect of the medication. Rhein [DB13174] is also an active metabolite known to have many protective effects.
Related reactions
0 records
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Compound notes
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