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Details

Stereochemistry ABSOLUTE
Molecular Formula C41H63NO15.C4H4O4
Molecular Weight 926.0088
Optical Activity UNSPECIFIED
Defined Stereocenters 20 / 20
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PROTOVERATRINE B MALEATE

SMILES

OC(=O)\C=C/C(O)=O.CC[C@@H](C)C(=O)O[C@H]1[C@H](O)[C@H]2[C@@H](CN3C[C@@H](C)CC[C@H]3[C@@]2(C)O)[C@@H]4C[C@@]56O[C@@]7(O)[C@@H]([C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@H]5[C@]14O)[C@]6(C)CC[C@@H]7OC(=O)[C@](C)(O)[C@@H](C)O

InChI

InChIKey=WIWCPBACAHRLCS-VNBGJTSYSA-N
InChI=1S/C41H63NO15.C4H4O4/c1-10-19(3)34(47)56-33-28(46)27-23(17-42-16-18(2)11-12-25(42)38(27,9)50)24-15-39-32(40(24,33)51)30(54-22(6)45)29(53-21(5)44)31-36(39,7)14-13-26(41(31,52)57-39)55-35(48)37(8,49)20(4)43;5-3(6)1-2-4(7)8/h18-20,23-33,43,46,49-52H,10-17H2,1-9H3;1-2H,(H,5,6)(H,7,8)/b;2-1-/t18-,19+,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37+,38+,39+,40-,41+;/m0./s1

HIDE SMILES / InChI

Molecular Formula C41H63NO15
Molecular Weight 809.9366
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 20 / 20
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Protoveratrine B is one of two alkaloids isolated from the plant Veratrum albumen. The main effect of both alkaloids is vasodilation in all vascular beds thereby reducing blood pressure. In the 1950's it was recognized that Protoveratrine B is the preferred compound which can be administered at significantly higher doses before the patient begins to vomit.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PubMed

PubMed

TitleDatePubMed
A comparison between protoveratrine A and protoveratrine B orally in arterial hypertension; a therapeutically important difference in activity.
1956 Dec 20
[Protoveratrine A-B in medical therapy of hypertensive disease].
1957 Dec 22
INHIBITIONS BY OUABAIN AND PROTOVERATRINE ON ACTIVE TRANSPORT OF L-DOPA INTO BRAIN SLICES.
1963 Apr
Medicinal history of North American <i>Veratrum.</i>
2014 Sep
Patents

Sample Use Guides

In Vivo Use Guide
Protoveratrine B was administered to hypertensive patients as an oral tablet. Doses began at 0.3 to 0.5 mg single daily dose and raised incrementally until a marked fall in blood pressure was observed or the development on vomiting prohibited further increase.
Route of Administration: Oral
In Vitro Use Guide
Brain cortex slices of adult guinea pig were incubated for 30 min with 0.1 mM L-dopa. Brain slices were then pretreated with 5 uM protoveratrine (10 uM to 10 mM) for 20 min at 27 deg-C. Slices then incubated with glucose and L-dopa at 37 deg-C. The inclusion of Protoveratrine caused a decrease in the accumulation of L-dopa compared to control.
Substance Class Chemical
Created
by admin
on Tue Oct 22 16:32:23 UTC 2019
Edited
by admin
on Tue Oct 22 16:32:23 UTC 2019
Record UNII
ZY7MZX91C8
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PROTOVERATRINE B MALEATE
Common Name English
CEVANE-3,4,6,7,14,15,16,20-OCTOL, 4,9-EPOXY-, 6,7-DIACETATE 3-(2,3-DIHYDROXY-2-METHYLBUTANOATE) 15-(2-METHYLBUTANOATE), (3.BETA.,4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.(R),16.BETA.)-, (2Z)-2-BUTENEDIOATE (SALT)
Common Name English
Code System Code Type Description
PUBCHEM
71587006
Created by admin on Tue Oct 22 16:32:24 UTC 2019 , Edited by admin on Tue Oct 22 16:32:24 UTC 2019
PRIMARY
CAS
16533-30-5
Created by admin on Tue Oct 22 16:32:24 UTC 2019 , Edited by admin on Tue Oct 22 16:32:24 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE