JERVINE HYDROCHLORIDE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H39NO3.ClH
Molecular Weight	462.064
Optical Activity	UNSPECIFIED
Defined Stereocenters	10 / 10
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

Cl.[H][C@@]12C[C@H](C)CN[C@@]1([H])[C@@H](C)[C@@]3(CC[C@]4([H])C(C(=O)[C@@]5([H])[C@@]4([H])CC=C6C[C@@H](O)CC[C@]56C)=C3C)O2

InChI

InChIKey=BTHSHLDGBOARGK-AVEQMEPMSA-N

InChI=1S/C27H39NO3.ClH/c1-14-11-21-24(28-13-14)16(3)27(31-21)10-8-19-20-6-5-17-12-18(29)7-9-26(17,4)23(20)25(30)22(19)15(27)2;/h5,14,16,18-21,23-24,28-29H,6-13H2,1-4H3;1H/t14-,16+,18-,19-,20-,21+,23+,24-,26-,27-;/m0./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15137822
Curator's Comment: description was created based on several sources, including: https://en.wikipedia.org/wiki/Jervine | https://www.google.com/patents/US20150259313

Jervine (11-Ketocyclopamine) is a naturally occuring steroidal alkaloid is derived from the Veratrum plant species. Jervine is a teratogen implicated in birth defects when consumed by animals during a certain period of their gestation. Over the Hedgehog signaling pathway Jervine effectively inhibit the tumor growth using three human tumor xenograft models including lung cancer, pancreatic cancer and basal cell carcinoma. Jervine has the potential to advance to a treatment for different tumors.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Hedgehog signaling pathway 11 Target ID: map04340 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12606278	Inhibitor 8297		50.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20013819 https://www.ncbi.nlm.nih.gov/pubmed/15137822	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Glycoalkaloids and metabolites inhibit the growth of human colon (HT29) and liver (HepG2) cancer cells.	2004 May 19	15137822
Critical time window of hedgehog-dependent angiogenesis in murine yolk sac.	2006 Mar	16414085
Antitumor activity of extracts and compounds from the rhizomes of Veratrum dahuricum.	2008 Aug	18570211
A study on the chemical constituents of Veratrum nigrum L. processed by rice vinegar.	2008 Jul-Aug	18636372
Accidental intoxication with Veratrum album.	2008 Nov-Dec	19021933
Smoothened adopts multiple active and inactive conformations capable of trafficking to the primary cilium.	2009	19365551
Ingestion of false hellebore plants can cross-react with a digoxin clinical chemistry assay.	2010 Jun	20586573
Antitumor and antiplatelet activity of alkaloids from veratrum dahuricum.	2010 Jun	20013819

Patents

Sample Use Guides

In Vivo Use Guide

Oral: 40 or 60 or 80 mg/kg once every day (during 21 days). Intravenous: 20 or 40 or 80 mg/kg once every day (during 21 days).

Route of Administration: Other

In Vitro Use Guide

Tongues treated with jervine at 10 μM exhibited a dorsal anterior tongue that was almost completely occupied by fungiform papillae.

Name

Type

Language

JERVINE HYDROCHLORIDE

Common Name

English

SPIRO(9H-BENZO(A)FLUORENE-9,2'(3'H)-FURO(3,2-B)PYRIDIN)-11(1H)-ONE, 2,3,3'A,4,4',5',6,6',6A,6B,7,7',7'A,8,11A,11B-HEXADECAHYDRO-3-HYDROXY-3',6',10,11B-TETRAMETHYL-, HYDROCHLORIDE (1:1), (2'R,3S,3'R,3'AS,6'S,6AS,6BS,7'AR,11AS,11BR)-

Systematic Name

English

JERVINE HYDROCHLORIDE [MI]

Common Name

English

(2'R,3S,3'R,3'AS,6'S,6AS,6BS,7'AR,11AS,11BR)-2,3,3'A,4,4',5',6,6',6A,6B,7,7',7'A,8,11A,11B-HEXADECAHYDRO-3-HYDROXY-3',6',10,11B-TETRAMETHYLSPIRO(9H-BENZO(A)FLUORENE-9,2'(3'H)-FURO(3,2-B)PYRIDIN)-11(1H)-ONE, HYDROCHLORIDE

Systematic Name

English

Code System Code Type Description

CAS

903508-18-9