SULFORAPHANE, (±)-

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 Search

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

Molecular Formula	C6H11NOS2
Molecular Weight	177.288
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23983898
Curator's Comment: The description was created based on several sources, including https://clinicaltrials.gov/ct2/show/record/NCT02880462 | https://clinicaltrials.gov/ct2/show/NCT02909959 | https://clinicaltrials.gov/ct2/show/record/NCT03232138 | https://clinicaltrials.gov/ct2/show/NCT01228084 | https://www.ncbi.nlm.nih.gov/pubmed/23685571 | https://www.drugbank.ca/drugs/DB12422

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 Target	Pharmacology	Potency
Nuclear factor erythroid 2-related factor 2 15 Target ID: CHEMBL1075094 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24053646	Inhibitor 8504	19080.0 nM [EC50]
Epidermal growth factor receptor erbB1 62 Target ID: CHEMBL203 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27135370	Inhibitor 8504	9000.0 nM [IC50]
Macrophage migration inhibitory factor 5 Target ID: CHEMBL2085 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25743213	Inhibitor 8504	2200.0 nM [IC50]
Glutathione S-transferase A1 1 Target ID: CHEMBL3409 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9288764	Activator 1447
Glutathione S-transferase A2 1 Target ID: CHEMBL2241 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9288764	Activator 1447
Glutathione S-transferase A4 1 Target ID: CHEMBL4933 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9288764	Activator 1447

Conditions

Condition	Modality	Highest Phase	Product
Schizophrenia 305 Sources: https://clinicaltrials.gov/ct2/show/NCT02880462	Primary	Phase III 665	Unknown Approved Use Unknown
Autism 20 Sources: https://clinicaltrials.gov/ct2/show/NCT02909959	Primary	Phase II 1147	Unknown Approved Use Unknown
Neurodevelopmental disorders 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02909959	Primary	Phase II 1147	Unknown Approved Use Unknown
Lung cancer 70 Sources: https://clinicaltrials.gov/ct2/show/record/NCT03232138	Primary	Phase II 1147	Unknown Approved Use Unknown
Recurrent prostate cancer 1 Sources: https://clinicaltrials.gov/ct2/show/NCT01228084	Primary	Phase II 1147	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A1 132 MRP1 116 CYP2E1 1060 P-gp 1741 CYP1B1 32 CYP1A2 2153	GSTA1 4	MRP1 74 GSTA1 4 MRP2 146 BCRP 101 P-gp 301

Drug as perpetrator

Target	Modality	Activity
BCRP 985	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17077187/	no
BSEP 554	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/34767876/	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10775323/	no
CYP1B1 93	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10775323/	no
CYP2E1 1146	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10775323/	no
CYP3A4 2633	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/10775323/	no
CYP7A1 7	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/34767876/	no
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12425469/	no
P-gp 1932	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12425469/	no
CYP1A1 272	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19202560/	yes
GSTA1 4	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/15090468/	yes
MRP1 232	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17618109/	yes
MRP2 625	inducer 1966 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1NzQ4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDQ4ODAyIn19 \| https://pubmed.ncbi.nlm.nih.gov/11264000/	yes
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/17618109/	yes

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
GSTA1 4	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/12756216/	yes

PubMed

Title	Date	PubMed
Sulforaphane for the chemoprevention of bladder cancer: molecular mechanism targeted approach.	2017-05-23	28423681

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:44:14 GMT 2025` Edited by `admin` on `Mon Mar 31 18:44:14 GMT 2025`
Record UNII	41684WL1GL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

SULFORAPHANE, (±)-

Common Name

English

(±)-SULFORAPHANE

Preferred Name

English

4-METHYLSULFINYLBUTYL ISOTHIOCYANATE

Systematic Name

English

SULFORAPHANE (±)-FORM [MI]

Common Name

English

BUTANE, 1-ISOTHIOCYANATO-4-(METHYLSULFINYL)-

Systematic Name

English

NSC-749790

Code

English

ISOTHIOCYANIC ACID, 4-(METHYLSULFINYL)BUTYL ESTER

Common Name

English

Code System Code Type Description

PUBCHEM

5350