reserpine
Trade name: serpasil
Approved
Apr 1, 1954
Reserpine is an alkaloid, isolated from the Rauwolfia serpentina plant and developed by Ciba pharma. Reserpine was approved by FDA for the treatment of hypertension and psychotic disorders. The drug exerts its effect by blocking two vesicular monoamine transporters, VMAT1 and VMAT2. The blockade results in vesicles that lose their ability to store neurotransmitter molecules. Neurotransmitters, thus retained in cytosol, are then neutralized by MAO. — NCATS
Clinical trial activity
7 trials · 14 clinical orgs · 48 marketing orgs
Earliest trial started Sep 1, 1980 (NCT00000499)
Timeline
1950s
- Apr 1, 1954
Earliest FDA Approval
- Apr 1, 1954
Novartis — NDA Secondary Org
- Mar 24, 1955
Sandoz — NDA Secondary Org
- Aug 12, 1955
Ciba — First NDA Organization
- Aug 12, 1955
Ciba — NDA Organization
- Oct 12, 1955
Lannett Company, Inc. — NDA Secondary Org
- Dec 11, 1958
Merck — Marketing Organization
- Dec 11, 1958
Merck — NDA Secondary Org
1960s
- Mar 9, 1960
Schering — Marketing Organization
- Mar 9, 1960
Schering — NDA Secondary Org
- Jun 20, 1960
Shire — Marketing Organization
- Jun 20, 1960
Shire — NDA Secondary Org
- Oct 15, 1963
Pfizer — Marketing Organization
- Oct 15, 1963
Pfizer — NDA Secondary Org
- May 8, 1964
Sanofi-Aventis — Marketing Organization
- May 8, 1964
Sanofi-Aventis — NDA Secondary Org
1970s
- Dec 22, 1971
Watson Pharmaceuticals — Marketing Organization
- Mar 30, 1972
MK Labs — Marketing Organization
- Apr 4, 1972
Solvay — Marketing Organization
- Jun 21, 1972
Halsey — Marketing Organization
- Oct 16, 1972
Barr Laboratories — Marketing Organization
- Dec 26, 1972
Hikma — Marketing Organization
- Jul 31, 1973
Whiteworth Towne Paulsen — Marketing Organization
- Aug 7, 1973
Marshall Pharma — Marketing Organization
- Sep 30, 1975
Medpointe — Marketing Organization
- Sep 30, 1975
Medpointe — NDA Secondary Org
- Dec 7, 1976
Bausch Health Companies — NDA Secondary Org
- Mar 10, 1977
Lannett Company, Inc. — Marketing Organization
- Feb 21, 1978
Everylife Foundation for Rare Diseases — NDA Secondary Org
- Nov 20, 1979
AmerisourceBergen — Marketing Organization
- Nov 20, 1979
Chartwell Pharmaceuticals — Marketing Organization
1980s
- Jan 1, 1980
Earliest Phase 2 Sponsor(trial)
- Apr 16, 1981
Sandoz — Marketing Organization
- Oct 22, 1981
Eli Lilly — NDA Secondary Org
- May 6, 1982
Mylan — Marketing Organization
- May 6, 1982
PHARMOBEDIENT — Marketing Organization
- Sep 7, 1983
Lederle — Marketing Organization
- Sep 7, 1983
American Cyanamid — Marketing Organization
- Jan 1, 1984
Earliest Phase 3 Sponsor(trial)
- Apr 10, 1984
Sun Pharmaceuticals — Marketing Organization
- May 10, 1984
West-Ward Pharmaceutical — Marketing Organization
- Jan 11, 1985
Ivax — Marketing Organization
- Mar 7, 1985
Teva — Marketing Organization
- Sep 20, 1985
Par Pharmaceuticals — Marketing Organization
2000s
- Jan 1, 2004
Earliest Phase 1 Sponsor(trial)
Indications
Mechanism of action
- Synaptic vesicular amine transporterINHIBITOR
SLC18A2 inhibitor
Combination products
diupres
with chlorothiazide
Also known as chlorothiazide-reserpine
diutensen-r
with methyclothiazide
hydromox r
with quinethazone
naquival
with trichlormethiazide
regroton
with chlorthalidone
Also known as demi-regroton
renese-r
with polythiazide
salutensin-demi
with hydroflumethiazide
Also known as salutensin
ser-ap-es
with hydralazine, hydrochlorothiazide
Also known as cam-ap-es, hydralazine, hydrochlorothiazide w/ reserpine, hydrap-es
serpasil-apresoline
with hydralazine
Also known as dralserp
serpasil-esidrix
with hydrochlorothiazide
Also known as h.r, hydropres, hydro-reserp, reserpine and hydrochlorothiazide
Approval history
- approvedApr 1, 1954
Chemistry & pharmacology
SMILES
CO[C@H]1[C@@H](C[C@@H]2CN3CCC4=C(NC5=C4C=CC(OC)=C5)[C@H]3C[C@@H]2[C@@H]1C(=O)OC)OC(=O)C6=CC(OC)=C(OC)C(OC)=C6- Mol. weight
- 608.6787 g/mol
- Lipinski Ro5
- 1 violation(s)
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral
- Availability
- Discontinued
Oral
Yes
Parenteral
No
Topical
No
Sources
- WikipediaReserpine ↗
- NCATS8B1QWR724A ↗
- ChEMBLCHEMBL772 ↗
- ChEMBLCHEMBL3559672 ↗
Also known as
- 3,4,5-trimethoxybenzoyl methyl reserpate
- 3,4,5-trimethoxybenzoyl methyl reserpate
- (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
- (3beta,16beta,17alpha,18beta,20alpha)-11,17-dimethoxy-18-[(3,4,5-trimethoxybenzoyl)oxy]yohimban-16-carboxylic acid methyl ester
- apoplon
- apoplon
- deserpine
- elserpine
- hiserpia
- hiserpia
- raudixin
- raudixin
- raudixin
- rau-sed
- rau-sed
- rauval
- rauwasedin
- reserpin
- reserpin
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- reserpine
- (-)-reserpine
- (-)-reserpine
- (−)-reserpine
- (−)-reserpine
- rivasin
- sandril
- sandril
- serpalan
- serpalan
- serpalan
- serpanray
- serpanray
- serpasil
- serpasil
- serpasil
- serpate
- serpate
- serpine
- serpivite
- serpivite
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT06199778 | N/A | Jun 1, 2022 | Allina Health, Zhengzhou University |
| NCT02684786 | Phase 1 | Mar 1, 2016 | Mayo Clinic |
| NCT03223272 | Phase 2 | Jul 23, 2015 | University of Alabama, Birmingham |
| NCT00267657 | Phase 1 | Jan 1, 2004 | National Institute on Drug Abuse (NIDA), University of California, San Francisco |
| NCT00033033 | Phase 2 | Jul 1, 2001 | Department of Veteran Affairs, National Institute on Drug Abuse (NIDA) |
| NCT00000514 | Phase 3 | Jun 1, 1984 | National Heart, Lung, and Blood Institute (NHLBI), National Institute on Aging (NIA), The University of Texas, Dallas |
| NCT00000499 | Phase 2 | Sep 1, 1980 | Kaiser Foundation, National Heart, Lung, and Blood Institute (NHLBI), National Institute on Aging (NIA), Rush University, University of Alabama, Birmingham, University of Pittsburgh, Washington University in St. Louis |
Organizations
Research & Development (14)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| National Heart, Lung, and Blood Institute (NHLBI) | Government | 2 | 2 | 2 | 1980 |
| National Institute on Aging (NIA) | Government | 2 | 0 | 2 | 1980 |
| National Institute on Drug Abuse (NIDA) | Government | 2 | 2 | 2 | 2001 |
| University of Alabama, Birmingham | Academic/Hospital | 2 | 1 | 1 | 1980 |
| Allina Health | Academic/Hospital | 1 | 0 | 1 | 2022 |
| Department of Veteran Affairs | Government | 1 | 0 | 1 | 2001 |
| Kaiser Foundation | Academic/Hospital | 1 | 0 | 1 | 1980 |
| Mayo Clinic | Academic/Hospital | 1 | 1 | 1 | 2016 |
| Rush University | Academic/Hospital | 1 | 0 | 1 | 1980 |
| The University of Texas, Dallas | Academic/Hospital | 1 | 0 | 1 | 1984 |
| University of California, San Francisco | Academic/Hospital | 1 | 0 | 1 | 2004 |
| University of Pittsburgh | Academic/Hospital | 1 | 0 | 1 | 1980 |
| Washington University in St. Louis | Academic/Hospital | 1 | 0 | 1 | 1980 |
| Zhengzhou University | Academic/Hospital | 1 | 1 | 1 | 2022 |
Marketing (61)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| American Cyanamid | For profit | MKTG | Sep 7, 1983 |
| AmerisourceBergen | For profit | MKTG | Nov 20, 1979 |
| BELL PHARMA | For profit | MKTG | — |
| Barr Laboratories | For profit | MKTG | Oct 16, 1972 |
| Bausch Health Companies | For profit | NDA2 | Dec 7, 1976 |
| Bowman Pharms | For profit | NDA2 | — |
| Bristol-Myers Squibb | For profit | NDA2 | — |
| Bundy | For profit | NDA2 | — |
| Chartwell Pharmaceuticals | For profit | MKTG | Nov 20, 1979 |
| Ciba | For profit | NDA | Aug 12, 1955 |
| Cycle Pharmaceuticals Ltd. | For profit | NDA2 | — |
| Eli Lilly | For profit | NDA2 | Oct 22, 1981 |
| Elkins Sinn | For profit | MKTG | — |
| Everylife Foundation for Rare Diseases | Academic/Hospital | NDA2 | Feb 21, 1978 |
| Halsey | For profit | MKTG | Jun 21, 1972 |
| Hikma | For profit | MKTG | Dec 26, 1972 |
| Hikma | For profit | SYN | Dec 22, 1983 |
| Hikma | For profit | SYN | Dec 22, 1983 |
| Impax Laboratories | For profit | NDA2 | — |
| Ivax | For profit | MKTG | Jan 11, 1985 |
| Lannett Company, Inc. | For profit | MKTG | Mar 10, 1977 |
| Lannett Company, Inc. | For profit | NDA2 | Oct 12, 1955 |
| Lederle | For profit | MKTG | Sep 7, 1983 |
| Lederle | For profit | NDA2 | — |
| MK Labs | For profit | MKTG | Mar 30, 1972 |
| Marshall Pharma | For profit | MKTG | Aug 7, 1973 |
| Medpointe | For profit | MKTG | Sep 30, 1975 |
| Medpointe | For profit | NDA2 | Sep 30, 1975 |
| Merck | For profit | MKTG | Dec 11, 1958 |
| Merck | For profit | NDA2 | Dec 11, 1958 |
| Mylan | For profit | MKTG | May 6, 1982 |
| Novartis | For profit | NDA2 | Apr 1, 1954 |
| PHARMOBEDIENT | For profit | MKTG | May 6, 1982 |
| Panray Corp. | For profit | NDA2 | — |
| Par Pharmaceuticals | For profit | MKTG | Sep 20, 1985 |
| Pfizer | For profit | MKTG | Oct 15, 1963 |
| Pfizer | For profit | NDA2 | Oct 15, 1963 |
| Pharmavite | For profit | MKTG | — |
| Puracap Pharmaceutical | For profit | MKTG | — |
| Rexall Drug Company | For profit | MKTG | — |
| Roxane Laboratories | For profit | MKTG | — |
| Sandoz | For profit | NDA2 | Mar 24, 1955 |
| Sandoz | For profit | MKTG | Apr 16, 1981 |
| Sanofi-Aventis | For profit | MKTG | May 8, 1964 |
| Sanofi-Aventis | For profit | NDA2 | May 8, 1964 |
| Schering | For profit | MKTG | Mar 9, 1960 |
| Schering | For profit | NDA2 | Mar 9, 1960 |
| Shire | For profit | MKTG | Jun 20, 1960 |
| Shire | For profit | NDA2 | Jun 20, 1960 |
| Solvay | For profit | MKTG | Apr 4, 1972 |
| Sun Pharmaceuticals | For profit | MKTG | Apr 10, 1984 |
| Tablicaps | For profit | MKTG | — |
| Teva | For profit | MKTG | Mar 7, 1985 |
| Teva | For profit | SYN | Nov 20, 1973 |
| Teva | For profit | NDA2 | — |
| Upsher-Smith Laboratories | For profit | MKTG | — |
| VALE | For profit | NDA2 | — |
| Vitarine | For profit | NDA2 | — |
| Watson Pharmaceuticals | For profit | MKTG | Dec 22, 1971 |
| West-Ward Pharmaceutical | For profit | MKTG | May 10, 1984 |
| Whiteworth Towne Paulsen | For profit | MKTG | Jul 31, 1973 |