RAUBASINE HYDROCHLORIDE

Possibly Marketed Outside US

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 Search

SMILES

Cl.[H][C@@]12C[C@]3([H])C(=CO[C@@H](C)[C@@]3([H])CN1CCC4=C2NC5=CC=CC=C45)C(=O)OC

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

Description
Sources: https://www.indiamart.com/proddetail/raubasine-6582993991.html | http://en.pharmacodia.com/web/drug/1_12936.html | https://link.springer.com/chapter/10.1007/978-3-642-66646-9_3 | https://www.ncbi.nlm.nih.gov/pubmed/6099269

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Alpha-2a adrenergic receptor 63 Target ID: CHEMBL1867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Antagonist 2778	8.2 nM [Ki]
Alpha-2c adrenergic receptor 37 Target ID: CHEMBL1916 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Antagonist 2778	5.0 nM [Ki]
Alpha-2b adrenergic receptor 27 Target ID: CHEMBL1942 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7562902	Antagonist 2778	14.5 nM [Ki]
Adrenergic receptor alpha-1 169 Target ID: CHEMBL1907610 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3021076	Antagonist 2778

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://en.pharmacodia.com/web/drug/1_12936.html https://www.ncbi.nlm.nih.gov/pubmed/790125 https://link.springer.com/chapter/10.1007/978-3-642-66646-9_3	Primary		Approved 8429	Lamuran Approved Use RAUBASINE is an antihypertensive drug used in the treatment of high blood pressure.
Cognitive disorders 8 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2093422 https://www.ncbi.nlm.nih.gov/pubmed/2093414	Primary		Phase I 428	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Inhibition of the alpha 1 and alpha 2-adrenoceptor-mediated pressor response in pithed rats by raubasine, tetrahydroalstonine and akuammigine.	1984 Oct 30	6099269
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Effects of four non-cholinergic cognitive enhancers in comparison with tacrine and galanthamine on scopolamine-induced amnesia in rats.	1992	1738791
Development of a pharmacophore for inhibition of human liver cytochrome P-450 2D6: molecular modeling and inhibition studies.	1993 Apr 30	8487254
Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus.	2005 Jun	15930738

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 HYDROCHLORIDE

Common Name

English

(19.ALPHA.)-16,17-DIDEHYDRO-19-METHYLOXAYOHIMBAN-16-CARBOXYLIC ACID METHYL ESTER HYDROCHLORIDE

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