Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C21H24N2O3 |
| Molecular Weight | 352.4269 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 4 / 4 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12C[C@]3([H])C(=CO[C@@H](C)[C@@]3([H])CN1CCC4=C2NC5=CC=CC=C45)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
| 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 |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| Biliary drug lithiasis: dipyridamole gallstones. | 1992 Nov 28 |
|
| Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus. | 2005 Jun |
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.
| Substance Class |
Chemical
Created
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on
Edited
Fri Dec 15 15:19:54 GMT 2023
by
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| Record UNII |
4QJL8OX71Z
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| Record Status |
Validated (UNII)
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ACTIVE MOIETY |
