PROTOVERATRINE A TANNATE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C76H52O46.C41H63NO14
Molecular Weight	2495.1357
Optical Activity	UNSPECIFIED
Defined Stereocenters	24 / 24
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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)CC.OC8=CC(=CC(O)=C8O)C(=O)OC9=C(O)C(O)=CC(=C9)C(=O)OC[C@H]%10O[C@@H](OC(=O)C%11=CC(OC(=O)C%12=CC(O)=C(O)C(O)=C%12)=C(O)C(O)=C%11)[C@H](OC(=O)C%13=CC(OC(=O)C%14=CC(O)=C(O)C(O)=C%14)=C(O)C(O)=C%13)[C@@H](OC(=O)C%15=CC(OC(=O)C%16=CC(O)=C(O)C(O)=C%16)=C(O)C(O)=C%15)[C@@H]%10OC(=O)C%17=CC(OC(=O)C%18=CC(O)=C(O)C(O)=C%18)=C(O)C(O)=C%17

InChI

InChIKey=MADHPJGTJKDOQS-ODGWTQRTSA-N

InChI=1S/C76H52O46.C41H63NO14/c77-32-1-22(2-33(78)53(32)92)67(103)113-47-16-27(11-42(87)58(47)97)66(102)112-21-52-63(119-72(108)28-12-43(88)59(98)48(17-28)114-68(104)23-3-34(79)54(93)35(80)4-23)64(120-73(109)29-13-44(89)60(99)49(18-29)115-69(105)24-5-36(81)55(94)37(82)6-24)65(121-74(110)30-14-45(90)61(100)50(19-30)116-70(106)25-7-38(83)56(95)39(84)8-25)76(118-52)122-75(111)31-15-46(91)62(101)51(20-31)117-71(107)26-9-40(85)57(96)41(86)10-26;1-10-20(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/h1-20,52,63-65,76-101H,21H2;19-20,23-33,45,48-51H,10-18H2,1-9H3/t52-,63-,64+,65-,76+;19-,20+,23-,24-,25-,26-,27+,28+,29-,30+,31-,32+,33-,36-,37-,38+,39+,40-,41+/m10/s1

HIDE SMILES / InChI

Molecular Formula	C41H63NO14
Molecular Weight	793.9372
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	19 / 19
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C76H52O46
Molecular Weight	1701.1985
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	5 / 5
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/15409589 | https://www.ncbi.nlm.nih.gov/pubmed/14455364 | https://www.ncbi.nlm.nih.gov/pubmed/13571173 | https://www.ncbi.nlm.nih.gov/pubmed/13785790

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A, the principal alkaloid of Veratrum album, has been used in the treatment of hypertension but has largely been replaced by drugs with fewer adverse effects.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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
acetylcholine metabolic process 11 Target ID: GO:0008291 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1159414 \| https://iccb.med.harvard.edu/files/iccb/files/prestwick2_knownbioactivelibraries_activities_website_09092015.pdf	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15409589 https://www.ncbi.nlm.nih.gov/pubmed/14455364 https://www.ncbi.nlm.nih.gov/pubmed/13571173 https://www.ncbi.nlm.nih.gov/pubmed/13785790	Primary		Phase I 438	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
23.5 ng/mL EXPERIMENT https://link.springer.com/article/10.1365%2Fs10337-008-0936-4	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
21 ng/mL EXPERIMENT https://link.springer.com/article/10.1365%2Fs10337-008-0936-4	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

AUC

Value	Dose	Co-administered	Analyte	Population
494.9 ng × h/mL EXPERIMENT https://link.springer.com/article/10.1365%2Fs10337-008-0936-4	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
44.7 ng × h/mL EXPERIMENT https://link.springer.com/article/10.1365%2Fs10337-008-0936-4	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
21.9 h EXPERIMENT https://link.springer.com/article/10.1365%2Fs10337-008-0936-4	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
21.4 h EXPERIMENT https://link.springer.com/article/10.1365%2Fs10337-008-0936-4	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

Doses

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/13460332	unhealthy, 40-56 years Health Status: unhealthy Age Group: 40-56 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13460332	Other AEs: Nausea, Vomiting... Other AEs: Nausea Vomiting Sources: https://pubmed.ncbi.nlm.nih.gov/13460332
1.4 mg single, oral Highest studied dose Dose: 1.4 mg Route: oral Route: single Dose: 1.4 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13378636	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/13378636	Sources: https://pubmed.ncbi.nlm.nih.gov/13378636
2.5 ug/kg single, intravenous Highest studied dose Dose: 2.5 ug/kg Route: intravenous Route: single Dose: 2.5 ug/kg Sources: https://pubmed.ncbi.nlm.nih.gov/13785790	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/13785790	Other AEs: Nausea, Vomiting... Other AEs: Nausea (5 patients) Vomiting (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/13785790

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/13460332	unhealthy, 40-56 years Health Status: unhealthy Age Group: 40-56 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13460332
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: https://pubmed.ncbi.nlm.nih.gov/13460332	unhealthy, 40-56 years Health Status: unhealthy Age Group: 40-56 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/13460332
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: https://pubmed.ncbi.nlm.nih.gov/13785790	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/13785790
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: https://pubmed.ncbi.nlm.nih.gov/13785790	unhealthy Health Status: unhealthy Sources: https://pubmed.ncbi.nlm.nih.gov/13785790

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OATP1B1 1079 OATP1B3 961

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
OATP1B1 1095	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNjk3NjY4IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMDU3NjkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]
OATP1B3 970	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwxNzQzMTIxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDIxMDU3NjkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes [Inhibition 10 uM]

Sourcing

Vendor/Aggregator	ID	URL
abcr GmbH	AB167916	http://www.abcr.com/shop/en/AB167916
ABI Chem	AC1L1RZ7
Alfa Chemistry	143-57-7	https://www.alfa-chemistry.com/cas_143-57-7.htm
Alfa Chemistry	AP143577	https://reagents.alfa-chemistry.com/product/protoveratrine-a-cas-143-57-7-4932.html
Aurora Fine Chemicals LLC	A17.912.463	http://online.aurorafinechemicals.com/info?ID=A17.912.463
BOC Sciences	143-57-7
Chemieliva Pharmaceutical Co., Ltd	PBCM0280320
Compound Cloud	8931
eNovation Chemicals	D512302	http://www.enovationchem.com/productDetails.asp?productID=D512302
Parchem	57928	https://www.parchem.com/chemical-supplier-distributor/Protoveratrine-A-057928.aspx
Sigma-Aldrich	P6385_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/p6385?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma Aldrich	P6385
Sigma Aldrich	P6385\|SIGMA
Smolecule	S567404	https://www.smolecule.com/products/s567404
ZINC	ZINC000085537146	http://zinc15.docking.org/substances/ZINC000085537146

PubMed

Title	Date	PubMed
Protoveratrine A in treatment of hypertension.	1957-09-14	13460332
The use of protoveratrine in the treatment of hypertensive vascular disease.	1953-10	13092044

Patents

Sample Use Guides

In Vivo Use Guide

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

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:43:44 GMT 2025` Edited by `admin` on `Mon Mar 31 20:43:44 GMT 2025`
Record UNII	8V09K74WY1
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

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.)-, TANNATE

Preferred Name

English

PROTOVERATRINE A TANNATE

Common Name

English

Code System Code Type Description

FDA UNII

8V09K74WY1

Created by admin on Mon Mar 31 20:43:44 GMT 2025 , Edited by admin on Mon Mar 31 20:43:44 GMT 2025

PRIMARY

PUBCHEM

165411850

Created by admin on Mon Mar 31 20:43:44 GMT 2025 , Edited by admin on Mon Mar 31 20:43:44 GMT 2025

PRIMARY

Related Record Type Details


					XP343X1HJU

PROTOVERATRINE A

ACTIVE MOIETY

Amount: