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

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.[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

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 TargetPharmacologyConditionPotency
8.2 nM [Ki]
5.0 nM [Ki]
14.5 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Lamuran
Primary
Unknown

PubMed

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.