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Details

Stereochemistry RACEMIC
Molecular Formula C6H11NOS2
Molecular Weight 177.288
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of SULFORAPHANE, (±)-

SMILES

C[S+]([O-])CCCCN=C=S

InChI

InChIKey=SUVMJBTUFCVSAD-UHFFFAOYSA-N
InChI=1S/C6H11NOS2/c1-10(8)5-3-2-4-7-6-9/h2-5H2,1H3

HIDE SMILES / InChI

Description

Sulforaphane is a naturally-occurring phytochemical belonging to the class of isothiocyanates. As the aglycone metabolite of glucosinolate glucoraphanin (sulforaphane glucosinolate), sulforaphane acts as an antioxidant and potent stimulator of endogenous detoxifying enzymes. This agent displays anticarcinogenic properties due to its ability to induce phase II detoxification enzymes, such as glutathione S-transferase and quinone reductase, thereby providing protection against certain carcinogens and toxic, reactive oxygen species. Broccoli sprouts contain large amounts of sulforaphane, which is also found in other cruciferous vegetables including cabbage and kale. Sulforaphane is under investigation for the treatment of Autism Spectrum Disorder and Schizophrenia.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
9000.0 nM [IC50]
2200.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown
Primary
Unknown

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
12 week treatment sulforaphane supplement 3-8 tablets daily, with dose depending upon body weight. The weight-based dosing schedule is as follows: 3 tablets (approx. 46.5 µmol SF) if <100 lb; 5 tablets (approx. 77.5 µmol SF) if 100-125 lb; 6 tablets (approx. 93 µmol SF) if 126-175 lb; 7 tablets (approx. 108.5 µmol SF) if 176-199 lb; 8 tablets (approx. 124 µmol SF) if ≥ 200 lb
Route of Administration: Oral
In Vitro Use Guide
Sulforaphane was evaluated in vitro for their cytotoxicity against five cancer cell lines (HepG2, A549, MCF-7, HCT-116 and SH-SY5Y). The cytotoxic activity in vitro was measured using the MTT assay. The MTT solution (10.0 mL/well) was added in culture media after cells were treated with various concentrations of compounds for 72 h, and cells were incubated for further 4 h at 37 C. The purple formazan crystals were dissolved in 100 mL DMSO. After 10 min, the plates were read on an automated microplate spectrophotometer (Bio-Tek Instruments, Winooski, VT) at 570 nm and 630 nm.