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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H24N2O3
Molecular Weight 352.4277
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAUBASINE

SMILES

C[C@@]1([H])[C@@]2([H])CN3CCc4c5ccccc5[nH]c4[C@]3([H])C[C@]2([H])C(=CO1)C(=O)OC

InChI

InChIKey=GRTOGORTSDXSFK-XJTZBENFSA-N
InChI=1S/C21H24N2O3/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/t12-,15-,16+,19-/m0/s1

HIDE SMILES / InChI
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

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Lamuran

Approved Use

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

Approved Use

Unknown
PubMed

PubMed

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

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.
Name Type Language
RAUBASINE
MART.   MI   WHO-DD  
Common Name English
TETRAHYDROSERPENTINE
Common Name English
AJMALICINE
Common Name English
NSC-72133
Code English
HYDROSARPAN
Brand Name English
ISOARTERIL
Brand Name English
RAUBASINE [MART.]
Common Name English
(19.ALPHA.)-16,17-DIDEHYDRO-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER
Common Name English
.DELTA.-YOHIMBINE
Common Name English
CIRCOLENE
Brand Name English
PYTETRAHYDROSERPENTINE
Common Name English
RAUBASINE [MI]
Common Name English
LAMURAN
Brand Name English
RAUBASINE [WHO-DD]
Common Name English
Code System Code Type Description
PUBCHEM
441975
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
CAS
483-04-5
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
IUPHAR
8746
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
WIKIPEDIA
Raubasine
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
EVMPD
SUB15107MIG
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
FDA UNII
4QJL8OX71Z
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
MERCK INDEX
M9507
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
207-589-5
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY
RXCUI
17205
Created by admin on Sat Jun 26 12:30:15 UTC 2021 , Edited by admin on Sat Jun 26 12:30:15 UTC 2021
PRIMARY RxNorm