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Details

Stereochemistry ABSOLUTE
Molecular Formula C41H63NO14.C2H4O2
Molecular Weight 853.9892
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTOVERATRINE A ACETATE

SMILES

CC(O)=O.[H][C@@]12C[C@]34O[C@]5(O)[C@H](CC[C@@]3(C)[C@]5([H])[C@@H](OC(C)=O)[C@@H](OC(C)=O)[C@@]4([H])[C@]1(O)[C@@H](OC(=O)[C@H](C)CC)[C@H](O)[C@@]6([H])[C@@]2([H])CN7C[C@@H](C)CC[C@@]7([H])[C@@]6(C)O)OC(=O)[C@@](C)(O)CC

InChI

InChIKey=DSDHWCGNLHADHK-XGTFUUGSSA-N
InChI=1S/C41H63NO14.C2H4O2/c1-10-20(4)34(46)55-33-28(45)27-23(18-42-17-19(3)12-13-25(42)38(27,9)49)24-16-39-32(40(24,33)50)30(53-22(6)44)29(52-21(5)43)31-36(39,7)15-14-26(41(31,51)56-39)54-35(47)37(8,48)11-2;1-2(3)4/h19-20,23-33,45,48-51H,10-18H2,1-9H3;1H3,(H,3,4)/t19-,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37-,38+,39+,40-,41+;/m0./s1

HIDE SMILES / InChI
Protoveratrine A, the principal alkaloid of Veratrum album, has been used in the treatment of hypertension but has largely been replaced by drugs with fewer adverse effects.

Originator

Curator's Comment: Protoveratrine was first isolated by Salzberger in 1890.

Approval Year

Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
21 ng/mL
12.5 μg/kg bw single, intravenous
dose: 12.5 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PROTOVERATRINE A plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
23.5 ng/mL
0.4 mg/kg single, oral
dose: 0.4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROTOVERATRINE A plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
44.7 ng × h/mL
12.5 μg/kg bw single, intravenous
dose: 12.5 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PROTOVERATRINE A plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
494.9 ng × h/mL
0.4 mg/kg single, oral
dose: 0.4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROTOVERATRINE A plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
21.4 h
12.5 μg/kg bw single, intravenous
dose: 12.5 μg/kg bw
route of administration: Intravenous
experiment type: SINGLE
co-administered:
PROTOVERATRINE A plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
21.9 h
0.4 mg/kg single, oral
dose: 0.4 mg/kg
route of administration: Oral
experiment type: SINGLE
co-administered:
PROTOVERATRINE A plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
3.6 mg 1 times / day multiple, oral
Studied dose
Dose: 3.6 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3.6 mg, 1 times / day
Sources:
unhealthy, 40-56 years
n = 2
Health Status: unhealthy
Condition: HYPERTENSION
Age Group: 40-56 years
Sex: M
Population Size: 2
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea
Vomiting
Sources:
1.4 mg single, oral
Highest studied dose
Dose: 1.4 mg
Route: oral
Route: single
Dose: 1.4 mg
Sources:
unhealthy
Health Status: unhealthy
Sources:
2.5 ug/kg single, intravenous
Highest studied dose
Dose: 2.5 ug/kg
Route: intravenous
Route: single
Dose: 2.5 ug/kg
Sources:
unhealthy
n = 10
Health Status: unhealthy
Condition: hypertension
Population Size: 10
Sources:
Other AEs: Nausea, Vomiting...
Other AEs:
Nausea (5 patients)
Vomiting (2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Nausea
3.6 mg 1 times / day multiple, oral
Studied dose
Dose: 3.6 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3.6 mg, 1 times / day
Sources:
unhealthy, 40-56 years
n = 2
Health Status: unhealthy
Condition: HYPERTENSION
Age Group: 40-56 years
Sex: M
Population Size: 2
Sources:
Vomiting
3.6 mg 1 times / day multiple, oral
Studied dose
Dose: 3.6 mg, 1 times / day
Route: oral
Route: multiple
Dose: 3.6 mg, 1 times / day
Sources:
unhealthy, 40-56 years
n = 2
Health Status: unhealthy
Condition: HYPERTENSION
Age Group: 40-56 years
Sex: M
Population Size: 2
Sources:
Vomiting 2 patients
2.5 ug/kg single, intravenous
Highest studied dose
Dose: 2.5 ug/kg
Route: intravenous
Route: single
Dose: 2.5 ug/kg
Sources:
unhealthy
n = 10
Health Status: unhealthy
Condition: hypertension
Population Size: 10
Sources:
Nausea 5 patients
2.5 ug/kg single, intravenous
Highest studied dose
Dose: 2.5 ug/kg
Route: intravenous
Route: single
Dose: 2.5 ug/kg
Sources:
unhealthy
n = 10
Health Status: unhealthy
Condition: hypertension
Population Size: 10
Sources:
PubMed

PubMed

TitleDatePubMed
The use of protoveratrine in the treatment of hypertensive vascular disease.
1953 Oct
Protoveratrine A in treatment of hypertension.
1957 Sep 14
Patents

Sample Use Guides

Out-patient Treatment of hypertension with Protoveratrine A: The duration of treatment has been from one month to as long as two years (mean nine months). The total treatment months were 155. The dosage employed varied from 0.5 to 3.6 mg daily. The drug was taken three times daily after meals and an additional dose often on retiring.
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: Protoveratrine A (10(-4) M), on the other hand, elevated the efflux of glutamate, GABA and possibly aspartate when these amino acids were synthesised from glucose, but not when acetate was the labelled precursor. https://www.ncbi.nlm.nih.gov/pubmed/913529
Protoveratrine A increased the release of gamma-amino[3H]butyrate from small slices of rat cerebral cortex. This effect increased with increasing protoveratrine concentration, reaching a maximum at 100 uM. 2. Removal of Ca2+ from the superfusing medium did not change the increase in release due to 10 uM-protoveratrine.
Name Type Language
PROTOVERATRINE A ACETATE
Common Name English
CEVANE-3,4,6,7,14,15,16,20-OCTOL, 4,9-EPOXY-, 6,7-DIACETATE 3-((2S)-2-HYDROXY-2-METHYLBUTANOATE) 15-((2R)-2-METHYLBUTANOATE), (3.BETA.,4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.,16.BETA.)-, ACETATE
Common Name English
Code System Code Type Description
FDA UNII
R1YW91CA2K
Created by admin on Sat Dec 16 09:35:21 GMT 2023 , Edited by admin on Sat Dec 16 09:35:21 GMT 2023
PRIMARY
PUBCHEM
91799751
Created by admin on Sat Dec 16 09:35:21 GMT 2023 , Edited by admin on Sat Dec 16 09:35:21 GMT 2023
PRIMARY