HYDRASTININE HYDROCHLORIDE

US Previously Marketed

First marketed in 1921

Details

Stereochemistry	RACEMIC
Molecular Formula	C11H13NO3.ClH
Molecular Weight	243.687
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.CN1CCC2=C(C=C3OCOC3=C2)C1O

InChI

InChIKey=DLNQCQJCIITVHC-UHFFFAOYSA-N

InChI=1S/C11H13NO3.ClH/c1-12-3-2-7-4-9-10(15-6-14-9)5-8(7)11(12)13;/h4-5,11,13H,2-3,6H2,1H3;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

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

Molecular Formula	C11H13NO3
Molecular Weight	207.2258
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/14398297
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/11582536 | https://www.ncbi.nlm.nih.gov/pubmed/16911722

Hydrastinine is a synthetic alkaloid prepared by various processes from either hydrastine, berberine, or narcotine. It exerts a strong stimulating action on the uterus of all species studied, including human. Hydrastinine and the closely related alkaloid cotarnine have been employed as hemostatics, particularly in abnormal uterine conditions. In the non-pregnant animal, hydrastinine in doses of 10 mg. depressed both tonus and activity, even after the section of the hypogastric. In the pregnant cat, it caused the uterus to contract. A stimulant action was also noted in the non-pregnant animal if nicotine were administered prior to hydrastinine. The rabbit uterus in situ was strongly contracted. Laidlaw believed that hydrastinine acted on the uterus both directly on the smooth muscle and also through its sympathetic innervation. Repeated administration of large doses for a period of time resulted in greatly increased amplitude of contractions which persisted after removal of the drug. The drug was patented by Bayer as a haemostatic drug during the 1910s.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Solute carrier organic anion transporter family member 1B3 16 Target ID: CHEMBL1743121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 8297
Solute carrier organic anion transporter family member 1B1 32 Target ID: CHEMBL1697668 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23571415	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Labor complications 8 Sources: http://jpet.aspetjournals.org/content/9/6/287	Primary		Basic research	Unknown Approved Use Unknown

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inhibitor 1852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
NTCP 34 OAT1 599 OAT3 642 OATP1B1 788 OATP1B3 706 OATP2B1 123 OCT1 512 OCT2 647 BSEP 402 BCRP 699 MATE1 306 MATE2 263 MRP2 383 MRP3 157 P-gp 1461

Drug as perpetrator

Target	Modality	Activity
BCRP 773	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
BSEP 403	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
MRP2 475	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
MRP3 207	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
NTCP 35	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
OAT1 603	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
OAT3 644	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
OATP1B1 803	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107, https://pubmed.ncbi.nlm.nih.gov/23571415/	no
OATP1B3 715	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107, https://pubmed.ncbi.nlm.nih.gov/23571415/	no
OATP2B1 126	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
P-gp 1650	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	no
MATE2 263	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	weak
OCT1 543	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	weak
MATE1 308	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	yes [IC50 82 uM]
OCT2 648	inhibitor 3277 Sources: https://ascpt.onlinelibrary.wiley.com/doi/abs/10.1002/cpt.2107	yes [IC50 95 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/32591416/	yes [Ki 37 uM]

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY565905	https://www.001chemical.com/chem/6592-85-4
AHH Chemical co.,ltd	MR-1006369	http://www.ahhchemical.com/product/MR-1006369.html
Alfa Chemistry	6592-85-4	https://www.alfa-chemistry.com/cas_6592-85-4.htm
Ambinter	Amb22732393	http://www.ambinter.com/reference/22732393
BLD Pharm	BD01212831	http://www.bldpharm.com/products/6592-85-4.html
Chem Scene	CS-0108783	http://www.chemscene.com/6592-85-4.html
ChemMol	99138005	http://www.chemmol.com/chemmol/99138005.html
Chemspace	CSSB00000065284	https://chem-space.com/CSSB00000065284
MedChem Express	HY-B1181A	https://www.medchemexpress.com/hydrastinine.html
Molcore	MC565905	https://www.molcore.com/product/6592-85-4
Smolecule	S606760	https://www.smolecule.com/products/s606760
THE BioTek	bt-436220	https://www.thebiotek.com/product/others/bt-436220

PubMed

Title	Date	PubMed
Chemical comparison of goldenseal (Hydrastis canadensis L.) root powder from three commercial suppliers.	2003 Dec 3	14640583
[Extraction and HPLC analysis of alkaloids in goldenseal].	2004 Mar	15969129
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.). 2. Palmatine, hydrastine, canadine, and hydrastinine.	2006 Jun	16780351
The origin of MDMA ("ecstasy")--separating the facts from the myth.	2006 Nov	17152992
Thin-layer chromatography/desorption electrospray ionization mass spectrometry: investigation of goldenseal alkaloids.	2007 Apr 1	17338504
Photochemistry and photocytotoxicity of alkaloids from Goldenseal (Hydrastis canadensis L.) 3: effect on human lens and retinal pigment epithelial cells.	2007 Jul-Aug	17645667
Significant differences in alkaloid content of Coptis chinensis (Huanglian), from its related American species.	2009 Aug 24	19703289

Patents

Sample Use Guides

In Vivo Use Guide

Rat LD50=104 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

PC12 cells were maintained routinely in RPMI 1640 medium supplemented with 10 % heat-inactivated horse serum and 5 % fetal calf serum plus 100 units/ml penicillin and 100 μg/ml streptomycin at 37 °C. PC12 cells (ca. 1 × 10^5 cells/cm2) were treated with hydrastine derivatives (5 - 40 μM) into the medium and then were incubated for 6 (-48) h in the presence of the hydrastine derivatives. The cells (ca. 1.5 - 2 × 10^5cells/cm2) were harvested with phosphate buffered saline and then were centrifuged. The cell pellets were used for the measurement of dopamine content, and the intracellular TH and AADC activities.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:05:20 GMT 2023` Edited by `admin` on `Fri Dec 15 16:05:20 GMT 2023`
Record UNII	S8253P6A1G
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

HYDRASTININE HYDROCHLORIDE

Common Name

English

HYDRASTININE HCL

Common Name

English

HYDRASTININUM MURIATICUM

Common Name

English

5,6,7,8-TETRAHYDRO-6-METHYL-1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, HYDROCHLORIDE

Systematic Name

English

1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, 5,6,7,8-TETRAHYDRO-6-METHYL-, HYDROCHLORIDE (1:1)

Systematic Name

English

HYDRASTININE HYDROCHLORIDE [MART.]

Common Name

English

Hydrastinine hydrochloride [WHO-DD]

Common Name

English

NSC-93766

Code

English

HYDRASTININUM MURIATICUM [HPUS]

Common Name

English

1,3-DIOXOLO(4,5-G)ISOQUINOLIN-5-OL, HYDROCHLORIDE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C78311