U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C41H63NO14
Molecular Weight 793.9372
Optical Activity UNSPECIFIED
Defined Stereocenters 19 / 19
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PROTOVERATRINE A

SMILES

[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=HYTGGNIMZXFORS-MGYKWWNKSA-N
InChI=1S/C41H63NO14/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/h19-20,23-33,45,48-51H,10-18H2,1-9H3/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A, the principal alkaloid of Veratrum album, has been used in the treatment of hypertension but has largely been replaced by drugs with fewer adverse effects.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
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
MI   WHO-DD  
Common Name English
CEVANE-3,4,6,7,14,15,16,20-OCTOL, 4,9-EPOXY-, 6,7-DIACETATE 3-(2-HYDROXY-2-METHYLBUTANOATE) 15-(2-METHYLBUTANOATE), (3.BETA.(S),4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.(R),16.BETA.)-
Systematic Name English
PROTOVERATRINE A [MI]
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.)-
Systematic Name English
PROTALBA
Brand Name English
(3.BETA.(S),4.ALPHA.,6.ALPHA.,7.ALPHA.,15.ALPHA.(R),16.BETA.)-4,9-EPOXYCEVANE-3,4,6,7,14,15,16,20-OCTOL 6,7-DIACETATE 3-(2-HYDROXY-2-METHYLBUTANOATE) 15-(2-METHYLBUTANOATE)
Common Name English
NSC-7526
Code English
Protoveratrine a [WHO-DD]
Common Name English
PROTOVERATRIN
Common Name English
PROTOVERATRINE
Common Name English
NSC-23865
Code English
PROTOVERINE 3-((+)-(2S)-2-HYDROXY-2-METHYLBUTYRATE) 6,7-DIACETATE 15-((-)-(2R)-2-METHYLBUTYRATE)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C221
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
Code System Code Type Description
FDA UNII
XP343X1HJU
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
NSC
7526
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
NCI_THESAURUS
C81361
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-602-9
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
NSC
23865
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105769
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
CAS
143-57-7
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
EVMPD
SUB36172
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
MERCK INDEX
m9278
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID301009391
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
SMS_ID
100000128725
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY
PUBCHEM
8931
Created by admin on Fri Dec 15 15:39:22 UTC 2023 , Edited by admin on Fri Dec 15 15:39:22 UTC 2023
PRIMARY