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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O3.ClH
Molecular Weight 388.888
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAUBASINE HYDROCHLORIDE

SMILES

Cl.COC(=O)C1=CO[C@@H](C)[C@H]2CN3CCC4=C(NC5=C4C=CC=C5)[C@@H]3C[C@H]12

InChI

InChIKey=YWPZOTNKHMBWPD-QAWKRFFXSA-N
InChI=1S/C21H24N2O3.ClH/c1-12-16-10-23-8-7-14-13-5-3-4-6-18(13)22-20(14)19(23)9-15(16)17(11-26-12)21(24)25-2;/h3-6,11-12,15-16,19,22H,7-10H2,1-2H3;1H/t12-,15-,16+,19-;/m0./s1

HIDE SMILES / InChI
Molecular Formula C21H24N2O3
Molecular Weight 352.4269
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

The Rauwolfia alkaloid, raubasine (ajmalicine), has been found to have broad application in the treatment of circulatory diseases, especially in the relief of obstruction of normal cerebral blood flow. In combination with other Rauwolfia alkaloids it has been used to lower high blood pressure. Raubasine is an antihypertensive drug used in the treatment of high blood pressure. It has been marketed under numerous brand names including Card-Lamuran, Circolene, Cristanyl, Duxil, Duxor, Hydroxysarpon, Iskedyl, Isosarpan, Isquebral, Lamuran, Melanex, Saltucin Co, Salvalion, and Sarpan. Raubasine acts as a α1-adrenergic receptor antagonist.

CNS Activity

CNS Active
4002
Curator's Comment: Behavioral studies showed raubasine to possess anticonvulsant properties against pentylenetetrazol- and bicuculline-induced convulsions in mice.

Originator

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
 8.2 nM [Ki]
Antagonist
2849
 5.0 nM [Ki]
Antagonist
2849
 14.5 nM [Ki]
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
Lamuran

Approved Use

RAUBASINE is an antihypertensive drug used in the treatment of high blood pressure.
Primary
Phase I
438
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
Disc. AE: Vertigo, Nausea...
AEs leading to
discontinuation/dose reduction:
Vertigo
Nausea
Epigastric pain
Skin rash (1%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
AEs

AEs

AESignificanceDosePopulation
Skin rash 1%
Disc. AE
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
Epigastric pain Disc. AE
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
Nausea Disc. AE
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
Vertigo Disc. AE
10 mg 2 times / day multiple, oral
Recommended
Dose: 10 mg, 2 times / day
Route: oral
Route: multiple
Dose: 10 mg, 2 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/2093414/
PubMed

PubMed

TitleDatePubMed
Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus.
2005-06
Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies.
1993-04-30
Biliary drug lithiasis: dipyridamole gallstones.
1992-11-28
Effects of four non-cholinergic cognitive enhancers in comparison with tacrine and galanthamine on scopolamine-induced amnesia in rats.
1992
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.
1991-01-01
Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine.
1984-10-30
Patents

Patents

JPH00892041A
6
JPH06296443A
2
WO2015048792A1
2

Sample Use Guides

In Vivo Use Guide
In the raubasine group (10 patients aged 47 to 81 years, including 6 cases of anacidity) there was after one and two weeks treatment with dialy doses of 90 mg raubasine a significant reduction of the raised vascular resistance and pulsewave velocity and systolic blood pressure in the internal carotid artery which indicate an improvement in cerebral haemodynamics.
Route of Administration: Oral
In Vitro Use Guide
In strips of isolated canine basilar arteries, previously labeled with 3 X 10(-7) M of either [3H]noradrenaline or [3H]serotonin, three consecutive periods of electrical stimulation (2 Hz) evoked a reproducible overflow of the respective [3H]amine. Increasing concentrations of raubasine (7.5 X 10(-7)-7.5 X 10(-6) M) did not influence the spontaneous 3H efflux but increased the stimulation-induced 3H overflow in a concentration-dependent way. The highest concentration of raubasine used (2.5 X 10(-5) M) caused an increased spontaneous 3H efflux but no longer augmented the stimulation-induced 3H overflow.
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:30:17 GMT 2025
Edited
by admin
on Mon Mar 31 21:30:17 GMT 2025
Record UNII
I0V9KZN41X
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(19.ALPHA.)-16,17-DIDEHYDRO-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE
Preferred Name English
RAUBASINE HYDROCHLORIDE
WHO-DD  
Common Name English
Raubasine hydrochloride [WHO-DD]
Common Name English
RAUBASINE HCL
Common Name English
AJMALICINE HYDROCHLORIDE
Common Name English
Code System Code Type Description
EVMPD
SUB15108MIG
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
SMS_ID
100000078629
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
FDA UNII
I0V9KZN41X
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
ECHA (EC/EINECS)
224-471-9
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
CAS
4373-34-6
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
EPA CompTox
DTXSID301349028
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
PUBCHEM
168978
Created by admin on Mon Mar 31 21:30:17 GMT 2025 , Edited by admin on Mon Mar 31 21:30:17 GMT 2025
PRIMARY
NIH
NCATS
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