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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H21NO6
Molecular Weight 383.3945
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDRASTINE

SMILES

[H][C@@]1(OC(=O)C2=C1C=CC(OC)=C2OC)[C@]3([H])N(C)CCC4=C3C=C5OCOC5=C4

InChI

InChIKey=JZUTXVTYJDCMDU-MOPGFXCFSA-N
InChI=1S/C21H21NO6/c1-22-7-6-11-8-15-16(27-10-26-15)9-13(11)18(22)19-12-4-5-14(24-2)20(25-3)17(12)21(23)28-19/h4-5,8-9,18-19H,6-7,10H2,1-3H3/t18-,19+/m1/s1

HIDE SMILES / InChI

Molecular Formula C21H21NO6
Molecular Weight 383.3945
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/26821251 | https://www.ncbi.nlm.nih.gov/pubmed/25609220 | https://www.ncbi.nlm.nih.gov/pubmed/2163278

Hydrastine is an alkaloid, one of the chief components of goldenseal (Hydrastis canadensis) which was discovered in 1851 by Alfred P. Durand. Goldenseal is unique from other hydrastine containing plants in that (-)-β- hydrastine is the only hydrastine isomer present, while the (+)-enantiomer is found in other hydrastine-containing plants. . While a number of therapeutic activities have been attributed to berberine, the pharmacological effects of hydrastine are less studied and its safety profile is poorly understood and to frame the relevant pharmacological effects of hydrastine within the specific stereochemistry found in goldenseal. Hydrastine has been shown to have several specific biological activities including, inhibition of tyrosine hydroxylase in PC-12 cells, a relaxant effect on guinea pig isolated trachea, and inhibition of several cytochrome P450 (CYP) enzymes. Toxicological studies performed on goldenseal powder in mice and rats indicate that at commonly used doses goldenseal supplements are non-toxic, thus its constituents are likely to be safe for human use when taken at reasonable doses. Despite goldenseal’s widespread usage, the pharmacokinetics of hydrastine in humans has not been adequately described. While it is difficult to determine the proper dosage range for any herbal product, a recent extensive survey of the literature suggests a daily dose of Hydrastis in the range of 0.9 to 3 g per day. Hydrastine has been reported to elicit abortifacient effects and induce preterm labor in pregnant women when taken orally.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
208 ng/mL
1.13 mg/kg single, oral
dose: 1.13 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDRASTINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
495 ng × h/mL
1.13 mg/kg single, oral
dose: 1.13 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDRASTINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.8 h
1.13 mg/kg single, oral
dose: 1.13 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
HYDRASTINE serum
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Screening for new compounds with antiherpes activity.
1984 Oct
Differential modulation of respiratory neuronal discharge patterns by GABA(A) receptor and apamin-sensitive K(+) channel antagonism.
2001 Nov
Effects of hydrastine derivatives on dopamine biosynthesis in PC12 cells.
2001 Oct
A validated high performance liquid chromatographic method for the analysis of Goldenseal.
2002 Mar
Individual and combined effect of (+/-)-alpha-hydrastine and (+/-)-beta-hydrastine on spore germination of some fungi.
2003
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.
2003 Dec 3
Method validation for determination of alkaloid content in goldenseal root powder.
2003 May-Jun
Human cytochrome p450 inhibition and metabolic-intermediate complex formation by goldenseal extract and its methylenedioxyphenyl components.
2003 Nov
Enantio-selective inhibition of (1R,9S)- and (1S,9R)-beta-hydrastines on dopamine biosynthesis in PC12 cells.
2004 Dec
Effects of (1R,9S)-beta-hydrastine on l-DOPA-induced cytotoxicity in PC12 cells.
2004 Mar 19
1H and 13C NMR signal assignment of benzylisoquinoline alkaloids from Fumaria officinalis L. (Papaveraceae).
2004 Oct
Capillary zone electrophoresis as a tool for the quality control of goldenseal extracts.
2005 Jun
Effects of (1R,9S)-beta-hydrastine on intracellular calcium concentration in PC12 cells.
2007 Aug
Inhibitory effects of (1R,9S)-beta-Hydrastine on calcium transport in PC12 cells.
2007 Jan
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells.
2007 Jul-Aug
Expanding the repertoire of small molecule transcriptional activation domains.
2009 Feb 1
Screening of a chemical library reveals novel PXR-activating pharmacologic compounds.
2015 Jan 5
Patents

Patents

Sample Use Guides

The disposition and metabolism of hydrastine was investigated in 11 healthy subjects following an oral dose of 2.7 g of goldenseal supplement containing 78 mg of hydrastine.
Route of Administration: Oral
A549 cells were incubated with the indicated concentrations of (-)-β-hydrastine for 24 h. The cells were then collected, rinsed with PBS, and suspended in staining buffer (10 μg/ml propidium iodide, 0.5% Tween-20, 0.1% RNase in PBS). The cells were analyzed using a FACS Vantage flow cytometer with Cell Quest acquisition and analysis software program (Becton-Dickinson and Co., San Jose, CA, USA).
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:08:43 UTC 2023
Edited
by admin
on Fri Dec 15 15:08:43 UTC 2023
Record UNII
8890V3217X
Record Status Validated (UNII)
Record Version
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Name Type Language
HYDRASTINE
MI   USP-RS   WHO-DD  
Common Name English
NSC-757430
Code English
Hydrastine [WHO-DD]
Common Name English
HYDRASTINE (CONSTITUENT OF GOLDENSEAL) [DSC]
Common Name English
HYDRASTINE [USP-RS]
Common Name English
HYDRASTINE [MI]
Common Name English
PHTHALIDE (S)-6,7-DIMETHOXY-3-(R)-(5,6,7,8-TETRAHYDRO-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-YL)-
Common Name English
(S)-6,7-Dimethoxy-3-(R)-(6-methyl-5,6,7,8-tetrahydro-[1,3]dioxolo[4,5-g]isoquinolin-5-yl)isobenzofuran-1(3H)-one
Systematic Name English
Classification Tree Code System Code
DSLD 1119 (Number of products:5)
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
NCI_THESAURUS C221
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C76031
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
WIKIPEDIA
Hydrastine
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
CAS
118-08-1
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
FDA UNII
8890V3217X
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
EPA CompTox
DTXSID9025409
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
PUBCHEM
197835
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
RS_ITEM_NUM
1313210
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
NSC
757430
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
ChEMBL
CHEMBL1256919
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-233-0
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
MESH
C013024
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY
MERCK INDEX
m6076
Created by admin on Fri Dec 15 15:08:43 UTC 2023 , Edited by admin on Fri Dec 15 15:08:43 UTC 2023
PRIMARY Merck Index
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
Related Record Type Details
ACTIVE MOIETY