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
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
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL1867 |
8.2 nM [Ki] | ||
Target ID: CHEMBL1916 |
5.0 nM [Ki] | ||
Target ID: CHEMBL1942 |
14.5 nM [Ki] | ||
Target ID: CHEMBL1907610 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Lamuran Approved UseRAUBASINE is an antihypertensive drug used in the treatment of high blood pressure. |
|||
| Primary | Unknown Approved UseUnknown |
Doses
| Dose | Population | Adverse 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Vertigo, Nausea... AEs leading to discontinuation/dose reduction: Vertigo Sources: Nausea Epigastric pain Skin rash (1%) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 |
Sample Use Guides
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 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.
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SUB15108MIG
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100000078629
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DTXSID301349028
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168978
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SUBSTANCE RECORD
